Spring is a time I find myself observing how so many elements of baseball translate to “real life”, and how true this is no matter the competition level. While the speed and polish improve from level to level, so many of the truisms remain consistent from how the game evolves from youth to high school to college and to ultimately the professional level.

Every sport provides learnings that apply to one’s worklife, but there’s something about the game of baseball that I find particularly relevant to what it takes to navigate the ambiguity and challenges of working in a company, especially an early stage company. Specifically, there are four characteristics inherent in baseball that I see embedded in what also matters for people working in a startup organization either as the CEO, a people manager, or an individual contributor.

Failure and Resilience

There’s a lot of failure in baseball. The best hitters succeed well below 40% of the time and the best pitchers can all recite countless outings over their career in which they got “lit up” by opposing hitters. Likewise, there’s a lot of failure in startups. Most of these companies fail, and the failure rate of startups is even lower than the batting average of the weakest MLB hitters.

If you can’t handle failing and aren’t willing (or able) to learn how to be resilient, then don’t play baseball or start/join a startup. In baseball, the line is “flush it”, a refrain used to remind the hitter to forget taking that called third strike so they can immediately refocus their attention on playing great defense and can restart preparing mentally for their next at-bat.

The same applies to what you do in a startup. Forget that customer product feature that bombed or that sales pitch that resulted in a “no thanks”. Flush it. Figure out what you’re building and shipping next, or shift your focus to how you’ll tweak that next sales presentation.

Repetition and Iteration

Baseball is a game of repetitions or “reps”. You can’t master the game just because you can run fast, jump high, or have amazing strength – just ask Michael Jordan. It’s a game that requires hitters take thousands of swings at thousands of pitches that move and dart in different directions and varying speeds. It’s a game that requires pitchers to throw thousands of pitches that they are endlessly trying to command moving in multiple directions and speeds.

Startup companies are also built on “reps”. Ask any startup founder or CEO how many times they have to iterate on their fundraising pitch. Most of these CEOs will tell you stories of the thousands of versions of their presentation they had to create over the course of their fundraising efforts, and the hundreds of meetings in which they presented those pitches to investors.

With each rep those CEOs got a little better; they told their company’s story a little more clearly and with increasing conviction and confidence. But they never stopped getting reps, they never stopped iterating, and neither does anyone in a startup no matter what your role or level might be. Like baseball, you’re constantly trying to perfect the imperfectable and, just when you think you’ve got it all figured out, you get smacked down. The pitch falls flat, the marketing channel doesn’t react as hoped, or the hiring strategy yields lackluster results. At that moment you know it’s time to tap into your resilience and get in some more reps.

Playing Every Out

Baseball has no clock (well, the pitch clock doesn’t really count). Both teams get the same number of outs and you learn pretty quickly that no matter the score or situation, neither team can hold the ball and run out the clock.

This is exactly why maintaining resilience and getting in your reps are so crucial. As Yogi Berra said so well: “It ain’t over until it’s over.”

This ethos applies so beautifully to life in a startup. While venture capitalists like to ask “what’s your burn, how much runway do you have?”, this doesn’t ever mean as a startup CEO you are on a defined clock. With any amount of capital raised, as a startup CEO you and your team have a certain number of outs you can play. You need to play every one of them because it may be the bottom of the ninth when you get the breakthrough you need, like figuring out product market fit or getting that first customer closed.

Unlike a baseball game that eventually ends once the losing team has used up their 27 outs, a startup has levers to create more outs it can play. Whether that’s raising more capital, slowing down the pace of investment, or both, your company can continually adjust the length of the game so long as you stay mindful that there’s no clock defining when the game’s over and that every “out” matters.

Individual and Team

Being resilient, focusing on getting reps, and playing every out are all elements deeply inherent in both baseball and startups, but my favorite dynamic by far is how both experiences combine the individual and team.

In so many ways baseball is the most individualistic team sport out there. The pitcher on the mound, the hitter in the batter’s box, and the fielder on the diamond are all alone, individual in their respective pursuit of getting the hitter out, getting on base, or successfully fielding the ball hit to them. At the same time, there are ten players (nine position players and a designated hitter) in the lineup at any time and it takes their collective team effort to score as many runs as possible when at bat while concurrently yielding as few runs as possible when pitching and playing defense.

The startup company is no different. Everyone plays a position in the field and hits in the lineup. The metaphor can be extended however you want. Maybe the CEO is the pitcher, maybe she’s the manager, or maybe the catcher, shortstop, and centerfielder represent the head of product, go-to-market and finance respectively. However you slice it, the theme is the same. Every functional role is critical in the company, and every individual has to make plays on defense and do their best job possible when it’s their turn to hit.

And yet, the team doesn’t succeed because of a single player’s performance, nor does it fail because of a single player’s error or strikeout. A team can – and often does – lose because the commitment to win isn’t held by every player, the individual effort isn’t contributed by every player, and the culture of “picking a teammate up” doesn’t exist within the team.

It’s this last point that brings it all together. Because the experience of playing baseball and working in a startup company are so challenging and full of failure on the individual level, the team ethos of supporting every player when they struggle can play an outsized role in how a baseball team or company navigates tough times. It’s the combination of CEOs that lead in this way, managers who manage in this way, and individual contributors who step beyond their individual efforts in this way that powerfully transforms a game of individual contributions into the result we all remember most – team success.

And perhaps no open source digital platform has helped as many businesses – through the power of Search Engine Optimization (SEO) – organically grow as Google Search has over the last 25 years.

So it makes perfect sense that AI optimization (AIO) is the next growth opportunity for every business big and small. Indeed, it feels as though for many businesses the race is on to create and push as much of their information into the frontier AI platforms in hopes that links to their brand appear in billions of AI conversations. And if this works, these businesses believe, they’ll reap the rewards from this new open source customer acquisition channel called AI.

I’m not so sure history will repeat itself here.

Google Search and the Open Web

Using content publishers and brand marketers as examples, the overly simplified evolution of Google Search goes something like this:

• In the early years publishers and brands could invest resources to reverse engineer how Google Search worked, learn how queries could be relevant to their business, and, as a result, generate organic traffic, audience, and potential customers. This is the general concept behind SEO.

• During this same period, Google invested billions to optimize its role as the “middleman” between publishers and brands, and their target audience and customers. This is the overly simplified description of how search engine marketing (SEM) evolved.

• Google’s financial aspirations pushed the company to make it harder for businesses to consistently succeed at the SEO game. Most notably the moving target for SEO success has been Google’s persistent schedule of “search update releases” designed to curb the volume of very low cost audience and customer acquisition traffic publishers and brands could garner. Concurrent with the narrowing of the SEO opportunity, more of the consumer search results experience has become filled with SEM-driven paid marketing placements.

Despite this not-so-subtle shift from SEO to SEM, you can still argue that Google Search remained an open, non-walled-garden environment. Why is this? Well, think of Google Search as a 2-dimensional (2-D) platform.

Search is 2-D because it’s presented in a single user interface, or doorway, that includes a single screen measured by your device’s height and width, and when the user clicks on a search result they are routed to a third dimension that exists beyond Google Search – whether the user gets there via an SEO or SEM link.

So based on the way history has played out in search, you can’t fault publishers and brands from looking at AI platforms as the next big traffic generating “open source” opportunity. But they shouldn’t.

AI Conversations and the New Walled Gardens

At first glance the parallel looks enticing. If you’re a publisher or brand, all your amazing content and intellectual property should be accessible by ChatGPT, Claude, or Gemini, and when it’s relevant to serve up your content in an AI conversation – boom! – users will find it, and happily click links to find more at your website. Not this time.

AI platforms like OpenAI, Anthropic, and Google are actually 3-dimensional, “3-D” versus 2-D like Google Search. What does 3-D mean here? Think of your prompt like a search query, and you enter it into a screen with height and width (2-D), but instead of getting a result that clicks you to a 3rd party for the third dimension, you enter the third dimension right there in the AI’s response.

And the loop continues inside the AI platforms, with each subsequent prompt, response, and ensuing conversation. Heck, you may never leave, get everything you need and never visit any of the sources ChatGPT, Claude, or Gemini used to help answer your questions. Welcome back to the AI walled garden.

What’s a Business to Do?

If you are a publisher, content creator, or IP generator that connects potential customers to a digital service you hope to get paid for, expect AI “walled gardens” to find this information and republish it in conversations - maybe with attribution and a link to your business - but likely not. Until we see how the copyright lawsuits that publishers like the New York Times have brought to the likes of OpenAI and Anthropic, it’s safe to assume your IP will stay in the AI ecosystem where the vast proportion of value will accrue to the AI platforms.

If you are a brand selling a product or service that can’t be fulfilled within the AI conversation itself, you’ll see the gap between AI “optimization” (AIO) and AI “marketing” (AIM) collapse way faster than the gap did between SEO and SEM. Google’s aggressive effort to inject their AI platform Gemini into the “search UI” is a clear sign they are replacing the 2-D model with a more lucrative 3-D model where Gemini subscriptions cover experiences you don’t need to leave Gemini to consume, and brands will continue to pay Google for customer acquisition through AIM instead of SEM. At the same time, OpenAI’s public admission that “ads” will be coming to ChatGPT clearly implies they’ll be working on the same calculus, trying to optimize the subscription revenue users pay them and the AIM revenue 3rd party businesses pay them.

Ultimately for CEOs and business leaders, the important question is determining how quickly AI platforms can disintermediate what you do, particularly if the IP that makes your business valuable becomes fully embedded within these AI environments. For many businesses, as counterintuitive as it sounds, the answer may be going back to building and maintaining their own “walled gardens” in an effort to directly acquire and engage your target customers. And even if that’s the answer for your business, be prepared to migrate a major portion of your marketing spend to AIM in order to grow and maintain your own healthy walled garden.

NextPlay>Forward AI Disclaimer: I very actively use artificial intelligence and large language models to generate the content you read here, but I do review it and edit it to make sure it can be generally useful to people who read it. Keep in mind that AI can make mistakes - check important information. Let me know if I make any errors and I will correct them.

The reality today is that it’s easier for companies to measure their AI ROI on the cost (COGS and OpEx) side of the P&L. In fact, many organizations have rolled out AI-based productivity tools, automated a few workflows, and have quietly (or not so quietly) noted that the same work is getting done with fewer people hours. That’s material learning for sure, but if that’s the whole story, you’re playing defense instead of offense with one of the most powerful tools your business has ever had access to.

CEOs should be prioritizing ways they can spur revenue growth within their AI ROI formula. Cost savings matter, but they’re the second-order benefit, and without top-line growth you’re just relying on AI to find expense reductions. And that approach basically becomes a race to the bottom.

So what can the revenue-first approach look like?

Start with what your customers are telling you they need, and ultimately what they’re most likely willing to pay you for. AI can synthesize customer feedback, support ticket insights, sales call patterns, and churn signals at a speed and scale that outpaces what teams can do on their own. The output of this investment in customer insights isn’t just a more robust dashboard, it’s a sharper view of the specific problems worth building solutions for, including the ones your customers haven’t figured out how to even fully describe to you yet. Companies that use AI here are surfacing product opportunities in weeks that used to take quarters to identify and act on.

Next, use these customer signals to prioritize and accelerate what you build. Once you’ve identified the problems worth solving, AI dramatically compresses the cycle from insight to working prototype and testable solutions. The question your product and engineering leaders should be answering isn’t “what can we build with AI?”, but they should be asking “are we building something a customer would pay more for, or pay us for the first time?” With this question at the center of their AI strategy, Intercom rebuilt their core product around an AI agent called Fin and the resultant revenue growth tells a compelling AI ROI story.

The third step is about using AI to accelerate the iterations between your product development and go-to-market motions. Get your portfolio of product updates in front of customers before they’re fully baked. Rapid prototyping with AI means your sales and marketing teams can put a working solution “concept” in your customers’ hands and work through the “last mile” tweaks with current or prospective customers. Whether you use dedicated forward deployed engineers (FDEs) or pull your best customer-facing team members into these customer build efforts, the test is the same: does the customer say “I’d pay for that” or at least guide the process to ultimately making that commitment?

Finally, imagine how your AI investments can be expanded to determine whether there are new customers who have the same problem. The same process that helps you deepen relationships with existing customers can help you identify adjacent market segments, model new buyer personas, and run faster go-to-market experiments against them. With a revenue-centered AI investment focus your organization has the potential to widen its addressable market, thus creating another path towards revenue growth.

Once your team has wired your AI investments to drive revenue growth, the cost savings opportunity then becomes more aligned with how your company is scaling enterprise value. AI-driven margin expansion comes from enabling your team (even while it might grow in number) to serve customers more productively, while also reducing what you spend on third-party software and tools. To create enduring and compounding value, sequence your organization’s focus on how AI boosts revenue growth first, and then margin expansion as a fast follow.

In the coming weeks, bring your leadership team two questions. Start with: “Where in our business are we actually using AI to grow revenue beyond our current operating plan targets?” Then follow up with the more challenging one: “For the dollars we’re spending on AI tools and services, what percentage of that investment can we connect to a specific revenue line?”

The answers will tell you everything about whether you have an AI strategy that’s driving future growth or merely an AI story built on “activity” but not lasting value creation.

NextPlay>Forward AI Disclaimer: I very actively use artificial intelligence and large language models to generate the content you read here, but I do review it and edit it to make sure it can be generally useful to people who read it. Keep in mind that AI can make mistakes - check important information. Let me know if I make any errors and I will correct them.

Relax. Let me give you the TL;DR on the latest AI doomer hits making the rounds: agentic AI drives the marginal cost of labor toward zero, frontier platforms deploy all the agents, rebuild every existing company in the process, and ultimately capture 99% of the wealth. And what does that mean for the rest of us? Well, that part hasn’t been explained particularly well. You’d be forgiven for thinking the phrase of the year so far is “we’re all f***ed.”

It’s not just vibes. A widely-circulated post from Citrini Research sketched out a pretty bleak two-year horizon for the economy. Block’s CEO recently announced he was laying off nearly half the company because AI can efficiently replace so much human labor, and he said he felt late doing it. And finally, every software platform that’s embedded itself inside Fortune 500 companies suddenly finds itself needing to explain why it won’t just be replaced by vibe coders inside those same companies. No doubt about it, the doom is arriving in ear piercing shock waves. And it’s going to get louder.

No wonder it’s never felt harder to be a CEO.

If you’re a CEO right now, you likely feel the walls closing in on you: on one side, your team is quietly (and sometimes not so quietly) wondering whether their jobs will exist in six months. On the other side, your board (mostly capital allocators) wants to know why you’re not doing more with less. Good luck explaining a hiring plan for the back half of 2026.

During World War II, Britain’s populace embraced the phrase “Keep Calm and Carry On” to boost morale in their darkest hours. CEOs need their own morale-boosting phrase right now. I’d suggest: Be Positive and Stay Optimistic.

But before we get to “Be Postive and Stay Optimistic”, let me share a few other “Be” traits CEOs might consider embracing in the weeks, months, and years ahead to help them navigate their unenviable job.

Be Contemplative

Carve out dedicated time every week to process what’s happening and sketch out strategic pathways that your company or organization might consider. Too often in times like this, you can get lost trying to just see your next footstep in the fog. But you have to find a way to get above the clouds and chart a future that may require some dramatic changes. Build this contemplation into your executive team meetings, too. Think in 180-day increments and keep iterating. It’s the only way to navigate when the rate of change and dislocation feel so accelerated.

Be Focused

Come back to the vision, mission, and values that define your company. Clarity about what you deliver for customers is your best north star as AI reshapes everything around what you and your team are trying to accomplish. More than ever, now is the time to perhaps do less, but do it exceptionally well.

Be Vulnerable

What’s happening right now isn’t like the invention of electricity or the fourth industrial revolution. It’s not like anything history can aptly be applied to as a comparable. We are watching the proliferation of intelligence capabilities for which nobody has figured out the ramifications, no matter how eloquently they craft a science fiction description of what 2028 will look like. Practically speaking, it’s okay to say that out loud to your team, and to acknowledge that your organization is still figuring out how human intelligence and AI intelligence will co-exist. And it’s okay to acknowledge that your organization may not grow headcount the way it once did, or may even shrink. They already know this potential outcome is on the table.

Be Accessible

Your people have questions about what AI means for them and for the organization. Show up for those conversations. The void created by silence from leadership is filled in immediately with buckets of anxiety poured in by your team. Each conversation you comes with a multiplier effect given teammates talk and compare notes with each other. So speak with each individual in a way that acknowledges their personal perspective, but that is also consistent as if you were speaking to the entire organization at an all hands meeting.

Be Decisive

Even in uncertainty, execution matters, and making decisions that need to be made will separate the organizations that move forward from those that become laggards or roadkill. Once you’ve built your plan, move on it. But be excellent at identifying the successes (and the failures) that result from your decisions so you and your team can course correct and implement the important decisions that follow. Yes, people prefer stasis and they hate ‘context switching’, but unfortunately those concepts largely disappeared as of November 2022.

And finally, and most importantly, as a CEO today:

Be Positive and Stay Optimistic

I get it, optimism feels really hard to embrace when you’re walking through quicksand with a blindfold on. But here’s the thing: this is how CEOs are actually wired. We sign up for the job to solve important problems, to create solutions, to believe that what we’re building matters, and to fight our way forward. New disruptive, scary, and world-reshaping technologies have historically expanded human capability and productivity, and, in turn, have created more wealth and abundance for people. That’s not naivety, that’s a repeatable pattern well documented in human history. Heck, it’s played out multiple times in just the last 150 years.

AI will change how your company works. It will change some of the roles on your team, and may even reduce the need for everyone on your current team. But the organizations who thrive through the AI-driven transformation will be the ones led by CEOs and senior executive teams who lead with a positive view of the future and an optimistic belief that their organization’s vision and mission must persist.

So that’s your most important job right now: Be Positive and Stay Optimistic. Maintaining this perspective and personality trait will become increasingly paramount for you as CEO given that it’s a safe bet the AI doomers will continue to beat their drums louder and louder.

NextPlay>Forward AI Disclaimer: I very actively use artificial intelligence and large language models to generate the content you read here, but I do review it and edit it to make sure it can be generally useful to people who read it. Keep in mind that AI can make mistakes - check important information. Let me know if I make any errors and I will correct them.

Being a CEO isn’t easy at any stage, but the job is vastly different if you’re running a public company (which I’ve never done) versus if you’re leading a venture backed startup that’s somewhere between zero and exit (which I have done).

Typically, the startup CEO profile looks like one of the following personas:

• Founder from a functional area of expertise (i.e. product development, engineering, etc.) who has to learn how to build a company working with functions they aren’t expert in and with investors they have sold on a big vision. This CEO may take the company all the way to exit or may hand off along the way to a CEO who fits the profile below.

• Experienced operator (who may or may not also be a first time CEO) brought in by the board to help a company navigate from some level of product / service usage (and likely some “issues” that need to be navigated) to an exit, which statistically speaking will most likely be an acquisition.

Given the complexity of the CEO job—and the reality that nobody gets a Bachelor’s degree in “Being a CEO”—it’s pretty common these days that folks (i.e. board members) will at some point recommend that the startup CEO work with a “CEO coach” who can help them navigate the twists and turns inherent in leading an early stage company.

So if you’re a startup CEO what questions might you ask to answer the “CEO coach” question?

Here are 5 questions that can help you sort it out:

1) “Do I even want or need a CEO coach?”

• Are there topics or questions you want to talk with someone about in a confidential manner, and do you have a sight line on what those topics and questions might be? I’ve met with many CEOs who felt they didn’t need a CEO coach, or perhaps weren’t “there yet” in understanding what a coach could help them with. Don’t sign up for a coach because someone told you to get one. Only lean into finding a CEO coach when you feel drawn to the idea of being able to talk about “things” with someone who’s 100% there for you, and you alone.

2) “Who can I talk to about anything?”

• This might be the best way to identify not only whether you should work with a coach, but who the right coach might be. Let’s face it, startup CEOs can’t (and literally don’t) talk to their co-founder(s), members of their executive team, their board members, their partner, or even their best friends about everything they are wrestling with at any given moment. (Well, they probably could tell their partner everything, but that’s likely not a great dynamic if you’re hoping to build a healthy long-term relationship). When you need to talk to someone other than that little voice in your own head, you might be ready to find a CEO coach.

3) “Do I really think I can talk to my board members about everything?”

• Part of what makes being a CEO so difficult is the collective opinion everyone around you has about how you’re doing the job. No matter how confident a startup CEO appears to those around them, they’re not actually that confident everything’s going to work out. Here’s the reality: the group you’ll spend the most time managing your confidence in front of is the group whose job it is to hire and fire you…your board. And this dynamic is more pronounced in an early stage company where your board members are primarily (or exclusively) your investors. What you need is an “independent independent”. More on this concept later.

4) “Do I think one of my independent board members can be my coach?”

• Sorry, but even if you add your mom to the board as an independent director, she has a fiduciary responsibility to all shareholders, including the preferred equity holding shareholders like her fellow investor board members. So if you end up telling your independent director (aka your mom) over dinner something like “I don’t know how to [insert one of the many things you don’t know how to do as a startup CEO]”, all that’s going to do is make mom think “Hmmm…maybe my kid isn’t cut out to be the CEO of this company.” See above: what you need is an “independent independent”. Again, more on this concept shortly.

5) “Do I have to pick between a ‘been there, done that’ former CEO as my coach or someone with a graduate degree in psychology who can ‘help me develop my leadership skills’?”

• This is a false choice. First, plenty of former CEOs who have been through what you’re dealing with can—and often do so very effectively—provide great insights around the “soft skills” that some CEOs feel can only come from a “psychologist”-type coach. Second, if you can’t find the right coach who can do both, then select a CEO coach who can address topics you want the most help with right now. That’s either someone who you can ask something like “how did you think about how much of your series B to invest in the core business versus new initiatives?” or it’s someone who you can ask something like “how can I get my product and go-to-market leaders to work together more effectively?” The good news is there are CEO coaches out there who can talk through both types of questions with you in a confidential setting.

So what do I tell a CEO when they ask me whether I think they should work with a CEO coach or not? Here’s how I lay it out for them:

• Every CEO needs someone they can talk to about anything—someone to whom they can ask the ‘How do I…?’ or ‘I don’t know how to …?’ type questions and not worry that they’ll be judged as not being capable of doing the CEO job when they do. I think this advice holds for any CEO, but is particularly helpful for “first time” CEOs who don’t fully realize the ‘multivariate calculus’ nature of what being a startup CEO entails.

• An ideal CEO coach as someone the CEO can think of as an “independent independent”: the person that they’ll get everything out of as if they were an “independent board director”, but who is fully “independent” and therefore in service first and foremost to the CEO. The value of this ‘consiligere’-like leverage that a CEO coach provides is difficult to describe until you tap into it during a company crisis or when you’re stressed the night before a board meeting.

• And a good CEO coach is a litmus test for your board and investors who may have been the folks recommending you work with a coach. Good board members and investors have seen the positive impact a CEO coach can bring to a company, and they don’t feel threatened that the CEO is talking to someone that they might never even meet. It’s the folks around your board who don’t embrace the privacy of this “CEO to CEO coach” relationship that you may need to wonder about.

If you’re in the midst of the startup CEO journey and climbing alone, I’d encourage you to re-read this post and listen to that voice in your head after you ask each of the questions above one more time. If you’re still feeling like “solo player” mode is right for you, great, no need for a CEO coach. But if asking yourself the questions above makes you anxious about walking the tightrope by yourself, make it a priority to find your “independent independent” in the coming weeks or months.

NextPlay>Forward AI Disclaimer: I very actively use artificial intelligence and large language models to generate the content you read here, but I do review it and edit it to make sure it can be generally useful to people who read it. Keep in mind that AI can make mistakes - check important information. Let me know if I make any errors and I will correct them.

When the WSJ piece “Your Next Boss: More Harmony, Less Authority” grabbed a recent click of mine, I made it through a couple paragraphs before the text did that not-so-subtle “fade out”, telling me that the full article is only for paying subscribers. I grew up on the free, ad-only supported internet, and I’m already paying for like six video streaming services plus cable, so the last thing I’m gonna sign up for is the digital version of a newspaper. Ah, but how brilliant to then find that the fine folks at the WSJ published under their “Noted” brand a summary of the article. Now I don’t know if this super short summary is targeted at cheapskates like me, or if it’s actually geared to the world of short-attention-span-theater consumers who couldn’t make it through the five minute read of the full article even if they were a paying subscriber?

It doesn’t matter, let me tell you how you might think about the evolving trend of bosses turning into coaches.

First, the thesis: Bosses need to become Coaches for their employees. The WSJ piece argues that this not so subtle shift in management science is due in part to the automation of routine tasks bosses no longer need to perform, and in part to the reality that leading and managing is more about collaborating across an wide array of experts than trying to be a command-and-control chief. I say it’s WAY more due to the latter —and besides, I can’t remember the last time I poured over a print out of somebody’s expense report? What’s happening rapidly across every organization is a confluence of dynamics that turn managers and company leaders into “conductors” versus “autocrats”. A few dynamics that support this trend include:

• Accelerating digitization and technological advancements across every type of business — think about how commonplace themes like data science, machine learning, and artificial intelligence have become in recent years;

• Hyper specialization of skills and knowledge within every department, and even sub-department within our departments — think about the precise consideration set of focus, custom tools, and actions items every single teammate in your company must process just this quarter;

• Ever widening knowledge and skill gaps between leaders — both at the functional level and certainly at the CEO level — and the experts that execute so many specialized and critical motions for a company.

So what’s really going on here? Well, recall all that talk over the last many years about how an organization’s most important asset is its people and how, despite that refrain, too many bosses spent too much time trying to personally shore up every technical competency versus investing their time in really getting know their people and how they can best help them. You know this boss-type, the one wasting a bunch of time trying to be their own mini versions of every VP on their team. Now’s the time for anyone who leads or runs anything to spend 99% of their time on being experts on people and how people come together to do great, really high impact things for other people — the ones we call our users and customers.

Try starting with honing these simple “Boss to Coach” steps:

• Start by taking some time to really know who you are as a manager and/or leader. Managers help team members deliver their best performance, while leaders help team members see the vision, goals, and cultural ethos that support team member performance and belonging. As senior startup company managers and leaders — including CEOs — more often than not our ability to coach team members stems from how our talents and strengths mesh with the talents and strengths of the people we work with most closely;

• Next, really get to know the people you work with most closely— your direct reports for sure, as well as their direct reports. Understanding the talents and strengths of your teammates allows you to more clearly see the most effective ways that your folks can come together to achieve the company’s vision;

• Indeed, fully understanding what you and your teammates bring to the table in terms of talents and strengths, enables you to most naturally shift from commanding boss to conducting coach. In this vein, the best thing you can do as a coach is to figure out how to support your team members as you collectively pursue the company’s vision in a way that most effectively combines their talents across strategic thinking, relationship building and influencing, and execution. Coaching at its best is done in a way that resonates with every one of your functional “experts” such that you honor, support, and shape their individual efforts in a way that makes the whole greater than the sum of its parts — and so the team achieves more than it ever thought it could.

In the abstract it seems obvious that gone are the days of the “Um, I’m going to need you to come in on Saturday…” boss. Today’s startup leaders must be wired to lean in with an ethos that’s all about “How can I support you in your role helping us achieve the outcomes we want as a company?” And the startup CEO needs to be able to context switch their coaching on two planes.

First, they must coach as a leader who can orchestrate the effort to develop a unifying vision and plan for where the company can go, who can ensure that the company is capitalized to advance towards that vision, and who can selflessly assist in developing a team-first culture that will resiliently pursue that vision. Second, the startup CEO must coach as a manager of senior executive experts who themselves are managing both vertically within their domains and horizontally in collaboration with the expertise that thrives around them.

As long as startup CEOs embrace coach over boss, team over me, and them over I, their companies will end up miles ahead of where they’d be if they don’t.

Originally published on Medium on February 23, 2021. This Substack version is maintained as the canonical archive.

Reflecting recently on how I think about my role leading and managing (yes, two different elements) our e-team, I came up with five layers that define how I view the important role each e-team member plays in a startup. In parallel, these five elements describe the way I best serve and support each e-team leader. For the purposes of the framing below, I’ll speak interchangeably in the context of both my role as a card-carrying e-team member, and as the “coach” for each of our e-team members. Of course, like any relationship, it’s critical that a healthy dialogue flows in both directions, so I’m always open to feedback from my e-team colleagues whenever they feel I can be more helpful to them individually or to all of us as a unified e-team.

It begins with an alignment on the vision, mission, values, and goals that we live by as a company and an e-team. While our vision, mission, and values persist over longer periods of time, our goals have shorter timeframes (e.g. annual and quarterly), and by definition they create the common north star — and sense of urgency — over these discrete periods that bring every functional group together. The e-team must ensure that clearly defined and measurable goals exist for the impact we strive to deliver for our users and customers, the sustainability we strive to create as a business, and the performance and belonging we strive to engender within every team member at Remind.

Next, each of our e-team members must be experts. They are the domain champions for product, engineering, sales, marketing, customer success, finance, and people operations — as well as for many sub-areas of expertise that evolve within these organizational groups. By extension, the people that our e-team leads are themselves even more expert at the important slices of what happens in each of these areas. While it might be the case early on in a startup that a CEO plays a dual role as CEO and functional expert (e.g. product or engineering), once the company has shifted into the “1 to X” phase, the CEO by necessity must shift fully into the “jack of all trades, master of none” mode.

Third, e-team members are not only domain experts, but they perform the equally important (and in some contexts, more important) role as people manager to those team members who report to them. So, not only is our e-team marketing leader or product leader asked to be experts in those domains, they are also asked to be great people managers or “coaches” to the individuals on their teams. As CEO, an important role I play is as a “coach” for my e-team colleagues in helping them as managers, an always challenging role given the constant forces that push and pull on a startup every day.

While the expertise and manager contributions from an e-team member are critical to a company’s success, it actually rests below the fourth ask made of every e-team member, that being they view the e-team as their “first team”. This by no means diminishes the importance of their work as experts and people managers, rather it represents an ask on behalf of the company that they bring their functional focus together with our unified goals in a way that enables us to continually evaluate our performance, processes, and priorities in the most objective way possible. When our head of sales voices the importance of an engineering investment and our head of finance highlights the need for a customer success initiative, these are the examples that illustrate how e-team leaders are collaborating with each other in a way that’s about putting the needs of the company and our collective team ahead of the needs (or wants) of any single department.

Finally, the layers above — and most certainly the fourth area just highlighted —rest firmly on a foundation of trust. If there’s one thing a CEO can most bring to an e-team (and by extension to an entire company) it’s a clear and continuous commitment to building trust. There’s no magic formula to building trust. It starts with being vulnerable across the e-team — sharing openly our backgrounds, our talents and strengths, and our lesser talents and strengths, including even our weaknesses. Trust also requires familiarity and repetition. This means spending more time together (yes, more Zoom meetings together five days a week post COVID), and being willing as an e-team to rely on the collective trust across the team when our work requires us to engage in hard conversations, work through conflict, and make difficult decisions.

It’s true, a startup CEO has too much to do — just like everyone else — yet nothing’s more important than how we show up to serve our e-teams. It begins with being aligned around a core set of shared goals, and then being there to help your e-team experts be great managers for their functional teams. From there it then requires setting a clear expectation that each e-team leader’s first team is the e-team, and that trusting each other on every level — and in every situation — is how executive leadership teams become the force multiplier for company success, as well as team member growth and development, for every individual in the company.

Originally published on Medium on February 8, 2021 This Substack version is maintained as the canonical archive.

In that post, most of what was described revolved around the Two Goals. First, how we lead with Impact, like any company should, as a way to define clearly the “why” that we all show up to do our important work each day. For Remind, Impact is reflected most clearly through our Vision which is “to give every student an opportunity to succeed.” Our Impact can be measured in multiple ways by the number of students, educators, and parents we support every day through their engaged use of the Remind platform.

In support of Impact lies the second goal, Sustainability. Through our focus on Sustainability we imagine how we might evolve our product development, go-to-market, and operations so that we build a business that can firmly stand on its own. Clearly, Impact and Sustainability co-exist — being able to positively Impact student outcomes in perpetuity can only happen by creating a Sustainable business. These Two Goals of Impact and Sustainability reinforce — rather than pull away from — each other.

But what about One Team? In many ways the easy approach is to describe One Team is “self evident”, that it’s just about collaborating cross-functionally and supporting each other in pursuit of our Two Goals. Similarly, it’s simple to further define One Team by the myriad of management literature and quotes that surround us on the topic of teams. (I will say, I have been known to utter in more than a few meetings a favorite John Wooden quote that captures the spirit of “One Team”: It’s amazing how much can be accomplished if no one cares who gets the credit.)

Without a doubt, a significant part of how we describe and express One Team at Remind comes through the many examples of collaboration that individuals and groups engage in together. We have committed to measure One Team through our two-times a year team engagement survey (TES) that asks important questions around team member engagement and performance, as well as team member sense of belonging that we strive to engender through our efforts to create a diverse, equitable, and inclusive workplace.

At the end of last year we decided to go even deeper with how we invest in One Team. We channeled the Delphic phrase “know thyself”, and we’ve made a companywide commitment to bring strengths based managing and coaching throughout our team. You could say that in order for us to really define One Team, we’re investing to “know thyselves” (all apologies to Socrates, Plato, Aristotle, and the like).

Specifically, we’re going deeper with Gallup’s CliftonStrengths and tapping into Gallup’s strengths-based coaching framework to support managers and individual contributor team members alike. By focusing on strengths-based development we aim to bring a shared language and vocabulary that we’ll weave throughout Remind in a way that will strengthen our One Team. For example, we are excited to see how explicitly talking about talents and strengths will enable a team member in customer success to really see and understand a team member in engineering or operations, and vice versa. Sharing openly our respective talents and strengths (as well as those areas where we may be less naturally talented) builds trust at the team member level through a vulnerability that stems from allowing our team members to see the core elements that define who we are.

As a CEO I am happy to share what Gallup defines as my “dominant” talents and strengths, and I look forward to seeing them reflected alongside the same list of dominant strengths for each of my Remind teammates. Similarly, I’m equally excited to share my “bottom” talents and strengths so people know the elements that are harder for me to naturally express and tap into as a leader. What’s most important is that my colleagues know that I commit to lean into my top talents and strengths in my efforts to serve fellow “Reminders” as well as in my efforts to serve our users, customers, partners, and shareholders.

For me, 2021 will be a year of growth that emanates from the strengths-focused conversations I will have with my teammates at Remind. These conversations will center around how we can continuously tap into — and elevate — our collective talents and strengths to advance our work in support of education. It’s exciting to imagine how our strengths-based development efforts will help Remind improve on the already deep collaboration ethos that serves as the foundation for our One Team, and how this companywide commitment will support a never ending effort to make our One Team stronger and even more resilient.

Originally published on Medium on January 25, 2021. This Substack version is maintained as the canonical archive.

Thinking about leadership in this way makes it easy for an article — like this story about a Superintendent from a major urban city school district who recently resigned — to grab my attention.

Despite the fair amount of detail shared in the story, there’s no way I or anyone other than this leader and her board members can speak to the details that may have led to the Superintendent’s departure. However, whenever I read about a situation like this, I reflect on how I’ve always viewed the relationship between an organization’s leader and their board. I believe that there’s a simple set of ideas that are fundamental to ensuring a strong partnership can be developed between a leader and their board.

First, it’s good to remember that the board hires (and therefore has the authority to fire) the CEO. The CEO’s boss is the board and that’s the simple fact even if nobody around the table specifically utters this reality, or if a formal “performance review” process is never put in place. (On this latter point, there’s a wide range of how CEOs might think about performance reviews. Simply put, don’t expect a formal performance review like those the rest of your team navigates one to two times a year. Think of every board meeting as your performance review.)

Second, the CEO runs the company, not the board. By “run” I’m talking about the CEO’s responsibility to play point in developing the company’s plan. This plan includes the organization’s vision, mission, and values, as well as a cogent set of goals and that development of a corresponding strategic operating plan that further defines where the organization is heading. Any time a board finds itself doing this work (other than providing feedback and perspective on the plan developed by the CEO and her/his team), something’s out of whack. Either the board (or specific members) have stepped outside the scope of their role, or the CEO is not doing their job.

Finally, how should an organization’s leader and board address any disconnect — either in the form of how a CEO and the board see the organization’s future path, the results to date versus this plan, or both? These questions about assessment speak to why it’s vital that a leader and the board establish clear commitments to objectivity, trust, and communication.

• Objectivity is about looking at the goals that the company has set out and assessing how the CEO and board feel about whether the company has achieved these goals. For example, either a revenue goal was achieved or it wasn’t. Either a product was developed and launched in the timeframe committed to or it wasn’t. There’s no room for subjectivity in how a CEO and board view performance versus plan. When an organization doesn’t achieve its goals when measured objectively, the elements of trust and communication serve to strengthen the partnership between a leader and their board.

• Trust defines the quality of the the relationship that exists between the organization’s leader and her/his board. Do the board members trust the CEO to craft a vision and strategic path for the company? Do the board members trust the CEO to build the team and instill a culture that gives the company the best chance to succeed? Do the board members trust the CEO to “field command” and adjust course when the environment surrounding the company adversely impacts the organization’s plan, and therefore requires that changes be considered. (I have no doubt that here have been many examples of this scenario playing out between leaders and boards in 2020.) And what about trust in the other direction? It’s crucial for the leader to trust that their board members will be there with support, ideas, experience, and a willingness to leverage their networks when the company needs it? Further, the leader must trust that the board will be open-minded and supportive of changes that she/he proposes when new realities come into view that alter the plan of record.

• Communication is about staying connected and sharing feedback with each other, especially as an organization’s “actuals vs. plan” play out. Board meetings are the key setting for this, but so too are conversations and updates between board meetings. The best CEOs communicate when needed — always mindful that the board doesn’t need play-by-play updates of what’s going on at the company. At the same time, the best board members know how many moving parts an organization’s leader is juggling at any given time and therefore appreciate that there’s an optimal cadence to communication with the CEO.

It’s indeed sad to see a leader resign from an organization particularly when, based on what’s shared publicly, I get the sense that something was amiss between the leader and the board. Perhaps the undercurrent that created the departure could have been avoided if the CEO and board where better aligned around their respective roles and responsibilities. Even with such alignment, however, departures can still occur if objectivity, trust, and/or communication don’t underpin how leaders and boards partner.

Originally published on Medium on November 23, 2020. This Substack version is maintained as the canonical archive.

I disagree.

These are my sentiments on why creating a successful company requires the duality of focus and hearing every voice, not the false choice that the former is sufficient without the latter, and they reflect how we will continue to build our company culture at Remind.

At this point I’m never surprised by the ebbs and flows in the narrative around company building that emanates from Silicon Valley. Always present in this narrative is the hope by some that the hard work of company building can be succinctly reduced to an exercise in perfecting algorithms that reject the reality that humans with hearts, souls, and voices are what make great companies.

Companies make difficult choices all the time. As leaders it’s vital that we never make false choices — that we never choose to tell those who join our company and help us pursue our vision and mission that they must adhere to a code of conduct that requires them to silence their voices as a way to create the optimal path to company success.

Impact and sustainability are not mutually exclusive goals. They are the dual goals that every company must define for themselves and pursue relentlessly in a way that continuously views sustainability as a goal in service of impact. A company can (and should strive to) create massive positive impact in the lives of its customers and users, and that same company can do so in a highly profitable and sustainable way. In fact, that’s how a company ultimately scales its impact.

Establishing a culture that emphasizes focus and performance is absolutely critical to a company’s success, and yet it’s the effort a company puts into ensuring that every team member feels that they belong on the team that completes the formula for creating a culture that maximizes the dual goals of impact and sustainability over the long-term.

A company makes a false choice when team members are asked to extract parts of their heart, soul, and, most importantly, their voice, as a pre-condition for entering the workplace. We’re not only fortunate at Remind that our work supports the success of K12 and higher education students, but we are also fortunate that we embrace our diversity of voice so that we can empathetically engage with our users and customers across a similarly diverse spectrum. It’s this very human reflection that enables us to continually make Remind better and more valuable.

When you strip the heart, soul, and voice from team members and thus remove the most essential human dimension from your team, you still might win a few games, maybe even a championship one “season” driven by the chance alignment of a collection of homogenized talent (and serendipitous market conditions). But you won’t build a culture that endures this way. You won’t build a dynasty.

I shudder to imagine a workplace where a working mother isn’t able to voice openly what she needs in support of her ability to be both a mother and a team member in our current work-from-home environment, or a workplace where an LGBTQ team member feels they must mute the anxiousness they feel about how shifts in our judicial system might impact their rights, or a workplace where a team member who identifies as a person of color is expected to silence any feelings they carry given the social injustices they witness and experience daily across our country.

Choices are hard to make, but making false choices are even harder to live and succeed with. This is why we’ll never ask any of our team members to check the essence of their humanity — their voice — at the door when they come to work each day at Remind. #OTTG: One Team, Two Goals. E pluribus unum.

Originally published on Medium on October 2, 2020. This Substack version is maintained as the canonical archive.

I watched the video on a Sunday evening after witnessing a weekend of youth basketball games (my daughter’s AAU team). For some reason the confluence between these two themes — two of my favorite things, Bill Murray and youth sports — compelled me the next morning after a night’s rest to reaffirm all that ever matters in life are two things.

It just doesn’t matter. That’s number one. Murray blurts it out so eloquently in the epic summer camp classic “Meatballs”, as he attempts to rally the Camp Northstar crew on the eve of their 2-day Olympiad versus the well endowed Camp Mohawk clan.

It really just doesn’t matter. Think about how much anxiety we wrap around what we do. This constant striving, comparing, and stressing places on overemphasis on our “ups” and our “downs”. Today we “win” — we’re awesome, life’s awesome, but tomorrow we lose, we suck and life’s shit. I’m not suggesting a life of Stoicism, but perhaps a bit more even-keeled perspective. Redefine success and failure not as opposite ends of spectrum. Think of them as adjacent to one another, separated by a mere nano ounce of serendipity.

This leads to the second point of all that matters in life. And that’s that all that really matters is the next play. Yes, I love sports and sports metaphors, but only those authentically derived from playing and competing. Being in the arena as Teddy Roosevelt described is where sports matters — not in the realm of today’s visceral pop culture layer that celebrates individual brand over contributor to team success.

What happens on the field, court, or pitch over and over approximates so well what happens at work and in our relationships, over and over. Stuff happens — some good, some not so good. Looking back in agony and anguish is a waste of time. All that matters is that we grab in the moment some learnings and turn our focus to the next play. The next shot. The next swing. The next coversation or decision.

It’s really pretty clarifying when you merge the lessons from Bill Murray with those taken from playing sports. When you realize it just doesn’t matter and you focus relentlessly on the next play, there’s no time for your mind to rathole on the past or on the wasted energy that comes from comparing yourself to what others are doing.

Keep this in mind.

Originally published on Medium on July 22, 2019. This Substack version is maintained as the canonical archive.

Now’s the time for the experts sitting outside the day-to-day reality that confronts those actually doing work in tech companies to provide actionable ideas that company leaders can actually employ — and that workers can simultaneously invest in—so that re-skilling can evolve in the face of AI’s emergence.

First off, let’s start by creating a simple and common understanding of what AI means. Parse for everyone in the company the idea that AI means enabling machines to do work more effectively than humans, and that machine learning (ML) and deep learning (DL) are more nuanced layers of AI that represent how machines develop more effective algorithms over time. It matters not whether these algorithms live in massive computational cloud installations or client side IOT hardware (or both), so long as they can do things humans shouldn’t be doing — or things we can’t accomplish on our own — in support of company goals.

So what might this look like in the context of re-skilling your team?

It means being explicit about how every team member comes to understand AI and how it might be employed to solve problems for your organization. For example, creating a simple approach to AI that utilizes data to rapidly develop and deploy predictions (which will continue to become cheaper as the insightful book “Prediction Machines” articulates), that in turn allow team members to apply judgements and decisions (based on those predictions) to enable rapid progress towards goals. Revisiting this iterative data > prediction > judgment (decision) loop creates an AI skillset that every team member can adopt and bring to how they do their own work.

Re-skilling your team for an emerging AI workplace also means people need to be simultaneously macro- and micro-minded. Macro-minded means teammates need to work at developing their ability to understand the strategic big picture that the company is building towards. What’s your big vision — what will your company be in 5, 10, or 25 years from now? Once a clear macro mental construct becomes solidified in everyone’s mind, shifting to the micro-minded framing becomes crucial. Breaking down the big idea into micro steps requires that each employee become facile in evaluating data analytics and insights in ways that support the daily march towards the big idea. As a tech leader there’s perhaps nothing more important in the age of AI than supporting your team’s ability to bounce from macro- to micro-mindedness in an effort to overcome every obstacle your company faces on its long-term path.

Finally, avoid generalized statements like those uttered by alarmist consultants. Take any comment you read or hear in a podcast per the vital need to apply AI to your workplace, (and the resultant requirement that your workforce needs to dramatically be re-skilled for a future we can’t imagine), as an opportunity to step into creating simple data, prediction, and judgement/decision loops. Develop these AI loops over and over, and in every department in your company — from engineering to sales. Then, use these basic AI loops to validate that your team is doing the hard work of toggling in unison from a macro-minded view of where you are heading, into the myriad of micro-minded activities that will increase your probability of success over the long haul.

Perhaps we are indeed heading to a future in which AI will replace everything humans might do, but the sooner we invest in really developing simple applications of AI within our workplaces and daily lives, the better we will get at understanding where the line can exist between the machines and us pesky humans. Taking an applied approach to how we develop within the company also brings hope that we’ll be more effective at steering machines towards human enhancing efforts, but that we might also steer our machines towards both unbiased and ethically appropriate ends.

Originally published on Medium on July 15, 2019. This Substack version is maintained as the canonical archive.

Such was the case for us at Remind not too long ago. You see we have more than 30 million monthly active users — teachers, students, parents, and administrators — who converse and share content with each other over our communication platform. We also have more than 1,000 distinct school and district customers who have purchased our Remind School Plan so that they might bring important benefits to their schools or districts like being able to reach everyone with important safety-first oversight and controls around the communication taking place throughout their community.

So it’s not too surprising that as we’ve scaled our company to these dimensions across users and customers — while simultaneously evolving the different departments that work to build and take our product to market — we can be susceptible to a bit of what I’d call “message entropy”. What exactly happens when your company contracts a case of message entropy, especially a case that becomes evident through a sudden flash fire of some inspired, healthy, perhaps a little animated, and hopefully crucial conversation about how everyone should be describing in unison what your company does?

Well, first off be glad that your team members are taking the initiative to engage in this dialogue with one another. Better to have a little disconnect and friction, then a company that’s not inspired to engage in this way. Keep in mind your company is constantly evolving and this should always be a recurring discussion topic across your entire team. That said, here are three specific messages we shared across our company to reconnect as a team when we recently experienced a case of message entropy.

Revisit your vision, mission, and values

• “First, we have created a strong foundation in our vision, mission and values that serve as the starting point for how we describe Remind. I wrote a post earlier this year that helps delineate how I parse the distinct purpose of a company’s vision, mission and values. For all of us, the high level “what” Remind does is captured in our Mission: Remind is building a communication platform that helps teachers, students, parents, and administrators work together. Now, as with everything we do at Remind, we can discuss whether this accurately captures what we do or whether we need to update it. I happen to like the simplicity and broad scope that this mission statement provides as a starting point for every conversation I have with people about what Remind does every day.”

Be flexible to customize your description per your audience

• “Second, even with the foundation of our VMV, we will find ourselves in conversations with specific audiences where we will need to tailor how we describe Remind. What we might say to a district CTO will be perhaps different from how we describe what we do to a district CAO (Chief Academic Officer). While our descriptions might not be dramatically different, we might emphasize different elements of Remind for these two individuals. Likewise, how we describe Remind to a potential investor will be a little different than how we might describe what we do to a potential partner who we’d like to encourage to integrate within Remind. As long as we use our VMV as the core starting point and do our best to capture within our broader messaging framework the evolving ways we might describe Remind to different audiences (or “personas”) we will be doing the best we can to describe what Remind does at any given time.”

Focus on the work your team has created and made available

• “Finally, we clearly live in a world of information overload —like everyone, I struggle with this reality every day. Yet I believe that Remind continues to work hard at creating the important information for all of us to do our best work. Oftentimes we may feel the information we need isn’t available when oftentimes it’s just a click or search query away. This is why it’s important to find, read, and internalize the important information we all collaborate to create for each other — whether that be a board presentation, a product roadmap, a collection of sales training materials, or our vision, mission, values; as well as the special ways we might augment our description of Remind for varied audiences. So before we question what does Remind do, take a moment to revisit our VMV statements, our broader brand messaging framework, and tap a colleague on the shoulder to bounce off them the way you’re planning to explain what Remind does to a person you’re about to meet.”

Originally published on Medium on December 23, 2018. This Substack version is maintained as the canonical archive.

This is also the time of year to look ahead. What are our goals — and priorities to achieve those goals — for 2019? How do we keep it simple, or said differently: “How do we do less better?” Anchoring to a single goal i.e. user growth, revenue growth, profit margin, helps create simplicity and alignment for everyone. Underpinning that single goal with the shortest list of imperative priorities is a great next step.

One major stepping stone for a company is the moment when everyone recognizes that the organization is ready to partner with the biggest customers in its industry. Said differently, this is the time when everyone must ask: “What does it mean for us to be enterprise ready?”

For Remind that means being able to support and serve the biggest public school districts in the country. This is both exciting and nerve racking. Each day now at Remind, in every meeting any of us attend, we implicitly — and explicitly — ask each other “what does it mean to really succeed with the biggest customers in K-12 education?” In a more general sense, every company aspires to get to this critical stage — the moment that this question becomes vital to every team member every day. Here are three succinct ways to think about being enterprise ready no matter what those enterprise customers look like to you and your company:

1. Build the product that can close enterprise customers

This is where every company starts. What are the core customer benefits that we need to deliver in order to even be considered a viable option for an enterprise customer. Questions abound here. What are the true “needs” that must be met i.e. what are “table stakes” for us to get a deal? How quickly can we reshuffle our product roadmap to have that product definition built and ready to ship to an enterprise customer? What do we need to do to ensure that our product or platform can work at the scale at which the enterprise customer operates?

When your company must shift gears to support enterprise customers, the days of building minimal viable products (MVPs) — the mantra in the early years for Silicon Valley startups —fade away rapidly in your rearview mirror. It’s time to dramatically up level your effort to build EVPs — “enterprise viable products”. For many companies this cognitive leap is daunting. For every company it’s a major cultural shift from a mindset that says “stuff might break, or not work, but it’s okay, because that’s how we’ll fix things and get better” to a mindset that says “that big customer expects big-time service level agreements (SLAs) and a platform that works better than their current solution.”

The sooner you and your e-team can begin down the road of building towards an enterprise ready product, the better. The reality is it will take longer than you think to build it; that it will take your marketing and sales team longer to sell it; and that your financial plan will only come into full view once these bigger enterprises become part of your customer set.

2. Develop the processes to retain enterprise customers

If step 1 is building your product or platform to enterprise scale and getting enterprise customers on board, then step 2 is all about developing the processes needed to delight these big customers while also ensuring that you continue to evolve what it means to be enterprise ready across a number of important areas that come into focus after you’ve closed the deal.

While the product, design, research, and engineering teams (Prod-Eng) will be central in building the product that closes the first deal, your “go-to-market” (GTM) team that spans marketing, sales, and success will be crucial to ensure these customers renew and expand their relationship with your company. Of course marketing and sales are central to step 1 above, but they are equally crucial here in the phase that centers around keeping customers happy and engaged. For example, your marketing team can see firsthand how these big customers are using the product, and can partner with your success team to prescribe ways to heighten customer engagement. Likewise, while sales team members will be focused on landing new enterprise customers, in the early days of bringing these bigger customers on board, they will be sought out by the buyer as a key go-to relationship.

Within the GTM team, the processes and interactions that your success team develops will be vital. Customer success teams can be multi-faceted — including implementation, user support, and customer success, among other job descriptions. However, each of these team members provides a valuable service for somebody in the enterprise customer’s organization that, if done well, adds to the trust the enterprise customer has in your company. In many ways, the processes you establish for how you implement your customer on boarding and then how you continue to monitor the success these enterprise customers experience with your product determines the probability of renewing and expanding the customer relationship before you even enter the renewal discussion.

While your Prod-Eng and GTM team members are busy scaling their efforts to support enterprise readiness, behind the scenes operates a third leg of the stool that delivers for your biggest customers: your business operations groups. Everything that your finance and accounting, data and business intelligence, people operations, and legal teams do to support your enterprise-sized customers adds to the long-term success you realize in this high-end segment of your business. In fact, a major part of what the business operations effort helps you assess — and then engage with your Prod-Eng and GTM teams to collectively level up — is how your company measures and addresses the combination of security, user content, and compliance risks.

3. Support your people to build meaningful relationships with enterprise customers

When it comes to how you and your company approach the topic of scaling up everything you do to become enterprise ready, the third — and most important — dimension that you must invest heavily in is how you engage your people in this effort. We all get comfortable in the status quo. Nothing feels better than the cozy feeling that “we’ve got this”, but that feeling’s akin to the mountain climber who reaches a base camp, only to realize there’s another camp further up the mountain. As a company, everyone must hold firmly to three beliefs when it comes to beginning the climb to that that next base camp called “enterprise ready”:

• everyone on the team must believe that enterprise readiness is critical to the dual, long-term impact and business outcomes you are trying to achieve together;

• everyone on the team must believe that your company can do this — that you can eventually get to the base camp together that represents delivering on a continual basis an enterprise ready product or platform; and

• everyone on the team must believe that your combined resiliency and “test and learn” ethos will get you past any storms of adversity that will inevitably test you on your ascent to reaching the goal of being “enterprise ready”

One last thought about how to stay centered on this immense challenge. If you and the team constantly put your customers first — essentially using them as your north star in this effort — you’ll never lose your way. If everyone on your team commits to listen to your customers empathetically and to respond to them authentically and with integrity, you’ll always be on the path to enterprise ready no matter how challenging that journey may feel at times. After all, it’s the “hard” — yet fulfilling — journey that we all aspire to take on.

Originally published on Medium on December 16, 2018 This Substack version is maintained as the canonical archive.

This year I ask that everyone take a moment to reflect on the things you’re truly thankful for, I mean TRULY thankful for. Yah motorized scooters being approved in San Francisco or the abundance of options we have for binge watching a never ending stream of scripted video programming doesn’t really count. Sorry.

I’m moved to “thank” three people who were there for me during my formative years — three individuals who left a mark in some way that stays with me today. See if you can do the same. Identify (1) an academic teacher, (2) a sports coach/drama instructor/music teacher, and (3) an advisor/mentor who each played a key role in your life. Craft a story or description this Thanksgiving of that person’s influence in your life and include that in your observation of Thanksgiving this year. Thanks for letting me share my three with you — and please share your three with me!

Academic teacher — Professor Ernie Stromsdorfer

As a college freshman at Washington State University, I was, like most 18-year-olds, pretty uncertain of what I was embarking on away from home. In particular, I recall being in awe of the academic presence that surrounded me on a large college campus. That Fall I somehow found myself in an introductory microeconomics course taught by a professor named Ernie Stromsdorfer.

As a capstone to the course we had to research and write a term paper on a topic that demonstrated our understanding of “micro-econ”. After meeting with Professor Stromsdorfer, he suggested a paper about how the “reserve clause” artificially depressed the player salaries of Major League Baseball players, and how it took a single player (Curt Flood) to challenge the reserve clause and ultimately open the floodgates to free agency and the rapid increase in player salaries that begin in the late 1970s across all sports.

What I remember about Professor Stromsdorfer is how much time he spent with me on the topic and the application to economics, how he genuinely cared that I really learn bones of the topic, and most importantly, how he made me feel like I could do well in college. He did so much to erase a lot of anxiety and self-doubt I had by simply taking the time — time that as a research professor he didn’t need to take. Of course, I still have that paper somewhere in my garage, all typed up on a real typewriter, with hand drawn supply-demand charts and all.

Sports coach — Steve Woods

This is the one that should be about my dad, but that’s a given. Besides, there are too my stories to share about dad’s influence on me as a coach. In addition to my dad I think a lot about Steve Woods. He was our high school wrestling coach and the JV baseball coach. Now since I played basketball, I was as far away from the wrestling mats as one could get. But Mr. Woods — like my dad — taught Social Studies, and he happened to be my homeroom advisor.

I remember being inspired by the fact that Mr. Woods was a NCAA Division-I collegiate wrestler at Oregon State University, where he won a Pac-8 championship his senior year. Legend had it that he also wrestled in a tough match versus the legendary Dan Gable. However, while upon further research that match versus Gable may have been an “urban” legend I cooked up in my own mind, it only added to the respect I had for Coach Woods.

It was actually in his role as JV baseball coach, i.e. my dad’s assistant coach, that he had the most impact on my personally. Here he was in a sport he knew virtually nothing about so he wasn’t there to impress me in the way he could if this were wrestling. Instead, he provided great perspective. Perspective of where sports really fits into the big picture. One time after a tough game he noticed that my head was down and I was taking it pretty hard. I remember him simply saying, “Hey, there are billions of people around the world who don’t give a shit about that game.”

For some reason that sunk in instantly, and that sentence has been a soundbite I go back to often. Coach Woods never used perspective setting statements to replace the priorities of working hard and committing yourself to do your best, yet those perspective inducing comments helped remind me that it was indeed the hard work and commitment that mattered, not the results on the scoreboard or stats pages.

Advisor/Mentor — Joe Story

After I made the move to finish my undergraduate studies at Pacific University in Oregon, ostensibly so I could play college baseball versus watch it from the bench in Pullman, WA, I met Dr. Joseph Story. Dr. Story was the head of the Economics Department at Pacific, but more importantly he became a central figure in my life during the final 3 1/2 years of my undergraduate years over which earned a double major in mathematics and economics.

For some reason Dr. Story was always willing to let me pop into his office, unannounced and unscheduled. I’m sure he has many memories of thinking “Oh, here’s Brian Grey again, I wonder want new academic pursuit he wants to chase or what new career path he’s mapping out?” But even if those thoughts rolled through his mind, he was always there to listen, advise, and encourage me as I struggled to put my finger on what would be next after college.

He supported me immensely as I took on the challenge of a major research study and campus-wide presentation that tried to make sense of the stock market meltdown of 1989. And he also supported me in my first post-undergrad effort to pursue a graduate degree in Economics, which while not ending in a PhD as originally planned, did end with an MA in Economics and me landing in California where I’ve been ever since.

Dr. Story left an impression on me in terms of how important it is as an advisor/mentor to always just “be there” — to be present. From him my biggest lesson learned has been to try to do the same for as many people as I can who reach out to me for help, a conversation, or specific guidance.

So this Thanksgiving I’m saying thanks to Professor Stromsdorfer, Coach Woods, and Dr. Story.

Originally published on Medium on November 22, 2018. This Substack version is maintained as the canonical archive.

These two important cultural elements — VMV and #OTTG — provide crucial foundations for our company culture and how we collaborate and work together on behalf of teachers, students, parents, and administrators across the K-12 and higher education spectrum. At the same time, VMV and #OTTG help spawn a number of other ways we can describe and talk about our work together. Here are ten that I personally like and believe are worth sharing:

1. One team, two goals is what matters above all else — everything we do should align with this framework

• As a company this has become a powerful way we bring everything together. No matter where you work at Remind, you’re an equal and important contributor to our “one team”. By extension, the concept of “two goals” creates simplifying clarity for team members that inspires and focuses our efforts. Our first goal is anchored around the “impact” that we strive to achieve in support of students, teachers, parents, and administrators; and the second goal defines the business objective of “revenue growth” that serves as a proxy for how we progress towards a reality in which Remind is able to perpetually exist as a sustainable platform supporting education across K-12 and higher education.

2. Live our vision, mission, and core values

• A friendly reminder shared in context — for example in a cross-functional team meeting — helps reconnect us to this important foundational layer at Remind. What’s so powerful about referring back to our VMV is how these layers can also be augmented and customized to the work happening in specific departments. For example, our engineering or customer success teams will each create their own examples for “Find a way” and “Create simplicity for others”, as well as for our vision “To give every student an opportunity to succeed.”

3. Work hard — value #4!

• Nothing replaces work ethic. I’ve written about this as a company’s value number “N+1”, meaning that no matter how many core values your company defines, the idea of working hard becomes, de facto, one last value that wraps around all the others.

4. Be here and be present every day

• We all have so much going on in our personal lives. At the same time, we’re all subject to an ever growing flow of content and information via our mobile devices that pulls our most scarce resource — attention— away from our most important work. Reminding ourselves to be present and focused on the work we are doing (and being compensated to do) is critical if we expect to deliver the results connected to our #OTTG.

5. Time is short — execute with energy, enthusiasm, and a sense of urgency

• This one’s related to #4, think of it as another way to frame it for everyone. In life we all get just a few opportunities to be a part of something special. Perhaps it’s the benefit of being a bit “older”, but I tell team members that the last thing you want to ever do in life is look back and regret that you didn’t do everything you could to make something as successful as it otherwise could have become.

6. Commit to hold yourself and your teammates to the highest standard of excellence

• We owe excellence to ourselves, to our colleagues, to our investors, and most importantly to the users and customers we serve. Highlighting instances where we could have done better — or situations in which we outright failed — shouldn’t be taken as offensive, it should be seen as supportive. Be sure to create an environment where doing your best work is the expectation, not the exception. And if you need help with some ideas of how to approach discussions when this standard isn’t being met, check out “Crucial Conversations” for a framework that might help everyone come together on this front.

7. Build every product, process, and relationship as a strong foundation for our future — don’t build flimsy

• This one came from our product and engineering team leaders, and I love it. It’s neatly connected to #6, but goes a bit deeper and more specific to the component parts (product, process, and relationships) that ultimately support the intertwined fabric that supports a company’s success. And I just love the last phrase “don’t build flimsy” — it provides such a powerful visual for the standards we must set here!

8. Making Remind successful comes first

• This one reaffirms the “one team” ethos embedded in #OTTG. Granted, in today’s “look at me” social media-driven culture, the importance and value of contributing to team success can often feel secondary to one’s desire to optimize personal outcomes. The reality, however, is that so much of what we build in the form of personal identity comes from the teams we’re a part of, and how successful these teams are as measured by the impact they impart on their industry — and the sustainability they’re able to achieve in delivering this impact. In the long run, it’s truly the case that “we first” > “me first”.

9. Communicate clearly and candidly with each other in an honest and non-confrontational way

• Yes, this one is so much easier said than done. Increasingly the norm in society is to retreat to polarizing positions, to define your perspective, dig in, and hold on tightly to your desire to “be right”. With this approach we all lose. Teams lose. Team members lose. Our users and customers lose. And, our ability to achieve our “two goals” fades away, slowly but surely. However, if we’re able to raise our line of sight to focus on team goals, make it about “we and us” versus about “me and I”, then we can create communication channels that take us in the right direction. Again, if you or your company need some formal help in creating this environment, bring “Crucial Conversations” into the picture.

10. Not every decision will be agreed with 100%; yet every decision must be supported 100%

• For many of us this is one of the hardest concepts to grasp, or at least support. It goes back to some of the themes above. If it’s about “me” then I’ll push for what I believe must be done and if that view doesn’t align with what the broader team decisions are, then I’ll stay silent. I’ll pretend like I’m on board even when I’m not and I’ll step away from all of the points above. Conversely, when I take the view that it’s always about “we” then I contribute my expertise and perspective with the rest of the team. And regardless of the decision or direction the team selects, I lean in with 100% support — even if that wasn’t the decision or direction I advocated. This dynamic is crucial for team success as well as for a team member’s personal and professional growth. Fortunatley, it’s easy to spot when teams and their team members operate in this way…and when they don’t.

I’m sure there are many other elements beyond the 10 highlighted above that we speak to and reference at Remind. Likewise, I suspect that folks at other organizations have many other novel themes they use to similarly help define how their team’s work together. I encourage you to think about other elements like those listed above (or use those listed above!), and apply them in a way that works best for your company or non-profit’s culture. Most importantly, invest the time in crafting at a minimum your VMV and a short list of supporting elements that all of you can come back to over and over as you progress on your unique #OTTG journey.

Originally published on Medium on November 5, 2018. This Substack version is maintained as the canonical archive.

Investing in learning how to fully engage in communication — or “crucial conversations” — starts with creating an awareness of the topic and its importance. Next, it takes commitment from everyone within an organization to agree that communication skills are those that everyone should want to improve. Finally, getting better at communication requires that a organization adopt a formal approach to how its team members engage in the crucial conversations that will amplify the collaborative efforts everyone puts towards companywide projects and initiatives.

At Remind we created awhile back a working group focused on helping foster the important relationship between managers and team members, aka the individuals a manager manages. Among the many things this manager development — or “MDev” — working group helps advance throughout our company is curriculum that we can all engage with to help deepen relationships in all directions within Remind. Recently, communication became one of those areas we decided to invest in more extensively, and as a result, we decided to adopt the communication framework described in the book “Crucial Conversations” to help us all enhance how we work together.

“Crucial Conversations” (or “CC” from here forward) establishes a thorough and research based approach that helps all of us talk to each other in a way that encourages two parties to achieve a meaningful outcome through dialogue in a way that removes tension, anger, frustration, anxiety, and essentially any emotion that otherwise might impair our ability to successively deliver and receive candid communication when we need it most. For sure “CC” is too long to fully summarize here in a single post, and as such I highly recommend that you buy your own copy and read it in its entirety. However, for those who might appreciate a simple, high-level summary to come back to as they continue to practice engaging in crucial conversations, well, consider the outline below your cheat sheet to “CC”.

1 What’s a crucial conversation, and how do you know you may be about to enter one or that you should work to create one?

The authors of “CC” identify three key elements that arise between two individuals (or groups of individuals) that you should look for as an indication that a crucial conversation might be in the offing:

• First, you find yourself in a situation where “opposing opinions” exist. This point’s pretty straight forward. For example, consider the situation in which your VP of Finance believes that your company should invest in product A, and your VP of Product believes that the company should invest in a very different product B.

• Second, “emotions run strong” between you and your counterpart. Staying with the example above, let’s say that discussions in executive team meetings, in cross-functional meetings, and even in one-on-one meetings between your two VP’s, have escalated to become quite heated per the “Product A vs. Product B” debate.

• Third, based on the context in which you and another colleague might become engaged, it’s clear that “stakes are high” as relate to the outcome of the conversation. Once again, play out the example above. Your company only has a finite amount of investment, thus you can only invest in either the Product A path or the Product B path, but not both (though as explained below, this last assumption is a false one).

As “CC” highlights, based on studying more than 2,000 projects and programs: “The path to high productivity passes not through a static system, but through face-to-face conversations.” So what do your two VP’s need to do next?

2 How to master crucial conversations through the power of dialogue

Yes, your two VP’s need to engage in real dialogue around the decision between the two product path options. Before engaging in real dialogue though, your two VP’s need to step back and make sure they don’t enter the discussion believing there’s a “fool’s choice” in front of them. A fool’s choice means believing that an either/or outcome awaits you in a dialogue. Your VP of Product mustn’t believe that “if we don’t go with Product B I’ve failed in my job”; nor should your VP of Finance enter the discussion with a belief that “if we don’t pursue Product A we’ll never hit our financial targets.” A crucial conversation built through true dialogue can only exist if both participants enter with an open mindset that’s not anchored to “either/or” or “win/lose” thinking.

Assuming both participants enter with an open mind, how do you create real dialogue? Let’s start with a definition:

Dialogue (n): The free flow of meaning between two or more people.

This is where I’m taking severe liberties — for the sake of creating an abridged version of the “CC” approach — with the full framework outlined in “CC”. That said, let me reiterate that you should read “CC” cover-to-cover so that this summary serves its purpose i.e. to help you “snap back into” crucial conversation mode when necessary. Given this caveat, here’s a simple, abbreviated four step process to help you and your partner engage in dialogue.

• Start with (your) heart. Simply put, this means being really clear with yourself what you want out of the dialogue. Ask yourself why you’re so “charged” by this interaction and what would make you feel better on the other side of the discussion? For example, the VP of Finance enters the discussion wanting a product decision that helps the company most accelerate revenue growth; while the VP of Product may enter the discussion hoping for a product path that ensures that the company will be able to capture significant market share from competitors.

• Make it safe. Nobody likes a dialogue with another individual when they don’t feel safe, therefore both participants must feel safe in order to fully share their perspectives, facts, and other information while in dialogue. This means that individuals who sit organizationally at a higher level may need to speak to this safety dynamic explicitly in order to ensure that other participants won’t be negatively impacted by what they say. For example, the VP of Product may feel less equipped to fully contribute for fear they don’t fully understand all the financial impacts implied by pursuing each product path. In this setting, the VP of Finance must take the lead in creating an environment that enables a discussion such that the VP of Product feels safe sharing all their information related to each product opportunity.

• Create a pool of shared meaning. Once a safe dialogue environment has been established, it becomes much easier for each participant to share their unique “meaning”. In this instance, meaning represents the collection of facts, perspectives, and other information salient to facilitating a full fidelity dialogue. Starting with facts is always a great way to begin as this allows the dialogue to commence in an objective versus subjective manner. The true power of each party filling the “pool of shared meaning” implies that when combined to the true underlying desires that each party brings to the table in terms of a desired outcome from the dialogue, this approach can illuminate real alignment between the participants around truly shared goals. For example, through a real dialogue the VP of Product and the VP of Finance might recognize that their respective desires to accelerate revenue growth and increase market share might be viewed as the same objective.

• Recognize when you’re ready to move to action. Again, I’m purposefully omitting a number of steps along the path here, but through a dialogue that’s “safe” for all participants — while also combining each participant’s desired outcome with their willingness to share personal meaning throughout the discussion — both parties may simultaneously recognize an opportunity to take action towards a desired outcome. “CC” provides crisp points on “deciding how to decide” e.g. are decisions made through command, consultation, voting, or consensus; and on how to document decisions and put them into action by assigning follow up tasks e.g. who will do what, by when, in what form of follow up, and through what form of documenting everything so nothing slips through the cracks? Back to our two VP’s for a moment. Through their dialogue, they may agree that based on their shared meaning, Product A gives the company the best opportunity to increase market share and therefore grow revenues faster than Product B. However, because they aren’t 100% certain given the limits to current facts and understanding — and because neither wants to make a “fool’s choice” here — they agree in parallel to invest significantly in Product A, while also investing a small “test case” amount that will allow them to further explore the opportunity related to Product B.

3 Always bring it back to two important levers

If there’s only one piece of the “CC” framework you internalize and come back to consistently, it’s the following two “levers” that are outlined at the end of the book. Essentially, think of these two levers as the simplest and quickest way to apply the “CC” approach in any setting where it might prove useful.

• Learn to look. Recognize whether the three signs that a crucial conversation might be appropriate exist, and then observe whether you are truly in a dialogue with another person or group. (One hint that you may not be fully in dialogue: Is the other person or some individuals in the other party exhibiting silence or violence during your interactions? If so, you’re not fully in dialogue.). Ask the question: “Are we in dialogue or have we moved away?”

• Make it safe. As you move towards establishing a setting for real dialogue — or you’ve already entered a state of true dialogue — keep your “make it safe” antennae constantly tuned to all participants. Again, two clear signs that the setting for a “safe” dialogue may not be in place are if a participant (or participants) remains in silence and/or acts out in violence. If participants don’t feel safe they likely won’t share all the meaning they possess, or conversely they may feel threatened and as a result will choose to react in a more violent manner. The “CC” framework provides a number of helpful tools for encouraging those who may be exhibiting silence or violence to feel safer in a dialogue and therefore participate in a manner that leads to a positive outcome for all.

The “Crucial Conversations” framework by no means represents the only approach people and organizations might employ to facilitate healthy and candid communication. Indeed, the most important step a company can take is acknowledging that real dialogue between and across your team is a vital part of how you work — and succeed — together. Once you’ve made the commitment to invest in company-wide communication, pick an approach and stick with it over time. That’s how your organization will reap the long-term benefits from really engaging in crucial conversations.

Originally published on Medium on October 7, 2018. This Substack version is maintained as the canonical archive.

Baseball became such a big part of my youth that I basically chose my initial college path based on my desire to play college ball. In fact, one of my lasting memories from baseball is pitching in college — or as my teammates would describe it — throwing batting practice for the opposing team. Yet despite an otherwise unspectacular Division III college career, I reflect on my time pitching and think how in many ways it was great training for life as a startup CEO. The parallels are striking.

It’s lonely on the mound. You, standing by yourself toeing a rubber slab, initiate action with each pitch and then watch as events unfold, pitch by pitch. Your teammates do so much to determine your success (more on this later). It’s equally lonely as a startup CEO. The same dynamic unfolds, just without you having to stand on a dirt hill. Instead, you initiate action not by propelling a white ball with red stitches, but by propelling audacious objectives onto a whiteboard or Google slide. Then, day by day, you encourage and challenge your teammates to perform amazing plays in order to reach your team’s lofty goals.

As a hurler, so much rests with the team behind you. Once you release the ball, you’re at the mercy of a shortstop’s ability to field ground-balls or a centerfielder’s ability to chase down a sinking liners. You coach your defenders to move to the left, to the right, to move up, to move back, to be ready, and to plan a couple plays ahead. You pat them on the back if they make an error and sometimes you have to yell at them to get their head in the game — all in a spirit to help them grow into great players. So it goes for startup CEOs. You rely on your team members, every single one of them. Can they make their plays, can they work together and support each other on the “field”? Like a pitcher, the startup CEO can do a lot to help players grow, yet at the same time, as pitchers and CEOs, our success rests so heavily on how well our teammates perform on their own along side us.

Pitching is one of those things that doesn’t look too physically demanding from afar, but it’s utterly exhausting. Strenuous bursts of energy that place undue stress on the body ultimately depletes you in every outing. Oftentimes you’ll glance over at the dugout and hear advice, encouragement, or even a dose of admonishment. The coaches and managers watching closely (or not?) from the sidelines bring different perspectives either from having watched a lot of games and, if you’re lucky, from having actually been a pitcher themselves.

For the startup CEO, the dugout of experts is your board. You do well to listen to them, take their advice, and like everything you process, fold it into the decisions you make around what “pitch” to throw next as a CEO. You’re lucky to have these people in your dugout, and the good ones know how hard your job is and that ultimately you’re the one on the mound dealing with everything. Ultimately they let you throw the pitch you think best at that moment in the game.

Every pitcher who has logged enough innings knows what it feels like when you have great stuff and pitch a great game. By the same token everyone of us who takes the mound has gotten smacked around by the opposing team. Success and failure go together in baseball — just as they do in startup companies. What matters most is how you as a pitcher respond to a rough inning or outing. Do you give up — letting a bad game crush your resiliency? Or do you bounce back and look immediately ahead to the next batter? It’s the same in a startup. Every great day or win is usually followed by a body blow of some kind. The CEOs who have been through highs and lows, and who know how to pattern match experiences (good or bad) to future prospects in an even keel manner are the ones who give their teammates the confidence to play forward.

Ultimately a pitcher needs to call their own game. Yes you rely on your catcher, (who in the startup world might rotate from day-to-day between your heads of product, sales, marketing, engineering, success, or finance), to offer up pitches you might throw. In fact, the best flow for a pitcher is when you can rely on your catcher to call a good game, you can rely on helpful advice from coaches in the dugout (they’ve seen lots of games and can bring some experience that’s potentially helpful), and you can rely on your teammates to make the plays around you pitch after pitch.

But whether you’re a pitcher or a startup CEO, you have to be willing to shake off your catcher and ignore the dugout every once in awhile. You have to have the guts — and heart — to throw the pitch you feel is the right one to throw, knowing that even if it gets hit, your team will make the play. And you have to be resilient in the face of failure. Always remember, each outing is a learning experience and so long as you love the challenge of pitching and being a startup CEO, the next batter you face is always digging into the batters box ready to take a swing at your next pitch.

Originally published on Medium on September 2, 2018. This Substack version is maintained as the canonical archive.

Let me share this value with a brief, recent story from Remind. At a recent all hands, one of our engineering managers took the stage at the end the hour. His message was simple. Paraphrasing a bit, he implored to everyone at our company to “rest and recharge this weekend — these next several weeks are going to be intense.” As soon as he completed his statement, one of our teammates blurted out, “are you going to do it?” The question’s meaning was clear — this team member knew that this engineering manager typically works weekends and late into weeknights to ensure what we are creating for customers exceeds their expectations, and she wanted to know he would too be taking some time to recharge and renew over the weekend.

Her question also confirmed for all of us the importance of what this engineering manager — as well as the rest of Remind embodies — in terms of the “+1” value of work ethic and effort (“WEE”). For certain, work ethic and effort most definitely define the “+1” that your company must add to any other “N” company values it defines. What’s great about WEE is how simple and powerful it is for your company. Here are three simple reasons why:

Everyone can work hard and commit to your company’s cause. You don’t need an Ivy League degree nor do you need to know Python to do what it takes to delight your customers and fully support your users. All you need is a “work hard” mindset — a mindset that understands how special your opportunity is and that staying up late on a weeknight to get a project completed or getting up early to do a few hours of work on a Saturday or Sunday morning is how you help your company succeed. Work ethic and effort exists in each of us, and therefore it truly does come down the adage “how bad do you want it?”

Another truism about work ethic and effort is how contagious it can become. For those working together towards a common mission and vision, working hard floats throughout your ranks like a “healthy” virus that inoculates everyone in every department. Everyone gets the bug to do more and achieve as much together as the company possibly can. At the same time, those teammates who, for whatever reason, don’t naturally amp their work ethic and effort may actually be less connected to the broader mission and vision your company is striving to achieve. As a manager, you want to quickly determine who brings work ethic and effort to your team and who doesn’t. Both groups are good people, and even friends, but it’s the former who will most help you reach your long-term goals, and it’s the latter who need to find another mission and vision to which they can apply their innate work ethic and effort.

The last element that makes work ethic and effort so special is the fact that, all else equal, WEE truly becomes the difference maker for a startup. Of course “all else equal” is that term economists throw around to give them an out when their theories don’t turn out exactly as predicted. In this setting, a startup team can exhibit an unbelievable work ethic and effort, and still “fail” in the eyes of the market because another competitor is better funded, started earlier, or just got a bigger dose of serendipity. However, when we assume “all else is equal” between companies, more often than not it is the company that works harder that wins. Do I have empirical proof of this? Of course not. Does anyone want to argue the point to the contrary? I highly doubt it.

When your startup revisits its mission, vision, and values — and when your company crafts an update to its strategic plan and roadmap — be sure to take stock of your team’s collective work ethic and effort. This is the “+1” difference maker value for your company. Thanks to the heartfelt question from the audience at a recent all hands meeting, it became clear that the manager up in front of the company serves as a shining example of the work ethic and effort at our company that, when multiplied by the same effort across every team member at Remind, will become the difference maker over the coming years for what we are able to create for educators, students, and parents.

Originally published on Medium on July 30, 2018. This Substack version is maintained as the canonical archive.

Yet here I sit at the end of another week on the road trying to figure out what the heck is happening? Yes, work’s busy — a business trip two weeks ago, a board meeting last week, and now a week-long east coast trip that’s got my circadian rhythm all whacked and my noggin toggling from strict adherence to a healthy diet to rash bouts of exhaustion that cripple my ability to mindfully grub.

That’s why I’m chalking these last few weeks up to my reptilian brain taking over — along with a slightly evolved ability to narrow my focus towards the most critical areas that need my attention for the sake of our company’s success. As a startup CEO dealing with so many moving parts — and so much ambiguity — this state of mind might qualify as one version of what psychologists call being in the “Zone”. Consider the behaviors and themes I’ve laid out below. They’re likely not too dissimilar from what most startup CEOs deal with, especially when on the road for pronounced stretches of time trying to accomplish important strategic progress with external parties while continuing to support and stay connected with everything happening inside the company — as well as on the home front.

Yet read these anecdotes closely and you’ll recognize that they truly are base-level survival and “thrival” instincts that are sometimes exactly what you need to be doing as a startup CEO when racing at full speed. Calling this mode being in the “Zone” is a bit much — I’d simply rather call it “doing your job” when it matters most.

Focus and adrenaline. You hit the road and your focus sharpens instantly. You prep well for the important meetings on the trip and nail the talk track for each conversation. Adrenaline kicks in under the radar and it’s what allows you to bounce out of bed at 6 a.m. eastern time, when your body knows it’s only 3 a.m. Of course, waking early might also be aided by the fact you forgot to pull the bedroom blinds and the sunlight zaps your face straight away! Either way, getting out of your “home” environment forces you to prioritize at another level knowing that many of your conversations will be with people you hope to impress and leave in a state of mind thinking to themselves “Wow, I want to work with that company!”.

Healthy eating goes out the window. Whatever diet or healthy eating regimen you’ve been on heretofore immediately falls to the wayside when you’re in this mode. One night you go from New York to D.C., arrive at a three star (ok, maybe a 2 star ) hotel and blindly order what’s advertised as a “Greek flatbread pizza”. What arrives 20 minutes later resembles something more akin to 6 pieces of pita bread stitched together, slathered with some Ragu sauce, and piled high with a white mystery cheese that to this day remains unidentified. But guess what? Yep, I scarfed it down like Famous Ray himself had hand delivered it from his Manhattan pizzeria.

Now, pay close attention to the two important corollaries intimately tied to the sudden drop in your healthy eating defenses:

• Corollary 1: Your tolerance for bad wine skyrockets. “Is it a heavy red?”, you hear yourself asking the bartender (at the same hotel that served you the pita bread pizza cheese thing), thus instantly signaling to everyone within earshot how low you’re willing to set the quality bar necessary to imbibe. And while it may not be the wine that comes from that oversized bottle with a footprint on the label (you know the brand I’m talking about here!), at this point you wouldn’t blanche one bit by a Malbec described as being “From one of America’s fasting growing wine regions outside of Santa Fe, New Mexico.”

• Corollary 2: This one I describe simply as the “hunt for DD”. Clearly, one of the evil ploys East Coast cities have unleashed on unsuspecting West Coast-ers like myself is to place a Dunkin Donuts outpost on literally every street corner, and in every train station and airport. Except when they don’t! I fell victim to a moment of weakness when — tired, starved, and blurry eyed one evening — I began walking aimlessly inside the Washington, D.C. train station in search of the “Dunkin Donuts” that showed up on Google Maps. After what felt like an hour (but was likely closer to 15 minutes) of traipsing the darkened halls of D.C.’s Union Station, I thought to myself : “For Christ’s Sake, it says Dunkin Donut’s right here across from the damn Aunt Anne’s pretzel place …where the hell is it?!!” Finally, I came to the painful realization — it was gone. Replaced by a freaking Sbarro’s Pizzeria. C’mon, that’s not even real pizza is it?!! So says the guy who ate hotel pizza bread the night before.

Forget trying to stick to a workout schedule. Once you have that first early wake-up call of the trip you’re immediately locked into a morning mode that’s absolutely not conducive to running, cruising the elliptical, or hopping on a SoulCycle. Plus, if you’re like me, by the time you’ve scheduled all the important meetings you want to make happen on the trip, the only time you have left during the day is literally the travel time from one meeting to the next. Thus, take solace in the fact that your workout schedule reduces to walking the streets of New York City, D.C., Chicago, or Boston, which if done in July produces ample sweat to make it almost feel like you dropped into a hot yoga class (sans the requisite Lululemon attire of course).

Clearly, zooming around the country can wreck havoc on your healthy lifestyle, especially when you’re in the midst of processing information about the rapidly changing industry dynamics that surround your business. With this in mind, there are three other important facets that may tweak your brain waves when you’re operating in this realm.

Clarity around important meetings and perspectives. Maybe it’s the unique ability our brain has to narrow its focus and tap into adrenaline, but when in this operating mode, you’re able to zero in on important external relationships and click with people. Now for me, maybe it’s the fasting I default to because I’ve over-scheduled my day, but more likely it’s the excitement of telling people the Remind story and how we’re helping so many teachers, students, parents, and educators collaborate more closely together. For each of us, when we’re able to peel away the other topics and distractions that cloud our focus, we can really nail the meetings that matter — and foster the relationships that help propel our companies rapidly forward.

Creativity gets zapped. This is the observation that actually triggered this post. While on the road over much of the last month — coupled with preparations for a board meeting and several exciting 3rd party conversations — I’ve noticed a decline in my ability to creatively step outside these more narrowly defined lanes through which I’ve channeled my attention. Which, by the way, is exactly as it should be. I’m just noticing that when my CEO brain turns it’s attention to the near, medium, and even long-term ramifications of really important issues and projects, the side affect is that a big chunk of what my brain might otherwise creatively ruminate on gets dialed back. Personally, this means the natural flow of topics I might write about — or new business ideas I might noodle on — that typically bounce around my brain are put on pause when I’m hunkered down.

Feeling alone. When you’re focused on the important path forward for your company, and you literally “hit the road” to help that cause, be prepared to feel lonely. The startup CEO job in general is designed to be a lonely one — there are always things you’re processing and thinking about that you might not have a clear outlet to discuss with someone. But in this unique operating mode you find yourself in, the notion of being alone goes deeper. For significant chunks of time you’re physically detached from family, friends, and your team. When you are “home”, you can still feel a little alienated given the time you’re still spending in meetings and conversations that take you away from time with your teammates working through operational priorities, or that take you away from time with your family. The way I’ve learned to deal with this dynamic is to know that during these windows I’m doing important work for my company — and my family — that will pay dividends in the future.

Remember, none of us operate in an accelerated mode like this all the time. Psychologists tell us we are actually in any mode that resembles a “Zone” for very limited amounts of time, but when we are, we can absolutely achieve new milestones and define new perspectives for our businesses and our lives. Traveling and engaging with the external world oftentimes triggers in me a unique set of feelings and behaviors, and as my examples above attest, these last few weeks have felt this way to me. I’ve been fortunate to engage in several weeks of really great meetings about Remind and to think more broadly about the future of the platform we are building in education. And while it’s been a bit lonely on the road, I’ve been emboldened by an amazing Remind team that’s executing together as “one team” focused on “two goals”, and by a family that supports me in the mission I’m on to help bring an important personalized learning platform into K-12 and higher education.

Oh, and on the health front, being on the road actually helped me get back into my intermittent fasting mojo, and I even mixed in a couple salads. And thankfully, my frustration from the D.C. train station was alleviated when I finally tracked down that elusive “DD” in Boston (as you’d expect), and treated myself to a donut — chocolate old fashioned of course!

Originally published on Medium on July 23, 2018 This Substack version is maintained as the canonical archive.