I recently completed a busy stretch of business travel that took me on the road for parts of four consecutive weeks. In general I hate being away from our home office, it makes me feel like I miss too much of the important day-to-day that goes into leading a startup. Yet at the same time, going on the road is crucial because staying exclusively inside your four walls can lead to a chronic case of “echochamberitis” — an ailment where you and your team convince each other that you have all the perspective and answers needed to succeed. That’s why it’s imperative for a startup CEO (and some of your team members) to periodically head out on the road so you can broaden your perspective in 3 important dimensions by spending important time with users and customers, partners, and investors.

Users and customers are the lifeblood of every company. Users are those individuals who engage and “use” your product or service on a daily/weekly/monthly basis. Like users, customers are a group of individual people who interact with your product or service on a consistent basis. Unlike users, however, customers are the folks that pay you to use your product or service — and they oftentimes make those purchase decisions based on the engagement they see from users who might have a need to use your service every day. That important distinction is enough right there to get you out of your office and on the road. At Remind, we benefit by having avid teacher, student and parent “users” as well as an increasing number of school and district “customers”. Our users and customers span the U.S.; they exist in large public school districts and schools, as well as in smaller, more specialized charter and independent schools, as well as related organizations where students, teachers, and parent engagement is crucial. We work diligently every day to deliver a communication platform that delviers deep engagement and connection between our customers (e.g. district and school leaders) and our most active users (e.g. teachers, students, and parents).

When I’m out visiting users and customers as I did on my most recent travels, I focus on two elements in those conversations. First, I do a lot of listening. I want to hear how our customers and users benefit most by using Remind, and what they wish we did more of to help them as educators and families. As CEOs, we’re often wired to believe we need to do all the talking, and if you do this with customers or users you walk out of the room having learned virtually nothing. The second thing I do in these conversations is ask questions, as many as I have time to ask in between the listening. The work our customers and users undertake daily requires that Remind be there for them specifically when students and parents need to be reached. Asking simple questions turns out to be a great way to probe areas that may not come up naturally in conversation or that might unlock a whole new level of enthusiasm from the customer who then blurts out “Oh, yah, it would be great if Remind could…” At that point I shift back into listening mode where I can capture more learnings to augment what our sales team, research team, and product managers are also hearing in their interactions with customers and users.

Nobody builds a business without partners. Think about it, there are dozens of activities that go on in your company today, many which are managed by a partner providing a service that you and your team would otherwise have to build. As important as these relationships are with the partners handling your site serving and ops needs, your document management, your data systems and reporting tools, your sales pipeline tracking, your accounting and finance operations, and every other detailed element of running your company, the partners I’m talking about here are the ones that you don’t work with yet. I’m talking about the partners that represent the next phase of where you might take your company. The partners that you’re not even sure make sense working with you and vice versa.

For Remind these partners represent the long list of education services that we see flowing through our communication platform today, a subset for whom we’d like to make it easier for our customers and users to discover and engage with every day. (On this front, Remind recently launched a significant step in this direction with 14 great learning services implementing the “share on remind” capability from their own service). Again, by staying in our office we’d never truly understand how these partners think about reaching their own customers, nor would we be able to deeply share how we see Remind evolving into a communication channel that supports the delivery of important learning services to students and parents.

One of the CEOs most critical responsibilities is to devote a portion of her/his time to explore future market opportunities. “Do we go into an adjacent market? Do we go international? Do we build a new value proposition for our current user base that would bring us more market share?” Imagining what these next phases might look like for Remind requires partnering with services like those we announced with our share on Remind effort last month, while at the same time deepening our understanding of how partner relationships benefit our users and customers. Only by meeting with — and talking to — potential partners, customers, and users will you reach the most informed answers to these questions, and if the CEO (and your team members) devote meaningful time to this effort you’ll create more value for these important stakeholders while also creating long-term value for your own shareholder employees and investors.

If users and customers are the lifeblood of a business, and partners help you assess and scale your future opportunities more efficiently, then capital represents the fuel your company needs to build a self-sustaining engine. This is why a meaningful part of every CEOs calendar must also be allocated to meeting with investors. I can hear a few CEOs out there groaning, “But why do I need to spend time with investors when I’m not fundraising?” Here are two important reasons why investor conversations need to be a recurring theme on the CEO’s calendar.

First, you’re always fundraising, even when you aren’t. Every conversation you have with an investor gives you an opportunity to refine your narrative in terms of how you share the vision of what you and the team are building together. You can never have enough “reps” doing this — especially in a world where the pace of change means that your narrative by necessity constantly evolves as a living and breathing organism. Take the opportunity to meet with as many qualified investors as possible to keep your saw sharp so when you’re in the market to raise a round, you can “cut deep” to tap the fuel you need for your company’s next phase of growth.

Continuously meeting with investors also provides critical macro perspective for a CEO that helps shape the strategic lens you bring to internal discussions with team members. Remember, investors spend their days talking to companies, seeing what’s working — and what’s not. They have a unique perspective on trends and even systemic shifts impacting specific sectors that you should be learning about on an ongoing basis. Like all perspectives, these investor views need to be absorbed in context. Some are more informed than others, some may or may not factor in operational realities, and some just flat out won’t apply to your business (at least in a timeframe that maps to your focus and priorities for the coming 12–24 months). As a corollary to the importance of always talking to investors, I’ll add that it’s advantageous to create a short list of investors whom you can always go to for feedback and perspectives, even (or especially) if they aren’t investors in your current business. These investor relationships are built over years, but they become invaluable to you as a CEO along your company’s journey, just as you provide invaluable leader and operator counsel for them in return.

So, what to do now? If you’re a CEO who is already consciously carving up your calendar to allocate a portion of your months to visiting customers, users, partners, and investors, great — keep doing it. However, if you are a CEO who would acknowledge that your comfort zone is staying close to home, digging down deep into the product roadmap and/or engineering build schedule, or diving into some other functional critical path for your company, take a step back for a second. Get out your notebook (or mobile phone note app, or wherever you use to track your priorities) and create a section for customers, partners, and investors. Jot down 3–5 names that pop into your head for each category and make it a point to visit each of them over the next few months. After that, make this a habit when you are planning your next quarter or two — your company will absolutely benefit by you hitting the road.

Originally published on Medium on December 10, 2017. This Substack version is maintained as the canonical archive.

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