I love it when an article’s title is so succinct as to be eye catching — delivering that perfect hook. Conversely, I hate it when that same article title pops up in a social media feed (or is shared via an internal Slack channel), only to lead me to a gated subscription wall. Thanks Wall Street Journal (and New York Times, and basically every branded content publisher). Sure, the digital publishing industry is trying to go direct-to-consumer-subscription in order to escape the death grip of Google and Facebook, but what then are those of us trying to comment and share perspectives from these compelling articles supposed to do?
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.


