The Inspiring Leader vs The Player Coach

Scott Galloway has an interesting take on the two types of effective leaders (starts at 26:14):

There are two types of effective leaders or managers.

The first is the “inspiring leader.” They can stand up in front of a group of people and distill down the North Star: this what we’re here to do, this is why you are here to do it, and this is why this is the right place and right time for you to be here right now. And it gives people a sense of connective tissue that they’re here for something bigger, and it says to them, “when you show up here, you are appreciated, and it was a smart decision to be here.” And they can paint a really exciting future.

Then there’s the “player-coach.” That person is so good at what they do, and takes a vested interest in other people’s success. My partner at my business, Katherine Dillon, is a player-coach. If someone is editing a document, she takes her chair and sits next to this person and says, “I’m going to show you how to edit a document. This is good, but this is where you got it wrong.” And she’s kind but very direct, and she teaches people to be much better players.

I’m the inspiring leader - I like getting up in front of a group of my employees and painting the vision. The inspiring leader is effective over the short term but not usually the long term.

The player-coach point reminds me of this excerpt from a blog post by Will Larson (”Grab bag of random thoughts”):

There are a number of executives out there who are very good at some things, but lack the flexibility to operate in varied environments. Sometimes this is because they are stubborn, and have a specific working style that they insist on following independently of the company. Another major contributor, in my experience, is executives who lack experience working in middle management.

Middle management is, of course, something that people often view as fake work, but it’s the critical work of translating an executive’s stated plan into a series of real plans that the company can actually implement. Executives who don’t understand this are doomed to create systems and processes that impede organizational execution, often screwing things up while claiming to improve organizational execution. Based on my experience, I don’t think you can be an excellent executive at a scaled (or scaling) company without middle management experience. ¹

I’ve seen many people become frustrated in the middle manager role (full disclosure: I am a middle manager) but I agree with Will that the reps are valuable. The challenges of the middle manager role are real: managing up and managing down, being further away from implementation details, needing to bridge the gap between an executive’s desires and pragmatic realities, etc. But assuming you have goals to continue to climb the career ladder, how else do you expect to coach and grow middle managers in future roles without this experience? The reps breed a deep empathy for what works and what doesn’t, which allows you to step into a role as a player-coach when it’s appropriate.

The notion of player-coach also speaks to the crux of what I mean when I say engineering managers must be technical enough to intervene. Honestly, my coding skills are stale - I haven’t meaningfully contributed production code in years, and the JavaScript zeitgeist changes every 10 minutes. But because I’ve spent years shipping complicated changes to production I have a lot of smells around things like rollout plans and the difference between real technical due diligence and lip service. Because I’ve spent years authoring technical roadmaps and documents like RFCs I can guide my teams through authoring their own. It’d be impossible to coach my reports through this work if my opinions weren’t rooted in meaningful reps.

One nuance in improving as a manager is minding the gap between being a player coach and a micromanager. The goal is to distinguish between showing someone how to do something versus doing the work for them. One strategy I use: I think it’s most productive to coach someone through improving an artifact they’ve made the first version of alone. For example, if I know someone is an inexperienced public speaker and wants feedback before presentation delivery, I’ll ask them to present at a dry-run the week before. Then I’ll duplicate the slide deck and coach them through any potential improvements using their slides as a baseline. ² The same goes for RFCs, engineering-all emails, etc. And then I give less oversight the next time, with the caveat that I’ll intervene if I need to.

I’m less sure about training the “inspiring leader.” I think you can absolutely become a better public speaker, which, like many things, gets better with practice. And I think it’s important for leaders to cultivate that skill. But inspirational public speaking is 90% message and 10% delivery. One question I ask often: “what’s the core narrative behind this work? Why should this matter to someone who is not you? How does this become a story of problems and outcomes and less about technical detail?”

An inflection point for me was when I realized that all of the best talks / podcast interviews / etc I’ve ever heard were stories. Inspiring leaders are storytellers, and even your frontend JavaScript build library upgrade has a compelling story. And that story is not a retelling of the Jira tickets, but rather the story of the before and after. What were the unexpected learnings? What were the hardest parts? That’s what stays with people.

I like the Galloway quote because it succinctly identifies the two aspirational qualities I often find myself admiring in others: the ability to stand up in front of a group of people and rally their enthusiasm behind shared goals/values, and the ability to scale execution across people and teams with a carrot and not a stick. Thinking about these two qualities helps me frame my own work by thinking about how I conduct myself, what I say yes to, and how I find opportunities for those who report to me.

Footnotes