Someone on my team told me they weren’t performing at their best because I didn’t have time to mentor them. I sat with that for a long time. It landed the way honest feedback always does, with a weight that’s hard to argue with and even harder to act on immediately, because the reason I didn’t have time was the same reason the work mattered so much.
For the past year and a half, I’ve been heads-down on Nakamoto, ruthlessly deprioritizing everything that wasn’t directly in service of shipping it. Personal life, side projects, the kind of open-ended conversations that make people feel seen and invested in, all of it got squeezed out. I live for moments like this, ecosystem-defining work that reshapes what’s possible, the kind of thing you look back on and know it mattered. And yet, that message sat with me in a way I couldn’t shake. It raised a question I hadn’t been asking: what does mentoring actually look like when you’re in the middle of a fight?
Peacetime Mentoring Is Easy
When things are calm, mentoring flows so naturally it can feel almost effortless. You have time for real 1:1s, the kind where you ask open-ended questions and actually listen to the answers. You can recommend books, pair on problems, help someone think through a career decision without glancing at your phone. You can hold space for ambiguity, sit with someone’s uncertainty, let a conversation meander toward insight. This is the version of mentoring that gets written about in leadership posts and management books, and it’s genuine, it works, it builds loyalty and growth. It’s also the easy part.
The harder question is what happens when the building gets intense enough that every hour has a cost function attached to it. When you’re shipping something that will define the ecosystem your team operates in, every meeting that isn’t about the release feels like a tax. The 1:1 that used to be a highlight of your week starts looking like thirty minutes you can’t afford, and even if you keep the meeting on the calendar, your mind is somewhere else. The mentee can feel it, too, the difference between presence and attendance.
The Player-Coach Trap
Professional sports figured this out decades ago. The player-coach role, where someone both competes and develops the team, has become essentially extinct. By 2013, only two clubs in all of English professional football still used player-managers. The NBA and NFL now prohibit it outright in their collective bargaining agreements. The reason is clear: as the game got more complex and the stakes got higher, the cognitive demands of competing and coaching simultaneously became untenable. You can’t read a defense and design a play at the same time, and trying to do both degrades both.
In tech, we still romanticize the equivalent. The engineering leader who’s deep in the codebase, shipping features, reviewing pull requests, whilst also running the team, growing people, setting technical direction. At a certain scale and intensity, that archetype stops being aspirational and starts being a well-documented failure mode. The manager becomes a “player-player,” hard-wired to take on work themselves, with coaching reduced to an afterthought, something done between deployments or deferred to the next quarter that never comes.
I fell into exactly this pattern during the Nakamoto push. I was building, shipping, unblocking, context-switching between architecture decisions and partner conversations and protocol governance. The mentoring defaulted to “they’ll learn by watching” and “we’ll catch up when things settle down.” Things don’t settle down during a battle, and watching someone work isn’t the same as being developed.
Wartime Mentoring Looks Different
Mentoring during a crisis can’t look like the peacetime version, and trying to force it into that shape does everyone a disservice. The shape has to change, and the change still develops people, just through different mechanisms.
Major General Fox Conner is widely considered the greatest mentor the U.S. Army ever produced, the person who turned Dwight Eisenhower from a frustrated young officer into the strategist who would lead the Allied invasion of Europe. Conner didn’t mentor Eisenhower in a classroom. He did it in Panama, whilst running an active brigade command in difficult conditions, over three years of daily operational work. He made Eisenhower write field orders for every aspect of the command, assigned him readings in military history, then discussed them in the context of real problems they were solving together. The mentoring wasn’t a separate track bolted onto the operational work; the operational work was the curriculum. Eisenhower graduated first in his class at Command and Staff School, and he credited Conner entirely.
Andy Grove’s concept of Task-Relevant Maturity from High Output Management gives this a practical framework. Grove argued that how you manage someone shouldn’t be static; it should flex based on where they are with the specific task at hand. When someone is new to a problem, you’re prescriptive and structured: clear objectives, frequent check-ins, tight feedback loops. As their maturity on that task grows, you pull back to coaching, clear on the what, hands-off on the how. At the highest level, you agree on objectives and get out of the way. The mentoring itself gets recalibrated for tempo rather than reduced. You don’t have time for open-ended career coaching during a battle, but you absolutely have time to be deliberate about how you delegate, how much autonomy you extend, and where you intervene.
Patton put it more bluntly: “Tell them what to do and they will surprise you with their ingenuity.” When the operational tempo is high, mentoring shifts from teaching to trusting. You set intent, you let people execute, and you course-correct when the execution diverges from the objective. The development happens in the doing, in the autonomy and the trust and the real stakes.
The best wartime mentors make the fight itself the training ground.
There’s a harder lesson buried in the military parallels, too. Lieutenant Colonel Hal Moore, before commanding the 1st Battalion at the Battle of Ia Drang, spent months developing every junior leader in his unit, from squad leaders up. When the unit was encircled and communications broke down under fire, those investments paid off; his junior officers and NCOs operated independently because Moore had built that capacity in advance. The implication is uncomfortable: some of the mentoring has to happen before the crisis. If you haven’t invested in someone’s development during peacetime, you can’t retroactively create that foundation under fire. The battle reveals what you built, and what you didn’t.
Trusted Lieutenants
The force multiplier I’ve come to rely on most is distributing the mentoring function itself. When you’re heads-down on existential work, you need senior people who can carry the development of others, senior ICs and tech leads who can onboard, pair, unblock, and grow the people around them. This is architecture, not abdication.
Bill Campbell, who coached Steve Jobs, Eric Schmidt, and Larry Page through some of the most intense periods in Silicon Valley history, understood this intuitively. His mentoring was never a separate workstream bolted onto the side of the real work. It was embedded in how the team operated: surfacing conflict, building trust between people, ensuring that the intensity of the work became a growth accelerator rather than a growth inhibitor. Campbell didn’t pull people out of the battle to develop them. He made the battle the development context.
What I Got Wrong, and What I’d Say Now
I keep coming back to that message. Two things are true at the same time, and sitting with both of them is the actual work of leadership at this level: I was right to go heads-down on Nakamoto. The intensity was warranted, the tradeoffs were real, and I’d make the same call again. And the person who reached out had a legitimate need that went unmet. Both of those things are true, and pretending otherwise, in either direction, is dishonest.
What I got wrong was the silence around the prioritization. I should have been upfront about what I could and couldn’t give during this phase, deliberate about connecting people to the lieutenants who could develop them, and honest about the fact that senior leadership during a battle looks fundamentally different from senior leadership during peacetime. The people who tell you they need more from you are usually the people worth investing in, and the right response is clarity, not guilt or defensiveness.
Sometimes the honest answer is “I can’t give you what you need right now, and here’s what I can offer instead.” That kind of honesty is the version of leadership that respects both the mission and the person enough to tell the truth. Over-promising availability you can’t deliver is worse than naming the constraint, because the person on the other side can feel the gap between your words and your calendar.
The Cost of Moments Worth Living For
I live for these moments, the ecosystem-defining, once-in-a-career pushes where everything else falls away and the work consumes you completely. The cost is real: personal life contracts, relationships get tested, the mentoring gaps accumulate in ways you don’t fully see until someone is honest enough to point them out. I don’t apologize for the choice, but I’ve stopped pretending it’s free.
The best mentors in wartime make the firefight itself a place where people grow, build systems and lieutenants that develop people even when they personally can’t be in the room, and stay honest enough to name the tradeoffs rather than pretending they’ve figured out how to have it all. The battle is the teacher, and the only variable is whether you’ve set your people up to learn from it.