On Leadership in the AI Era

The distinction between real Leadership and Executivism is more important than ever.

In my early 20s, I had one of the most formative experiences of my life working at a summer camp in the San Bernardino Mountains. Most groups brought their own counselors who already knew their kids. But almost every week, one or more groups would come up short on adults. As one of the younger team members, I got stuck with what everyone considered the least desirable job: backfill counselor for the “overflow kids.”

This meant taking 6-9 kids I’d never met under my care for a week at a time. Most of the time, I worked with young boys aged 8 and 9. Having my own kids now, I have no idea how I managed to care for six 8-year-olds at the age of 20. But I did. And I did it well. Every kid under my guidance had a great week. Not because I let them run wild, but because I made sure they had a real connection with every kid in our tent.

I remember one kid vividly. He had a rough first two days. He was a total nightmare to the other boys in our tent, so they treated him like shit in return. On that second day, I asked him to run the treehouse ropes course with me. He opened up about his household, his siblings, how he was viciously bullied back home. I offered him something simple: “Just be at camp this week. Be a dork with our tent. Forget about everything back home for a few days.” To my surprise, he did. He was willing to go outside his comfort zone to just have a good week. The following days he led the charge during “cleanup time” every morning, getting the other boys to participate and make the tent better for everyone. He volunteered for KP duty and made friends with one of the kids who was really homesick. He became the MVP.

This story is the earliest exploration I had of real leadership. I didn’t recognize it at the time, but that set the foundations for how I operate today. Leadership isn’t about authority. It’s about connection, understanding, getting into “the work” yourself, and inspiring people to become their best selves.

That 8-year-old didn’t follow me because I was “the counselor.” He followed because I saw him, understood him, spent time doing kid stuff with him, and gave him space to transform. The other boys didn’t clean up the tent because I made them - they did it because one of their own showed them it mattered and replicated what I had already modeled.

Artwork courtesy of Luis Palomares.

The Two Approaches

From the moment you start your career, maybe even before, you face a choice most don’t even recognize they’re making. There are two fundamentally different approaches to influence and leadership, and they take you to two completely different, incompatible places.

Approach 1: Real Leadership

This is leading through competence and modeling. You build trust through capability; your influence is earned through demonstrated mastery. People follow you because they learn from you, because you can actually help them get better at their craft, and because you know what “good” looks and feels like. This is the engineer who other engineers ask for help, the designer whose work becomes the reference standard, or the analyst whose insights change how the team thinks. Before you have any formal authority, you are already leading, because you can do the work better than most and you help others do it better too. This is Andy Grove visiting manufacturing plants, teaching technical courses, and staying involved with operational details several levels below him. This is Steve Jobs staying involved in product design. This is the engineering lead who can still ship features when the team is underwater. Your value comes from making your team more capable, not from coordinating their inputs, outputs, and process.

Approach 2: Executivism

This is leading through hierarchy and politics. You build power through organizational structure. Your influence comes from position and people follow you because they have to, because you control resources and promotions, and because you’ve mastered the performance of leadership even if you can’t do the actual work. This is the person who masters managing up instead of mastering the craft. It’s the manager whose main skill is organizational maneuvering, the VP whose calendar is meetings about meetings, or the executive who can’t answer technical questions without deferring to someone who reports to them. Your value comes from coordination and from navigating organizational power dynamics.

Why Executivism Exists: The Managerial Feudalism Problem

Executivism doesn’t emerge in a vacuum. It takes seed in a specific organizational structure that anthropologist David Graeber called “managerial feudalism.” In feudal times, lords demonstrated their power and status through the size of their retinue - servants, advisors, guards, and attendants. The more people in your entourage, the more important you were. Your wealth wasn’t measured by what you produced, but by what you could appropriate and then redistribute to maintain your power base. Modern organizations operate in a very similar way. You hire lots of people, grow your organization to meet hypothetical demand. However, it’s not because you need more people to ship product, but because having more people reporting to you makes you more important. Your compensation is tied to headcount, your status in the organization is determined by the size of your org, and your position in internal power struggles depends on your ability to command resources.

Graeber called this the proliferation of “bullshit jobs”, roles that exist not to produce value but to maintain the hierarchy. Flunkies who make you look important, goons who fight your internal battles, box tickers who create the appearance of process, and taskmasters who manage the managers. An entire architecture of power built on top of the functional work of the organization, not integrated with it. And within this structure, Executivism flourishes.

The playbook writes itself: master the performance of leadership, build your fiefdom, manage through coordination rather than capability, win through politics rather than results, and distance yourself from “doing” as you climb. This is why some organizations teach a version of “leadership development” that’s really Executivism training. Why the path to VP runs through management, not mastery. And why senior leaders who stay technical are seen as anomalies.

In organizations with thousands of people, who can tell the difference between an executive who understands the work and one who just coordinates it? The system doesn’t select for operational competence. It selects for people who can maintain the hierarchy. For decades, this was just how organizations worked at scale. If you wanted to build something big, you needed management layers. You needed coordination. You needed executives who could navigate complexity through organizational skill rather than operational knowledge.

And now AI is changing everything.

The AI Inflection Point for Leadership

Something remarkable is happening, a new generation of startups is building companies that would have required hundreds of people just five years ago - with teams of less than ten. Not by working harder. Not by cutting corners. But by fundamentally rethinking what’s possible when operators have AI-augmented capabilities and workflows. The examples are everywhere: Startups deliberately keeping engineering teams at 7 developers while competitors scale to 40+, achieving similar product capabilities. PostHog operating with fewer than 50 people but shipping like a company 10x their size. VCs now seeing startups hit $100M in ARR with 10 people in 3 years, all kinds of metrics that would have been impossible in the pre-AI era.

What makes these teams work? They’re not led by executives. They’re led by operators. People who understand the work deeply enough that they can use AI to extend their own capabilities rather than hiring layers of people to coordinate. Technical founders who can personally ship features while also setting strategic direction. These teams don’t have project managers, program managers, scrum masters, or VPs of Ops. They have people who can do the work, augmented by AI that makes their impact broader and deeper.

This model makes Executivism obsolete.

In a team of 5, you can’t hide behind coordination theater. Everyone knows what everyone else is doing. There’s no room for people whose primary skill is managing up and down. There’s no place for executives who’ve forgotten how to ship. If your 5 reports quit tomorrow, could you actually do their work with help from gen AI? If you can’t do the jobs of 5 people with AI helping you, how can you possibly run an organization of 5,000?

The old answer was: “Through hierarchy, through delegation, through organizational design.” But that answer assumed you needed layers of people to translate strategy into execution. AI is making those layers unnecessary. Small teams of operators are shipping what used to require armies. If you wanted to build something big, you had to give up doing the work you loved. You had to become a coordinator, a politician, a performer. The price of impact was losing touch with the craft. AI breaks this equation. You can stay an operator and build something that matters. You can scale impact without scaling away from the work.

Be a real leader, get your hands dirty

Jobs and Grove proved you could stay deeply operational while running massive organizations. But they were exceptional. Most leaders couldn’t maintain that level of technical mastery AND set strategic direction AND manage thousands of people. AI makes what they did achievable for strong operators, not just generational talents. The operational leadership that used to require world-class capability is now within reach of good engineers, good product leaders, and good operators who use AI well.

The camp counselor model isn’t just possible at scale now - it’s the competitive advantage. You can achieve massive organizational impact while keeping teams small enough for real human leadership. You can see people, understand them, work alongside them, help them transform... AND build something that reaches millions. AI brings humanity back into leadership. It eliminates the size constraints that forced us into less humane structures in the first place - large fiefdoms of organizations. We don’t have to sacrifice understanding for impact. We don’t have to become Executivists to build something “big” that matters. For the first time in the history of organizations, the most effective model and the most human model are converging.

What This Means in Practice

If you’re a founder: Design against Executivism from day one. Hire operators over coordinators, people who can teach the team something, not just coordinate them. Keep teams small enough that you understand the work. Before you add a management layer, ask if you could build AI capability instead. Watch for roles that exist to make someone look important rather than deliver value.

If you’re an emerging leader: Stay operational even as you advance. Use AI to extend what you can personally do, not to replace expertise, but to keep you grounded in the work. Resist the performance trap when people tell you to “act more like a leader.” Real leadership is felt in results, not in how well you perform the role. Build T-shaped capability: deep expertise in your domain, broad competence across the stack.