The Long Game: Growing Engineering Managers

Alex had been on my team for two years. Strong engineer. Shipped consistently. Other engineers came to her with questions. When we had a particularly gnarly incident, she was the one who stayed calm and walked everyone through the problem.

One day in our one-on-one, she said, "I've been thinking about management."

This is the moment where a lot of managers get it wrong. They either pump the brakes too hard ("Are you sure? It's really different from engineering") or they fast-track the person into a role they're not ready for. I've done both. Neither works.

What I've learned is that growing a manager takes time, intentionality, and a willingness to let someone change their mind along the way.

Start With the Person, Not the Path

Before you can help someone become a manager, you need to understand who they are. Not just their work performance—their values, their motivations, what they want from their career and their life.

This sounds obvious. It's not.

Most career conversations I've observed focus on the immediate: What do you want to work on next quarter? Where do you see yourself in two years? What skills do you want to develop? These are fine questions, but they're shallow. They assume the person already knows what they want and just needs help getting there.

The better approach is to understand someone's story. Where did they come from? What do they care about? What does "meaningful work" mean to them? What are they afraid of? When do they feel most alive at work?

Kim Scott's Radical Candor has a framework for this that I've found useful. She calls them "career conversations," and they're structured around three discussions: the person's life story, their dreams, and a plan to connect those dreams to their current role. The key insight is that you can't help someone grow if you don't understand what growth means to them.

The point is: keep regular career conversations. Explore goals. Build enough trust that people tell you what they actually want, not what they think they're supposed to want.

When Someone Shows Interest

So someone says they want to explore management. What now?

The worst thing you can do is immediately start talking about open roles or headcount.

What works better is to build a shared understanding of what management actually is. Not the title, not the org chart—the work. The day-to-day reality of it. Because the thing people imagine when they say "I want to be a manager" is often nothing like the actual job.

Camille Fournier's The Manager's Path is the best resource I've found for this. It walks through each level of engineering leadership—from tech lead to VP—and describes what the work actually looks like. Not in a theoretical "here are the competencies" way, but in a practical "here's what your day will feel like" way.

When I have someone interested in management, we read it together. Not all at once—maybe a chapter a month. After each chapter, we talk about it. What surprised them? What made them excited? What made them nervous?

This is where you start learning whether management is actually right for them. The person who lights up when reading about one-on-ones and feedback is different from the person who lights up when reading about system design and technical strategy. Both are valid. They just point to different paths.

One thing I've learned: be explicit about what flavor of engineering management your company values. Some organizations want tech-lead managers who still write code and lead architecture decisions. Others want people managers who focus primarily on coaching and organizational health. Some want both. If you're not clear about this, you're setting someone up for a job they didn't sign up for.

The Apprentice Model

Before someone becomes a manager, let them practice being one—for real, with actual responsibility.

Give them a small team. Make it official enough that the team knows this person is their manager, but structured enough that you're still providing close oversight. This isn't shadowing or running the occasional retro. This is the job, at a smaller scale.

The key is making sure they go through at least one full planning cycle and one performance cycle. These are the two hardest parts of management, and you can't really understand them until you've done them.

Planning forces you to make tradeoffs. What are we building? What are we not building? How do you negotiate with stakeholders who want more than you can deliver? How do you communicate priorities to a team that might disagree? Your apprentice manager needs to own these decisions, make mistakes, and learn from them while the stakes are still relatively low.

Performance cycles are harder. Writing reviews is the easy part. The hard part is having honest conversations with someone about their growth, their gaps, the things they don't want to hear. It's sitting across from someone who's underperforming and deciding whether this is a coaching problem or a fit problem. It's calibrating your assessments against other managers and defending your reasoning.

Throughout all of this, you're providing feedback and guidance. Weekly one-on-ones at minimum, probably more frequent at the start. You're watching them run their team meetings and debriefing afterward. You're helping them prepare for difficult conversations and then asking how it went. You're catching mistakes early, before they become expensive.

And here's the part most managers forget: you have to provide an explicit out. Make it clear from the beginning that going back to IC is not a failure. It's a valid outcome. Some people will go through this process and realize they don't want to do it full-time. That's not a waste—that's the system working.

Graduation

When someone makes it through the apprenticeship—when they've done the planning, done the performance cycles, gotten your feedback and incorporated it, and still want to keep going—it's time to make it official.

This part is straightforward. You expand their scope. You give them a full team, or you formalize the one they've been running. You update their title. You announce it to the organization.

But don't skip the ceremony. It matters.

Acknowledge what they've accomplished. Not just "congratulations on your new role," but recognition of the specific work they did to get here. The hard conversations they had. The planning cycles they ran. The mistakes they made and learned from. This is the culmination of months of intentional development, and it should feel that way.

I also find it useful to reset expectations at this point. The apprenticeship had training wheels—close oversight, smaller scope, an explicit safety net. Now those come off. They're a manager, fully accountable for their team's results and their people's growth. The relationship between you and them shifts. You're still their manager, but the dynamic is more peer-like. You're there for guidance when they need it, not for constant supervision.

The Long Game

Growing managers is slow. It takes months of career conversations to really understand someone. It takes more months of reading and discussing to build a shared understanding of the role. It takes two or three quarters of real apprenticeship—with planning cycles and performance reviews—to give them genuine practice. And then, finally, graduation.

This feels inefficient. It's not.

The alternative is transitioning people who aren't ready, or moving people into jobs they don't actually want. That's expensive. They struggle, their teams suffer, they either burn out or get managed out, and you're back where you started—but now with collateral damage.

The managers I've grown intentionally, the ones who went through this full process, are still managing years later. They knew what they were signing up for. They had time to develop the skills before the stakes got high. They made an informed choice. And when they graduated, they were already operating at the level—the title was just recognition of what they'd already become.

The ones I rushed? Maybe half of them are still in management. The rest went back to IC roles, or left the company, or are struggling in jobs that don't fit them.

If you're a manager of managers, this is some of the most important work you do. Not hiring externally—though that matters too—but growing the leaders who are already on your team. The ones who know your codebase, your culture, your people. The ones who just need time and space and structure to figure out if this path is right for them.

Give them that time. Do the career conversations. Read the books together. Let them apprentice with real responsibility. Provide the out if they need it. And when they're ready, graduate them properly.

If they decide management isn't for them along the way, celebrate that too. You've helped someone avoid a mistake, and you still have a great engineer who now understands what their manager deals with.

That's not a failure. That's the process working.