Whether You CAN Is Learnable. The Issue Is Whether You WANT To.

We left the office, bought some coffee, and started walking down Stadiou from Omonia toward Syntagma. You could say it was an awkward 1-on-1—away from the office, meeting rooms, notes and laptops. We were talking about management. What makes a good manager. What makes a bad one. Sixty-six minutes in, my colleague had said it: I feel I can’t do it at all. He was talking about people management—the trial we were talking about, the responsibilities we had scoped, the boundaries we’d set, the ramp we had built. This wasn’t impostor syndrome, some abstract version of it. He was experiencing the concrete fear that he wasn’t cut out for it; haven’t we all gone down this road when we took our first steps.

On the walk I reframed it. Whether you can is learnable. The issue is whether you want to.

I’ve been doing this for quite some time—management, in various positions and capacities, industries, companies. That reframe is what I’ve learned. It’s the seed of this post. It’s what I’ve spent years watching.

Stay a while and listen.

The Same Conversation

The same conversation has played out in different rooms, different companies, different faces, different times. I’ve seen people who are extremely strong technically get pushed toward leadership—and fail catastrophically. Not because they couldn’t learn the skills, but because we tell them that leadership is the only way to go above and beyond. The raises, the promotions, the power, the recognition. We present management and leadership as an evolutionary trait; if you don’t adapt, you’ll stay on the front lines forever. A senior engineer with a regular paycheck, having no effect on the organisation—you, your tasks, and a constant sprint to deliver the new feature, the optimisation, the fix to a regression.

Thus we model it. We run the tryout. We assume the only thing between them and the role is confidence, or role clarity, or specs, or breadth of scope.

We treat I don’t think I can and I’m not sure I want to as the same problem. They aren’t.

Can is capacity. Want is desire.

You can train capacity. You don’t get to train desire into someone who doesn’t have it—it cannot happen. You shouldn’t try. We’ve tried. We’ve failed in the past.

The no-shame exit ramp isn’t a consolation prize. It’s the actual design that works for everyone. When you pair it with clear delegation of intent and authority, people can step back without shame.

I Didn’t Learn That From a Book

I’ve held various positions in various industries and I’m proud that I’ve been a factory worker, carrying euro-pallets in warehouses, gathering grapes, tobacco and olives when I had the need to. The dynamics are the same whether you’re working a blue-collar or a white-collar job. If the one who leads the crew is inherently incompetent—lack of soft skills is incompetency—the crew will become as incompetent as the one that leads them. There’s a brutal historical example: after the Battle of Kleidion in 1014, the Byzantine emperor Basil II had thousands of Bulgarian prisoners blinded, but left one eye in one man out of every hundred so that he could lead the ninety-nine blind back to their tsar. The one-eyed leading the blind. When the leader is barely fit for the role, the whole column follows at that level.

I’ve seen the senior who went manager because it was the only way to get a raise, spent two years and came to understand that their tech skills had atrophied, and went back because he didn’t like it. I’ve seen the lead who said yes to the title and no to the work—everyone could feel the no. I’ve seen the ones who left a company rather than say I don’t want this out loud, because the only alternative on offer was stay IC and watch your ceiling drop. The ones who stayed often became the managers everyone complained about. Tenure must not guarantee leadership. Tenure measures time in seat, not desire to lead and not fitness for the job. When we promote because someone has been there longest, we’re not selecting for capability—we’re selecting for survival. The result is the one-eyed leading the blind, and the crew becomes as incompetent as the one at the front. If the only reason someone is in the role is that they outlasted everyone else, the system is broken.

In every case, the system had one right answer: Step up. You know what?

The system was wrong. Both outcomes are on the system.

The Trial We Designed

So when my colleague and I designed his trial, we baked the pivot in from day one. Not try this and we’ll see—he already held the position, but in a limited capacity. We said: try it properly, and if it doesn’t fit, we’ll adapt the work to the person, not the person to the work. The exit isn’t failure. The exit is one of the two valid outcomes. No performance review penalty, no PIPs, no narrative that he couldn’t do it. We ran the experiment; that was the result.

What kind of manager would I be if I didn’t put people where they can succeed and step back when the path isn’t for them?

Three Weeks In

Three weeks in, the data is coming in. He’s catching PRs, calling out problematic behaviours, taking decisions in his domain—his own to take—without having to run them by me. I could write this as a victory lap—see, the trial works—but I ain’t. The trial might not work. The point isn’t the outcome. We’re doing this without pretending it will work. Success, in this case, isn’t outcome-oriented—it’s the value we obtain from exploring another domain, the leadership and management one. We design for success, we work towards success, no matter the actual outcome.

My First Steps

That reframe didn’t come from a playbook. It came from my first steps—and from the moment I understood that can and want are not the same thing.

The first time I took a managerial role it was out of sheer need. My manager went on maternal leave and there was no one to run the operation. We, the ICs, didn’t think we needed a lead; we thought it was business as usual. Then higher management called me and said I was the interim manager so fuck-ups would stop. Was I the one with the longest tenure? Sure. I also had a deep understanding of the operation and my way with people—a couple of years on the front lines of customer service and support. They thought I was cut out for the job. I said let’s give it a try; it was supposed to be temporary.

It was weird every day. Managing people who had been colleagues—same trenches, same trauma, beers and shop talk. It was painful to show them their mistakes and try to help them grow. You’d ask: wouldn’t you already be doing that, as the most senior of the crew? The truth is, ten years later with a clearer picture, I was already doing it. I was the X/O; I didn’t get promoted to C/O but I was the acting one. Did everything go according to plan? No—and that wasn’t in the package. I was there to lead, not manage. And I led. Sailing on and on and north across the sea.

When I switched jobs I went back to IC. Back then I thought: screw this, I’ll go for a junior position and allow myself to relax. That was the plan; between us, I still think about it from time to time. There was a vacancy and I offered to fill the gap—no title, no raise, no shenanigans. My motto was to set myself up for obsolescence. I was there not only to lead or manage but to help more junior members grow, make myself obsolete, let them take on my responsibilities so I could move to the next challenge. It took time. It was painful. And again I was there, saying I’m not cut out for it, I don’t want to do it—people have grown, they can take it from here. Back to IC.

Back to management a year later. Stronger, more determined. I’d had enough of idle reverie; I decided to take my life in my own hands. Am I a good engineer? Most probably. Is my team composed of engineers who are better than me? That’s for sure. So what do I have that makes me cut out for this role? The soft skills that only come through experience, pain, mistakes, understanding. You stop optimising for CPU cycles and memory and start optimising for people’s output. You still do reviews—architectural, security, business. You still write code from time to time, but only when something genuinely needs you or to fill a forty-five-minute gap between demanding meetings. You prototype so you don’t get left behind and turn into another I don’t understand this, can’t we use an iframe?

I had a talk with my manager the other day. I told him straight: have you digested that neither you nor I are developers anymore? It hurts, but it’s the truth. We’re not developers. We’re engineering managers—we manage the people who produce the code, we help them grow, we listen, we understand their problems, we give them solutions, we escalate, we protect. I’ve been the guardian angel of a crew of twelve strong for the past two months; soon I’ll be out on paternity leave, expecting my second. I’m seeding what needs to be reaped. A proper culture, empowerment, the ability to speak up, to push back, to criticise the higher ups. All of that can be taught by a book, but it has to be experienced. Joining a call with a mid-level engineer and demanding that they challenge you and push back whenever necessary—I do that. I may be the captain of the ship, but I ain’t infallible. I’ve got a ton to learn from my team, just as they have from me.

Don’t Be a Hypocrite

Don’t be a hypocrite. You’re another person in a leadership position. It’s a war out there and you need your crew to win; if you’re John Rambo, tough luck—this is the twenty-first century. Teach them that can and want are not the same. Teach them to challenge you. Give them space and time to grow. Perform the course corrections that are absolutely necessary. Seed the culture they’ll thrive in, not the one that suits you. And if you don’t go to therapy, it’s high time you did. If not therapy, talk to others in the same position. Build a support network. People are strange; you’ll need support, you’ll need to talk, you’ll need to vent. You’ll build trust by listening.

The First Day in the Army

The first day in leadership is like the first day in the army. The boots kill your legs, the food is awful, the bed is uncomfortable and there’s an unexplained smell in the barracks. You’ll make it. And if you don’t—make sure the exit plan is something completely acceptable and promoted. If it isn’t, it’s not you. It’s the culture.

There’s a difference between knowing the path and walking the path—Morpheus to Neo, in the Matrix. We’re walking it.