On Growing People

I have a shelf full of books about leadership. Radical Candor, The Manager’s Path, The Culture Map, The Introverted Leader.

I’ve done the training courses, watched the videos, sat in the workshops where you role-play difficult conversations with a colleague who’s trying not to laugh. All of it useful. I’m glad I did it. But none of it, not a single page or module or framework, prepared me for the actual moment you’re sitting across from someone and need to say something they don’t want to hear.

There’s a version of Amara’s Law that I think applies to management, though I’ve never seen anyone frame it this way. Amara’s original observation was about technology: we overestimate its impact in the short term and underestimate it in the long term. I think the same thing is true of conversations. We overestimate the impact of easy conversations in the short term, the praise, the check-ins, the “great job on that project” moments, and we underestimate the impact of hard conversations in the long term. The ones where you tell someone something honest that they’re not ready to hear. Those are the ones that actually change the trajectory. I know this because someone did it for me, and I’ll be forever grateful she did.

The reset button

I was a few years into a role, my dream role at the time, performing well enough by most measures but wearing down. One of those situations where you’re technically doing the job but the job is slowly doing you in. My manager at the time pulled me aside and said something I didn’t expect: “Maybe it’s time to hit the reset button.”

That’s it. No framework. No sandwich method. No carefully worded HR-approved script. Just an honest observation from someone who’d been watching closely enough to see what I couldn’t see myself. I didn’t fully appreciate it at the time, honestly it stung a bit. But I took the advice. I moved on, and that move shifted my career from delivery into pre-sales, from purely technical work into business thinking. A completely different path opened up because one person chose to say the uncomfortable thing.

The cost of honesty

The thing I didn’t appreciate until much later: it was against that manager’s own interests to say it. This is the part that most leadership books skip right past. A manager isn’t just a people leader, they’re running a business. They have targets, headcount plans, attrition metrics, maybe a stack ranking to fill. When I walked out the door, that manager had a hole in their team, a recruitment cycle to kick off, and a gap to explain upward. The easy move, the self-preserving move, would have been to say nothing and let me grind along for another year hitting my numbers.

They said it anyway.

I’ve been on the other side of this enough times now to know how rare that is. I’ve watched managers handle people badly, not because they’re bad people, but because the system makes it really hard to be good at this part. I’ve seen high performers pushed out because a manager needed to put someone below the line on a report and had no real understanding of how the person was actually performing. I’ve seen poor performers promoted because they ticked the right boxes and played the right games. I’ve seen someone leave a company and have their exit handled so poorly that it cemented a permanently negative view of the place, exactly the outcome everyone should be trying to avoid.

In almost every case, the common thread was the same: the manager cared more about how they looked than about what the person across the table actually needed. And before you judge them too harshly, understand what they were dealing with. Every honest conversation carries a business cost. Telling someone “this role isn’t right for you” means volunteering for pain, losing a team member, explaining the attrition, finding a replacement. Keeping a disengaged person in their seat avoids all of that, at least for the next quarter. The system rarely rewards managers for doing the right thing by their people when it conflicts with the business metric. Most management training teaches you conversation techniques but completely ignores the fact that having the conversation at all often works against your own interests.

The managers who have those conversations anyway aren’t following a model from a book. They’ve just decided, consciously or not, that the person matters more than the metric.

A different kind of growing

I had a different kind of growing moment at another point in my career, one that taught me something else about how people develop. I was going through a period where I kept ending up as the dissenting voice in interview loops, saying no to candidates when everyone else was saying yes. It was getting to me. Was I too harsh? Were my standards off? Was I just bad at evaluating people?

I sought out a director in another part of the business and asked for help. What I got wasn’t what I expected. They didn’t tell me I was wrong, and they didn’t tell me I was right. They helped me see that the other interviewers were making logical, sound decisions, just shaped by different experiences and expectations than mine. My perspective wasn’t wrong, it was just different. And that was OK.

That conversation didn’t change my mind about anything specific. But it changed how I thought about disagreement itself. I still carry that with me. The best mentoring I’ve received has never been someone telling me what to think. It’s been someone helping me understand why I think the way I do.

The other side

Not all of it lands, though. When I left one role earlier in my career, my manager at the time got angry. Visibly angry. Told me I was making a backward step, that I was throwing away what I’d built. I know now that the anger had nothing to do with my career and everything to do with the hole I was leaving in their business plan. They were processing their own problem out loud and calling it advice. I left anyway, and it turned out fine. But I remember how it felt, and I remember thinking: if I’m ever in a position to have this conversation with someone, I want to do it differently.

Passing it forward

I’ve since had the “maybe it’s time to move on” conversation with a couple of people I’ve mentored. Both times it was hard. Both times I could see they weren’t in the right place, that the job was grinding them down, and that they couldn’t quite see it themselves because when you’re inside the thing it’s almost impossible to get perspective on the thing. In both cases the short term was rough, it always is. But the long term worked out.

I’ll be honest, it was easier for me because I wasn’t their manager. I had nothing to lose. No headcount gap, no recruitment cycle, no awkward conversation with my own leadership. A manager saying the same thing is choosing to take a hit, and I don’t think we talk enough about how much that choice costs them. The tension between “do right by this person” and “do right by this business” is real, and pretending it doesn’t exist is how we end up with managers who optimise for self-preservation and call it leadership.

I don’t have a five-step framework for this. But I do think a leader’s job isn’t about hitting this quarter’s numbers. It’s about steering someone’s career in a direction they might not understand yet. Sometimes that means telling them they’re doing great and to keep going. Sometimes it means telling them the thing nobody else will say. And sometimes, if you’re being really honest, it means telling them that the best thing they can do is leave.

A company isn’t your life. But sometimes it’s hard to see the distinction until someone outside your own head puts it into real words. The managers who do that, the ones who choose the person over the metric, they’re the ones you remember. Not because they followed a framework, but because they cared enough to say the hard thing when staying quiet would have been easier for everyone, especially them.