You promoted your best engineer. Now what?

The philosopher Brianna Wiest wisely said that the question is never what should you do - it's why aren't you doing it. Whenever I'm brought in to coach someone who is underperforming in a leadership role, my first question is never what are they doing wrong. It's what is holding them back from doing what they need to do. The answer almost always lives in their career up until that point.

Technical people - engineers, product managers, developers - are, in their domain, often extraordinary. The problem is that the same singular focus that made them brilliant individual contributors is exactly what makes the transition to leadership so hard. They have spent years being rewarded for what they can do alone. Now their job is to get performance out of other people. That is a different skill set entirely, and most of them have had almost no exposure to it.

Before we get to any of that, though, there is a more fundamental step. One that is deceptively simple and therefore almost always skipped.

Get crystal clear on what the role actually is.

The question I use for this is: explain your role in a way that a seven year old could understand. I have sat in rooms with very senior leaders who cannot do this. Not because they aren't intelligent - they are - but because leadership is abstract, and when we don't truly understand something, we reach for jargon to cover the gap. The problem is that you cannot perform something you cannot define. And a leader who can't define their role will default to the role they came from - which, for a technical leader, means doing the technical work themselves and quietly ignoring everything else.

Once there is clarity on the role, you can have an honest conversation about the barriers to performing it. For anyone in a leadership role, the same things tend to trip people up - holding others to account, having direct conversations about underperformance, choosing what not to do in favour of what they know they have to do, managing time and energy in a role with no clear edges. These aren't character flaws. They are gaps - the result of a career that simply didn't require those muscles until now.

Some coaches will tell you to focus on strengths and work around the gaps. I don't take that view. Muhammad Ali (we think it was Muhammad Ali) said it's not the mountains ahead that wear you out, it's the pebble in your shoe. A leader who can't hold their team to account is carrying a pebble. Left alone, it will tire out the leader, the team, and eventually the business.

The third step is strategy - how to develop or offset those barriers over time. But none of it works without the feedback that makes it possible. Not the comfortable kind. The kind that is timely, specific, and honest enough to confront the gap between where someone is and where they need to be.

These conversations are rarely easy. But they are the way to help the new leader improve.