"Being let down is part of the job"

One of the guarantees of leadership is that people will let you down. But the other, less comfortable truth, is that you’ll let people down too.

I think back to that same individual who was under scrutiny during a push to speed up delivery. They were responsible for safe deployments, but I had asked them to think more strategically about performance testing. They struggled with that, and I was frustrated.

What I didn’t realise was the lengths they were going to just to keep things moving. They were manually running our flaky platform tests over and over, ensuring that deployments went out tested. It wasn’t sustainable, but it was an act of commitment in a messy situation.

Looking back, I let them down. I didn’t support them enough to grow the strategic side of their role. And I missed the human element in that evolution, the emotional work of moving from an individual contributor to someone who could hold teams to account. For them, it felt easier to pick up the slack than to step into that new authority. My job was to help them bridge that gap, and I didn’t.

And that’s the nature of leadership: we’ll let people down, even when we don’t mean to. The question is what we do next, do we sit with the disappointment, or do we use it as a moment to learn and adjust?

Because the guarantee isn’t that disappointment will happen. The guarantee is that it can lead somewhere better, if we let it.

Until next time,
Dermot
The Messy Middle.

✉️ Enjoying The Messy Middle?
If this sparked something useful, consider forwarding it to a colleague or friend, it might help them too.

If someone sent this email your way and you’d like to get it direct, you can sign up here.