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I'm Dermot Kilroy

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Featured from The Messy Middle

Insights and practical guidance from the trenches of engineering leadership

Aug 26, 2025

Intent Is Invisible, Impact Is Real

When I think back to the email I received from the boss with a long list of issues that happened during my holiday...

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Aug 22, 2025

The trap of thinking ahead

As leaders, we’re told to prepare. Think things through. Anticipate problems. But there’s a trap in this. When we spend time alone turning a problem over, we come into the room with...

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Jan 10, 2025

I’m disappointed isn’t feedback

You’ve probably said it, or at least thought it. A bug slipped through review, and a Team Lead catches it. Later, they told me: “I told the team members involved that I’m disappointed...

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Apr 7, 2025

When Your Team Doesn’t See the Fake

I was talking to someone who played under-19 basketball for England. At that level, the game is sharp, every move counts. But when he dropped down to the lower leagues, his usual tricks stopped...

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May 9, 2025

It’s all in the interactions

I’m currently reading Complexity and Organisational Reality by Ralph D Stacey. For those unfamiliar, it’s a book, published in 2010, that challenges the idea that we can manage organisations through clear plans and control. Instead, it suggests that management is...

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May 13, 2025

Maybe politics isn’t a dirty word after all

A couple of days ago, I shared this line from Stacey: “The effective leader is a skilled participant in the ongoing ordinary politics of daily life.” At the time, we focused on how leadership lives in real-time interaction. But I’ve been coming back to that word: politics...

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Hello,I'm Dermot Kilroy

Featured from The Messy Middle

Intent Is Invisible, Impact Is Real

The trap of thinking ahead

I’m disappointed isn’t feedback

When Your Team Doesn’t See the Fake

It’s all in the interactions

Maybe politics isn’t a dirty word after all

Get insights like these delivered daily

Hello,
I'm Dermot Kilroy