Why I’ve Never Lost a Direct Report in 23 Years. I've still never really worked it out. But..........

When Jeff and I kicked off Who2, one of the first things we agreed on was simple: we’re only as strong as the team we build around us.

I’ve been leading teams for over two decades. In 23 years, I’ve never lost a direct report. Not one. People have been promoted, moved on in their careers, and gone on to bigger things but no one has ever left because they didn’t want to work with me or the team anymore.

That’s not luck. That’s trust. When people asked for time off, I never once asked the reason. Not once. I assumed they knew why and that's all that mattered to me. If it was for a holiday I did get a little FOMO. 

Here’s the thing: if you spend your energy trying to be the smartest in the room, you’ll miss the real point. The job of a leader isn’t to prove you know it all. It’s to build an environment where good people want to stay, thrive, and push for more.

At Who2, it’s no different. Jeff and I know we can’t do everything ourselves (although we sometimes try). What we can do is set the tone:

• We will trust people to do the job we will hire them to do

• We will back them when they get it right, and when they get it wrong. We win and lose together, always

• We make it clear that work is about progress, not perfection. If perfection was real, Adam and Eve would still be here

The insurance world is full of clever products, shiny systems, and endless meetings. But the truth is, none of that matters if your team doesn’t want to come in on Monday. I hope I've never had a colleague who had the 'Sunday night dread'. 

23 years without losing a direct report isn’t about me, or Jeff, although this article may seem like it is. It’s about creating a culture where people believe in what you're building and where they know the person above them has their back. Always know your people! 

That’s what Jeff and I are carrying into Who2. Trust the team, keep them close, and the rest follows.

Want to work from the moon? - crack on 

Want to bring your dog to work? - crack on 

Want to wear a Mickey Mouse outfit? - crack on

Just help us to build something incredible. Together.

The views expressed in this article are those of WHO2 Global Ltd and do not constitute professional advice. All content is for informational purposes only.