What's holding your team back?
For 25 years I've asked one question in almost every one-on-one. Now I'm asking you, and every week I'll answer one situation: what's usually behind it, and one first move.
By Paul Hepworth, author of The Compounding Team
For 25 years I've asked some version of one question in almost every one-on-one: what's holding you back from doing your best work?
I've asked it in formal one-on-ones, over Zoom, and in the hallway. I've asked it of people who didn't report to me, when I could just tell from their eyes that they were stuck.
Why I'm asking now
Right now it feels like everybody else is winning, and AI is supposed to make everything easy. But if you lead a startup, you know the reality:
- Your team isn't moving as fast as it needs to.
- Quality is slipping, or it's hard to manage.
- Trust between your teams is wearing thin.
- Revenue is hard to earn.
- And you're carrying more than anyone sees.
Here's what I've learned: it's almost never just you. I've needed help at every stage of my career, from managers, peers, mentors, and people outside the company with fresh eyes. The things that kept me up at night turned out to be keeping other leaders up too.
How this works
- You send me what's holding you or your team back. Anonymous is fine, and you decide how I share it.
- Every week I pick one and answer it in a short video: what's usually behind it, and one first move.
- If it's outside my lane, I'll bring in someone I trust who's been there.
Teams get better one opportunity at a time. Let's work on yours.
Go deeper
- In the book
- Chapter 4: Continuous improvementTeams get better one opportunity at a time. That's the idea this series is built on.
Questions
- What is What's Holding Us Back?
- A weekly video series from Paul Hepworth, author of The Compounding Team. Each week he takes one real situation someone is facing at work and answers it: what's usually behind it, and one first move.
- Who can send in a situation?
- Anyone with something at work in the way: founders and CEOs, executives, managers, and individual contributors. It can be a problem with a team, a decision nobody will make, or a goal you can't see a way to reach.
- Can I stay anonymous?
- Yes. You choose how anonymous to be. A fully anonymous submission stores no name, email, company, or IP address, and identifying details are changed before anything appears in a video.
- How do I send mine?
- Use the form at iterationiq.com/whats-holding-us-back. Paul reads every submission himself and picks one a week to answer.
Transcript
So what's holding your team back from doing its best work? For 25 years, I've asked some version of that in almost every one-on-one. Formal, on Zoom, in the hallway, even from people that didn't report to me, who I could just tell in their eyes, they were stuck.
Right now, it feels like everybody else is winning. But are you? Is your team? AI is supposed to make everything easy, right? But if you lead a startup, you know the reality. Your team isn't moving as fast as it needs to. Quality may be slipping or is challenging to manage. Trust between your teams may be wearing thin. Revenue can be hard to earn. And you're carrying more than anyone sees.
Here's what I've learned. It's almost never just you. I've needed help at every stage of my career, from managers, peers, mentors, people outside the company with fresh perspectives. And the things that kept me up at night, turns out, were keeping other leaders up too.
So I'm asking you one question, as if we're in a one-on-one. What's holding you back? The link is in the comments. Anonymous is totally fine, and you decide how I share it. Every week, I'll answer one. If it's outside my lane, I'll bring someone in I trust who's been there.
Teams get better, one opportunity at a time. Let's work on yours. So what's holding your team back from doing its best work? I can't wait to find out.
What's holding your team back?
Send me your situation. Every week I answer one: what's usually behind it, and one first move. Anonymous is fine.
Send yours →