How to Run a Leadership Retrospective

Written by Dave Bailey

Brené Brown, author of Daring Greatly

Learn how to run an effective leadership retrospective that will engage your team, help them give feedback, and improve their performance.

Every time you don’t share how you’re feeling with a colleague, you’re taking out emotional debt. You’ll have to pay it back eventually, but it will cost you more to have the conversation later rather than sooner.

Emotional debt accumulates rapidly on every team, and your leadership team is no different. Sadly, there’s no Xero or QuickBooks keeping track of the debt and it’s pretty invisible, particularly to leaders.

What if I told you I could reduce the emotional debt in your leadership by 90% — and it would take just one hour of everyone’s time each week?

Stop it, Dave,’ I hear you collectively say. ‘That’s impossible.’

Well, it is possible. I call the meeting a ‘round-robin retro’ and it’s the most important meeting you aren’t regularly having with your team.

The structure is dead simple, so let’s take a look at it. 

Part 1: ‘What went well?’

One-by-one, each person gives a single, specific, one-sentence answer to the question, ‘What went well?’ Once everyone in the room has done this, go around again . . . and again, until people have voiced everything that’s gone well.

The facilitator’s role is crucial here. They must:

  • Take notes
  • Acknowledge each answer — ‘Thanks for sharing that, John.’
  • Maintain a fast pace — ‘Barbara, it’s your turn.’
  • Cut off any discussion — ‘We’re here to listen. We’ll talk about improvements later.’
  • Nudge for more responses — ‘Come on, what else went well?’

Part 2: ‘What didn’t go well?’

You can follow exactly the same format for this question. Remember, the objective is to listen, not solve, and the facilitator’s role is to make the environment safe enough for everyone to share their grievances without the risk of being shot down.

You might be tempted to start a round-robin session with the negatives — but I encourage you not to. Starting with the positives instead promotes a grateful and appreciative mindset. It helps people stay upbeat and avoid catastrophising when they come to discuss what isn’t going well.

At the end of this session, tally up the number of good things and bad things, and share them with the team. ‘This week, there were 31 things that went well, and 24 things that went less well.’

Part 3: ‘What will we change?’

You won’t have time to solve everything in a 60-minute meeting. So instead, ask the team this:

Based on everything you’ve heard, what could we change next week that would most improve our team dynamic?’

Have that discussion. Ideally, you’ll come away with one change all team members can agree and commit to . . . for one week only. Why one week? Because (a) you don’t know if your improvement will work, and (b) virtually everyone can commit to one week.

Time spend listening is time well-spent

Round-robin retros can help you and your team have vulnerable conversations—and this builds trust and connection. Brené Brown captures it perfectly in her book Daring Greatly:

Connection is the energy that is created between people when they feel seen, heard and valued—when they can give and receive without judgement.’

The strange truth about emotionally-charged issues is that sometimes just being listened to solves the problem. Not always, but often. The question is, can you afford to take one hour out of your week to listen to your teammates? Or rather, can you afford not to?

Continue reading about managing a team:

Originally published Nov 11, 2020, last updated Aug 19, 2021

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About Dave Bailey

Hi, I’m Dave Bailey and I coach tech CEOs from Series A to pre-IPO. Join 20,000 entrepreneurs who receive my new essay every week. 

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