The 5 Most Powerful Debrief Questions and Why They’re Important

Box of Crayons
3 min readNov 15, 2017

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Debriefing should be a significant part of any project because, oddly enough, we learn more from an event or project once it’s all over than we do during its execution. And yet we often finish something and move on without meeting to discuss and reflect on the way things went down.

But there really is value in doing that — and there’s an art to it too. You don’t want to gloss over the good or the bad; you want to find out what worked and what didn’t. Moreover, you want to be able to learn from it.

Think about the way a sports coach draws up their plans. Only after watching the team play can the coach see what works and what doesn’t and then plan accordingly for the next game.

As a manager and coach (albeit of the non-sporting kind), you’re doing the same thing when you debrief.

Your best bet is to ask a few powerful questions post-project that focus on learning and community building, rather than on measuring success. Don’t set this up for failure by making it a finger-pointing affair; rather, consider it as a way to find out what worked and what didn’t.

So let’s take a look at those questions:

1. What were we trying to do?

This is when you might repeat the goals of the project, and reiterate what you were all trying to achieve. It can be as simple as going over the original plan.

2. What happened?

As I’m sure you know, what we plan isn’t always what ends up happening. As Eisenhower said, “Plans are useless, but planning is indispensable.”

Use this question to find out what actually happened. Sure, you see things one way, but, assuming that other people were involved, there are various perspectives. This question helps gather the facts of it all — and the opinions too. This can initiate a moment of reflection. Just remember, though, to capture specific instances rather than using this question to call out a time when someone might have done something wrong.

3. What can we learn from this?

Some learning moments will be obvious (“The registration process took too long; there wasn’t enough signage at the event”); others will be less specific and require a little more exploration (“Why did we take on this project, when it’s on the fringe of our organization’s focus?”).

It’s easy to point to the flaws of a project or event, but it’s more worthwhile to start with what’s been working and go forward from there.

Knowing what works and then looking for answers about the aspects that are still puzzling will lead you to moments of discovery — learned insights — and help you come up with solutions. Be clear and concise about what still needs working on.

4. What should we do differently next time?

This question is important because it makes the learned insights stick. It puts a thought in your mind that you’ll remember as you embark on the next project and think toward the next debrief. This discussion reminds us of the gathered wisdom we can use moving forward, instead of falling into a pattern of doing things the “usual” way.

5. Now what?

Now for the practical stuff. A debrief might lead to actions that need to be taken, and this is where you can decide who should do what. Set up accountability — decide on actions, set up tasks and determine deadlines.

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Box of Crayons
Box of Crayons

Written by Box of Crayons

Box of Crayons helps organizations transform from advice-driven to curiosity-led.

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