We need more retrospectives...
We just finished a major initiative at work. Months of planning. Weeks of execution. Tons of effort from multiple teams.
It’s done. Everyone’s exhausted. And the immediate reaction from leadership?
“Great. What’s next?”
No pause. No reflection. No conversation about what worked or what we’d do differently next time.
Just straight into the next thing.
This happens constantly. We finish projects, close out initiatives, survive busy seasons. And we immediately move on without ever stopping to ask what we actually learned.
I don’t think we take enough opportunities for retrospectives at work. We never go back to look at things that went well. And more importantly, things that didn’t go well.
For HR, these moments can be the most important. They help us gather valuable insights we wouldn’t otherwise get.
Think about the last major project you worked on. A system implementation. An organizational restructure. A company-wide policy rollout. Whatever it was.
When it was over, did anyone sit down and ask what actually happened? Not just “did we hit the deadline,” but what went smoothly and what was a mess? What decisions helped and which ones created unnecessary problems? What would we do completely differently if we had to do it again?
Probably not. Because by the time something’s done, everyone’s ready to move on. The team is tired. Leadership wants to focus forward. And suggesting we spend more time talking about something that’s already finished feels like dwelling on the past.
But here’s what happens when you skip the retrospective. You repeat the same mistakes next time. The things that caused friction in this project will cause friction in the next one. The process that didn’t work will get used again because nobody officially acknowledged it didn’t work.
You also miss what actually created success. Maybe something worked really well and you don’t even realize why. Maybe someone found a workaround that saved the project but leadership never heard about it. Maybe there’s a practice worth replicating but it stays buried because no one took the time to surface it.
I watched a company roll out a new performance management system. It was rocky. Really rocky. Managers were confused. Employees were frustrated. HR spent weeks putting out fires.
When it was finally over, everyone wanted to forget it happened. Leadership declared it a success because it got done. HR was too burned out to push for a debrief. And the team moved immediately to the next project.
Six months later, they rolled out a new compensation structure. Same problems. Same confusion. Same fires for HR to put out.
Because nobody ever stopped to ask what went wrong the first time. Nobody captured the lessons. Nobody documented what should have been done differently.
So they repeated it. And it was just as painful the second time.
Here’s what that costs you beyond just repeating mistakes. Your team stops improving. They’re working hard but not getting better because there’s no mechanism to learn from experience. They’re stuck in a cycle of just getting things done without ever refining how they get done.
Your best people get frustrated. The ones who see the patterns, who notice what’s not working, who have ideas for how to do it better next time. They’re watching the same problems happen over and over while leadership keeps declaring things a success and moving on.
Eventually they stop speaking up. Or they leave for places that actually want to learn.
And you lose institutional knowledge. The person who figured out the workaround leaves. The insight about what almost derailed the project never gets documented. The next time you do something similar, you’re starting from scratch instead of building on what you learned.
So why don’t we do retrospectives?
Time. Everyone’s already behind on the next thing. Taking time to look backward feels like a luxury we can’t afford when there’s so much ahead.
Discomfort. Retrospectives mean acknowledging what didn’t work. And that means someone made a decision that caused problems. Someone dropped the ball. Someone’s process created friction. Nobody wants to be that person in the conversation.
The illusion of forward momentum. Looking ahead feels productive. Looking back feels like dwelling. Leadership especially wants to focus on the future, not rehash what’s already done.
From my perspective, this is short-term thinking disguised as urgency. We think we’re saving time by skipping the retrospective. But we’re actually wasting time by repeating the same problems.
Here’s what I think needs to change. Make retrospectives a non-negotiable part of finishing anything significant.
Not a nice-to-have if there’s time. A required step before you close out the project and move to the next thing.
And don’t make them complicated. You don’t need a formal process or a consultant or a three-hour workshop. You need a conversation. Ninety minutes with the right people in the room asking three questions.
What actually worked? Not what was supposed to work according to the plan. What actually worked in reality. What decisions made things easier? What practices should we keep? What surprised us in a good way?
Get specific. “Communication was good” doesn’t help. “The weekly fifteen-minute check-ins between the project lead and department heads caught problems early” is useful. That’s something you can replicate.
What didn’t work? And be honest about it. What created unnecessary friction? What decision seemed right at the time but turned out to be a problem? What would we absolutely not do again?
This is where the discomfort comes in. But frame it right. You’re not looking for who to blame. You’re looking for what to learn. The goal isn’t to make someone feel bad. It’s to make sure you don’t repeat the mistake.
What would we do differently next time? This is where you turn observation into action. Based on what we learned, what’s the concrete thing we’d change? What’s the process we’d adjust? What’s the decision we’d make earlier or differently?
And then document it. Not in some elaborate report that nobody will read. In a simple summary that lives somewhere accessible. So the next time someone’s planning something similar, they can actually benefit from what you learned.
Picture this. You just finished a difficult hiring process for a critical role. It took longer than expected. There were miscommunications. Some steps felt redundant while others got skipped.
Instead of just being relieved it’s over, you schedule a retrospective with the hiring manager, the recruiter, and HR. You spend an hour walking through what happened.
You realize the job description was too vague, which led to misaligned candidates early on. You discover that the hiring manager would have appreciated more coaching on what to look for in interviews. You identify that the feedback loop was too slow, which extended the timeline.
You document this. And the next time you’re hiring for a similar role, you start with a more specific job description. You build in time for hiring manager prep. You tighten the feedback timeline.
The second search is smoother. Not perfect. But better because you learned from the first one.
That’s the power of a retrospective. It’s not complicated. But it requires someone to actually do it.
Think about the last major thing your team finished. An initiative. A busy season. A difficult project.
Did anyone stop to ask what you learned? Or did you just move immediately to the next thing?
If it’s the second one, you’re probably going to repeat whatever went wrong. And you’re definitely missing whatever went right that’s worth doing again.
You don’t need permission to run a retrospective. You just need to schedule it before everyone forgets what actually happened.
What’s the last thing your team finished that you never debriefed? And what are you still repeating because nobody ever stopped to ask if there was a better way?