To plan or not to plan? In early-stage startups, the answer is often no. Things move fast, priorities shift constantly, and formal planning can feel like a waste of time. But as the company grows, planning starts to take shape. First, it’s a rough sketch to give people direction. Then it becomes more structured, with goals, estimates, and coordination across teams. Eventually, planning becomes a central part of how the company operates.

That’s when the question shifts. Planning is no longer something you do on the side – it’s a big deal. So you start asking: how do we make our planning process better? Did we plan well? Did we follow through?

And so, like with any important process, you run a retrospective.

But here’s where many teams get stuck. A good retro is only as useful as the question it tries to answer. And when it comes to planning, the default question – did we stick to the plan? – can easily lead you in the wrong direction.

Sticking to the plan isn’t necessarily a sign of success. Sometimes it means you stayed focused and executed well. But other times, it means you ignored new information, missed better opportunities, or spent too long on work that no longer mattered. The goal of planning is to help you make smart choices, not to trap you into following them blindly.

This article is a practical guide to running better retrospectives. 

We’re using planning as the example, but the principles apply to any retro: launches, processes, team dynamics, or business outcomes, to name a few. 

So when you look back on your quarter, don’t just ask what got done.

Ask whether your planning actually supported the outcomes you wanted. That starts by asking the right questions, but it doesn’t end there. 

Let’s take a closer look.

Frame the Question

When most people think about a retrospective, they immediately run into what worked well and what didn’t. It’s actually more of the latter, but we’ll get to that later on.

But asking what went well or poorly only makes sense if you know what you were trying to achieve. The framing question sets the direction for the entire discussion. Get it wrong, and you might improve dramatically – but in the wrong direction.

Take planning, for example. If your goal was to help the team stay focused and make a business impact, then the right retro question might be: Did our planning process support good decision-making along the way? But if you instead ask if we stuck to the plan, you’re judging yourself on discipline rather than effectiveness. You might conclude that you need to plan harder into the details when, in fact, you should be planning more strategically.

This isn’t just a planning problem. It’s true for any kind of retro: for launches, ongoing business results, processes, team rituals, even communication. Whatever you’re looking back on, take the time to define the purpose first. What were you trying to achieve? What did success look like? That’s your lens.

Bottom Line Results

Once you’ve defined the right question, start with a clear, honest look at the results. No explanations, no justifications – just the facts.

Did you achieve what you set out to achieve?

But make sure you’re looking at the right facts. This ties back to how you framed the question. If you’re retroing your planning process and the goal was to enable better decisions along the way, then a list of what got delivered isn’t the point. It might be relevant, but usually not as a first-order topic.

You’re not judging effort or output. You’re checking whether the outcomes matched the goal you were actually aiming for.

This step might feel uncomfortable, especially if things didn’t go as planned. But avoiding the truth doesn’t make it less true – it just makes it harder to improve. The goal here isn’t to make anyone feel bad. It’s to see clearly.

Highlight the Good

Many teams skip this part. If something went well, the thinking goes, why bother analyzing it? There’s also a natural tendency to focus on what went wrong – that’s where the pain is, and that’s what we want to fix.

But it’s just as important to stop and highlight what worked. Not to make you feel good or brag, but to make it conscious and help it stick.

If success was a happy accident, chances are you won’t repeat it. If it came from the way you work, but you’re not aware of it, others can’t learn from you. And even you might not realize what to preserve next time.

Bringing the good into the light gives you something to hold onto. You can double down on it. Refine it. Teach it. Improve it. But it all starts with knowing what it is.

Admit the Bad

This is the part most retros tend to focus on – what went wrong. But even though it’s common, it’s not always done well.

If you want this part to be useful, don’t make it about blame. Talk about yourself. What didn’t work in how you operated? Where did you miss the mark? This doesn’t mean others don’t have their own share, but the most powerful thing you can do is take responsibility for your part.

When everyone on the team takes that same approach, something amazing happens. You shift from defensiveness to growth. Everyone learns faster. Everyone levels up.

And here’s the real secret: owning your misses gives you power. If it’s yours, it’s also yours to change.

Be as honest with yourself as you can. Not to beat yourself up, but to get better. You may become the person who makes it safe for others to do the same. And no matter what happens next quarter – or with the next team you lead – that’s growth you’ll carry with you.

It’s About You

This is where the real learning happens.

It’s not enough to say what went well or what didn’t. You need to ask yourself: what allowed things to go well? And what contributed to the misses? Without that, you’re just reporting the news, not understanding what created it.

Let’s say you hit your goals this quarter. That’s great, but why? What did you do that made the difference? Maybe you had unusually clear goals. Maybe you tracked progress closely and adjusted along the way. Maybe your team showed up with urgency and supported each other through tough moments.

Those are the real levers – and if you can name them, you can repeat them.

The same goes for what didn’t work. Don’t stop at saying something failed. Ask yourself what led to it. Was it unclear ownership? A lack of regular check-ins? Avoiding a hard decision for too long? These are the patterns you can take responsibility for and improve.

When you do this well, you walk away not just with a story about the quarter but with insight about yourself. About how you lead, how you operate, and what kind of environment you help create.

That’s the kind of learning that pays off, quarter after quarter, team after team.

Pick One of Each Kind

Talking about what worked and what didn’t is important, but on its own, it doesn’t change anything. Implementation is what matters. And for that, you need focus.

Retrospectives often surface a long list of insights and ideas for improvement. That’s great. But if you try to act on all of them, you’ll end up acting on none of them. Change requires attention, and attention is limited.

So pick just one. One thing to preserve. One thing to do differently. Not more than that.

You don’t need to worry that all the other insights will disappear. Just talking about them raises awareness. Your team is more likely to notice those patterns next time they show up. But if you want real, lasting improvement – the kind that compounds – you need to choose your one next step and commit to it.

Think about what happens if you take one meaningful step every quarter. Or even every month. Over time, that’s the difference between a team that talks about learning and a team that actually evolves.That kind of progress is not slower. It’s just deliberate, consistent, and incredibly powerful.