You Either Win or Learn (Here's How to Do Both)

At some point this year, something didn't go the way you planned.

A client didn't come back. Deal fell through. Or project went sideways.

A hire didn't work out. Or a launch flopped.

You probably noticed. You may have been frustrated. You might have vented about it. And then you moved on to the next thing.

Here's what you probably didn't do: sit down and actually figure out what happened.

Most business owners skip this step.

And I get why. Looking at what went wrong feels like dwelling on failure. It's uncomfortable. It feels negative. It's easier to just keep moving forward and focus on the next opportunity.

But here's what you're missing:

The things that didn't work are carrying information your marketing budget can't buy. They tell you where your process broke. Where expectations were misaligned. What type of client or project you should probably stop taking. What you need to change before it happens again.

If you're willing to look at them.

The Framework the Military Uses

The military has a framework for this. It's called an After-Action Review, or AAR.

After any mission, project, or engagement, successful or not, they sit down and answer four questions:

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What was supposed to happen?
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What actually happened?
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Why was there a difference?
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What are we going to do differently next time?

That's it.

No blame. No excuses. No covering your ass. Just honest assessment.

What was the plan? What was the outcome? Why was there a gap? What changes?

If it's good enough for people making life-or-death decisions, it's good enough for your business.

Why You Either Win or You Learn

There's a phrase I love: You either win or you learn.

If something went well, great. You won. Now figure out why so you can do it again.

If something didn't go well, you didn't fail. You learned. Now figure out what you learned so you don't make the same mistake twice.

The only real failure is not learning from it.

But most business owners treat losses like something to forget as quickly as possible.

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A client doesn't come back? Move on to the next lead.
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A project goes over budget? Just work harder next time.
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A hire doesn't work out? Try again with someone else.

They never stop and ask: Why did that happen? And what am I going to change so it doesn't happen again?

That's the difference between repeating the same mistakes over and over and actually getting better.

How to Run an After-Action Review

You can run an AAR on anything. A lost client. A failed project. A hire that didn't work out. A launch that didn't hit its numbers. A deal that fell through.

Here's how:

1. What was supposed to happen?

What was the plan? What did you expect? What was the desired outcome? Be specific. Not "we thought it would go well." What exactly were you trying to accomplish?

If it was a client engagement: What was the scope? What were the deliverables? What was the timeline? What was the expected outcome for them and for you?

If it was a hire: What role were they filling? What problems were they supposed to solve? What did success look like in the first 90 days?

If it was a deal: What was the expected close date? What was the pricing? What was the scope of work?

Write it down. The plan. The expectation. The goal.

2. What actually happened?

What was the actual outcome? Where did it go off track? When did you first notice something wasn't right?

No spin. No justification. Just the facts.

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The client didn't renew.
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The project went 30% over budget and took twice as long as planned.
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The hire lasted six weeks before you realized it wasn't working.
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The deal fell apart in the final proposal stage.

What actually happened? When did it start to go wrong?

3. Why was there a difference?

This is where the learning happens.

What caused the gap between what was supposed to happen and what actually happened?

Was it a bad process? A misaligned expectation? A gap in communication? A wrong assumption you made going in? A skill you didn't have? A client or person that wasn't the right fit?

Look for the root cause. Not the surface symptom.

Surface symptom: The client didn't renew. Root cause: We never had a conversation about what ongoing work could look like. The engagement ended and we just assumed they'd reach out if they needed us again.

Surface symptom: The project went over budget. Root cause: We didn't define scope clearly enough upfront, so the client kept adding things and we kept saying yes.

Surface symptom: The hire didn't work out. Root cause: We hired for skills but didn't assess for culture fit or communication style. Dig one level deeper than the obvious answer.

4. What are we going to do differently next time?

Based on what you just learned, what changes?

Be specific. "Communicate better" isn't a change. "Add a midpoint check-in call to every project to surface issues before they become problems" is a change.

"Hire better people" isn't a change. "Add a working interview to the hiring process where candidates do real work before we make an offer" is a change.

"Set clearer expectations" isn't a change. "Add a scope definition document that both parties sign before work begins, and require a change order for anything outside that scope" is a change.

Make it concrete. What's the actual change you're making to your process, your system, or your approach?

What I Found When I Did This

About three years ago, I ran an AAR on every client I'd lost in an 18-month stretch. Four clients. Different industries. Different budgets. Different personalities.

But when I looked at how those relationships started, the structure was almost identical. What was supposed to happen: We'd been brought in to fix a specific problem. Fix the problem, deliver the result, relationship continues.

What actually happened: We fixed the problem. We delivered the result. And then the relationship just drifted. No next project. No ongoing retainer. They went quiet. We moved on.

Why was there a difference: We had no process for what happened after the project ended. No offboarding conversation. No discussion about what ongoing work could look like. We just assumed that if they needed us again, they'd reach out.

What we changed: Added a clear offboarding process to every project. Two weeks before the end of any engagement, we have a conversation about what's next. Not a sales pitch. A strategic conversation. What are they working on next? What challenges are coming up? Does it make sense for us to continue working together?

Since I made that change, I haven't lost a client that way.

That one AAR was worth thousands of dollars in recurring revenue. And I only found it because I was willing to look at what went wrong instead of just moving on to the next thing.

Run AARs on Your Wins Too

Here's the thing most people miss: You should run AARs on your wins, not just your losses.

When something goes really well, when a client is thrilled, when a project comes in under budget and ahead of schedule, when a hire exceeds expectations, stop and ask:

What did we do differently that time? And how do we do it again?

Because if you don't capture what worked, you can't repeat it.

You'll just chalk it up to luck. Or assume you're doing it all the time when you're actually not.

Run an AAR on your best client engagement this year.

What was supposed to happen? What actually happened? (even better than planned) Why was there a difference? (what did you do that made it work so well?) What are we going to do to make that the standard? (how do you build that into every engagement?)

That's how you get better. Not by accident. By design.

Why Most People Skip This

Here's why most business owners don't do AARs. It feels like you're focusing on the negative.

But you're not. You're extracting the lesson so you don't repeat the mistake.

And if you run AARs on wins too, you're also capturing what's working so you can do more of it.

The only way to get stuck is to keep making the same mistakes without learning from them.

The only way to stay average is to have wins and not understand why they happened. AARs fix both.

Make It a Habit

Here's the assignment: Run an AAR on one thing from this year that didn't go the way you wanted.

Work through the four questions:

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What was supposed to happen?
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What actually happened?
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Why was there a difference?
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What are we going to do differently next time?

Write it down. Don't just think about it. Write it.

Then make one change based on what you learned.

And if you really want to level up, run an AAR on something that went really well.

Figure out what you did right. And do it again.

You either win or you learn.

Both are valuable.

But only if you actually stop and figure out which one happened.