Don't Waste a Good Failure

Last week, we talked about giving people decision-making authority.

We talked about moving decisions closer to the people with the information, expertise, and context to make them well. We talked about trusting people to use their judgment, even when they might choose a different path than we would.

But there is something we have to acknowledge if we are actually going to do that:

Sometimes they're going to get it wrong.

So are you.

So am I.

That is the deal.

You cannot build a team of confident decisionmakers while simultaneously expecting everyone to make the right decision 100 percent of the time.

If we want people to take ownership, exercise judgment, solve problems, and try new things, we also have to create an environment where learning is valued more than perfection.

That means we need to get a whole lot more comfortable with failure.

Failure Is One Heck of a Teacher

I have made some mistakes in my life that I can pretty confidently tell you I will never make again.

When I was in high school, I once washed a load of clothes with bleach instead of laundry detergent. (Don't ask me how the smell didn't tip me off.)

Needless to say, that did not end particularly well for my clothes. But you know what? I learned. To this day, I double-check what I am pouring into the washing machine.

Fast forward to adulthood, and the stakes of my mistakes got a little higher.

At one point, I decided to switch service providers. I found a new provider, worked through the details, and signed a new contract.

There was just one small problem... I hadn't thoroughly read the fine print on my existing contract.

Whoops.

Suddenly, I had committed myself to a new agreement while still being contractually obligated to the old one.

Was that fun?

Absolutely not.

Did I learn from it?

Ohhhhh yes. You better believe I read the fine print now.

And that is the funny thing about failure. Someone could have told teenage me a hundred times to double-check the bottle before pouring something into the washing machine. Someone could have reminded adult me to carefully review every detail of a contract before signing another one.

But experiencing the consequences myself? Those lessons stuck.

Failure has a way of making learning incredibly memorable.

And while I certainly don't recommend bleaching your wardrobe or accidentally signing overlapping contracts as a professional development strategy, I do think there is an important leadership lesson in both: Sometimes experience teaches us something that instruction alone simply cannot.

Failure Is Only Valuable If We Learn From It

I want to make an important distinction here. Creating a learning culture does not mean we start high-fiving every time someone screws something up.

There are mistakes that have serious consequences. There are situations involving safety, ethics, finances, legal requirements, or people's well-being where leaders absolutely need appropriate safeguards.

And repeated mistakes without reflection or behavioral change are not learning.

Failure alone does not create growth, but reflection after failure does!

The goal is not to celebrate the failure itself. The goal is to make sure we extract the lesson from it. If something goes wrong and we immediately move on, blame someone, hide it, or simply fix the problem without examining why it happened, we have paid the price of the mistake without receiving any of the value.

Don't waste a good failure.

Always ask what it came to teach you.

Your Reaction Teaches the Team What Happens Next

Think about what happens when someone walks into your office and says:

“I messed up.”

That moment matters... A lot. Because your first reaction teaches them what to do the next time something goes wrong. If your immediate response is anger, blame, embarrassment, or interrogation, what have they learned?

...Probably not the lesson you intended.

They may learn instead:

Hide mistakes.

Fix problems before the boss finds out.

Don't take risks.

Don't try something new.

Wait for approval so someone else owns the decision.

And suddenly we are right back where we started last week (Week 34: Clarify Decision Rights)

We gave people decision-making authority, but taught them that using it is dangerous.

Instead, imagine responding with: “Okay. Walk me through what happened.”

That does not mean there will never be accountability. It means curiosity comes before judgment. You are trying to understand before you react.

What information did they have?

What assumption did they make?

What didn't they know?

What did the system contribute?

What would they do differently next time?

Those questions turn an uncomfortable moment into a learning opportunity.

Move From “Who?” to “What?”

When something goes wrong, some organizations rush toward: Who did this?

There are certainly situations where individual accountability matters, but if our goal is organizational learning then we need to ask more questions than that.

What happened?

What conditions allowed this to happen?

What did we assume that turned out to be wrong?

What information were we missing?

What should we change because of what we now know?

That last question is especially important because learning should change something.

Maybe you update a process.

Maybe you communicate differently.

Maybe you add a checkpoint.

Maybe you stop doing something altogether.

Maybe the only change is that someone now has experience they did not have before.

If we keep experiencing the same failure without changing anything, we are not learning. We are just repeating.

Learning Requires Psychological Safety

This is where so much of the work we did earlier in this challenge comes back around.

Remember psychological safety (week 14)? This is exactly why it matters!

People need to believe they can say:

“I don't know.”

“I made a mistake.”

“I need help.”

“I tried something and it didn't work.”

“I disagree.”

“I think our current approach is wrong.”

Those statements contain incredibly valuable information, but you will never hear them if people believe honesty will be punished. A learning culture requires enough trust for people to expose what they do not know.

That requires leaders to model it, too.

Say:

“I don't know.”

“I got that wrong.”

“I changed my mind.”

“That didn't work the way I expected.”

“Here's what I learned.”

Leaders do not undermine credibility by acknowledging that they are still learning. They demonstrate that learning is something everyone does.

Learning Isn't Only About Failure

We should also be careful not to associate learning exclusively with mistakes. Some of our best learning comes from success.

A project goes exceptionally well.

Great!

Don't just celebrate it and immediately move on.

Ask:

Why did that work?

What did we do differently?

What conditions contributed to the outcome?

What should we repeat?

What could another team learn from this?

Organizations are often much better at conducting postmortems when something goes wrong than examining why something went right.

Both contain valuable information.

Learning cultures are curious about results, not just problems.

Create Learning Loops

If you want to encourage learning, build reflection into the way your team works rather than hoping people find time for it. It does not need to be complicated.

After a project, initiative, event, or significant decision, spend ten minutes asking:

What worked?

What didn't?

What surprised us?

What did we learn?

What will we do differently next time?

That's a learning loop.

Experience > Reflection > Lesson > Adjustment > Try Again.

Without reflection, teams can have years of experience without necessarily becoming much better.

The goal is not simply to accumulate experiences. The goal is to convert experience into wisdom.

Make Learning Part of the Work

Leaderss might initially think of learning as something separate from work: Training. Conferences. Books. Webinars.

Those things absolutely have value, and next week we are going to talk much more about intentionally investing in people's development.

But learning also happens inside the work itself.

Every project contains information.

Every customer interaction teaches us something.

Every decision creates an outcome we can examine.

Every mistake exposes an assumption.

Every success reveals something worth repeating.

Exceptional leaders build teams that notice those lessons.

Here are a few ways to create that kind of culture:

• Ask “What did we learn?” as routinely as “Did we finish?”

• Debrief projects, including successful ones.

• Share lessons across the team so one person's experience becomes everyone's knowledge.

• Talk openly about your own mistakes and what they have taught you.

• Give people opportunities to experiment where the risk is appropriate.

• Change systems and processes when learning reveals something isn't working.

• Celebrate improvement, not just perfect outcomes.

  
  

None of this requires a massive organizational learning program. It really only requires intention and curiosity.

Be Careful What You Reward

Culture is shaped by what leaders pay attention to.

If you only recognize flawless execution, people will work hard to appear flawless.

If you reward certainty, people will become reluctant to admit they don't know something.

If every failed attempt is treated as poor performance, people will naturally choose safer options.

...But if you recognize thoughtful experimentation, honest reflection, improvement, knowledge sharing, and the courage to raise a concern? People learn that those things matter!

One of the best questions an exceptional leader can ask themselves is:

“What behavior am I unintentionally teaching people to avoid?”

If you say you want innovation, but punish unsuccessful experiments, you do not have an innovation culture. If you say you value transparency, but react badly when someone brings you bad news, you do not have a transparent culture. And if you say you want people to learn, but don't give your time to teach them something, you do not have a learning culture.

Failure Should Produce Something

Here is perhaps the simplest way I think about all of this: A mistake should buy you something.

If you are going to pay the price of getting something wrong, get the lesson.

Get the improved process.

Get the new knowledge.

Get the better question.

Get the changed behavior.

Get something.

My bleach incident bought me the habit of checking what I'm pouring into the washing machine. My service-provider mistake bought me a lifelong habit of reading the fine print.

Some lessons are obviously much more consequential than others, but the principle is the same.

We are going to get things wrong. Our employees are going to get things wrong. Our organizations are going to try things that do not work.

The question is not whether failure will happen, but rather, "What will we do with it when it does?"

Build a Team That Gets Smarter

Over the past several weeks, we have been intentionally moving leadership away from the center of everything.

We gave people ownership.

We clarified priorities.

We protected those priorities.

We reduced unnecessary urgency.

We clarified who has the authority to make decisions.

Now we have to give people room to learn from those decisions. The goal is not to build a team that never gets anything wrong.

...That team does not exist.

The goal is to build a team that gets smarter every time something does: A team that reflects.

A team that shares what it learns.

A team that adjusts.

A team that is willing to say, “That didn't work. Here's what we're going to do differently.”

And a team that knows their leader will hold them accountable without expecting them to be perfect.

That is what a culture of learning looks like.

Next week, we will take that one step further. Once you create an environment where learning is safe and expected, exceptional leaders begin asking a more personal question:

How can I intentionally help each person on my team grow?