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Losing well: How honest reflection turns defeat into a growth

“I have not failed. I’ve just found 10,000 ways that won’t work.” – attributed to Thomas Edison

Let’s be honest: Failure stings and stinks. No matter your role, you’ve probably felt the gut punch of watching a project misfire, losing out on a key client, or realizing efforts missed the mark. When things go sideways, it’s human to want to move on quickly. Many teams bury frustrations and quickly shift their focus, hoping that momentum will heal their wounds. However, pushing past failure without proper reflection seems like a missed opportunity, doesn’t it? When you study teams that adapt and outpace competitors, there’s a noticeable pattern: not fewer failures, but better learning. The best teams aren’t perfect, but they lose exceptionally well.

Let’s take a look at how losing well can fuel lasting progress and smarter innovation and how to transform setbacks into real momentum.

Why we avoid failure and miss the gold

There’s an unspoken pressure to perform flawlessly. Perfection is rewarded and mistakes are typically not celebrated. While striving for excellence isn’t a bad thing, it’s easy for teams to equate imperfection with weakness and to see loss as a threat rather than an asset. But think about this:

Innovation thrives on experimentation
Experimentation guarantees failure along the way
Growth is the result of honest reflection

Avoiding mistakes doesn’t make a team stronger; it quietly erodes resilience. When failures are hidden, teams repeat blind spots and compound small errors into bigger ones. On the flip side, teams that openly reflect on defeats learn faster and recover stronger. Research on psychological safety (Google’s Project Aristotle, 2012–2015) shows that when people feel safe to admit missteps without fear, teams collaborate and outperform peers.

The defeats that teach the most

Not all failures are created equal. Some are careless, driven by lack of process or attention. Others are courageous, rooted in calculated risks or bold experiments. Only the latter have the potential to boost team learning. Celebrate those, and see careless ones as signals for better process.

Lost opportunities

Maybe you spent weeks tailoring a proposal, only to watch the prospect choose a competitor. Rather than shifting blame, dig into the detail:

What signs or signals did you miss?
What did the winning team do better?
What assumptions guided your strategy?

Feature flops

Perhaps you launched a product update with fanfare and high expectation but saw usage plateau or feedback turn sour. Resist the urge to blame the market or end users.

Were you actually solving the right problem?
Did you test enough, and with the right audience?
Were you listening for real user friction, or just echoing internal assumptions?

Team misfires

Maybe communication broke down on a deadline, you missed a key deliverable, or morale slumped. These misfires are often swept aside with generic retrospectives, but there’s so much value in the specific questions:

Where were expectations or roles unclear?
Did feedback dry up at a key moment?
Did anyone flag the issue early, and how did the team react?

Reframing mistakes from shame to strategy

A healthy learning culture meets mistakes with honest inquiry, not finger-pointing. Instead of “Who messed up?”, start with “What do we know now?”. Here’s how resilient teams process loss:

Lead with genuine interest and curiosity

Brené Brown, in Dare to Lead, argues, “Clear is kind. Unclear is unkind.” Openly naming failure removes the shame and creates pathways for learning. Try questions like:

“What do we know now that we didn’t before?”
“What surprised us?”
“Where did we make assumptions?”

This frames loss as valuable and insightful data, not defeat.

Distinguish two types of failure

Avoidable: Slips due to lack of clarity, miscommunication, or skipping process.
Exploratory: Outcomes of smart experiments where risk was expected.

Reward honest reporting of both, but celebrate exploratory failure. True innovation requires teams to risk getting it wrong and report back.

Capture what you learn

Verbal debriefs fade fast. Build a habit of short write ups after every meaningful loss:

What did we try?
What didn’t work?
What signals pointed to the issue?
What will we do differently next time?

This simple practice builds a searchable database of “lessons learned”, turning memory into an asset.

Make space for losing well

Learning from defeat requires deliberate cultural cues. Here’s how to create psychological safety and normalize loss as fuel for growth:

Model learning from the top

When you admit your own misjudgments or openly review a failed project, you give your team permission to do the same.

Try language like:

“This didn’t go as planned. What can we learn from it?”
“The effort matters. The result surprised us, but I’m proud we went for it.”
“This is a data point, not a disaster.”

Make reflection public

Some team insights will be sensitive, but when possible, share mini case studies internally.

What we tried
What didn’t go as planned
What we learned
What we’ll try next time

Public reflection removes stigma and amplifies key lessons.

Recognize learning behaviors

Most organizations reward achievement. Start also rewarding the mindset and actions that drive better outcomes over time:

Spot and recognize when someone calls out risk.
Celebrate quick course corrections after a red flag.
Share wins from teams that pivoted due to lessons learned from prior refusal.

Recognition shifts focus from outcomes alone to continuous improvement.

Turning mistakes into momentum

Turning reflection into forward progress requires more than just good intentions. Here are some quick tips to get started

The 5 Whys

Start with the surface explanation and ask, “Why?” five times.

Example:

Why did we lose the RFP? Because our proposal didn’t clearly address the client’s top priorities.
Why didn’t it address their priorities? Because we misunderstood what mattered most to the selection committee.
Why did we misunderstand? Because we didn’t speak directly with a stakeholder before submitting.
Why didn’t we speak with one? Because we assumed the RFP document provided enough context.
Why did we make that assumption? Because we were focused on meeting the deadline and didn’t want to slow the process with outreach.

You’ll often find the true root is three or four whys deeper.

Hold a (blameless) postmortem

Frame postmortems as system and sequence reviews, not blame sessions.

What happened and in what order?
What were the contributing factors?
Where could the process have caught the problem/error?

Avoid naming and shaming. Focus on gaps in process, communication, or understanding.

Share learning case studies

At the end of a project, write a brief snapshot detailing:

What worked
What didn’t
What you’ll change in future attempts

Give a platform for team members who raised a red flag or pivoted quickly.

Make learning a routine

Consider a Slack channel, Notion board, or short section in team meetings to regularly share “lessons from last week.” Small, honest updates build team memory.

Moving forward

The difference between teams that plateau and those that bounce back higher lies in their willingness to examine what happened, honestly and intentionally.

Effective teams:

Ask better questions about every loss
Make learning public and persistent
Celebrate those who surface insights, not just successes

If you can shift your culture from loss-avoidant to learning-forward, defeats become data, fuel, and even a quiet kind of advantage. Every loss, when analyzed with honesty, is one less blind spot and one more step in the right direction.

Failure is only failure when you refuse to look at it. Otherwise, it’s necessary and invaluable research.

What are your tips for using failure as an opportunity?

The bias for action when certainty is out of reach

In an earlier post, “Re-considering the No,” I reflected on how easily we default to no, especially in moments that require change, risk, or vulnerability. That post was about the internal calculus we make when faced with the unknown, and how saying yes, even if it’s a tentative, nervous yes, can open doors to creativity, connection, and possibility.

But what happens after the yes? If “Re-considering the No” was about cracking the door open, today’s reflection is about what it takes to actually step through it. That next step requires cultivating something I’ve been hearing more and more in recent conversations: a bias for action.

The hidden cost of overthinking

In my experience, we tend to reward intellectual rigor. We value planning, stakeholder input, and alignment, and rightfully so. But sometimes, those very strengths can often morph into stagnation. We get caught in analysis loops and hypothetical what-ifs. We seek consensus when what’s needed is the courage to make a move. We become so focused on getting it “right” that we end up not doing anything at all.

A bias for action counters that by asking: What if starting imperfectly is actually the most strategic move I can make?

And here’s the truth most of us know deep down: clarity tends to come from action, not the other way around. The project plan doesn’t reveal the sticking points but the first iteration does. The meeting doesn’t uncover misalignment, but the actual collaboration does.

Motion as a catalyst for learning

I may be stating the obvious: A bias for action doesn’t mean acting without thinking. It just means that we’re using motion as a mechanism for discovery. This can happen in many different ways. For example, you might spin up a prototype for something that’s not on the roadmap yet, ship an early version of a new feature and let usage data influence the next iteration, or put yourself on the hook for a webinar before you’ve done all the research needed.

Do these actions carry risk? Of course. But they can also be the most effective way to uncover the next step.

As Amelia Earhart once said, “The most difficult thing is the decision to act. The rest is merely tenacity.”

This simple truth reminds us that the first move, however small, is often the hardest. But once momentum is on your side, everything changes.

Leading through action

As a leader, modeling a bias for action is one of the most powerful ways to build agility and resilience within your team. When your team sees you moving forward, and making adjustments when needed, they feel permission to do the same.

I’ve watched more than once how action can spawn energy. One draft inspires another, one customer outreach reveals a new opportunity, one slightly awkward team experiment can be the origin of a new practice or services offering. These moments don’t happen because the idea was perfect but because someone had the courage to move.

Leadership often requires creating conditions in which movement and action is encouraged and even expected, even if you don’t always have all of the answers.

As a Cy Wakeman fan, I like to remind myself of this quote: “Stop arguing with reality, and start leading what’s next.” It reframes change from something to fear into something to harness.

Reconnecting to “Re-considering the No”

In “Re-considering the No,” I wrote about how saying no too soon can rob us of growth. But now I’ll add this: Saying yes and then not acting is just a slower version of the same problem.

We tell ourselves we’re on board, give a thumbs up in Slack, nod in meetings, or add to an idea. But if those ideas never get acted on, if the yes never becomes movement, then we’ve only postponed the no. A yes without action is like planting a seed and never watering it. A bias for action is what turns that yes into progress.

Don’t get me wrong. I need to listen to my own advice more frequently and ask myself “Is there something I’ve said yes to but haven’t moved on?” or “What’s a small step I can take immediately to build momentum?”.

When in doubt, move

Action is not about busyness or bravado, but about building momentum, no matter how big or small. It’s about trusting that movement and direction will teach you more than inaction or delay. So next time you find yourself nodding at a new idea, agreeing with a bold suggestion, or sensing that yes rising in your throat, commit to taking the next step, and then take it.

What about you? How do you practice bias for action?

Developing resilience in the face of adversity

Adaptability to ever-changing circumstances and the ability to recover quickly from adversity are two characteristics that define resilience, which happens to be one of the most transferable and desirable skills you can foster. As a leader, helping your team members develop resilience doesn’t just increase your chances of success, it can also play an impactful part in their personal and professional development. But of course, we have to start with ourselves and continue to train our resilience muscle, because there’ll always be adversity and unexpected challenges that we need to be able to handle in a much more productive way. Here are some ideas:

Focus on your locus of control

When faced with adversity, our knee-jerk reaction might be to freeze, vent, or capitulate, even though we know perfectly well that none of these behaviors are going to improve the situation. Cy Wakeman, in her reality-based leadership lessons and her No Ego podcast, frequently reminds us “Don’t outsource your happiness and well-being to external circumstances”. It’s a great framework on which to build resilience. Start with separating what happened from you as a human being, as difficult as it may be. Next, try not to go down a rabbit hole of speculating about other people’s intentions (“They only did this to me because they don’t respect me”). Then, focus on what’s in your control. What can you do to work within the parameters of the changed reality? What can you do to take on this challenge and mold it into new opportunities for yourself or your team?

Keep a log of lessons learned

One of the positives of adversity is that it might teach you valuable lessons. As Winston Churchill once stated, “Never let a good crisis go to waste”. How about keeping a log of your lessons learned from situations big and small? What has the adverse situation taught you about your industry, your company, your profession, and about yourself? Were there signs that you ignored? Was the situation avoidable? If so, what are you going to do differently? If not, what are the best strategies for embracing the change? Are your team members struggling with the adverse situation? How can you help them? Whose behavior is worth emulating?

Build a supportive network

Depending on the nature and severity of the adversity you’re facing, you need to pick the size and make-up of your support network. Be sure to surround yourself with people who can lift you up and help you figure out a game plan. Consider keeping a safe distance from anyone who seems to offer a sympathetic ear, but actually stokes negativity. Your network may consist of colleagues, peers in your professional circle, your family, friends, mentors, or even experts in the area in which your adversity occurred. Just don’t isolate yourself.

Practice gratitude

Adversity might cause you to hit the snooze button in the morning and/or to say out loud that you’re “just not feeling it”. We’ve all been there, and we all know that this approach rarely works. How about making yourself start your day by thinking about (and writing down) something that you’re looking forward to and that you’re thankful for? Maybe schedule something that you’d be looking forward to, whether it’s a massage, date night, or a hike. Keeping a gratitude journal and a lessons learned journal can also get you out of a slump when you read it back to yourself.

Train yourself in adaptability

As creatures of habit, change is hard, even if it’s a positive one. Facing adversity, it’s even more challenging. As we’re building up our ability to adapt quickly, even little experiments in breaking our attachment to routines can be useful, such as taking a different route to work or parking in a different spot. In fact, attachment to tangible and intangible things and our vision of the future often impairs our ability to be as resilient as we could be.

There’s no such thing as being “too resilient”. It’s a quality and a skill that can greatly reduce suffering, make you more successful, and even enable you to help others be more resilient in the face of adversity.

What about you? What are your thoughts on developing resilience?