personal-development

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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?

Why Leah Williamson Is the Leader Every Team Deserves

I’ve been a massive soccer fan all my life, and have always wanted to do a leadership spotlight in the world of soccer. Leah Williamson was an easy choice, as there are many lessons to be learned from her leadership approach, even for seasoned leaders, and certainly for me.

Leadership isn’t always about being the loudest voice in the room. Sometimes, it’s about thoughtful action, quiet confidence, and a deep sense of purpose. Leah Williamson, captain of the England women’s national team and a cornerstone for Arsenal, where she’s played since she was a kid, shows what modern leadership truly looks like. Her influence extends far beyond the football pitch, offering a powerful lesson in leading with intelligence, empathy, and authenticity.

Leads through intelligence, not impulse

Williamson’s leadership begins with the way she plays. As a defender, her greatest strength is her ability to read the game. She anticipates attacking moves before they happen, positioning herself and organizing her teammates to neutralize threats with calm efficiency. You won’t often see her making desperate, last-ditch tackles because her football intelligence means she’s usually already a step ahead. Although you can count on her to be your last line of defense any time.

This composure under pressure is a hallmark of her captaincy. She leads with a steady hand, providing a sense of control and stability that resonates throughout the team. Yet, when the moment requires decisive action, she has the courage and skill to step in. This blend of calm anticipation and assertive action defines her on-field presence.

Elevates everyone around her

A great leader makes others shine brighter. Williamson consistently elevates her teammates through clear communication, constant encouragement, and leading by example. Players often speak of the confidence she instills in them, creating a secure and organized backline where everyone feels empowered to perform at their best.

This supportive leadership was instrumental during England’s historic Euro 2022 victory. Thrust into the captaincy just months before the tournament, she fostered a resilient and united squad. Her focus was never on her own performance but on building a collective strength that could withstand the pressure of a major final. This year, Williamson made history again by leading England to their second consecutive Euros win, a first for the team and a testament to her exceptional ability to inspire and unite those around her.

Champions the team over self

Humility is a rare but powerful leadership trait. After lifting the Euro 2022 trophy, Williamson immediately shifted the focus to her teammates, the coaching staff, and the fans. Her words highlighted the shared effort and belief that brought the team to victory. For her, the captain’s armband is not a symbol of status but a responsibility to serve the group. This team-first mentality builds trust and creates a culture where every member feels valued.

Uses her platform for good

Off the pitch, Leah Williamson is a dedicated advocate for causes she believes in. She uses her influential platform to speak out on gender equality in sport, mental health awareness, and the importance of inclusivity. She approaches these complex conversations with the same thoughtfulness and conviction she brings to the game.

She speaks not as a celebrity seeking attention, but as a person committed to making a positive impact. Her willingness to be vulnerable and authentic makes her advocacy powerful and relatable, inspiring a new generation of athletes and fans to stand up for what is right.

Proves introverts can lead powerfully

Leah Williamson is living proof that you don’t need to be extroverted to be an outstanding leader. She is often described as quiet and thoughtful (“I’m not very social,” she once said about herself), preferring to listen and observe before stepping in. Yet, this reflective approach allows her to connect deeply with her teammates and understand what the group needs.

Leah recognizes the importance of genuine connection, even in the smallest moments. For example, she started drinking tea simply to spend more time with her teammates, using those shared breaks to build trust and camaraderie. Her willingness to step outside her comfort zone for the good of the group shows true adaptability and emotional intelligence. Through these everyday acts, Leah demonstrates that leadership is about creating bonds and making others feel seen. Sometimes, a cup of tea and a listening ear can be just as powerful as a rousing speech.

She is also known for being exceptionally well spoken and well mannered, traits that shine through in press conferences. Leah consistently greets each reporter who asks her a question and always thanks them after she responds. These small gestures reflect her respect for others and highlight yet another way she leads through kindness, humility, and professionalism.

What makes Leah even more relatable and authentic as a leader is her willingness to laugh at herself and openly admit her own quirks and weaknesses. She’s not afraid to share that she’s actually terrible at riding a bike or that she only eats plain foods, lighthearted confessions that endear her to fans and teammates alike. By being open about these little things, she breaks down barriers and shows that you don’t have to be flawless or larger-than-life to be respected. This self-deprecating humor and honesty make her approachable and reinforce the trust she builds within her teams.

Understands the value of balance

While Leah gives absolutely everything on the pitch, as evidenced by the many injuries she’s battled throughout her career, she also recognizes the importance of being well-rounded beyond football. Off the field, she’s found meaningful ways to recharge and grow. Leah is an accomplished children’s book author, sharing stories that inspire young readers. During the COVID lockdowns, she took on an entirely new challenge: learning to play the piano. Her dedication paid off in a truly remarkable way, leading to a performance with the BBC Concert Orchestra. These pursuits show that, even for someone at the height of their sport, cultivating interests outside of football is vital. Leah’s commitment to growth, both as an athlete and as a person, sets a powerful example for anyone striving to be their best self.

Redefines modern leadership

Leah Williamson represents a new model of leadership, one that values empathy over ego and intelligence over intimidation. She proves that quiet confidence, thoughtful action, and a genuine connection with others are incredibly powerful tools. Her style is a masterclass in leading with heart and purpose, demonstrating that true strength lies in authenticity.

Her influence reminds us that leadership is not about command, but about inspiration. By leading with her values, Williamson doesn’t just guide her team to victory. She shows us all a better way to lead.

What about you? Which athlete’s leadership style do you admire and learn from?

Speaking up: How to share feedback with leadership thoughtfully and effectively

For most of us, giving feedback “up the chain” can feel intimidating. Whether it’s your team lead, your VP, or the CEO, it’s easy to second-guess yourself: “Is this worth bringing up?”,“What if I sound like I’m complaining?”, “Will this actually change anything?”

I venture to say that most leaders want and appreciate your feedback not because it’s always easy to hear, but because they know they can’t fix what they don’t know. And when delivered thoughtfully and with care, your feedback becomes a powerful tool for driving improvement and creating a better workplace for everyone.

Here are some tips from personal experience to help you speak up effectively and constructively.

Start with the intent, not the gripe

Get clear on your reason why you’re giving constructive feedback. Are you trying to improve a process? Make communication clearer? Prevent customer churn? Framing your feedback as a desire to make things better, rather than just airing frustration or venting, makes it far more actionable and easier to receive.

Instead of “These meetings are a waste of time”, try: “Maybe we could tighten up the agenda and finish with clear next steps, so our meetings feel more productive and energizing.”

Perhaps instead of “People don’t pull their weight on projects,” you could say: “I think we could be even more effective if we set clearer expectations and ownership for each project phase upfront.”

Or instead of “Why are you letting this person get away with…”, consider “I’m concerned that when expectations aren’t consistently reinforced, it can create confusion or frustration for the rest of the team. Can we talk about how we want to handle situations like this?”

Be as specific as possible

Vague feedback like “we need better communication” leaves leaders guessing. It’s best to give real-world examples and describe the impact. Specifics make it easier to understand the issue and start solving it.

Here’s an example: “During the last launch, a lot of us didn’t know about the changes until clients started asking questions. A heads-up would have helped us feel more prepared and confident.”

Offer a suggestion for finding a path forward

Personally, I don’t like the phrase “Don’t come to me with problems, come with solutions.” You need to be able to voice a concern without having a perfect solution figured out. That said, even a basic suggestion shows that you’ve thought about the issue in good faith, and it invites a collaborative response.

Example: “Could we do a five-minute rundown of key initiatives during team meetings so we stay aligned?”

Even something as simple as, “Would you be open to brainstorming solutions together?” keeps the door open.

Speak for yourself, not for a group

When giving feedback, it’s often tempting to strengthen your position by saying something like,
“Everyone feels this way” or “A lot of people are frustrated.” Sure, it probably feels safer, because it implies that you’re not the only one with a particular concern, and you may think that it will make your point more compelling. But it can also backfire. Saying ‘everyone’ can make leaders feel attacked and put them on the defensive, which can shut down the conversation before it even starts. Consider owning your perspective with confidence, and use language like “I’ve noticed’, “From my experience”, or “Something I’ve been concerned about lately”.

This approach helps keep the conversation grounded in your firsthand experience and invites dialog rather than a dynamic of defending against “everyone”. It also tends to feel more genuine and can even encourage others who feel the same to add their voices without pressure.

A quick example would be going from “everyone thinks this new process is a disaster” to “I’ve found this new process a bit challenging because…I’d love to brainstorm some ideas to make it smoother”. Big difference!

Pick the right time and channel

Context matters. Some feedback is best shared face-to-face, while other points can be captured clearly in writing. Don’t bury important feedback in a quick chat message that could get lost, especially when leaders are often juggling hundreds of messages and carving out heads-down time for high-priority work.

If the feedback is significant, ask for time directly and be clear about your intent, like “There’s something I’d love to talk through with you. Do you have a few minutes this week?”

For less urgent feedback, asynchronous options like Slack, internal surveys, or feedback forms can work well, as long as you make sure the message is easy to spot and digest.

Assume positive intent

Not every decision will go your way. No leader will get it right 100% of the time . And sometimes, they simply can’t share all of the information with you. My recommendation is to focus on what you know for sure, and try not to speculate.

Starting from a place of curiosity rather than confrontation helps keep the conversation productive and collaborative.

Thoughtful feedback creates clarity, uncovers blind spots, and helps foster better and more effective working relationships. If you care about your company and your team, speaking up with respect and purpose is one of the most valuable things you can do, because it helps everyone.

Giving feedback to leadership doesn’t have to be intimidating. When you focus on intent, specificity, and collaboration, you turn feedback into a tool for growth for yourself, your leaders, and your organization.

What about you? What are your tips on how to give feedback to leadership?

Start with intention: Why planning your day out loud actually works

There’s a moment every morning that quietly determines how the rest of your day will go. It’s not when you open your inbox. It’s not your first meeting. It’s that moment, before the noise sets in, when you decide what kind of day you’re going to have. That’s why I’m a firm believer in starting the day with a realistic, intentional plan and in posting that plan right when your day begins, not hours into it. This isn’t about reporting in or logging hours. It’s about leading your own day with clarity, honesty, and purpose.

This post is about the power of being proactive and about starting on purpose rather than drifting into reaction mode.

Daily stand-ups still hold up

Years ago, I wrote a post called From a Hard-Core Advocate of Daily Stand-Ups, and everything in it still holds true.

Daily stand-ups work because they:

Force you to reflect on how the previous day went
Help you begin your day with focus
Surface blockers and competing priorities in real time
Create small moments of accountability that compound over time

And here’s the key: they only work if they happen at the beginning of your day. Not mid-morning or after your meetings. If your update isn’t shaping your day, it’s just commentary. Not a tool.

If live stand-ups aren’t possible, the next best thing is this:

Have everyone post a short, focused update in Slack as soon as they start working.

Why it has to happen first

When you wait until later in the day to plan, your day’s already been hijacked. The meetings, messages, and fire drills have already dictated your focus.

Posting a morning update before you dive in forces intentionality, puts you in the driver’s seat, and signals to you team where you’re focused and where you may need support.

Plan with honesty and realism

Let’s be blunt: you’re not going to accomplish 20 meaningful things in one day. So don’t write your update as if you will.

Your daily plan isn’t about documenting everything you could do. It’s about identifying what really matters today. The 2–5 high-impact priorities that deserve your time, attention, and energy.

Being honest with yourself matters here:

Is this task truly important or just easy to check off?
Is this list realistic given the meetings and energy you actually have?
Am I setting myself up to succeed or to feel behind?

As Greg McKeown puts it in Essentialism: “You can do anything, but not everything.”

The value of daily planning isn’t in ambition. It’s in alignment.

What a good update looks like

Your update should be written by you, in plain English, and at the start of your day. Not by a tool. Not copied from a ticketing system. Not written in project-speak or tech jargon.

It should answer:

What did I plan to do yesterday? Did I follow through? If not, why not?
What am I focusing on today, and why does it matter?
Is anything blocking me or shifting my focus?

Tools don’t think, but you do

Most of us use project management systems that populate our tasks automatically. And while those are helpful for visibility, they’re not your plan.

If you let a tool dictate your priorities, you’ll end up reacting to deadlines instead of leading with intention.

Writing your own update forces you to pause, prioritize, and communicate clearly, not just to others, but to yourself.

Reflect honestly and learn from the patterns

At the end of the day (or the next morning), check in with yourself:

Did you stick to your plan?
If not, what got in the way? Were your priorities realistic?
Did you let urgency overtake importance?

Honest reflection is what turns this from a routine into a leadership tool. When you regularly notice what’s working and what isn’t, you get better at planning, better at staying in your lane and better at protecting time for what matters.

This isn’t about micromanagement or checking boxes. It’s about building a habit of purposeful work, starting with a plan, crafted by you, in your own words, at the very beginning of your day.

And it only works if you’re honest with yourself. If you know you’re not going to get to 20 things today, don’t write down 20 things. Start early and in a truthful way.

Because real momentum doesn’t come from doing more, it comes from doing what matters, on purpose.

lead up

Invested leadership in the age of instant gratification