company culture

a burnt meal, band aid, crumpled paper, and a broken tool

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?

7 pitfalls of Slack (and similar tools)

Slack and similar messaging platforms, like Teams and Mattermost, promised frictionless communication, faster collaboration, and a reprieve from endless email chains. And to be fair, they’ve delivered, but not without their own set of challenges. These communication platforms can just as easily cause dysfunction as they can drive productivity. Here are some common pitfalls.

1. Expectations of always being on

The problem:
Real-time chat fosters the illusion that everyone should be instantly reachable. That constant hum of notifications creates low-level anxiety and can kill deep focus.

Example scenario:
Jasmine is a UX designer who starts working at 8:00 AM and wraps up by 5:00 PM. But her manager often messages her at 9:30 PM with “quick ideas.” Even though Jasmine doesn’t have to respond, she feels pressure to and it’s wearing her down.

Mitigation:
Normalize using Slack’s “Do Not Disturb” feature. Set team guidelines like “no messages after 6 unless urgent” and encourage scheduling messages with tools like Slack’s built-in delay feature. Confession: I spend way too much time on my laptop, and often respond to messages outside of regular hours. I’m even guilty of posting outside of those hours. However, there is no expectation that I expect a response at those times. (Note to self: I need to remind my team of this).

2. Important info gets buried

The problem:
Slack can’t distinguish between what’s urgent and what’s just active. Critical updates often disappear under a pile of less important chatter.

Example Scenario:
The engineering team shares a Slack message in #product-news:
“API v1.2 will be deprecated in 30 days. All third-party integrations need to migrate to v2.0.”
Within a day, the message is swallowed by a stream of stand-up check-ins and demo GIFs. A partner success manager never sees the post and doesn’t notify a key enterprise customer, resulting in broken integrations and an angry escalation.

Mitigation:
Use tools like Slack’s “Highlight Words” feature to alert people to terms like “deprecation,” “urgent,” or “migration.” Better yet, integrate Slack with your CRM or ticketing system to automate critical alerts to the right people since you should not rely on a single Slack message as your system of record.

How to set up Highlight Words, click your profile picture in the top right of Slack and select Preferences -> Notifications. Scroll down to My keywords and enter the words you want to track, separated by commas.

3. Slack becomes the default

The Problem:
Slack messages can easily be misread or misinterpreted, since you don’t see someone’s facial expression or hear their tone. Plus, they’re often very short.

Example scenario:
After a tense customer call, the customer success manager starts a thread criticizing the product team’s recent release. The product lead replies defensively. Within minutes, the conversation derails and now it’s visible to the majority of the company.

Mitigation:
Create clear guidance: feedback and conflict resolution should happen in 1:1 video chats or designated retrospectives. Use Slack for transparency, not tension.

4. It erodes focus

The problem:
Notifications and context-switching fragment focus, leaving team members busy but not productive.

Example scenario:
Daniel blocks off 9–11 AM for deep work on a strategy deck. But he gets pinged 8 times in 30 minutes with questions, requests, and check-ins. He never hits flow state and ends up working late to finish the deck.

Mitigation:
Support “focus hours.” Encourage team members to pause notifications, mute non-critical channels, and respect scheduled work blocks. Deep work should be protected, not penalized. I struggle with this often, as I have to resist the urge to respond, especially when someone pings me directly. When you feel like you can only be productive outside of work hours, it’s a problem that needs to be addressed.

5. Channel chaos

The problem:
When there are too many channels or unclear norms and naming conventions, people don’t know where to find or post what.

Example scenario:
Three team members post updates about the same client in #client-discussion, #sales-wins, and #random-client-notes. No one sees the full story, and someone accidentally duplicates work already done.

Mitigation:
Audit and consolidate your channels. Create clear naming conventions like #client-[name], #proj-[initiative]), #success-help-and-feedback. Make a simple channel guide part of onboarding.

6. Unconscious exclusion

The problem:
Fast-paced Slack culture can exclude people who aren’t always online, aren’t native English speakers, or need more time to process and respond.

Example scenario:
During a fast-moving brainstorm in Slack, the extroverts dominate with rapid-fire messages. Maria, a thoughtful team member who prefers time to think before weighing in, ends up not contributing, even though she had a great idea the next morning.

Mitigation:
Encourage async participation. After a brainstorm, ask for additional input later in the day. Use threads and “summary” messages to recap discussions for those in other time zones or working styles.

7. The “reply reflex”

The problem:
In many Slack cultures, people feel pressure to acknowledge or respond to every message , even when the message is clearly just an FYI. What should be a quick, high-signal update turns into a noisy thread filled with tangents, opinions, and questions that don’t need to be answered.

Example scenario:
A marketer posts in #company-updates:
“FYI, the user conference microsite just went live! Feel free to share the link with customers. No reply needed.”

Within minutes, the thread fills up:

“Wow, I can’t believe it’s that time again already.”
“Looks awesome!”
“Does the pink color match the one on our main site?”
“The banner image looks a bit blurry.”
“What are we doing for SEO?”

What was meant to be a simple status update now feels like a kickoff meeting and creates extra noise for teams that aren’t even involved.

Mitigation:
Normalize the idea that not every update needs a response. Use “No reply needed” or “NRN” explicitly for FYIs. Encourage emoji reactions for lightweight acknowledgment. And when someone does need feedback or input, make that ask intentional and clear. Otherwise, help your team practice restraint and focus.

As powerful as Slack and other tools can be, they can also influence your culture in detrimental ways. Be mindful, and continue to establish ground rules and expectations.

What about you? Which pitfalls have you experienced first hand and what helped you overcome them?

When it’s been a tough week: honesty or spin?

We’ve all had them, those weeks that knock the wind out of you. A missed opportunity, an unexpected client loss, a launch gone sideways, a painful conflict. Whatever the cause, there are times when work feels heavier than usual. In those weeks, the pressure to spin positivity is real. I try not to.

Not because I believe in wallowing, or in dragging the team down by being a Debbie Downer. But because honesty is far more valuable and powerful than pretending things are better than they are.

Lessons are hiding in the hard weeks

Hard weeks don’t just hurt, they can also be learning opportunities. They illuminate blind spots, reveal what’s not working, and force clarity around what matters most, but only if we’re willing to face them directly.

As leadership expert Brené Brown puts it: “Clear is kind. Unclear is unkind.” – Brené Brown, Dare to Lead

Being honest about a loss or a failure isn’t a weakness. It’s a commitment to learning. It’s saying: This didn’t go as planned. Let’s understand why so we can do better next time.

Simon Sinek reminds us: “The most effective leaders are the ones who can tell the truth, even when it’s hard, because that truth clears a path to progress.”

Lead with honesty and resilience

Being honest doesn’t mean being dramatic or dwelling in negativity. It means acknowledging what’s hard, owning the impact, and offering a way forward.

You can say: “This was a really tough week. We didn’t hit the mark. But here’s what I’m doing to get us back on track and here’s how you can help.”

That kind of leadership invites ownership and builds a sense of safety. It tells your team that we can handle this together. Learning how to develop resilience in the face of adversity is one of the best gifts you can give your team and yourself. It also helps us focus on the most important things rather than engaging in discussions or activities that are not moving the needle.

Trust your team to rise to the occasion

Your team doesn’t need you to be endlessly upbeat. They need you to be transparent. When people understand what’s at stake, most will step up if they’re given the chance. But if they’re led to believe everything is fine, they’ll either be caught off guard later or continue under false assumptions.

That’s not just inefficient, but downright unfair.

Don’t hide the hard stuff, but instead be clear, candid, and real. Not just because it’s the right thing to do, but because it builds a culture of trust, growth, and accountability.

Some weeks are tough. Losses are tough. But they’re not the end if you don’t let them be wasted. They’re often the beginning of the next chapter if we let them teach us.

What about you? How do handle communication when it’s been a rough week or two?

customer communication involves all departments

There’s no such thing as over-communicating when it comes to your customers

If there’s one thing I’ve been saying at nauseam in internal conversations: There’s no such thing as over- communicating when it comes to your customers.

We’ve all experienced first hand how some organizations treat customer communication like a one-lane road, owned and operated solely by the customer success or support team. But the truth is, our customers don’t experience our companies in silos at all, so why shouldn’t operate that way? When you open up communication across teams and create visibility into what customers are experiencing and sharing, you can build a culture that’s not just customer-friendly, but customer-obsessed, which is a much better place to be in.

Here’s why I think it matters, and how you can start fostering a that culture.

Create a dedicated Slack channel

Nobody wants more meetings, so you can start with a cross-functional Slack channel for customer insights. This can be your internal hub for things like:

Good news: big wins, unsolicited praise, successful launches
Red flags: early signs of dissatisfaction, usage drops, missed expectations
Complaints: even if they’re tough to hear. You need to share what’s really going on without sugarcoating.
Challenges and blockers: recurring issues, misalignments, confusing parts of your product
Aha moments: when a customer uses your product in a brilliant, creative, or unexpected way

Don’t restrict access to the channel. Invite Sales, Product, Services, Marketing, and Leadership, and really anyone who touches or impacts the customer experience. You might be surprised by the insights that come from someone who isn’t a Customer Success Manager. A marketer may have seen a trend. A developer might immediately understand the root cause of an issue that the customer is reporting. An account executive might chime in with helpful background from the buying journey. If you’re worried about overloading your team with messages, just make it clear that not everything requires an acknowledgement, let alone a response.

Make customers a part of the weekly conversation

Sharing updates in Slack is a good start, but not everyone looks at those updates all the time, and you don’t want to miss the opportunity to drive change. Make some space in your weekly company updates or all-hands meetings for a quick customer snapshot. It doesn’t need to be a full write-up or polished presentation, just a few minutes to surface recurring themes, such as

Are multiple customers asking for the same functionality?
Did a recent update excite users or confuse them?
Are there usage patterns indicating onboarding gaps?
Were customers not aware of a newly implemented feature or a service that you offer?

These patterns should inform roadmap conversations, onboarding optimization, and sometimes even hiring.

In addition, encourage your team to stay informed and curious about what’s going on in your customers’ world that may not have anything to do with your product or service. We share at least three articles about our customers every week in our weekly updates, because it makes us appreciate everything that our customers do and how they make the world a better place.

Break down the walls between roles

One of the most impactful things you can do is give everyone the opportunity to interact with customers, especially when they can add unique value. For example, let your engineers sit in on customer success calls. Encourage your marketers to attend quarterly business reviews. Invite your product leaders to join customer onboarding calls. Empower your sales reps to loop in implementation developers earlier in the sales process (if they have the bandwidth, of course).

The point is not to flood your customers with too many touchpoints, but to bring more clarity, more empathy, and more value to every interaction. When customer knowledge lives in silos, things tend to fall through the cracks, issues get repeated, feedback loops can break down, and your teams make assumptions based on partial or outdated information.

But when customer communication is shared, celebrated, and acted on:

Product decisions feel less speculative
Marketing becomes more relevant
Support becomes more proactive
The team starts speaking the customer’s language
Empathy grows

You can create alignment not just on what you’re building, but who you’re building it for. Make everyone listen to your customers. Because when your whole company becomes part of the customer conversation, you build stronger relationships, better products, and a clearer sense of purpose.

What about you? How much communication about your customers is too much?

lead up

Invested leadership in the age of instant gratification