Mistakes I Hope You Don’t Repeat
Mistakes I Hope You Don’t Repeat
There’s a special kind of wisdom that only comes from falling flat on your face in front of your boss, your team, or a packed conference room while trying to pretend you meant to trip over your own PowerPoint clicker. That kind of wisdom doesn’t come from books. It comes from mistakes loud, public, slightly traumatic mistakes that leave just enough scar tissue to become a leadership lesson.
I’ve made a few. Okay, more than a few.
In my early leadership days, I treated mistakes like bruises uncomfortable, avoidable, and best covered up. But over time, I started treating them like receipts. Every one was proof that I was in the game, learning the rules the hard way.
This post isn’t a confessional. It’s a favor. These are the mistakes I hope you don’t repeat not because you’re smarter than me (though you probably are), but because you deserve to spend less time redoing things that don’t work and more time building things that do.
Some of these mistakes are common. Some are a little too personal. All of them are expensive if ignored. So grab a coffee, a notepad, or some shine depending on what hour it is and let’s talk about six of the dumbest leadership moves I made so you don’t have to.
Mistake #1: Hiring for Skill, Not Fit
The high-performing salesman who burned down our culture
If I could sum up this lesson in one line, it’d be: “Sometimes the wolf you let in is wearing a suit but it’s monogrammed, and the initials are E.G.O.”
Let me introduce you to a guy I hired early in my professional leadership journey. We’ll call him Max, mostly because “Walking Red Flag” feels too on the nose.
On paper, Max was a slam dunk. Former top salesperson. Big energy. Said all the right buzzwords. He knew how to handle objections, close business, and he had that kind of bravado that makes recruiters weak in the knees. I should’ve run the moment he referred to himself in the third person, but I didn’t. (All jokes aside) I had targets to hit and I wanted to win and needed a strong proven sales professional – that wasn’t Max.
Max got the job.
And to his credit he did perform. At least, if your only metric of performance is revenue and chaos isn’t on the dashboard.
But from day one, the problems started to show. Max didn’t just bring his talent he brought a Saturn sized ego. He thought operations existed to slow him down. He treated account managers like personal assistants. Meetings weren’t discussions; they were one-man TED Talks. And when someone disagreed with him, it was less “let’s find alignment” and more “how dare you challenge the king.”
Execution suffered immediately. His promises to customers didn’t line up with what we could actually deliver. Our ops team was scrambling to make up for his cowboy-style commitments. Meanwhile, morale in the department dipped like a rollercoaster with loose bolts.
Here’s the kicker: Max wasn’t dumb. He just didn’t care about anyone else’s job. He saw success through the narrow lens of “I sell, therefore I win.” And he couldn’t, or wouldn’t, understand that we relied on each other for success. He refused to build with us. Instead he eroded the foundation we stood on.
I pulled him aside multiple times. Tried the coaching route. Gave him direct feedback. Asked him to collaborate. He always nodded, threw around a few buzzwords like “synergy” and “team buy-in,” and then returned to treating every cross-functional partner like an obstacle to overcome.
The team started to check out. They avoided him, delayed projects, and vented in hushed tones behind closed doors. I knew something had to be done because I could see the Max fatigue from the rest of the team.
And that’s when it hit me: I had hired someone who sold well but cost us everything else.
Look, we all make hiring mistakes. But this one taught me something foundational: a single person can produce results and still be an organizational liability. Especially when they treat collaboration like a speed bump and see their coworkers as competition.
The worst part? I had seen glimpses of this in the interview process. He cut me off mid-sentence once to correct a detail I didn’t need corrected. He laughed a little too hard when I asked about past failures. He dodged questions about team dynamics by telling me how amazing he was.
It was difficult to trust my gut back then, so with his background and the needs of the District I made the call.
So here’s the hard truth I had to learn: high performance doesn’t excuse low character. And it doesn’t justify hiring someone who can’t or won’t play well with others. Culture isn’t a perk it’s the operating system. And if one line of corrupted code walks in wearing polished shoes and a nice watch, the whole thing crashes.
Eventually, I had to let Max go. Not because of sales numbers, but because of what those numbers were costing us everywhere else. The day he left, the team breathed again. It was subtle, but real like we had finally stopped bracing for impact.
These days, I don’t just look for skill. I look for self-awareness. I look for people who know the job and the company aren’t just about them. If someone can’t describe a team win without using the word “I” eight times, I move on.
Because building a high-performing team means hiring people who elevate others not just themselves.
Mistake #2: Thinking Leadership Is About Authority (or Friendship)
It’s actually about trust! And trust is built in the hard moments
I used to think leadership was about getting people to like you… or at the very least, listen to you because of your title.
Spoiler: It’s neither.
There was a time early in my career when I swung between two extremes: I either wanted to be the team’s favorite sibling relatable, supportive, easy to talk to; or I tried to assert authority with the classic “I’m the boss, that’s why” approach. It was a real leadership rollercoaster, and it led me to a place where I thought I would gain respect by out working everyone on my team. Shocking as it sounds that didn’t work either.
When I tried to lead through friendship, I’d didn’t avoid hard conversations. but I would downplay the issues. I’d give my team too much space even if they were clearly struggling or creating friction because I didn’t want to “hurt the relationship.” I thought that friendship would encourage people to do the right thing, the hard work.
It didn’t.
And when I swung the other way and tried to lead with pure authority, it was worse. I would make commands with little insight, adjust peoples schedules before speaking with them. Commit team members to additional account visits or site walks. I made decisions in isolation and expected the team to just roll with it. Roll they did right past me on their way out the door.
After struggling leading my first team for sometime, working 10-12 hours a day because if I did it they could too. Because if I worked more than them they would respect me. Because if I wanted to lead them i had to be the best. A pivotal moment struck, I was faced with a situation that required me to admit my mistake take ownership of what happened and deal with a team member that was impacted because I hadn’t been a great leader. The outcome: I gained his trust, and respect. That’s when everything changed and I learned that leading is about Trust. Authority and Friendship cant do what trust can do.
And trust isn’t built during the easy weeks. It’s built when things go sideways. When the customer is furious, when the deadline is a flaming mess, or when a team member screws up and you don’t throw them under the bus.
Trust is built when your team knows:
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You’ll give them the truth, even if it’s uncomfortable.
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You’ll fight for them when it counts.
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You’ll own mistakes instead of dodging them.
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You won’t disappear when the heat gets turned up.
Another example: I had an account manager under me who made a pretty serious error that cost us a deal. It would’ve been easy for me to shift the blame onto him entirely, especially because he was the final step before things went wrong. But the truth was, I hadn’t provided enough guidance or feedback leading up to that point. I’d been too hands-off, assuming he had it covered.
So instead of letting him take the fall alone, I took the hit with with our team and our leadership team and owned my part. I could see the impact this had on my team immediately. They saw that I wasn’t just there to bask in the wins I was there to shoulder the losses, too.
That moment bought me more credibility than a year of pep talks and free pizza ever could.
Now don’t get me wrong: trust doesn’t mean softness. It doesn’t mean you let things slide or avoid accountability. But it does mean being willing to walk into tough moments with your team and not around them. It means facing issues head-on instead of hiding behind titles or pretending everything’s fine.
Eventually, I learned that trust grows in the exact moments most leaders avoid—when you have to say, “This isn’t working,” or “We need to talk about something difficult,” or “I don’t have all the answers, but I’m going to figure it out with you.”
That’s leadership. That’s where trust lives.
So, if you’re out here trying to win people over with charm or control them with a title, let me save you some heartache: it doesn’t work. You’ll either burn yourself out trying to be everyone’s buddy, or you’ll alienate your team by swinging the command-and-control hammer too hard.
Instead, get good at building trust. Learn how to say the hard thing with respect. Show up when it’s uncomfortable. Share credit. Own failures. Admit when you don’t know something.
Trust doesn’t require perfection, it just requires presence, consistency, and a little courage.
You don’t need to be liked. You don’t need to be feared. You need to be trusted.
That’s what people follow.
Mistake #3: Fighting Fires Instead of Fixing Problems
Why being the hero isn’t always helpful
If you’re a leader and you’ve never felt like a firefighter, congratulations—you might be the first. For the rest of us, there’s that adrenaline rush of jumping into chaos, stomping out the flames, and emerging with soot on your face like, “See? I saved the day.”
For a long time, I thought that was leadership.
I thought being the first one on the scene, solving the problem, and getting everything “back on track” was the gold standard. After all, the more fires I put out, the more valuable I must be… right?
Spoiler: wrong. So wrong.
The truth is, the more time I spent fighting fires, the less time I spent figuring out why things kept catching fire in the first place.
At one point in my career, I was practically living in crisis mode. Every issue—whether it was a customer complaint, a missed delivery, or a frustrated teammate—got my full, immediate attention. I’d drop everything to fix it. I’d send the emails, make the calls, patch the process, calm the customer.
And you know what? The team loved me for it. At first.
“Travis handles it.”
“He always has our back.”
“He’s the one who gets stuff done.”
It felt good. I felt needed. Useful. Heroic, even. But here’s the problem with always being the firefighter: you never actually stop the fires from happening.
I was putting on a performance, not leading a transformation.
Eventually, the same issues started popping up again. And again. Because while I was busy throwing water on the flames, I wasn’t fixing the faulty wiring that kept setting the place ablaze.
Worse, I had unknowingly trained my team to depend on me for everything. Why take ownership of a broken system when they could call me and I’d fix it? Why work through tension with another department when they knew I’d jump in and smooth it over?
I wasn’t empowering them—I was enabling them.
And here’s the kicker: I started to burn out. The more I firefought, the less strategic I became. I was constantly reacting, never proactively planning. And the business? It stayed stuck in a holding pattern because we never actually evolved—we just survived.
One turning point came during a particularly chaotic month. Three major client issues hit back-to-back. Each one could’ve been prevented. But instead of addressing the root causes—bad handoffs, unclear responsibilities, and a lack of follow-through—I dove in like usual and muscled through them.
We hit our targets that month. But we lost a great team member who felt overwhelmed and under-supported. And I lost a bit of my edge because I was too deep in the trenches to see the bigger picture.
That’s when I realized: it’s not enough to solve problems. Real leadership means preventing them.
So I started shifting my mindset. Instead of asking, “What needs to be fixed today?” I started asking, “Why does this keep happening?” I created space to zoom out, analyze patterns, and bring the team in to fix systems—not symptoms.
We mapped workflows. We clarified roles. We added some simple process guardrails that kept common issues from spiraling out. And you know what? It wasn’t sexy. It wasn’t dramatic. But it worked.
The fires didn’t disappear overnight. But they stopped feeling like emergencies. They became signals—early warnings that helped us course-correct before we needed a full response team.
And perhaps most importantly, the team grew. Because when I stepped back from being the hero, it created space for them to step up.
So here’s my advice if you’re still in firefighting mode: take off the helmet. Put down the hose. And stop pretending your calendar full of emergencies is proof of your importance.
Instead, lead like a forest ranger. Look at the whole ecosystem. Ask hard questions. Solve root problems. Train others to spot the sparks before they become infernos.
You’re not here to save the day.
You’re here to build a better one
Mistake #4: Mistaking Busyness for Effectiveness
Because a full calendar isn’t the same as a full impact
For a long time, I was proud of how “busy” I was. I had the color-coded calendar, the back-to-back meetings, the overflowing inbox, and the classic leadership posture of speed-walking down hallways like I was late for my own deposition.
I genuinely thought it meant I was killing it.
Busy meant important, right? Busy meant productive. Busy meant leading.
Except it didn’t. What it really meant was: distracted, disconnected, and occasionally one Starbucks away from a nervous episode.
The truth hit me the way most leadership truths do, after a few polite warning signs and one not-so-polite reality check.
Let me set the scene: I was leading a sales team and juggling about 87 tasks per hour. We were chasing aggressive growth, onboarding new customers, managing legacy ones, and I was in “always-on” mode. I had fallen into that trap where you think leadership means being available 24/7, solving everything instantly, and measuring your worth by the number of Teams calls you survive in a day.
And I wasn’t the only one. My sales team was doing the same thing. They were working their tails off, crushing hours logged, calls made, emails sent. From the outside, we looked unstoppable. And we were hitting targets. Being highly active was working; or was it?
My reps were logging tons of activity but not building real rapport with clients. They were transactional, not relational. And I was no better. I had stopped having regular check-ins with half my team. I watched the metrics and let it guide who I spoke to.
One rep finally told me, “Travis, I feel like i only hear from you when I need to do something or I need to improve”
That cracked my shell.
So I took a step back. I looked at how I was spending my time, and more importantly, how it was felt by the people who reported to me.
And what I realized is this: busyness is not a badge of honor—it’s a warning sign.
It’s what happens when you fill your days with motion instead of meaning. When you confuse speed with direction. When you manage a team by spreadsheet and forget that actual people are attached to those metrics.
I started making time for conversations again. Not just updates or standups but real, human conversations.
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“What’s working for you right now?”
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“Where are you stuck?”
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“How’s your energy this week?”
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“What’s one thing I can take off your plate?”
Nothing revolutionary. Just consistent, honest check-ins that weren’t about tasks they were about my team.
Same with customers. I asked the sales team to slow down and focus on quality. Not five emails a day but instead thoughtful conversations. Not “just touching base” emails but “here’s how we can help” solutions.
And guess what? Things got even better!
Customers felt heard. The team felt supported. And I—shockingly—felt less stressed because I wasn’t spinning in circles chasing tasks that didn’t actually move the needle.
Now when I see a packed calendar, I don’t automatically assume someone’s effective. I ask, “Are you actually connecting with your people? Are you creating space for strategy? Are you thinking, or just reacting?”
Because effectiveness isn’t how much you do, it’s how much matters.
Leadership isn’t won by getting your inbox zero or the most meetings attended. It’s earned by clarity, communication, and making the people you lead feel like they matter more than your calendar.
So if you’re too busy to talk to your team this week, or too buried in emails to hear what a customer is trying to say; pause. Look up. Take back control of your time.
Because nobody builds a legacy out of being “busy.”
They build it by being present.
Mistake #5: Avoiding Difficult Conversations
The longer you wait, the messier it gets—just ask Josh
Let me level with you: Hard Conversations are almost always worse in your head than in reality.
As a younger leader, I hadn’t realized that yet, so I would delay, over prepare or even just glaze over challenging topics. I believed that if I just gave things time, they’d work themselves out. That people would “get the hint.” That issues would smooth over with enough positive reinforcement, pep talks and KPI reviews.
And sometimes, sure, that works. But more often, avoiding the hard conversations just gives small problems time to become BIG ones.
Let me introduce you to Josh. Josh was the walking, vaping embodiment of why avoidance doesn’t work.
Josh was a new hire who came in confident borderline cocky, if we’re being honest. He talked a big game, showed up with enthusiasm, and assured everyone he was going to “own his territory.”
Spoiler: the only thing he owned was a vape pen and a shocking amount of self-delusion.
Almost immediately, Josh started missing the mark. He skipped customer visits. He ignored sales goals. His communication was thin, and when it did happen, it usually came with a side of sarcasm or thinly veiled condescension.
And then, the pièce de résistance: he vaped during meetings.
Yes. Meetings. As in, during team calls, mid-discussion, casually exhaling like he was headlining a jazz club.
Now, you’d think that would’ve triggered an immediate correction. But no I delayed. I rationalized. I convinced myself he just needed time to adjust. That he’d come around. That addressing things too soon might “discourage him.”
What I didn’t realize was that my silence was permission.
By not saying anything, I told Josh, loud and clear, that what he was doing was fine.
And he believed me.
So when the time finally came to sit him down and explain that he was missing expectations, underperforming, and actively frustrating the team he was shocked. Like deer-in-a-LED-headlight shocked.
Because I had let him walk around thinking everything was great for weeks.
And that was on me.
He didn’t take the feedback well. In fact, it went sideways fast. He got defensive, combative, and refused to take responsibility. And while yes, that reaction told me a lot about Josh, it also told me something uncomfortable about myself:
I had waited too long.
And that’s the bigger mistake here, not hiring Josh, not even the vaping (though wow) but waiting. Waiting to be honest. Waiting to provide clarity. Waiting to lean into a conversation I knew needed to happen.
This happens to so many leaders. We tell ourselves we’re giving someone “space” when really, we’re just avoiding discomfort. We’re scared of confrontation, scared of emotion, scared of making things awkward.
But awkwardness now is better than a disaster later.
Here’s what I’ve learned (the hard way):
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Early clarity prevents late-stage conflict.
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Avoidance isn’t kindness it’s confusion.
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Accountability conversations don’t get easier they get heavier.
And ironically, most people actually appreciate the directness if it comes with respect and a genuine intent to help.
Now, I don’t wait. If there’s a misalignment, I speak to it early. Not with aggression. Not with shame. Just with clarity. “Here’s what I’m seeing. Here’s what’s expected. What support do you need to get there?”
It’s not about being harsh, it’s about being honest.
Because the cost of avoidance is never just one person.
It spreads. It tells your top performers that mediocrity is tolerated. It erodes trust. And it makes every future conversation harder because you’ve trained people not to expect honesty from you.
So if there’s a Josh in your world right now; maybe not vaping, but definitely missing the mark. Ask yourself this:
Have you been clear? Have you had the real conversation?
Or are you just hoping it’ll fix itself?
Because it won’t.
And the longer you wait, the more dramatic it gets.
Mistake #6: Failing to Share the “Why” (and Treating Everyone the Same)
Fair doesn’t mean equal. It means human.
If you want to watch a team slowly disengage, just start handing down decisions without explaining them. Add a dash of blanket policy enforcement, top it off with a “that’s just how we do it,” and boom instant morale killer. Serve cold with a side of turnover.
Its easy to make this mistake, especially early in the leadership journey We tend to focused on structure, consistency, and keeping everything neat and predictable. We want everything to be fair. What I didn’t realize was: equal isn’t fair. Equal is uniform. Fair is personal.
Let me explain.
Back then, I believed I had to treat everyone the exact same way in order to be seen as a good leader. Same rules. Same style. Same communication. Same management approach. That felt safe. Impartial. Clean.
But people aren’t clean. They’re complex, layered, and wildly different in what drives them. Some are motivated by recognition, some by autonomy, some by a clear career path, and some just want to get home in time to make dinner and not be micromanaged into a coma.
And if you don’t understand that, if you don’t take time to learn what actually matters to each person, you’ll miss the mark. Even if you think you’re being “fair.”
For example, I once had two high-performers on my team. One was very private, highly independent, wanted space to work, and just needed the occasional acknowledgment that they were doing a good job. The other craved collaboration, mentorship, and regular feedback, they needed to feel connected to the mission and the team.
So what did I do?
I treated them both the same.
I gave them identical goals, the same cadence of check-ins, the same bonus structure. I figured, “If it’s fair on paper, it’s fair in practice.”
Spoiler: it wasn’t.
One quietly burned out. The other started shopping their resume. And both eventually sat me down and said some version of, “I don’t feel seen here.”
That one hurt. Because I liked them. I thought I was doing the right thing. I thought I was being fair.
But fair isn’t giving everyone the same thing. It’s giving people what they need to succeed.
And that starts with understanding why they’re here in the first place.
This brings me to the second part of the mistake: not sharing the “why.”
People will do a job. They’ll show up, follow instructions, and hit the numbers, at least for a while. But if they don’t understand why something matters? If they don’t know how it connects to the bigger picture, or how it helps the customer, or how it advances the mission, they won’t bring their best.
They’ll bring compliance. Not commitment.
I’ve made decisions before, about territory realignments, sales strategy shifts, or even team restructures, where I thought, “This is clearly the right move.” And maybe it was. But I failed to bring the team into the decision-making process. Or I didn’t explain the rationale well. Or I shared the what without the why.
And when that happens, even the best ideas land with suspicion.
Suddenly it’s not strategy, it’s politics. It’s not leadership, it’s micromanagement.
You lose trust, not because you made the wrong call, but because you made a quiet one.
These days, I slow down before rolling out a change. I explain it. I give context. I invite questions. Not because I need permission, but because people deserve understanding.
I also make it a point to ask every team member, “What do you want out of your time here?” Not in a cheesy HR kind of way, but with real intent. Some people want to grow into leadership. Some want stability. Some want to learn new skills. And guess what? When you tailor your approach to those goals, when you lead like a human being instead of a policy manual you unlock potential you didn’t even know was there.
Bottom line?
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Don’t treat everyone the same, treat them with the same level of intentionality.
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Don’t assume silence means agreement.
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And don’t just hand people the “what.”
If you want buy-in, give them the why.
Because when people understand their role, believe in the purpose behind it, and feel like their unique needs are recognized you don’t have to push them.
They’ll pull you.
Closing: You’ll Still Make Mistakes | Just Make Better Ones
If there’s one unifying theme across these six mistakes, it’s this: leadership isn’t about avoiding missteps, it’s about learning, adjusting, and not dragging a whole team through the same hole twice.
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I’ve hired the wrong person because I chased performance over fit.
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I’ve led with authority and friendship before I earned trust.
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I’ve worn the firefighter cape like a badge while ignoring broken systems.
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I’ve confused motion for meaning and filled calendars instead of connection.
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I’ve avoided hard conversations until they exploded in my face.
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And I’ve treated everyone the same in the name of fairness, only to lose what made them unique.
Each one of these mistakes came with a price, sometimes in budget, sometimes in morale, sometimes in sleep. But they also came with growth. And that’s the part I wouldn’t trade.
The truth is, you’re going to screw up. So am I. The goal isn’t perfection it’s awareness. Self-awareness. Team-awareness. Situational-awareness. Because if you can name the mistake, you can fix it. Or at least keep it from becoming your brand.
If you’re a new leader, take this post as a heads-up from someone who’s stepped on the rake more than once. And if you’ve been leading for years, consider this a gut-check: are you still making these mistakes? Are you justifying them because “that’s how we’ve always done it”? Are you willing to try a better way?
Leadership is a long game. And the best leaders aren’t the ones who avoid mistakes, they’re the ones who outgrow them.
So go ahead: mess up. But mess up with purpose. And when you do, pull your team in close, own it, and say the most powerful sentence in leadership:
“That one’s on me. Let’s make it better together.”
Thanks for reading. Now go lead like you’ve made a few mistakes and learned something from every single one of them.
