5 Things I Wish I Had Done Differently as a Leader

I’ve been reflecting recently on my leadership journey. I still think of myself as a leadership practitioner more than a theorist. But if I’m honest, that has shifted some. Since leaving my long-time career and becoming, essentially, a solopreneur, I don’t lead a team anymore in the way I once did.

That reality has caused me to look back on the years when I really was in the thick of leadership. Most of those memories are good ones. But when I reflect honestly, I also see things I didn’t do very well.

So I thought I’d share five of them here. Not because I enjoy reliving my mistakes, but because maybe my hindsight can help someone else lead better in the moment.

1. Trying to add value to everything

Sometimes as leaders, we just need to say, “Okay.”

As a team member, I was a high performer with strong perfectionist tendencies. When I became the boss, that combination made me want to improve every idea, document, or work product my people brought me.

Most of the time, I probably did add value. But that’s not the whole story.

With the benefit of hindsight, I can see how exhausting that must have been for my team. Even when I was “helping,” I was also subtly sending the message that their work was never quite good enough. That was never my intent. I simply wanted our team’s output to be as strong as it could possibly be. But in doing so, I often prioritized excellence in the product over encouragement for the people producing it.

In my pursuit of perfection, I sometimes took the wind out of their sails. I turned their ideas into our ideas and, too often, into my ideas.

What I’d do differently now:
I’d let good enough be good enough more often. I’d resist the urge to tweak everything. I’d still step in when there was a major mistake, a serious blind spot, or a pitfall only experience could help them avoid. But otherwise, I’d be quicker to say, “Great job,” and let them keep moving.

2. Assuming my people were like me

This one is subtle.

Of course I knew other people were not literally like me. But I don’t think I fully appreciated just how different they were from me in the ways that mattered most.

The teams I led included people from different backgrounds, cultures, and perspectives. But we also had enough in common that I think some deeper differences were easy to miss. We all worked in the same environment. We shared many assumptions. And I think those commonalities sometimes masked the reality that people could see the world very differently than I did.

Looking back, I can see that I often led people as though their motivations, reactions, and thought processes were basically the same as mine. They weren’t.

I remember one team member in particular whom I never really understood. I struggled to relate to her, and if I’m honest, I struggled to see the value she brought to the team. Then I came across this quote from Abraham Lincoln: “I don't like that man. I must get to know him better.”

That line stuck with me.

I wouldn’t say I disliked her, but I absolutely should have tried harder to understand her. People are complicated. Everyone has a story, and none of those stories are exactly like mine. The more I understand and value those differences, the better I can lead.

What I’d do differently now:
I’d get curious faster. When I don’t understand someone, I’d treat that less as a frustration and more as an opportunity. The people who think like me usually confirm what I already know. The people I struggle to understand may have much more to teach me. My job would be to set aside my ego, engage them as a fellow human being, and work hard enough to understand what makes them tick.

3. Not getting out of my office enough

If you’re reading this, you’ve probably heard of MBWA: management by walking around.

I had heard of it too, and to be fair, I did practice it… sort of.

I’m a natural introvert, so getting out of my office and making the rounds always took some effort. I built the habit of getting up from my desk every morning and every afternoon to check in on my team. But if I’m honest, it often felt more like checking a box than genuinely connecting with people.

I liked my people, and I usually enjoyed the small talk. But I was also very aware of myself, very aware of not wanting to be a nuisance, and usually trying to get back to my office as quickly as possible.

That was backward.

At the time, I acted as though the most important part of my job lived inside my computer. In reality, the most important part of my job was sitting in those cubicles I hurried past twice a day. It was always the people.

What I’d do differently now:
I’d spend less time glued to my desk and more time being present with my team. I wouldn’t just do a quick fly-by. I’d slow down. I’d linger. I’d make sure people knew I was available. And I’d put more effort into knowing them as whole people, not just employees.

In other words, I’d make it less about checking in and more about building relationships.

4. Not coaching enough

This is one of the mistakes I feel most strongly about now.

The older I get, the more I appreciate the value of coaching. I’ve seen it in my own life. I’ve had coaches help me recognize blind spots, challenge unhealthy thought patterns, and start doing the hard work of changing habits I didn’t even realize were hurting me.

Looking back, I can see that I did not coach my people nearly enough.

Part of the problem was that I didn’t fully understand the value of coaching until fairly recently. I didn’t know what I didn’t know when I actually had a team in front of me.

But part of the problem was also that I underestimated my people.

I assumed, probably incorrectly, that many of them were basically content with where they were and might resist being coached. I think I subconsciously equated coaching with criticism, and maybe I assumed they would too. But that was unfair. I know I have areas where I need to grow, and I welcome help when it’s offered well. I should have recognized that many of my people likely felt the same way.

Instead, I too often defaulted to minimal feedback throughout the year and then tried to cram a year’s worth of input into one 30-minute discussion every October.

That wasn’t leadership. That was avoidance with a calendar invite.

What I’d do differently now:
I’d coach early, coach often, and coach with genuine belief in the person in front of me. I’d stop treating coaching as something reserved for poor performance and start treating it as one of the main ways leaders help people grow.

5. Not celebrating enough

Work is hard. That’s why they pay us.

And yes, compensation matters. But that doesn’t mean celebration doesn’t.

One of the unwritten rules in many workplaces is this: people can do a hundred things right and hear nothing, but let one thing go wrong and suddenly the boss appears. That’s a terrible pattern, and I’m not sure I pushed back against it enough.

I recently read an excellent article from Eric Barker on happiness, and he referenced a powerful idea from philosopher Arthur Schopenhauer. Barker summarized it this way: “You cannot be grateful for what you experience as owed.”

That’s powerful.

If I, as the leader, assume my people simply owe me timely, accurate, complaint-free work, then I’m far less likely to be grateful for what they contribute. Whether they technically “owe” that performance is beside the point. The point is that I can choose how I experience it.

I can treat consistent, high-quality work as routine and expected, or I can see it for what it is: something amazing. Something worth noticing. Something worth appreciating.

What I’d do differently now:
I’d celebrate more. I’d express more gratitude. I’d look for reasons to recognize people when things went well instead of mostly noticing when they didn’t. I’d bring donuts. I’d order pizza. I’d create more moments of encouragement.

And sometimes, I’d celebrate for no particular reason at all.

After all, any occasion is a good occasion for cake.

Final Thoughts

So there you have it: five things I would do differently if I had the chance.

I can’t go back and lead those teams again. But I can reflect honestly, learn from what I got wrong, and share those lessons with others. That’s part of growth too.

I hope something here gives you food for thought. And I hope learning from my mistakes helps spare you a few regrets of your own.