How My Optimism Led to My Most Expensive Leadership Mistake

Optimism is an entrepreneur’s greatest asset. Unchecked, it becomes your most expensive habit.

I am not someone who gives up on people easily. For most of my life, I considered that a point of pride. I could see potential in someone that they couldn’t yet see in themselves, and I was willing to stay in that belief longer than most. Leading with a big heart felt like a strength. It is the kind of quality that builds loyalty, develops people and creates cultures where employees grow.

What I didn’t understand for a long time was that this same quality had a shadow side. I wasn’t just seeing people’s potential. I was making decisions based on a version of them that didn’t exist yet. And I was giving second chances, third and fourth — not based on evidence of change, but based on my own stubborn faith in the person I was convinced they were becoming.

My most expensive mistake was employing someone who performed well for their first six months, successfully led their previous award-winning company and showed the potential for becoming a leadership force that could help take my company to the next level. They were promoted, and their new title went to their head.

Their behavior changed, not for the better, and I was willing to believe their “reasons” for it. They snapped at a colleague? They’re under pressure. They didn’t follow company policy? They had extenuating circumstances. They hadn’t responded to coaching? They just needed more time.

Each individual act of grace was defensible. The pattern was the problem. Others in the company were watching, questioning my judgment and wondering if our long-held standards still applied. It caused my best performers to become frustrated and disengaged with each passing incident. One of my top salespeople even threatened to quit unless things changed.

The right decision became unavoidable. Letting the problem employee go was long overdue, and when it finally happened, the relief of the rest of the staff was immediate and unmistakable.

Maya Angelou said it plainly: When people show you who they are, believe them.

I have quoted that line more times than I can count. I have nodded at it in conversations, shared it with friends navigating hard situations and used it as a kind of wisdom shorthand. But for years, I failed to apply it to myself and my business. When employees don’t live up to their potential (or the story you’ve told yourself about their potential), failing to admit it puts your credibility as a leader at risk. Lesson learned, the hard way.

USC’s Mark Schroeder has studied this tendency carefully. He describes it as charitable interpretation — seeing others as protagonists doing their best within their circumstances. His research shows it’s a genuine virtue: It helps us avoid writing people off too quickly and creates space for real growth. But his research also identifies a tipping point, a threshold where the generosity of your interpretation stops reflecting reality and starts replacing it.

That’s the moment Angelou’s line stops being abstract wisdom and becomes a direct challenge.

This is the trap hiding inside entrepreneurial optimism. Thinking about the world differently is a core virtue of every successful founder. You see the product before it’s built, the market before it emerges, the team before it’s performing. Projection is the founding act of every company ever launched. The problem starts when you direct that same skill at an individual person and refuse to update it when the evidence stops cooperating.

I’m not someone who others would describe as conflict-avoidant. I’m direct and willing to have hard conversations. But I lead with a big heart for the people I hire — and that combination creates its own blind spots. Over time, I’ve had to build a set of rules to keep my optimism honest. If you recognize yourself in any of this, take note.

Always assume positive intent, until they prove otherwise

Start every relationship and every performance conversation from a place of good faith. Most people aren’t trying to fail or manipulate you. They’re navigating their own pressures, gaps and limitations.

Lead with the assumption that they want to do well. It costs you nothing, and it sets the right tone. The keyword, though, is until. Positive intent is the starting point, not a permanent override of what someone’s behavior is actually telling you.

Use data as a second set of eyes

Check the fulfillment of their potential against the numbers. Missed targets, recurring complaints, performance patterns and psychometric assessments either confirm that your belief is warranted or reveal what may already be painfully obvious to everyone else.

There’s an important difference between being willing to have hard conversations and looking for a fight. When the evidence is in front of you, you’re not seeking conflict. You’re just telling the truth.

Allow for a mistake. Once.

People learn by doing, and doing sometimes means failing. Give people room to get things wrong, own it and grow from it. That’s not weakness; that’s how high-performing cultures are built. But the same mistake made twice is a different conversation entirely.

The first time is human. The second time is a choice. Letting it slide again doesn’t protect the person; it signals that accountability is optional. That’s not kindness. That’s a failure of leadership.

Don’t let your open heart become an open door for manipulation

This one is uncomfortable to say out loud, but it has to be said. When you’re known as a leader who believes in people, extends grace and gives second chances, some people will respect that deeply. Others will quietly learn to work it. They will underperform, apologize convincingly and reset the clock. If you find yourself having the same conversation with the same person more than twice, stop asking what’s wrong with them and start asking what’s wrong with you.

Angelou’s line is deceptively simple. Believing people when they show you who they are doesn’t require cynicism. It requires a specific kind of courage: the willingness to let the evidence update the story, even when you loved the story you had.

See what’s possible in people. Fight for it, even. But when someone shows you who they are today, give them, and the others you count on, the respect of believing it.

Optimism is an entrepreneur’s greatest asset. Unchecked, it becomes your most expensive habit.

I am not someone who gives up on people easily. For most of my life, I considered that a point of pride. I could see potential in someone that they couldn’t yet see in themselves, and I was willing to stay in that belief longer than most. Leading with a big heart felt like a strength. It is the kind of quality that builds loyalty, develops people and creates cultures where employees grow.

What I didn’t understand for a long time was that this same quality had a shadow side. I wasn’t just seeing people’s potential. I was making decisions based on a version of them that didn’t exist yet. And I was giving second chances, third and fourth — not based on evidence of change, but based on my own stubborn faith in the person I was convinced they were becoming.