How My Optimism Led to My Most Expensive Leadership Mistake

Opinions expressed by Entrepreneur contributors are their own.

Key Takeaways

- Believing in people’s potential is a great quality, but repeatedly excusing someone’s negative behavior based on “who they could become” can lead to poor leadership decisions and real organizational costs.

- Always assume positive intent until someone proves otherwise, use data as a second set of eyes, allow for a mistake (once), and don’t let your open heart become an open door for manipulation.

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