Your Best Employee Will Disappoint You
It’s going to happen.
Your best employee—the one everyone trusts, the one who consistently delivers, the one you’d hire again in a heartbeat—will eventually disappoint you.
They’ll make a poor decision.
They’ll say something they wish they hadn’t.
They’ll miss a commitment.
They’ll have a bad day.
They’ll exercise poor judgment.
Not because they stopped being a great employee.
Because they’re human.
Somewhere along the way, many organizations began confusing excellence with perfection. We celebrate authenticity, encourage people to take ownership, and tell our teams it’s safe to learn from mistakes. Yet when someone we’ve admired stumbles, our evaluation can shift from “They made a mistake” to “Maybe they’re not who we thought they were.”
Those are very different conclusions.
A few weeks into my role at BecomeMore, I experienced something that caught me off guard.
At our staff meetings, every person shares two things: a Highlight—something that went well over the past two weeks—and a Spotlight—a mistake, misstep, or failure that taught us something.
Everyone participates.
New employees.
Seasoned consultants.
Even our CEOs.
The first time I was uncomfortable.
Admitting a failure, especially in front of people you respect, leaves you feeling exposed. Every instinct tells you to soften it, explain it away, or quickly move on to what you learned. We spend so much of our professional lives trying to demonstrate competence that publicly acknowledging where we fell short feels almost countercultural.
But then something unexpected happened.
No one rushed to judge. No one tried to rescue the person sharing. We simply listened. We learned. And then we moved on.
In that moment, I realized something important: the purpose wasn’t to celebrate failure. It was to normalize humanity.
Because if we expect people to take risks, stretch beyond their comfort zones, and grow into better leaders, we have to expect that they’ll occasionally disappoint themselves—and us.
That’s not evidence of a weak culture.
It may be evidence of one strong enough to tell the truth.
Brené Brown writes that vulnerability is the birthplace of courage, innovation, and learning. You cannot ask people to take meaningful risks while simultaneously expecting them never to disappoint you. Those ideas cannot coexist.
Organizations often say they want courageous employees. We encourage people to speak up, challenge assumptions, innovate, and take ownership. But courage comes with uncertainty. It comes with imperfect decisions. It comes with moments we wish we could do over.
If we expect authenticity without the possibility of disappointment, we’re not really asking people to be authentic.
We’re asking them to perform.
None of this suggests that accountability should disappear. Some actions have serious consequences, and leaders have a responsibility to address them. But accountability and grace are not opposites. The strongest leaders know how to hold both at the same time.
A single decision deserves evaluation.
A person’s character deserves perspective.
Your best employee will disappoint you.
The question isn’t whether it will happen.
The question is what you’ll do when it does.
Will you define someone by their worst moment?
Or will you evaluate what you’ve always asked them to evaluate in others—a pattern of integrity, a willingness to own their mistakes, and the courage to keep growing?
Because the organizations that learn the fastest aren’t the ones that make the fewest mistakes.
They’re the ones that make it safest to tell the truth about them.
And one day, if you lead long enough, you’ll need that same grace yourself.