When Leadership Isn’t Fun

Let’s talk about something that isn’t fun, but is absolutely necessary for anyone leading a team.

What happens when you have to write someone up?

I recently had to do this with a teammate. It wasn’t personal, and it wasn’t dramatic. But it was necessary. And while it’s never easy, it is part of my job.

I always begin these conversations with a simple and honest opener.

“I have some not-fun things to talk about.”

That sentence sets the tone. It lowers the emotional temperature and communicates that what comes next is about responsibility, not punishment.

I believe that part of leading well is being just and fair. That means I clearly explain the issue, hold space for questions, and follow up the conversation with written documentation. The write-up is then emailed to the teammate for signature, so there is no confusion about what was said or what expectations were given.

Set a timeframe and a standard

A write-up should never feel open-ended. I tie each write-up to a timeframe. For us, it begins with a 90-day probation period. During that time, the write-up is considered active. If the same issue occurs again, the consequences become more serious, and the probation period is extended.

We also follow a three-strikes policy, but time and context matter. If someone has been with me for several years and has one isolated write-up from two years ago, I usually do not count that as an active strike unless the same behavior repeats.

However, there are situations where the violation is serious enough that it must never happen again. In those cases, I say so very clearly in the meeting and put it in writing. There is no gray area. If it happens again, we part ways.

This is part of the job

I expect everyone to do their job.

And part of my job is holding people accountable when they do not.

Managers often struggle with this because it feels uncomfortable. But enforcing rules is not about being unkind. It is about maintaining the standards that make your business and your team strong.

You can and should approach these conversations with kindness, professionalism, and clarity. But here is something important to remember.

You are not responsible for how someone reacts.

You are responsible for how you lead.

Now let me ask you something.

If you write someone up and then find out they are telling other teammates that it was unfair, how do you handle it?

• Do you address it directly?
• Do you let it go?
• Do you clarify with the team?
• Do you reinforce expectations again, more clearly?

There is no one-size-fits-all answer, but your response matters. These are the moments that shape your team’s culture and trust. How you lead in these situations is what earns or loses respect.

If this is something you are dealing with right now, reach out. I would love to help you think it through and support you in doing it fairly and confidently.

With you in the hard stuff