I’m an emotional/empathetic (and perhaps doormat) person and owner, and I have an employee that I think I have to fire. They’ve taken 4.5 months off this calendar year (that I’ve said yes to, covered for, found coverage for). I’ve said yes because I wanted to give them that time and figured it would come back around. But it hasn’t. It’s also so stressful for me to cover these shifts.

Some advice I’ve gotten that’s helpful:

• Your behavior sets the expectation for everyone around as to what’s allowable and ok. If there’s an example they can point to of you doing something then it’s ok to do always.
• The mentality is that the employees on their best day will be only as good as you are on your worst day.
• You need to treat the employee with care and respect even when they don’t treat you that way. Don’t let other people’s actions dictate your behavior.

I think I am doing all of these things, but it’s so frustrating that this person has no sense that just because I can cover their shifts doesn’t mean it doesn’t burden me and others. It’s a well paying job if done full time, like $75k year. I already cut their hours in half to part time because I could not physically work extra hours. It wouldn’t be so bad if they expressed any interest in reciprocation of covering shifts. I’ve asked and been rebuffed many times.

I did set a policy of not allowing more than 24 days off after the initial issue, but because we hired a new person to help them out (issues at another business and they needed a job fast), problem employee immediately capitalized on it and asked for more vacay even knowing this policy. I again, said yes, my bad.

Now that person I hired I like better. They have higher tickets, know more about the product, are a better employee while also being skilled in the way the other employee is. They also have an acute sense of how much time off is fair. They’re just vibing the industry we work in a lot better.

I’m sure the advice will be something like “it’s hard, but just fire them.” Am I misinterpreting something? Should I have done something different like say no to their vacation requests just because I don’t want to? We’re so small, like 2 front facing people, coverage is me or basically no one. How do I handle this inevitable conversation? I have actually never fired anyone before because we’ve had so few employees in our time with this business. I know it’s stupid, but if anyone has any resources on the structure of the conversation I need to have with problem employee. I’d appreciate it.