The hardest part of entrepreneurship and leadership is having to let people go. It freaking sucks. After more than 15 years of running a business, it hasn’t gotten any easier. I agonize over these decisions, and in many cases, I spent the night tossing and turning in preparation for what I would have to do the next day.

When letting someone go, you carry a pit in your stomach. You second-guess yourself and try to convince yourself that maybe things might be different.

I have read in the past that people are like plants and companies are like biomes. Recently I have been comparing hiring and firing decisions to feet and shoes. I have often heard glowing reviews of specific running or casual shoes. Then when I put them on my feet, I find myself thinking, “This doesn’t feel that great.” Likewise, I have recommended to others specific brands of shoes that I absolutely love, and the shoes haven’t fit right for them.

Similarly, sometimes we don’t fit right with a particular company. In most cases, it’s a misfit of core values or the concept of GWC that I love: Some people may not Get It, Want It or Have the Capacity to Do It.

I have found myself wanting to apologize to certain people for letting them go because I care about them. But if a decision is right, don’t spend time apologizing.

Here are my best tips for letting someone go:

1. Do it in person.

2. Show empathy and give them grace. (Unless you are already an A-hole, then your kindness will be perceived as fake.)

3. Treat the person as a human being with a family.

4. Be brief and direct.

5. Communicate the personnel change effectively with the rest of the team.

Letting people go is a necessary but difficult part of being a leader. Hopefully these thoughts help you as you handle those important decisions.