Sometimes employment just isn’t the right relationship between an individual and a company. This can be the case despite the best intentions of both parties, their efforts, and the skills of the individual not withstanding. I think these situations are some of the most difficult to handle of all employee relationship challenges.

There are lots of reasons you might have to fire someone. An employee who’s consistently not performing, or is putting projects and client relationships at risk is relatively easy to let go. Not fun, but pretty straightforward. Someone dishonest or unethical would be even easier, I imagine (thankfully, I’ve yet to face that situation). The more difficult cases are when reality clashes with aspirations.

Keeping your physical office environment open, and your practices and culture transparent and collaborative may take care of poor performance and bad matches without direct action. Few people want to stay in a situation where it’s apparent they either don’t fit well or they aren’t pulling their weight. If you don’t have people hiding in cubicles or solo-ing on all their work, a mismatch will be apparent to them and everyone else. Whether they move on of their own accord, or you need to help them on, the culture tends to maintain itself and bad matches don’t accumulate.

The talented person who wants to be part of the team but for whatever reason simply doesn’t fit is the toughest firing I’ve faced. The well-worn advice to “hire slowly, fire quickly” doesn’t help here. Because of the tricky nature of “fit” it’s very easy to spend months talking, worrying, experimenting, helping, reflecting, giving feedback and negotiating. If you weren’t willing to make that effort you’d probably not be a good boss or have a decent workplace. After all, everyone has their moments and their quirks; it would be self-destructive and unreasonable to fire someone without careful thought and consideration.

But there comes a time when you need to give up the struggle. When you do, I’ve found it helpful to think about two things. First, remember your obligations to your other employees. Second, think about the problematic employment relationship as a struggling, dying creature. Firing is like putting the suffering beast out of its misery; it’s a difficult but humane action to take. Once you’ve made up your mind, be as generous with severance as you can, be honest with your former employee, and try to help them find a better match.