When should you encourage an employee to resign?

It requires a good relationship. I’ve only done it once, but my relationship with the former employee improved. We both knew it was inevitable and so I helped them move on.

They use me as a job reference.

In our case the employee had hit a wall and couldn’t move forward so a change of scenery was necessary.

Very difficult conversation, but when an employee is not successful in a position and does not seem to be able to turn things around it can be more kind to help them find a better fit in another role.

When it’s really not working out for you or for them.

With a role I lost last year, I wanted to keep them because it was the only resource that I had out in France, but at the same time I was pushing them out. I said, “It's going to pain me to have to backfill that role, but if you're not seeing what you're supposed to see from the folks you're working with on a daily basis, then I will figure it out.” I helped him with anything he needed, including coaching, which I do a lot. I coach folks on building the skills and confidence to make the move they want. Who's in control of your life, what you learn and how you learn it are some of the hardest things to realize.

I've been in my company for eight years and I’ve never had to fire anybody on my team. I'm proud of that because I've had employees who got offers elsewhere with higher salary, but they would stay because they felt they belonged. On our team, they are appreciated as human beings. They believe in what the IT team's trying to do, and they see the levels they can grow into. I did have some employees who learned everything we have to offer and they would tell me about accepting an offer. In those cases I’d say, "I'm sad to see you leave, but I totally understand because you've outgrown this place."