Teju: As a leader, it’s hard to provide feedback to my teammates for weaknesses that I actually share with them. Do you have any advice on doing this?

Jane: First, giving feedback is always difficult, but especially so when it’s about someone’s weaknesses and not their strengths. Actually, I think you’re at an advantage if you’re providing feedback for a weakness you share. You’ll be able to give concrete examples of the tactics you’ve tried to overcome it and how you’ve become more successful by doing so. Genuinely relating with their situation is an opportunity for you to create a more personal link with one of your employees.

Teju: In my role leading a startup, one specific example of this is fear because everyone in the company is doing something we haven’t done before. Would you advise being open and honest with your teammates in this situation?

Jane: You should never be afraid to be honest with your teammates. In my experience, it really connects with people and creates even more loyalty. In the situation you’re describing, you do need to create a safe place for your team. Even if they’re taking a chance and they’re out on the ledge, your team needs to know that you’re standing with them and if something goes wrong they won’t be pushed over by themselves. That’s really part of what starts to build a team. It’s when you push the fear factor, take chances, and chart new waters. In doing so, it’s also very important that your teammates understand what you’re concerned about, what you’re expecting of them and how they’re part of the solution.