10/20/2025

Mentoring a Very Timid Employee

Examining this and two other tricky workplace dilemmas

Inc.com columnist Alison Green answers questions about workplace and management issues—everything from how to deal with a micromanaging boss to how to talk to someone on your team about body odor.

1. How to mentor a very timid employee

I'd love some advice about how to help out a very timid staff member, let's call her Jane. Jane and I have 1-1 weekly professional development meetings where I can offer support, mentorship and advice. She is not my direct report and we don't work in the same department so our workflows never cross; our company culture is that each senior staff member (i.e., me) has regular mentoring meetings with some junior employees.

Jane is very, very timid. She doesn’t feel like she can advocate for herself in her own team, and she doesn't push back when she’s given unachievable deadlines. If she knows she cannot meet a deadline, she tries to anyway because she does not want to say no to her team leader. This results in Capital S stress for her, and a missed deadline for the team.

Please select this link to read the complete article from Inc.