how to mentor a very timid employee

A reader writes:

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 can’t meet a deadline, she tries to anyway because she doesn’t want to say no to her team leader. This results in Capital S Stress for her, and a missed deadline for the team.

Recently, Jane ended up crying in my office, totally overwhelmed by her workload, and feeling like she’s not able to do anything about it. I investigated with her team leader, Kate, who told me that Jane always produces brilliant work, even if it’s sometimes after a deadline. Her team has nothing but positive feedback about Jane’s work ethic, even though it seems like she often works overtime to try and meet a deadline (something else that causes her stress). All in all, it seems to me like a supportive team environment. Kate and I are peers, and I know for a fact that she is an incredibly supportive leader who would not react badly to Jane speaking up at the right time.

Kate and I have tried for months now to give Jane some ways to help her communicate to her team members when she’s struggling, and how/when to speak up when she’s given a deadline that she knows is unachievable. The problem is that Jane is so timid that she refuses to actually carry out any of the ideas that we discuss in our meetings. She just says that she “doesn’t think she can say that to Kate.” Jane’s stress levels are getting worse, and I’m at a loss with what to try next.

I answer this question — and two others — over at Inc. today, where I’m revisiting letters that have been buried in the archives here from years ago (and sometimes updating/expanding my answers to them). You can read it here.

Other questions I’m answering there today include:

• I gossiped and upset my coworker
• Is pushy networking the new norm for college students?

The post how to mentor a very timid employee appeared first on Ask a Manager.