How Do I Mentor a Very Timid Employee?

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.

Here’s a roundup of answers to three questions from readers.

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 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.

Green responds:

Well … you can try giving her specific language, role-playing it with her, and setting specific plans  that you then check back about (“you were going to say X to Kate at your 4 p.m. meeting — did you? why not? so what next?”). You can also name the pattern for Jane — “We’ve worked on this for months but you haven’t implemented any of the ideas we’ve come up with. What do you think would really help?”

But if you’ve already tried those things, I think it’s likely that you can’t fix this. Mostly it needs to come from Jane herself, although Kate is also better positioned to fix it if she wants to.

Ideally Kate needs to ask Jane some probing questions about her workload and take a fresh look at it herself, check in on Jane’s progress toward deadlines earlier in the process, and give her explicit instructions about how she wants her to handle it when something is in danger of going off-track. Is your role one where it would be appropriate to suggest those ideas to Kate or even set up a meeting for the three of you, or are you really just supposed to be coaching Jane behind the scenes?

It’s also possible Jane mostly just wants a place where she can vent. If that’s the case, it’s useful for you to know that so you aren’t racking your brain for a way to move her to action.

2. I gossiped and upset my coworker

I was talking with a manager in another department when she expressed frustration with one of her employees — not that much, just that she is dealing with a lot. Soon after, I saw an ad for that person’s position posted, and I talked about it with a coworker in my department. I came in Monday to a full-blown rumor mill situation with that employee thinking they were being fired and their manager upset that I had talked about it! I take full responsibility; I was the one who spoke about it and that’s on me, regardless of who spread it afterwards. I apologized to the employee and their manager and said I truly didn’t mean to upset them and am so sorry they had to deal with it.

I’m not a gossiping person! I mostly stick to myself, but I made a poor choice and hurt someone. How do I let my colleague and the hurt employee know that this won’t be a pattern without completely walling myself off from everyone?

Green responds:

I know this isn’t a satisfying answer, but now that you’ve apologized, the only real way to show it is by demonstrating it through how you operate and that takes time. Going forward, be scrupulously professional and discreet and you should be able to repair any reputation damage.

But also … that manager who shared her frustration with you about the employee? That was a bigger breach than anything you did. She’s the one who had the real responsibility for discretion. Yes, you shouldn’t have shared what you heard, but she shouldn’t have said it to you in the first place. If she’s the person who chastised you, I hope she acknowledged her own responsibility as well.
(On top of that, if she’s already advertising someone’s position when they don’t know they’re going to be replaced, there are bigger problems here — although it’s not clear if that’s what the ad was.)

3. Is pushy networking the new norm for college students?

I’m curious about some interactions I’ve had with a student from my alma mater who has been contacting me for networking and “advice.” I’ve always been more than happy to pay it forward for students from my school and do networking coffees and have helped them with recommendations and getting internships before, as I work in a somewhat difficult to enter public policy field, but I’ve been thrown for a loop with this latest student.

We met up once and the student used the whole time to talk about himself and all the people he knew in the city where I’m located and didn’t ask me questions, but I still gave him the usual advice I give students. I was not impressed, but this student has sent me several emails over the past year to “update me” on his GPA, where he was moving, his extracurricular activities, etc. At one point I didn’t respond quickly enough and he messaged me on LinkedIn saying he’d been trying to contact me and hadn’t heard back.

Is this the new norm for college students now? I understand things are very difficult for those graduating right now. I’ve been polite in my responses, but don’t feel like I need to respond to every email, and I’m curious how you would handle it.

Green responds:

Nah, this isn’t a new norm. This is just one obnoxious guy!

There is advice out there for people to stay in touch with those they’ve networked with, and for early-career networkers to let people who helped them know how things are going as time goes by. Maybe that’s what’s he’s doing. But the level of pushiness is all him.

His “I haven’t heard back from you” message actually gives you a good opening — you could respond to that and say, “Glad to hear you’re doing well. I’m swamped these days and behind on correspondence. Best of luck in whatever comes next for you!” And then give yourself permission to stop replying to future messages if it’s not a relationship you want to maintain.

Someone could argue it’s better to be straight with him (“You’re coming across as demanding more of my time when you didn’t make good use of our meeting last year”), but I don’t think that’s a burden you need to take on. It’s not on you to explain to him why his approach is wrong, although you certainly could if you wanted to.

Want to submit a question of your own? Send it to alison@askamanager.org.