update: how to mentor a very timid staff member

by Alison Green on December 29, 2021

It’s “where are you now?” month at Ask a Manager, and all December I’m running updates from people who had their letters here answered in the past.

Remember the letter-writer asking how to mentor a very timid staff member? Here’s the update.

My update is a mixed bag. We’ve been working from home in lockdown since August (we’re not in the USA) and my timid mentee has had a pretty rough time over the lockdown between some bad mental health, not being able to see her family, the stress of lockdown and a heavy workload. The issue that I wrote about originally was her being too timid to communicate with her team, push back on workloads and deadlines that she finds unachievable, or ask for more information when she doesn’t have enough to go on. This has become even more important during the lockdown, as not being in the office together, we’ve all had to work on our communication skills via online chat channels. My mentee continued to be timid, and eventually hit rock bottom after an incredibly stressful project in which the deadlines were tight. Hitting rock bottom seemed to ‘wake her up’ to the reality of needing to be vocal and speak up when something is unclear or unachievable.

I’m happy to say that she’s eventually become much more vocal about advocating for herself since then. I wish it hadn’t taken such a large fall to get there, but I’m happy that we did. I’m also happy to say that since she’s started speaking up and communicating ahead of time that some deadlines were not achievable for her, the team has got a much better idea of how long tasks take her and what sort of timeframes are realistic when assigning her work. I think that we’ve all gotten better at planning a project with enough time that she can complete her part of it without undue stress, and I hope that this is the start of a positive cycle for her.

I’m so grateful to you and the commenters who pointed out that fixing this issue would need to come from her, not from me – that’s exactly what happened in the end, even if it was a painful process.

Side note – she recently told me “You challenge me and I dread it… but I always value it.” I think that’s good feedback???

Have a great holiday season Alison, your team and commenters.

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{ 23 comments }

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  2. AppleStan*

    OP, I promise you, that’s AMAZING feedback from Hermione. Kudos to the hard work she’s put in and the time you’ve put in so that she improved.

  3. Lana Kane*

    “Side note – she recently told me “You challenge me and I dread it… but I always value it.” I think that’s good feedback???”

    I got similar feedback from an employee and I took it as a huge compliment. Dreading being outside of your comfort zone is normal – what’s not always so normal is seeing the value in it. It sounds like you are doing that in ways that are supportive, make sense, and actually help people grow, rather than increase their fears. That’s not easy!

    1. Meep*

      I have a love-hate relationship with criticism. I actually love it. I hate the way a lot of people give it, because it is often poorly done and any constructiveness can be bogged down by vagueness. By that I mean, “I don’t like it.” I am fine with “I don’t like it” so long as it has a “because” attached. Most people have a hard time saying what they don’t like. I once went to bat for a color scheme I didn’t even care for because the way one guy was disparaging it (calling it “ugly” and saying whoever picked it was an idiot) sent my blood boiling. Up to that point, I didn’t pick it. What did I care if it was changed? Insult someone’s intelligence? I will go barbarian princess on you.

      Therefore, I totally get her feeling of dread before being pleasantly surprised and even relieved.

      Accepting and providing criticism are both arts few people have mastered.

      1. Lana Kane*

        I would have done the same! “I don’t like it, but now? It’s my FAVORITE and I will fight you.”

    2. Your Local Password Resetter*

      I get the feeling. Criticism and challenge is painful and terrifying and hurts me to my core, but it’s also really helpful and not getting any just makes me constantly anxious instead.

      1. Elizabeth West*

        I felt that way after my editor’s main feedback for Book 2 was “Wow!” I’m like, wasn’t there anything else you wanted to say? Did that mean you like it or did it suck? TELL ME!*

        I’m with Meep; just a plain “I don’t like what you did” without any reason seems arbitrary. If a boss is impressed with my work and wants to throw stuff at me that will build on my skills, that’s great. If she thinks certain aspects of it need improvement, I want to know so I can work on them. Don’t leave me in the dark, because it’s scary in there.

        *she liked it

    3. The Other Dawn*

      I wish so hard my team would see the value in being challenged. For the most part, they don’t. And I have no idea if that’s something I develop within them or not.

  4. IndustriousLabRat*

    Her feedback is wonderful; it shows a certain level of courage simply to vocalize that at all. Positive growth, for sure.

  5. Jack Straw from Wichita*

    As a coach, I am forever telling my performers/athletes–If you are pleased and happy with me all the time, I am not doing my job. That is GREAT feedback. :)

  6. Gray Lady*

    That’s very good feedback. If she were really made seriously uncomfortable rather than passingly uncomfortable with your manner, she wouldn’t have felt free to say even that much. She’s just acknowledging that negative feedback is never easy to hear, but you do a good job giving what she needs.

    1. Not So NewReader*

      So agree. OP this will become clearer as you move along. You are doing a good job with this employee, keep doing what you are doing. I predict your next “problem” will be that you think your employee respects you more than you deserve. To that I say, it’s HER experience she is reflecting back to you and you don’t have to feel that you deserve it. Just be gracious, that’s all.

  7. ecnaseener*

    Yes, that’s definitely good feedback!! Of course she dreads it, it’s HARD and really scary for her, but she knows it’s helping her! Well done, you sound like an awesome mentor.

  9. Jennifer*

    I wish it hadn’t taken her hitting rock bottom before she saw that she needed to change, but I definitely get it because I have been there.

  10. 80HD*

    I have ADHD and this employee sounds a lot like me (not diagnosing her, just saying that I hardcore relate). Part of my executive dysfunction means that I’m not great at telling how long something’s gonna take me to do. Some things take me way less time, some take way more, but either way factoring in communicating with my teammates and boss is a whole extra set of multiple steps that are very difficult to include. I have a lot of empathy for her!

    1. Elizabeth West*

      I have the same issue with dyscalculia. After doing a thing a few times, however, I can usually give a rough estimate of the length of time for that task. It’s in my nature to build in a cushion, though, because something will ALWAYS come up. Either way, I have to tell people; they can’t read my mind.

    2. PT*

      Prior abusive work environments, too.

      Me: Please do not feed the llamas French fries, they eat hay and it could make them very sick.
      Boss: HOW DARE YOU TALK BACK TO US YOU ARE NOT A TEAM PLAYER YOU ARE TRYING TO SABOTAGE OUR TEAM WHY ARE YOU COSTING US MONEY BUYING THE LLAMAS HAY YOU’RE CLASSIST NOT EVERYONE KNOWS LLAMAS EAT HAY YOU SHOULD BE MORE CARING AND NURTURING AND EDUCATE PEOPLE YOU SNOB

      Next boss: OK but why didn’t you speak up when you saw Marketing feeding the llamas French fries?

    3. Ariaflame*

      When giving advice to new research students, (or to be honest a lot of students but more focused on the research ones), we often suggest they consider how long they thing something should take, and then multiply that by 3 or 4. Especially when you are new at something, things will always take longer than you think they will.

      1. RebelwithMouseyHair*

        Yup. I do that systematically for any task I’ve not done before. Although I only double it then round it up, rather than multiply by three or four. Then again I’m no spring chicken so I think I’m probably a whole lot faster than most students.

  11. n.m.*

    I’ve given feedback like that to my PhD advisor. It’s a good thing! Sometimes the process of growing intellectually or professionally can feel like pulling teeth but it is important and we feel it’s value enough that we keep doing it!

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