update: I poured all my time into helping an employee … and I’m so discouraged by how it ended

by Alison Green on December 21, 2023

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.

There will be more posts than usual this week, so keep checking back throughout the day.

Remember the letter-writer who had poured all their time into helping an employee and was discouraged by how it ended? Here’s the update.

Reading the submission now nine months later, I can see that I was too personally invested/emotional about the whole situation, which many readers (rightfully) picked up on. Even still, so many readers were kind and thoughtful, and encouraged me not to get jaded as I continue in managing people in my career.

I took your advice about spending significant energy on hiring the right person for the role, and spent an exhausting six months hiring someone for the job. We had many candidates that probably would have been “fine,” but I didn’t want to repeat the cycle of over-managing someone who was just not the right fit for the role which, ultimately, was the crux of Wanda’s issues; she had many strengths but this job was not the right one for her. Even though the search was long and somewhat tedious, I also got to spend a lot of time covering for the role, and learning the parts that could use fixing, seeing which areas might need more managing, and streamlining some processes that were set up long before I arrived for the new person when they started.

Happily, we did hire a person who has been a great fit for the job, and who has exceeded every goal or standard set thus far. In fact, it appears she’s even become bored in the role, and now I get to approach a new management challenge of helping someone upskill in the workplace. This in and of itself has made me more confident; the tension in the role was more a Wanda issue than a me issue. However, my insecurities about the whole situation still creep in, and I sometimes find myself second guessing management decisions I make — am I overdoing it if I check in on this project? Are they feeling unsupported if I don’t? I hope with time and the right people I’ll continue to gain confidence and strike the right balance of it all. I’ve taken a lot of opportunities to learn from and observe the great managers in my own workplace, and to reflect on the good managers I had — especially the ones I had when I was in the entry-level admin role I now manage.

Just want to say thank you again to all the kind commenters who boosted my spirits and said “been there, done that.” Thank you also for posting my question so that I could get some very valuable feedback from people not as close to the situation as me!

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{ 13 comments }

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  1. Forested*

    OP, if you ever read these comments, please know that your original letter helped me SO MUCH with figuring out a situation with a lovely report who ultimately wasn’t a good fit for their responsibilities.

    1. Slow Gin Lizz*

      Wow!!! The real reason for AAM right here, to help everyone and not just the LWs! (But definitely also the LWs.)

  2. I should really pick a name*

    am I overdoing it if I check in on this project? Are they feeling unsupported if I don’t?

    The best solution to this is to ask them, because the amount of checking in/support that is wanted is going to vary from person to person.

    1. ENFP in Texas*

      I will echo this 100%! One of the best things my manager asks me during our 1:1s is “What else do you need from me? What can I do to make sure you feel supported?” Even if the answer is “Nothing right now”, the fact that she asks and I know I can answer makes me feel supported!

  3. Eldritch Office Worker*

    I’m so happy to get an update on this one! I’m glad things are going better, OP.

    “I sometimes find myself second guessing management decisions I make — am I overdoing it if I check in on this project? Are they feeling unsupported if I don’t?”

    You know, this isn’t necessarily a bad thing. It’s good to think over your decisions and how they impact people. Management isn’t a one size fits all deal, and when people get too entrenched in their own management styles they sometimes fail to account for the fact that different situations, and different people, have different needs.

    You shouldn’t second guess yourself so hard that you get decision paralysis, and that’s the thing that gets easier with confidence. You make decisions and you’re pretty sure they’re fine, defensible decisions at the end of the day. But it’s good to reflect on if there was a better option, what your pattern of decision making looks like, and if what you’re doing is ultimately getting the results you hope for.

    It sounds like you’re doing awesome.

  4. Sara without an H*

    Hi, LW — I went back and looked at your original letter. Been there, done that, bought the t-shirt. You made every mistake I also made as a newbie manager. There’s a powerful temptation to think that, if you were a really, really good manager, every employee would thrive. It doesn’t work that way.

    From your description, I agree with you that Wanda was miscast for her role. (I don’t remember where I first read that expression — probably here at AAM — but it made me feel much better about a lot of things.) And I think you made a shrewd decision to focus on making a good hire to replace her. As to how closely to manager your new hire, talk with her about this, along with some discussions about how she wants to develop her career and what kinds of opportunities you and your firm can provide.

    You have set yourself up for long-term success as a manager. Congratulations!

  5. Sloanicota*

    To be brutally honest, and I say this with sympathy as someone who over-thinks things, I’m surprised it would take six months finding the perfect “fit” for … an entry-level admin job? I thought until that point that this might be some kind of in-demand specialist or other hard-to-fill role. Managing entry level people is tough; the turnover is high and the return on investment is low. But I don’t know that finding the perfect fit is the solution TBH.

    1. Notell*

      Exactly. OP made at least two new mistakes.

      1. It shouldn’t take anywhere near that to hire for an entry level job and

      2. The OP hired someone grossly over qualified who is now bored 3 months in. Now that person will likely looking to move up or out soon and the cycle repeats again.

      OP really needs some help with basic people management and hiring.

    2. WittyReference*

      This jumped out at me, too. If OP’s new hire is bored, they’ll probably leave soon. Taking 6 months to fill an entry-level role is A Lot.

    3. Skytext*

      I thought the same thing. As soon as I read the line about how she had many candidates who were “fine”. How many times have we heard Alison talk about how it’s usually better to hire the “fine” candidate rather than spend months searching for the mythical “perfect” candidate. And look what happened! That “perfect” candidate was actually too good for the role, and quickly (in three months!) outgrew it. This LW sounds eager to do a great job, but the overthinking and overinvesting she demonstrated with Wanda reappeared in her “exhaustive” job search (for an entry level admin???). But with time, experience, perspective, and advice from Alison she should become an awesome manager.

    4. Liana*

      I hope I’m wrong… but if the new person is bored already, I wonder if they chose someone overqualified this time.

  6. Ms. Murchison*

    LW, I think you might need some job coaching or a mentor yourself, because to be frank it still sounds like you’re overdoing it. As Sloanicota raises above, it took you six months to fill the position? Because you were looking for perfect and passed over several acceptable candidates? It’s not exactly surprising that your new hire got bored quickly; both letters seem to suggest you take things to extremes and need a hand getting some perspective. Good luck.

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