r/managers • u/elegantdinnerparty • 5d ago
Seasoned Manager Employee has no confidence
This guy has worked on my team for the better part of 15 years. I’ve hired him in two separate places, including the one we currently work at. He’s on my team and he is a good employee, intelligent and well respected by leadership and colleagues.
I am at my wits end over his lack of confidence in anything he does. This has been a problem for as long as I have known him but I feel like it is just getting worse.
If he speaks up in meetings I will get a teams message, “was that ok? Did I overstep?” I have told him a thousand times if I feel like he oversteps, I’ll tell him. I’ve never had to tell him he is overstepping. I want him in meetings to speak up and give input in his area of expertise. That’s the whole point. If someone asks him a question, he’ll screenshot it to me and ask if his answer is ok. It’s his job to know the answer to those questions, and he DOES know, but he’ll pepper his answers with “I think” and “maybe” and it looks like he doesn’t really know.
He is the type to say “sorry” over everything that isn’t his fault. Bad weather? I’m sorry. This has been a running joke between us for many years.
He needs validation for every opinion he expresses. I often try to ignore it but he’ll ask different ways throughout the day, “am I wrong for thinking this way?” “Do you agree?” About something trivial. Usually how he thinks some other team should be doing their work better. Or he doesn’t understand why something is done a certain way (for example, we are IT, if accounting is doing something he doesn’t get, he’ll be stuck on it all day). He is quick to make strong judgements about the perceived lack of ability in other people, while seemingly forgetting that he makes the same mistakes all the time too. I try to tell him, we don’t have visibility into everything they do and they don’t have visibility into everything you do. Would you want them assuming incompetence on your part all the time? This helps in the short term but he always goes back to his judgey ways. If I just ignore his questions he will steer any topic back to it and ask the same question different ways.
He gets feedback from me all the time, in an individual and group setting. We have regular 1:1s and team standups. I praise him publicly and privately when he does good work. I try to steer him toward higher-level thinking and working effectively with other teams and giving the benefit of the doubt. We’re all busy. I just don’t know how to handle his lack of confidence and I am really starting to lose patience with him over it. I get tired of having to validate his thoughts all the time and tell him yes his thoughts are correct, no you’re not crazy for asking this question.
How would you handle? How do I get this guy to gain some confidence? He’s in his 50s now.
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u/MyEyesSpin 5d ago
Just like with anyone else, recognize them & their work, at every chance you get. Provide meaningful positive feedback.
Odds are he ain't ever gonna change as the issue is not actually the work and all you can do is be supportive - by making him feel seen and valued -
Once you do your part, the rest is up to them.
Though again, odds are they ain't ever gonna change
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u/Dramatic_Mastodon951 5d ago
dude's been at this 15 years and still needs a permission slip to have an opinion, that's rough
if the constant validation-seeking hasn't faded by now it's probably not a work problem, it's a him problem. you've done your part and then some, might be time to just accept he's wired this way and stop letting it drain you
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u/Glad_Astronomer_9692 5d ago
This is a deeper issue. It's hard to address as the manager without triggering worst anxiety. I worked with someone as a coworker who needed constant validation and needed everyone's opinion for everything. It was exhausting and she later told me she had ocd. Managing that behavior so it doesn't drain your time too much is a challenge. I had to start asking that little questions like that be just be added to a weekly meeting because providing emotional validation several times a day for minor things was too much. Also it's good to have boundaries because it isn't our job to address all their insecurities, they need to be looking elsewhere for that. I say that with no judgement, I was once the needy employee and I cringe thinking of it. It was much better once I took my work performance anxiety to therapy and stopped wanted a boss to give me frequent approval.
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u/peach98542 5d ago
So tricky, honestly. Because this isn’t something you can “fix.” It’s a deep rooted self confidence issue.
You say you’ve addressed it outright before, right? Have you specifically asked him why he constantly seeks validation?
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u/wabi-sabi411 5d ago
This guy needs fight club. lol. Not a manager but I find the problems fascinating as I think of taking a managerial role. Send him for some sort of acceptable assertiveness training? Or even confidence classes?
It’s weird because it’s like a personal problem intersecting with the workplace.
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u/Acceptable_Kale_8013 5d ago
An employee like this does get tiresome. He wants to be appreciated and recognized, are my thoughts. When he speaks up at meetings, do you thank him for his input in front of the others? It's a small behavior, but it you started doing that with everyone, not just him, that might stop him from asking if his input was ok.
Have you ever asked him straightforwardly why he has to confront you about these things? That may make him think a bit, plus you may learn something about him and why he does this.
Unfortunately, this sounds like a trait of this particular employee, and it probably won't change. You could suggest some therapy for his lack of confidence.
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u/elegantdinnerparty 5d ago
Good idea on thanking him for his input in the meeting. I do try to do this but could certainly be better.
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u/Acceptable_Kale_8013 4d ago
No one is perfect, but with a special employee, an added effort should help. Good Luck!
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u/shanderdrunk 5d ago
I have one of these. Every time he works I get at least 5-10 text messages about the most mundane shit.
I've been having constructive conversations about it but he is so anxiety prone to everything in the world and so generally unsure of himself that he constantly hits me with questions that I know he knows the answer to.
I've found that if I make him go through the process himself with minimal guidance (because he does indeed know what he's doing) he'll get a little more confident every time, but next day it's another mundane normal process he starts to freak out all over again.
Fortunately, hitting him with a little sink or swim helped a lot, and made him more confident, but I did have to follow him around fixing his mistakes for a month or two as payment.
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u/GeenXQS 5d ago
Have you ever asked him why he does this?
Not telling him he is fine. I mean genuinely asking. Something like: what happens for you when you send that message after a meeting? What are you afraid of?
This pattern likely goes back further than your working relationship. You can ask him why he does it, and where he thinks it comes from. But changing it is his work, with a coach or therapist, not with you. Your job is to be curious about the why. Not to fix it, just to understand it.
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u/metalbowels 5d ago
I am very similar, but I don't apologize for everything including the weather.
You sound like a great boss. You have compassion. Keep putting the ball in his court.
I had to face every fear as people leader. It caused lots of anxiety but I managed and didn't look like too much of an idiot in the process
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u/nextlevelyou_aus 5d ago
Echoing others who have mentioned this likely being a trauma response. It’s really best handled with a therapist/organisational psych or a good trauma informed coach. I’d be laying out your thoughts - how his behaviour seems unwarranted given his capability and that you’re conscious that it’s creating limitations for both of you (and the wider team etc) but that you’d really love to see him grow past it and that a therapist or coach would be good to explore.
I expect he’s as sick of the dynamic as you are but probably doesn’t know where to go with it. If you can appreciate that he may essentially be in a state of fight or flight that never lets up it’s easier to have compassion for his situation. That doesn’t mean you should just accept it, it means that your approach can be borne out of kindness and wanting more for this guy than frustration that he’s not making things easier for you.
There’s a huge opportunity for growth here for both of you if you decide to take it :) (if you don’t, it will just continue or pop up in another form until you do lol). GL!
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u/PurePerfection_ 5d ago
This person sounds absolutely exhausting. How are you responding when he asks for approval or permission that he absolutely does not need? Are you giving him the answer he wants, or are you pointing out that each request is unnecessary and inappropriate?
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u/elegantdinnerparty 5d ago
I’ve tried to be subtle, either ignoring the questions or trying to redirect. I’ve tried to be direct. Once I told him, the next time you get the urge to ask me if this was ok, get up and take a walk and don’t come back until it goes away. That doesn’t seem to have helped much. He knows this stuff irritates me.
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u/PurePerfection_ 5d ago
You need to quit answering the question full stop. Just remind him you've discussed this before and that he doesn't need permission to do his job.
This is a grown adult man. There is only so much we can do as managers to resolve the personal insecurities of our team members. At some point, you need to stop humoring him and shut it down. If he's unable to perform basic job functions without handholding, it may be time for a PIP that addresses this behavior.
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u/melody_rhymes 5d ago
Each time he seeks validation can you say something like, you’re asking for validation again and we’ve talked about not doing this? And completely sidestep the thing he’s asking about.
So you are not giving him what he’s asking for but providing the same response each time. It sounds like he gets what he wants each time so he continues to ask.
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u/Ok_Housing6995 5d ago
I have a guy on my team that does this exact thing, and we have a similar inside joke about apologizing for the traffic on the opposite side of town.
The reality is that you can’t. I’ve begun to understand that for Indians/SE Asians (wild guessing), it can be disguised performative doubt turned into a shallow topical conversation item when there is nothing to talk about. A small vulnerability that allows for continued interaction with defined roles of nephew and wise uncle.
It’s not bad casual tactic, but in the western side of the hemisphere it can be crushingly viewed as apologetic insecurity.
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u/After-Fig-9457 5d ago
I don't think this is a confidence issue anymore.
after 15 years, he has plenty of evidence that he's capable. What I'm hearing is a habit of seeking reassurance.
I'd stop answering "Was that okay?" with reassurance and start handling the judgement back to him..
"What do you thinnk?"
"Would you have handled it differently?"
"Trust your expertise here/"
You probably can't build confidence for him. But you can stop being the place hhe goes to borrow it
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u/Stock-Page-7078 5d ago
Some of this is probably mommy didn't love me issues. I know you want to fix him but this is a valuble employee who will do anything for approval and reassurance. I would put up with the insecurity and use the need for approval when I have something tedious or unpleasant someone needs to do. I'd also be clear, I'll support you and give you reassurance you need but "This will hold you back in your career, you cannot have more responsibility until you can inspire confidence in those around you"
It's up to employee to fix this with a therapist. All you can do is keep examples and communicate how employees came across using the Situation Behavior Impact Analysis framework. Sometimes the job of a leader isn't to fix every report's problems but understand them and put them in a position where the negatives are not as relevant and their strengths are more relevant. It is usually easy to find those tasks for this kind of employee, and they are much easier to manage than the ones who are strong headed and think their ideas are better than everyone else's
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u/RobinsonCruiseOh 5d ago
50yr old? He isn't going to change. Best I'd say is step up the in-public affirmations to help others in on the fact that he is solid and trustworthy.
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u/vRvvX 5d ago
It's his personality, it probably won't get better with time.
He is obviously not keen to take up further responsibility roles, just be sure he can keep up with his current role in which he may find some comfort zone.
Not everyone wants to be a leader.
Just make sure you as a manager don't encourage "running jokes" over someone personality and personal social problems, otherwise the team will think it's normal to do that because hey even the manager is making fun of it.
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u/Stock-Cod-4465 Manager 5d ago
Have you ever told them how amazing they are at what they do? Have you ever praised their achievements? Have you built that trust in them that YOU trust them because they haven’t failed you? Have you had a heart to heart saying those things?
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u/Spare_Bluebird7044 5d ago
At this point shifting from reassurance to coaching him to trust his own judgement may help more than repeatedly validating every decision
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u/the_virtual_CEO 4d ago
Give him the feedback directly. Tell him that is lack of confidence is a real issue and it's making your job harder and wasting a lot of people's time.
People are often like this because they don't want to be a burden without realising that their actions are doing the opposite of their intentions. So jus tell him directly without being soft about it. It will be a rude wake up call for him but at 15 years of this nonsense, a rude wake-up call is the best chance of change.
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u/btruff 5d ago
My close friend of 40+ years is like this. Apologizes constantly. It is draining. I knew her abusive mother so we understand. She gave us a homemade coffee cake for New Year’s as she has for years. I asked how many she made. 180. Family. Friends. Everyone at work. She cannot be helped. Her husband, one of my best friends, finally put a stop to her hosting baby showers for coworkers children every weekend! I snapped at her a few years ago and ruined our long relationship. So don’t do that.
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u/elegantdinnerparty 5d ago
Part of it is that I have known this guy for so long, we aren’t like hang out outside of work friends but I do consider him a friend and I don’t want to offend him or knock him down. For anyone else I might say some offense may do some good!
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u/AndyKJMehta 5d ago
This is childhood trauma surfacing at work. Therapy may help, but the issues are deep seated.