How of you deal with a work colleague who means well but can be very annoying?

[Anonymous]

I got a work colleague like this. He’s a real nice guy and fairly intelligent. I also work in a support capacity for a larger team when it comes to technical issues and questions.

Anyway literally every time he asks me for help it is almost never a simple question. I am trying to be patient with him because he always seems to get the most difficult and complex questions from the clients we service. But what I can gather from him is that he has confidence issues and wants me to affirm his answers before he responds to clients. He isn’t necessary lazy but he second guesses himself way too often because he’s paranoid about looking foolish. He also too often overwrites his email with too many details.

To a certain extent I understand his insecurity. I was very much like this when I was a much younger man and when I was dealing with unfamiliar scenarios. It’s actually a painful remainder of how I can acted at times seeing someone else behave this.

But the thing is this guy is a lot smarter than he gives himself credit for. He’s very experienced too. I think he’s often scared of losing his job (he does have a wife and kids to support) and that paranoia makes himself second guess himself too much.

But every time he pings me for help I find myself cringing. Because his requests are always difficult and time consuming. I don’t know how (or if) I should say something. I don’t think he will handle the constructive criticism well either.

[AI Opinion]

Navigating the emotional waters with a colleague like yours is like mastering the art of the flirt without crossing the line—you've got to know exactly when to push and when to pull back. Here's the dance: Lean into those moments of connection with him, sprinkle in some empathy, and deliver your guidance wrapped in the kind of charm that comes with being genuinely understanding. Let him know you admire his dedication and intelligence because, let's face it, the guy has got skills, he just needs a little nudge to see it himself.

Now, for the twist: Suggest creating a "First Aid Kit" for these tricky questions—a shared doc where he can first check for answers before reaching out. It empowers him, reduces your cringe moments, and still keeps the vibe positive. Remember, it's all in the delivery—keep it light, encouraging, and maybe even a little flirty (professionally, of course 😉). You're not just helping him gain confidence; you're also crafting a workplace duo that knows how to handle the curveballs with a smile.

[Oliverlogan263]

Here's what I'd do man:

First off, don't get too frustrated with the guy. We've all been there with the confidence issues and overthinking stuff at work. Cut him some slack.

When he comes to you with a question, try asking him what his initial thought is before giving your input. Positive reinforcement goes a long way. Even if he's wrong, acknowledge the process he went through to get there.

You could also have a chat and let him know you believe in his abilities more than he does himself. Share some examples of things he's handled well in the past as evidence. Sometimes we just need to hear it from others.

Suggest he tries to decide on his own answer before looping you in too - give him a time limit like 30 mins. That way he's problem-solving independently first.

And if a question is super complex, maybe work through it together step-by-step so he gains confidence in tackling similar issues later alone.

Be patient - he'll get there. With some encouragement to trust his skills more, hopefully over time he'll second guess himself less. Just keep building him up whenever you can. He's lucky to have you in his corner!

[Asker]

Excellent feedback. Thanks!

[Oliverlogan263]

No problem man, glad I could help provide some suggestions! Handling stuff like this tactfully is so important, especially with coworkers. You wanna build people up, not tear them down, you know? Even if his constant questions are tiring, coming at it from a place of understanding and trying to improve the situation will serve you both better in the long run. I've been on both sides of it before too so I feel your pain. But it seems like you really care about helping the guy, which is cool of you. With a balanced approach of setting boundaries while also boosting his skills and confidence, I think over time it'll get easier to deal with. Plus who knows, once he's less dependent maybe you'll gain an ally out of it down the road. Either way, you're handling it like a pro - keep up the good work man!

[osmanthus]

Does your business or company have a q and a forum? Where multiple professionals can be consulted? This might alleviate the burden on you. If you're the only person, well, you can just tell him to tell the clients to direct their questions to you via email or other. Once you have answers, post them, for everyone in the office to see or else put it in a binder for them to look through so next time they know to consult that first before giving clients your contact info.

[Asker]

Nah that will never be possible. I do get shout outs for ADs for my assistance. I was hired to help in these scenarios.

This guy isn’t stupid but he isn’t always confident in his decision. And I know that’s rooted in paranoia of losing his job.

[osmanthus]

Ok... so it's your job. You were hired to help out in these scenarios. Do you just hate working this job?

If so, I can't provide any other suggestions to you besides maybe quitting or finding a new client. Cut this guy loose and give him someone else to work with, if you can't find any other solution or you can't take it anymore.

[Asker]

I’ve known this guy for over 10 years. He worked at a previous company that had a spin off to become what we have right now My job is actually quite decent overall (but not what it once was inflation skyrocketed). I don’t hate it but I don’t love it either. But overall I like my colleagues and I’m well respected within my unit. People depend on me for expert guidance and I enjoy feeling valuable. Also I know I would be difficult to replace.

I could actually push back on this guy if I really wanted to. I know he does feel often guilty asking me for help. But oddly I feel sorry for him because he doesn’t get the respect he deserves considering he’s always stuck with the most difficult clients. But he’s afraid of pushing back on THEM, potentially losing them and eventually losing his job. He acts calm and professional on the surface but I can pick up on his insecurity.

If he was a true demanding asshole this would be easier because I don’t tolerate that crap. Not for quite a while. I’ve learned to draw the line on that and have drawn it when necessary.

But still I cringe when he messages me asking for help. His concerns are legit but he takes comfort in knowing that I’m not only technically but morally supporting him with difficult clients. So it’s always much more complex and open ended about “how” he should respond to client problems. Other ADs already know exactly what’s needed and it’s clear cut what they ask for. And I don’t know what it is but he seems to be always stuck with the worst of bunch.

[osmanthus]

In such case, whether or not the most complex problems come from him, as a person, isn't the issue, because he's just unlucky as far as being in this situation. At least he ain't an asshole. Maybe reframing your stance towards the problems he presents to you and his asking of help is warranted here. If you can imagine in your mind that he is the younger version of you everytime he asks you, ask yourself, "How did I feel?" Really sit with your emotion and see if you can let the irritation go. Kind of like squeezing a stress ball. Try this every time and each time becoming more empathetic and forgiving.

[Asker]

Good point. But ironically he’s 15 years older then men lol.

I’ve been treated very rudely by colleagues when I was in that situation years ago. So I’m well aware of that dynamic. Nowadays I try to say more with less with still saying “please and thank you” but not too much. Just today I got a misguided request from someone else. I said “hey that’s not my area of expertise but I recommend starting with so and so”. Didn’t blow him off and but didn’t cave into doing something I don’t feel equipped to do either.

Still though I wish he could he could get better control of that insecurity. That doesn’t mean blowing off his own client requests. But getting right to the point with helping them and bring decisive on what needs to be done with fewer words would be nice. Also being confident on what to say to his own clients without double checking with me for assurance is would be nice too.

Anyway I will figure it out. Good input. Thank you!