I'm part of a small team (4-6 members) with a flat hierarchy in a niche industry. The "boss" (the executive and also our manager) sits in another room as he's managing other teams as well, and therefore doesn't pick up on everyday details and team dynamics.

We got a new hire about a year ago, let's call him Oscar. To sum up Oscar, at first glance he gives the impression of being qualified for his role and he manages to get the job done (sort of), but cooperating and interacting with him is very difficult and straining.

Some of most pressing gripes with Oscars include, but are not limited to:

  1. Unavailability

    • Not willing to come in even 5 minutes early or stay 5 minutes late, when the situation requires it once every few months
    • Evading contact while working from home
  2. Claims a task is done, while a review by a coworker shows the result lacks required level of quality.

  3. Claims a procedure is safe, while a review shows that he spent only minimal time to do the necessary research - much less than required. (Once we almost lost our most critical data, which would have effectively destroyed our department)

  4. Refuses to share information

  5. Oscar makes it difficult to collaborate on a common task, and almost impossible to fill in for him in his absence

  6. Regarding statements directed through Oscar towards our whole team, Oscar doesn't convey the message accurately and clearly, such that someone else has to awkwardly again ask at the source.

  7. Oscar makes inaccurate or misleading statements to outside parties in our team's name.

Our boss is generally approachable and open to remarks and discussion.

Question: What is the appropriate and sensible way to enter into an open discussion with the boss about our concerns when working with Oscar?

Depending on an unknown fact whether the boss is aware of the problem with Oscar, the discussion should lead to following outcome:

  • (The boss isn't aware of the problem with Oscar): Then the boss will take the concern seriously and eventually act upon it,
  • (The boss has known all along): Then the boss discloses this fact to us and ideally at least reveals what the game plan is.
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    Before we answer - I have a key Question: what is your ideal outcome? The Boss fires Oscar? The Boss puts Oscar on a PIP to stop being difficult? The Boss moves Oscar to isolated work loads? We need this answered. Commented Mar 12 at 19:58
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    Maybe I'm missing something but isn't the answer "Just ask"? Explain the issues you had, use concrete examples identifying the outcomes he's caused (either problems or where the rest of the team had to cover) and ask what he thinks you should do. Focus on the problems and not the personalities Commented Mar 12 at 21:23
  • 4
    @TheDemonLord A question "How can I make my boss do a specific thing that I decide" would be answered "You can't". The expectations the OP has seem perfectly reasonable to me. They want their boss to act to address the situation, and (correctly imo) recognise that it's their boss's job to determine what the appropriate action would be.
    – Player One
    Commented Mar 13 at 0:06
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    I suggest to remove the 5 mins early or late part. Outside of work hours is outside of work hours. I doubt that this significantly contributes. Commented Mar 13 at 14:24
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    @infinitezero, I agree completely. Not only that remark is petty, but I can pretty much guarantee you that even if that particular issue gets resolved, Oscar will still remain pretty useless as an employee. Commented Mar 13 at 22:11

4 Answers 4


I see a good escalation path as going like this.

  1. Be super clear with Oscar about one single incident. "Nobody could reach you for 3 hours yesterday when you were working from home. That meant that [whatever happened like you couldn't answer an urgent client question, or production was down, or someone couldn't work on their top priority. Be specific.] Next time this happens I'm going to [boss] to tell them I can't reach you." Optionally, include "if you let us know you're going afk or heads down on a coding spike or whatever it will make things easier for us." That's optional because it might not be true.
  2. If the exact same incident happens again, go to the boss. Present it as you did to Oscar. "Nobody has been able to reach Oscar today and we've been trying since [time]. This has caused [consequence.] What should we do?"

This is an important pause point. Is the underlying problem Oscar's deficiencies, or that they are bottlenecks for you? For example, why is important information being relayed through him when he's not good at relaying it in a way you can all receive? One reason would be "nobody knows he's not good at that." Why is his unavailability when WFH a problem for anyone else? Does your system not have a way to "route around" someone not being available?

  1. If a different problem arises, raise it to Oscar first, with the same wording. "You didn't mention the backup requirements when you summarized your one-on-one with x, and that caused [consequence]." You're not speaking from a "you're in trouble" place of authority nor "I'm telling on you!" peer. You're showing the consequences to you personally of what you see as a deficiency in Oscar (which may be a deficiency in your system or something else.)

  2. When you need to report a second incident to the boss, it's ok to briefly refer to the fact it's a second one. "Sorry to bother you boss, but I wanted to let you know the reason for the fire drill yesterday. Oscar knew we were supposed to x, but didn't tell anyone else, so we didn't do it, and then the client called asking where it was. I know it sounds like I'm just complaining about Oscar all the time, but we've had two problems this week/month and they both happened to concern him, that's all."

  3. Once you escalate to your boss, leave it with your boss. You can keep telling Oscar "you did this thing, which caused this result. Please don't do that thing to me any more" if you want, but don't follow up with your boss to see what's going to happen with Oscar or whatever. You can of course report new incidents, and it might be helpful to do so, unless your boss says they don't want any further reports.

Sometimes people are just in the wrong role, and with a little adjustment they can find a happy place on the team. Sometimes people are going through a rough patch outside of work, and not able to be their best at work, but come back stronger and appreciating the place that understood. Sometimes people are coasting or lazing and a kick in the pants fixes that. Sometimes people are mad about other things and practicing on the job retirement as a result. Oscar may improve, or may leave, and you may never know exactly why, but then again you probably don't care as long as one of those two things ends up happening.

  • Not willing to come in even 5 minutes early or stay 5 minutes late

Not everyone is. This will be factored into his performance reviews. NOT YOUR PROBLEM; accept it and move on

  • Evading contact while working from home

Judgmental. You don't know if he is "avoiding" or just highly focused on what he is doing and not accepting interruptions. WRONG FOCUS; if you need him to respond within a specific amount of time ask your manager if that is a reasonable expectation and if so could the manager take it up with him. Be sure you have logs of every time you reach out and how long he takes to get back to you, or this may be dismissed as a biased reaction... and because that gives the manager a concrete basis in which to say either he's being slow or you're being unreasonably impatient.

  • Claims a task is done, while a review by a coworker shows the result lacks required level of quality.
  • Claims a procedure is safe, while a review shows that he spent only minimal time to do the necessary research - much less than required.

Have you worked with him to help review his code and teach him how to avoid these errors? Nothing should be committed to the code base without at least an opportunity for review. Nothing should be committed without running existing regression tests and writing new ones as necessary.

  • Refuses to share information

Refuses, or doesn't know how, or doesn't understand that it's part of the job? Again, education may be what's needed, along with requirements that design and implementation be documented.

  • Oscar doesn't convey the message accurately and clearly.
  • Oscar makes inaccurate or misleading statements to outside parties.

Again, sounds like he's a bit out of his depth and needs education in how to take a complete and accurate problem report, and in how to communicate with customers (including learning to say "I'm not sure, but I'll get you that answer" rather than guessing). Or needs better language skills. Or should not be assigned customer-facing tasks in the first place. Don't just complain about his weaknesses; figure out how to address them or avoid them.

You have a great opportunity here to build your reputation as a mentor. And if you tell your manager you're doing this and can show some success it will look great on your performance evaluation. But that starts by recognizing that rather than just complaining you need to actively engage, guide and teach, and need to exercise some patience and compassion in the meantime. Plus making sure the individual is assigned tasks not too far beyond their capabilities.

This is all assuming your description is accurate. You probably want to run this by your manager and get the mentoring role made official before meddling too much.


While the ship might have sailed on this, I want to impose a slight frame challenge on this: is Oscar aware about it?

Before you escalate you should make sure to tell Oscar first. If he was given the impression that what he was doing was fine or good enough, than there's little incentive for him to change anything.
Instead you should teach him to do work at an acceptable level, i.e. he himself will have to fix it, until it is acceptable. If he has to do it over and over again he should soon realise that it's faster and easier to be more careful next time before submitting something unusable.
If the project gets delayed and your boss asks, simply state "we're waiting on Oscar to complete part X".

For the unavailability issue, just let him know that you tried to reach him for something urgent yesterday at 14:00 and the team calendar didn't show him being absent. This should remind him that it's not ok to just do whatever when working home. If this continues you can just ask your superior about it: "hey I'm trying to reach Oscar, do you know anything?"

This way you're stating facts, make no blame and also don't "rat somebody out". It's then up to your boss to decide if they want to take any action.

  • 1
    That's a good point. I'm sure Oscar knows what he's doing. However I'm not certain that he's aware of the consequences on the teams morale. Be it as it may, there is nothing else left than escalation. We're all peers, we can not give him "orders" and when we express any shortcomings he simply refuses to do anything beyond his own judgement.
    – Zipper
    Commented Mar 14 at 2:22

My gut tells me, there needs to be some finesse about it and I should not just bluntly unload without any qualm"

To expand on a comment the way to clean the air, is to "just tell him". But as you said, it's important to phrase it correctly, in order to achieve a good outcome. With this in mind I'd focus on:

  • stick to facts
  • be curious, not judgemental, as to what your boss might have done/known already.

For sticking to facts, there's lots of good writing online about giving feedback. It's normally aimed at giving feedback to the person affected, but the principles are similar for talking to a manager;

  • explain the situation where you saw the behaviour
  • describe the behaviour,
  • explain the impact the behaviour had (a project was delayed, someone had to work late, etc),
  • explain what the behaviour could be different next time.

The focus is very much the behaviour, not the person. That means you're focussing on what's really important, and it's less likely you'll be seen as having a personal grudge against the team member.

For being curious, you're already doing that, because you mentioned that you wondered if you're boss is aware but is worried about hiring a replacement. By being curious and not just assuming they're unaware/don't care, you're less likely to put them on the defensive and make them feel like they have to justify something ("why haven't you fired him yet?"). You're also making yourself part of the solution, by trying to find out all the facts, before charging in to say something like a PIP is the only answer.

  • Right, feelings (other than curiosity) are a big impediment in the workplace. Check them at the door. Commented Mar 15 at 14:38

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