The gist of the situation is this:

  • the company I work for got sold

  • my manager used to be CEO, now he has people he’s reporting to. We are both programmers and we are working together on projects

  • the people he reports to push us to do estimates on completely unknown scopes. For example, we are working on a project that uses a messaging queue, and none of us ever worked on anything like it. Then they hold us accountable for the dates we set. Even though we state that’s those are wild guesses

  • he doesn’t push back and instead says things like: ‘We have to get our shit together. If you don’t do your part of the project, I am going to hack a solution and ship it without your part”. Where I am responsible for most of the work and on his end he just calls my API endpoint.

  • the product is complex and every time we touch something, new issues arise and he fails to acknowledge that it’ll take more time to do and he doesn’t increase the project timeline

Overall, it looks like he is more concerned with doing whatever his managers say without looking at well being of the team. We had a meeting with the developers of the company that owns us, and I specifically asked about how they estimate time and how they track their time. They said they don’t do it because it’s too hard and it’s giving them any benefits.

I really don’t want to change jobs. I like my colleagues, I like the projects and I am always learning new things. I just feel like this situation is new to my boss as he never had to report to people with more power about his subordinates and he worries more about how they perceive him and not worries that his employees will quit.

I am thinking about telling him that I am not happy with what’s going on and explain why I am unhappy.

Any thoughts?

  • 1
    It is really strange that you have to do estimates and others don't. To fight that you can play out in following way. When they ask for the estimates think about every little thing that may come out and estimate max than you would think it would take, then quadruple the number. Then add some time to account the specs change (yeah, yeah this never happens). When getting asked why your estimates are so high go into the details on why would it take so much and stay close to your numbers. Keep in mind there are always going to be distractions, etc.
    – AlexanderM
    Jun 30, 2019 at 22:44
  • 1
    Join or form a union. This is a question of democracy and power in the workplace, which is fundamentally a bigger and more structural question than the interpersonal relationship between you and your immediate manager.
    – iono
    Jul 1, 2019 at 10:18
  • No, find a new job and that will make it clear
    – Max A.
    Jul 1, 2019 at 12:31

4 Answers 4


Simply telling him you are unhappy, while true, isn't particularly constructive. You say you don't want to change jobs so by extension you are more interested in "fixing" your current situation.

Overall, it looks like he is more concerned with doing whatever his managers say without looking at well being of the team.

While I can sympathize that this is causing you problems I'm sure it's no picnic for him either - he's gone from having near autonomy day-to-day to once again having a "boss" and this takes some adjusting to - as you mentioned this is new for him and there's bound to be a period of adjustment. At the moment it sound like either he has swung too far towards keeping the new boss(es) happy or possibly they are giving him an disporportionately hard time.

Obviously the current situation can't continue indefinitely so you need to focus on ways you can improve things. Just telling your manager that you are "unhappy" doesn't do much for that. Instead I'd suggest talking to him about ways you can resolve the issues and going from there.

the people he reports to push us to do estimates on completely unknown scopes

Ideally you'd address the scoping problem itself - who does have the answers to the questions? Is there any way you can contact the appropriate people before giving the estimates?

Then they hold us accountable for the dates we set. Even though we state that’s those are wild guesse

If you're giving wild guesses then that's a problem - an estimate might be unavoidably inaccurate if your simply don't know what you don't know but that being the case you need to err on the side of caution, do some quick research on the subject matter come up with what you thing the worst case is and multiply it by 1.5, if your boss queries it being on the high side explain that there's unknowns and if you can get better scoping you will be able to give a more accurate one but failing that you want to make sure you meet or exceed the estimates rather than going over.

Also as you get more into the swing of technologies that were previously unfamiliar you'll get more of a feel for how long things take.

Trying to estimate development stuff sucks - it's a complete minefield a lot of the time but it's not a concept that's going to go away any time soon. Businesses need to be able to plan timescales for things, even if only roughly.

  • Yes I completely agree with this: While I can sympathize that this is causing you problems I'm sure it's no picnic for him either I think he needs time for adjustment and I am too emotional about this whole thing. I should take a breath and give it a couple of months to see what happens. Fortunately market for programmers is very appreciative, so if it doesn't improve I am confident I'll be able to switch jobs easily.
    – bobek
    Jul 1, 2019 at 13:21
  • When you don't know what you'll have to develop, hope for the best but prepare for the worst.
    – T. Sar
    Jul 1, 2019 at 16:01

I am thinking about telling him that I am not happy with what’s going on and explain why I am unhappy.

Any thoughts?

What would you expect to accomplish by telling your manager that you are not happy?

If you just want to talk, and get his take on the situation, then it makes a lot of sense. If you expect him to stop doing what his managers say, then I suspect you are wasting your time.

I've been part of many acquisitions. Middle managers often get caught in a tough position - they want to protect their team as much as possible, but sometimes that means working with the new upper management and figuring out how to satisfy them at the same time.

When my company was acquired, I always attempted to figure out what my team could do to be successful. Sometimes that meant just doing what we had always done. More often, it meant coming up to speed on the acquiring company's methods and culture and trying to get my team on board.

It was never easy. Sometimes it was successful. Quite often, people left (including me).

One way to look at it is "would you choose to work for the acquiring company if you were on the market?" Often the answer is "No."

  • 1
    The thing is, I would definitely want to work for the company that acquired us. It's a great company. I think I just need to give it time for 1. My manager to adjust and 2. For me to adjust. Thank you for your answer Joe.
    – bobek
    Jul 1, 2019 at 13:24

That depends a bit on how good your relationship with your manager is. In healthy relation ship, that's perfectly ok to talk about, if you follow some simple guidelines

  1. Don't make it a complaining session. Make it about a problem and finding a solution.
  2. Make sure you understand what your goal is and what different outcomes are acceptable for you. Think this through BEFORE you have the meeting
  3. Understand your options and do your homework. If you are seriously considering leaving, it wouldn't harm to to clean up your resume and apply to a few positions up front, so you can get an understanding what the current employment situation looks like.

Let's say you have this all worked out: schedule a 1:1 with your boss and walk him through your thought process

  1. State the problem as objectively as possible. Don't blame, don't gripe, don't dwell on the root cause, just state the problem and show data if you have it. Example: "Our current track record of scoping work has been pretty poor. For project XYZ we estimated 2 sprints but it took 4 and even then I had to work nights and weekends".
  2. State what the impact of the problem is and what would happen if it doesn't get fixed. Example "that's not working for anyone: the main company is unhappy since delivery dates shift and I'm unhappy since it generates a lot of stress and impacts the quality of my work"
  3. Suggest some solution and explain why the current approach (if any) doesn't work. Example: "Just working harder is not going to fix it. I feel we need to get better at scoping. Perhaps we could get some training or tools to help with this. Maybe we can get a resource from the mother company to support or coach us through the process. I was trying to understand their process, but I didn't get very far.
  4. State your acceptable outcomes. "I would love to get better at this, but I need help: training or coaching for example" "If we can't improve our scoping I need some way to protect my free time and get the work load to a sustainable level". "if we can't improve scoping more project slips are inevitable. We need a process to deal with this in a sustainable way"
  5. Ask an open question and start listening: "What do you think we should do ?"

As the discussion progresses, you need to hold your ground. Make a list of potential evasive answers and practice your reply to them. Example: "Boss: This is just temporary, in two weeks it will be fine". "You: Sorry, but I don't think so. This has been going on for a year now and I see no signs of improvement. Unless there was recently a significant change that I don't know about, I don't see how this can get better". etc.

  • Thank's so much for your reply. I decided to let it sit for a while but I'll definitely come back to your answer when I am ready to have the talk.
    – bobek
    Jul 1, 2019 at 13:22

About your estimates: An estimate is an estimate. If your estimates are perfect then it is 50% likely that you finis earlier, and 50% likely that you finish later. Apparently your new management doesn’t get that; when they ask for an estimate they actually want a 100% guaranteed delivery date. Obviously a 100% guaranteed delivery date is later, so you adjust your “estimates”. But not to what people want to hear, not to when you would like to be finished, but to the time when you can guarantee it’s finished. 100% guaranteed even with several unexpected problems happening.

About technical debt: What you say that every change causes unexpected problems means you have huge amounts of “technical debt”. How many thinks do you need to know to make a change that should be harmless without breaking things? You can fix this by refactoring code, or by documenting. Each takes time, documenting is safer. But you have self imposed delivery dates that don’t leave you any time.

You can tell your ex-CEO all this. Explain to him that he is setting himself, you, and the company up for failure. Maybe he’ll make changes. Or you can tell his superiors that his estimates are totally unreasonably, basically backstabbing him in the hope to get his job. Or you can start looking for a new job in a more sane place.

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