I work in a company that's extremely chaotic and absolutely not modern in terms of IT technologies and processes.

I worked in 5+ companies before but haven't experienced anything like that before. Basically, it's a major disaster and the causes are clear, although I wouldn't like to go into them now.

Now I have a new employee. When recruiting him I did signal what the situation is. I also asked him situational questions ("What would you do if ...") to find out what his reaction to the situation would be.

Now he is onboard and I see he is getting more and more shocked and frustrated with what he's got to work with. I understand this frustration since my reaction was exactly the same. Actually he's asking the same questions I asked after I started. I make it clear to him that I understand what he's frustrated about but also that it's a long way to change it - I don't want to lie.

Apart from that, he is very good, picking up things quickly. I'm happy with his performance.

At the same time, I have reasons to think he might be looking for a new job because of his frustration. Realistically speaking he would get similar money (probably 5-10% less, but that's not a huge difference) but have a much easier job at another company.

What can I do to make him stay? A salary increase isn't an option. I try to stress the potential to learn and transform things in the current setting, but I'm not sure that's convincing. Our relationship is good and I don't expect him to do unpaid overtime.


Why I want him to stay: I've had several people quit quoting the issues mentioned here or unable to work in these conditions. I can't afford to have another one.

  • 1
    What have senior management said to you when you reported to them that you have a retention problem due to the technologies (and processes) they've chosen? (Unless you are senior management of course...) Oct 4, 2020 at 8:22
  • @PhilipKendall, they see it as quitting employees' lack of skills/ maturity.
    – BigMadAndy
    Oct 4, 2020 at 8:36
  • 3
    "What can I do to make him stay? A salary increase isn't an option. I try to stress the potential to learn and transform things in the current setting, but I'm not sure that's convincing." What have you managed to transform in your tenure here?
    – Aida Paul
    Oct 4, 2020 at 8:46
  • 1
    @JoeStrazzere, I'm a realist and I know I can run into a similarly bad situation elsewhere. Bad bosses, unreasonable expectations, lack of investment, I've seen a lot. I'm first trying to fix it and learn as much as I can in the process. If it doesn't work I know what I should do.
    – BigMadAndy
    Oct 4, 2020 at 11:27
  • 1
    It would seem like the only one not learning, is the employer. Sometimes you find employers are so fixed in their views, that only a life-threatening haemorrhage of cash will change their ways, and some would sooner go to the grave than change.
    – Steve
    Oct 4, 2020 at 11:36

5 Answers 5


I make it clear to him that I understand what he's frustrated about but also that it's a long way to change it - I don't want to lie. Apart from that, he is very good, picking up things quickly. I'm happy with his performance.

With a little bit of conjecturing it sounds like you are saying "Don't worry about it, management is dealing with this, until then do do your job and trust in management. Everything is fine." Your developers won't trust in management, since management already let the situation turn into what it is today.

Instead you want to send the message: "I know it is a mess, and we need your help to fix it. Let me get the support you need."

Ask your developers what their biggest impediments are and which of those are most easy to solve. Pick the top priority item and let developers find a solution. Don't limit it to technical solutions explicitly include changes of more organisational nature, like "Have marketing communicate campaigns earlier" or "Block releases if tests fail". Then ask them "What do you need from me?". Don't do the work for them but be their voice when talking to upper management, or unblock them where you can:

  • If they need 2 servers for a new test environment make sure they get it
  • If they want to propose a change in workflow, find the right person who can make a decision on it
  • If they need every developer to follow the coding guidelines, enforce it as a policy

These things won't be over night successes and probably need multiple iterations to work, but now your (more senior) developers have an active role in the transformation. It stops being a developer vs. management thing.

Try to be biased on changes that you can do locally in your part of the organisation. Maybe you cannot hold your whole organisation to high testing standards, but you certainly can make it for code owned by your department.

Finally make sure that the work done on improving the current situation is recognized. It is not something you allow them to make them happy, it is something you encourage because it will increase efficiency and has a high impact on business numbers. Make sure people have time to officially work on this and are not supposed to do it in their spare time. Push for the priorities you agreed on.

  • 2
    "If they need 2 servers for a new test environment make sure they get it" That's what I'm trying to do. But then my boss comes and say: "I won't give you 2 servers. You don't need it". Discussions bring nothing. My team members know I'm on their side but I have limited power here. I could act against my bosses' wishes and I'm trying to do that whenever it's possible but I can't do something they explicitly told me not to. My solution is not consulting them on as much as possible. But they want to be consulted on most decisions.
    – BigMadAndy
    Oct 4, 2020 at 9:02
  • 8
    Your job as a middle manager is to translate from your developers to upper management. You need to either make management see why they need those servers, have your developers understand why they cannot be bought and what the alternatives are they can work with, or a good compromise solution. If you agree with your developers, but are not doing enough to make management understand, from their eyes you will be part of the problem.
    – Helena
    Oct 4, 2020 at 9:34
  • 5
    This probably should be its own question, but you need to make it clear to management that you need those changes, not to make developers happy, but because they will make a positive impact on the bottom line. "We believe we can save 10 developer hours per week [show a link to an internal survey for data], which translates to 4000$/month by renting two servers for together 200$/month"
    – Helena
    Oct 4, 2020 at 9:40
  • 2
    @Helena at this point you could probably even say "We either pay for 2 new servers or for the recruiting process for another developer again" and that should be case enough given how expensive hiring a new employee is.
    – Erik
    Oct 4, 2020 at 11:16
  • 5
    @Erik you could, but 1.) it is hard to show evidence that this is what will make people quit, and 2.) it can create the impression that testing servers are just something you give to developers to make the unreasonable and spoiled developers happy. You want management to trust in their developers actually making the right decisions for business.
    – Helena
    Oct 4, 2020 at 11:20

Given the situation, I'd really focus on you instead of "your employee". I hope that answering the following questions may lead you to set achievable and satisfying goals.

  • Why are you calling him "your employee"? You are not his employer and he is just a colleague and a member of the team you lead.
  • Why do you really want him to stay? Pay isn't that great and the job is a mess.
  • (most important) Why do you want to stay and fix all this mess?

It looks to me that you really care about your company in a genuine way. However, it's also apparent that you were not grant much power. You need to realize that the company isn't yours and you have little to none way in changing its culture. Your goal is not to redeem the situation. You just have to do your job.

Bottom line:

  • You should not try to convince him to stay. That should be a byproduct: if the job is great, he is going to stay, otherwise he'll leave. He is the judge about it. You also don't want to trick him in a way that eventually hurts his career path.
  • You should stop caring that much about the company. Report any problem to the management and state clearly that you are not going to reach project goals if some conditions are not met. Let them be aware of the fact that there is a reason why a lot of people are leaving.
  • Consider carefully pros and cons of your situation. Leave emotions aside. The company isn't yours. And btw, you can afford another people leaving. The company might not, but, again, the company is not yours.
  • You just have to make your best effort in doing your job, but no more than that. If you see it falling, communicate it to the management. If they don't want to act, fine, it's their decision. Take your decisions consequently.

Your comments said more than your post on this, so I'll bring one up:

I can't get rid of these frustrations... I've got rid of those I was able to get rid of. But my bosses' explicit decisions prevent me from getting rid of the rest.


Actually he's asking the same questions I asked after I started.

It is painfully clear that you are not able to fix the situation. If you did, the same issues would not still be outstanding as they were when you joined up.

Whether it's because the boss is inept or it's because you don't know how to properly explain those issues doesn't really matter.

I make it clear to him that I understand what he's frustrated about but also that it's a long way to change it - I don't want to lie.

Given that you are unable to get what you need from your boss, how is this a long way to change, and not the likely reality that it's likely to never change at all? That certainly is how I would view it from employee's perspective when I have a manager who did not fix the issues he had when joining in, and now is telling me about extremely vague "long way to change it" with nothing concrete to back it up. That's also likely why your promises of being able to change things are falling on deaf ears as talk is cheap and lack of progress counteracts it.

What can I do to make him stay?

The way you describe it there is very little you can do.

You cannot offer him anything to directly offset the mental anguish caused by the job which could come in form of better salary, more robust holidays package, other bonuses. You also are unable to fix the underlaying problem, at least not in a timely fashion.

As far as I can tell your only move is complete transparency.

This is when you communicate to employees exactly what you have tried to do to solve the problem and what was the outcome. You are also then open to input and help in attempt to solve the problem. With that approach the employee is not being given empty words, but can see actual actions taking place and has the power to shape said actions. And it's a big difference between being told about something supposedly happening and being directly involved in it.

A high risk strategy for sure, because if the employee is now on the fence, maybe seeing just how stubborn your boss is may make up his mind about leaving. But then on the upside he may offer great insight on how to actually approach the boss in more successful way. You won't know until you try.

  • Any downvoters interested in adding a comment?
    – Aida Paul
    Oct 4, 2020 at 10:38
  • one addendum: when OP is planning on sitting this out and changing it in the long haul with this strategy, it's an option to ask the dev to bring up the problems he encountered in an exit interview. That way you can slowly gather data to support your understanding that all the little problems are what causes the high turnover (and associated cost). Being honest towards the dev can help in that as it makes it more reasonable to ask for honest exit interview feedback (if the dev only ever hears promises why should they open up with honest facts then). (only when they actually leave of course^^) Oct 4, 2020 at 17:43
  • If you were my boss, I'd be frankly grateful for your honesty, and, for as long as I stayed, you'd have my earnest loyalty. But then I'd start applying to other jobs. Life's too short to waste challenging upper management, especially in IT, where so many companies are more than willing to throw resources at you in exchange for a decent level of commitment and professionalism. But I like your strategy: since he's going to find out on his own anyway, go ahead and try to gain his trust, at least.
    – Ramon Melo
    Oct 4, 2020 at 20:45
  • @RamonMelo Something to keep in mind that quitting a job within first 1-3 months is generally not a good look, it puts a pretty sizeable flag to most recruiters, and if you have few entries like that it starts to become a burden questioning the judgement. So just outright leaving ASAP is probably not the employees first goal (if it is, he is lost anyway and nothing will save it), but I would not blame anyone for putting the feelers into the market all the same.
    – Aida Paul
    Oct 4, 2020 at 20:50
  • 1
    Surely, but there are ways around it: networking, leaving it out of the resume, building personal projects. But make no mistake: leaving is not this employee's first goal at all. On the contrary, he's clearly motivated and devoted to the job. His frustration comes from not being able to commit deeper into his work. Which is why being open about it might work, he might be swayed by the challenge and persuaded to stay working with someone he trusts. Or the exact opposite. High risk, as you said.
    – Ramon Melo
    Oct 4, 2020 at 21:06

You need to fix something. It sounds like you're very aware that words saying "it'll get better in the future" are all well and good but don't actually improve anything. Find out what his biggest frustration is and do whatever you can to get rid of that frustration. Then go to work on the next frustration.

I'd still expect him to leave though; it sounds like this job just wasn't the right fit for him. So what can you do to stop this happening in future if you can't change the company culture? My only suggestion is to change the sort of people you hire - some people want a dynamic work environment with the latest technologies and tools, and they don't sound like a good fit for your employer. Other people are happy just to turn up, put up with whatever's there and get paid at the end of the day - they're the sort of people you're looking for. Look for people who have had a steady job with a larger organisation, possibly those who seem to have reached their potential and aren't getting rapidly promoted any more.

  • I can't get rid of these frustrations... I've got rid of those I was able to get rid of. But my bosses' explicit decisions prevent me from getting rid of the rest.
    – BigMadAndy
    Oct 4, 2020 at 8:54
  • Time to sort your CV out as well then... Oct 4, 2020 at 8:56
  • 2
    @BigMadAndy either convince your boss with repeated arguments and clear documentation why their decisions cost the company money and therefore need to be changed, live with the crap you have or leave. Oct 4, 2020 at 17:36
  • One caveeat with finding people that are happy in the place like it is -> the result will be that it will get even crappier and cost of changes in that system will rise and rise. If you want to change, you need someone that wants that too, but perhaps also someone that is patient and determined enough to make that change happen over time instead of expecting it to happen over night. Oct 4, 2020 at 17:38

If options for making the work environment are genuinely exhausted then you still have a few levers available to pull to make the workplace more attractive.

  • Be genuine and transparent - Be open with your team about challenges and what you are doing to resolve things. If they see you are trying your best to help them, they will give you more slack.
  • Reduce workload and free up time for learning and development - This will make your place an attractive place to stay for 1-2 years to gain experience before going onto something better
  • (A bad one but hey...) Adjust hiring to better suit the place - Not everyone is super ambitious, want to work with the latest tech and go somewhere. Some people are happy to stick to tech they know and focus on other things e.g. family. Select people who have put up with bad environments in the past.

Not exactly a great set of levers but plenty of places like this do exist and people make careers out of it. It sounds like you do care and realise the bad practices. So maybe a better question is - why do you stay at your current workplace.

You must log in to answer this question.

Not the answer you're looking for? Browse other questions tagged .