I work (first "sidejob", 2 years) for a company who's offering me freelance work. It's great. It pays extremely well.

There's a person in a management position who organizes our orders. Previously the communication and cooperation went smoothly, friendly and just great, with the manager and the team. It made me put in the extra effort or work when they needed, help them with questions, etc. It wasn't part of my task, but I enjoyed it and felt valued.

However the company itself has, to my idea, a high turnover rate (I suspect from underpaying their employees/lack of growth opportunities, risk averse business model, not my problem), and they had some struggle in filling the management positions.

I cooperate much worse with the new person in the management position compared to the previous 2. Previously I felt appreciated and not "used". However this new person tends to not show appreciation, make me feel used, and gives feedback that is unnecessary harsh to the degree the team turns to me for guidance more often. There is a general vibe that she feels she needs to milk every margin, at the expense of others (what I do, and the company itself is already very profitable). She got promoted from within the company and has close ties with the one who runs the company. I feel like she wants to "prove" herself, but what she does is very counterproductive.

I am not in the position to give her direct feedback, and hints given to her would been taken as a harsh personal attack.
I am playing with the idea of sending the head of the company just a message with the scope of "Hey I've worked with your company for 2 years, and with great pleasure. I felt appreciated and went along well with previous managers, however the current one is a bit of a hassle, and is therefor reducing my work pleasure. I don't know how to give her the feedback directly, just so you know, good luck with it".

I've made enough money to be able to lose the job, but it would be a pity. I don't want to ruin work relations, being well aware it's actually none of my business. I am an outsider, and it's kinda weird the way I want to inform them about the dysfunction of one of their employees. But then besides the job, it seems I've nothing to lose. How would a company react to such a message? And would there be a possible reward in being this directly as an outsider, unrelated to the manager in question?

  • Not sure if this is the case, but are you doing work that overlaps with the work of the full time employees? This can produce some asymmetrical feelings among different individual employees/ managers of the client . . .
    – Pete W
    Apr 28, 2021 at 13:02
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    "I am partially wondering if the reputation of someone who's super efficient, brutally honest and unconvential but odd, might be most rewarding." - maybe if you are playing a cop in a fictional TV show. Apr 28, 2021 at 15:10
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    While there are times for it, IMO brutal honesty does not work for most people most of the time. A lot of the stuff people write here on SE, for example, would be foolish to say IRL except with people who have known you long enough to trust that you are being unusually direct for a good reason. That said, being uncompromising about strictly technical matters is a good thing, but even then, how you say it matters.
    – Pete W
    Apr 28, 2021 at 15:10
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    Just wait for the next manager...
    – Laurent S.
    Apr 28, 2021 at 19:49
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    What do you hope to gain by sending this email? What do you (realistically) think they'll do? It may be better to ask a question about how to achieve whatever you want to achieve directly (assuming it's something other than "fire her") instead of asking about your proposed email. If the email has no goal, then you definitely should find one first. Are there any specific problems with dealing with her that you feel can potentially be changed? It might also make sense to ask a question (or two) about those instead. Apr 28, 2021 at 21:08

6 Answers 6


This is a business relationship. Whether it is a comfortable one or not should not be the main focus. The relationship no doubt has contractual terms?

If you are not contractually obliged to deal with this individual then just stop dealing with them. Deal with someone you like better.

If you are obliged, then try to communicate as much as you can via email. That way your conversations are always on the record, and it should be clear if any one party is being unreasonable.

If you are obliged to have face to face meetings with this individual, be transparent to them when you think they are wrong. It is perfectly valid in a business relationship to have disagreements about how work gets done. You can do this without emotion, just the facts.

Definitely do not try to give them "feedback".

Ultimately how this individual behaves is not up to you, and you will have little influence over it. I guess you need to decide whether dealing with them is worth the cash you are billing them to do it.

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    "be transparent to them when you think they are wrong" - to a reasonable degree, yes. If they're wrong about something that doesn't matter and doesn't have any further-reaching consequences, that might not be worth speaking up about. If you've already told them they're wrong, it's not constructive to say that again. If they already committed to a decision (bought something, signed a contract, etc.), it probably doesn't help much to tell them they were wrong to do that: focus on things they can actually still change. If disagreeing always goes badly, stop doing that or change your approach. Apr 28, 2021 at 20:15
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    An occasional battle-axe personality is no big deal, as you said, if it's possible to limit interaction. But the problem here is a Machavellian manager in a leadership position who is "milking every margin at the expense of others". That's extremely destructive not only to the well-being of co-workers but also in terms of their productivity and turn-over. OP should eventually leave and cite this manager as the core reason for their departure and why. Just tolerating it for the money only works for so long, one cannot pretend they don't have emotions.
    – teego1967
    Apr 29, 2021 at 13:18

I understand OP's position - sometimes it is hard to look at a situation that has gotten worse, you can see the problem and what would help (this manager becoming less abrasive & more helpful) and you want to be able to help improve the situation or pass on your solution. However as most of the other answers are pointing out, this is not something that is part of OPs duties for the company or their responsibilities so they probably cannot and should not do much.

If OP was friends with the head of the company, then it might be possible to have a quiet conversation with them (nothing in writing!) just suggesting they look at the manager's style. Alternatively if OP decides to stop working with the company altogether then as a consultant they are in a position to give "exit feedback" that an employee might not, but I still wouldn't specifically mention anything from the current manager (Manager C) For example

I greatly enjoyed working with your company under Manager A & Manager B, however I am no longer having as much fun and have decided to move on.

If the Head of Company is already concerned about Manager C that will point them in the right direction, if not anything you say is not going to matter anyway.

Outside of those possibilities though, the best option is just to deal with the awkward manager as best you can. If turnover there is so quick, they may be replaced soon anyway.

  • A side note is, my previous managers were young and overqualified (especially one of them), yet the current one is not, thuse less likely to leave/switch positions. So to some degree I might just been lucky.
    – Gerben
    Apr 28, 2021 at 23:47
  • +1 good approach. I would not even mention Manager A & B in the e-mail. Just state that your business relationship with the company has changed for the worse lately, and that you find yourself unable to work with them under the new circumstances. If they receipient of your e-mail is interested in what you are saying, they will be able to figure out the cause of the problem.
    – Theo Tiger
    May 14, 2021 at 10:26

Bad idea.

She got promoted from within the company and has close ties with the one who runs the company.

... hints given to her would been taken as a harsh personal attack.

I am playing with the idea of sending the head of the company

What do you hope to accomplish? Going over her head would be seen much more as a personal attack than any comment you would give her face to face. If she also 'has close ties' with them, no good will come of it. The head will likely see you as a trouble-maker, tell your manager, and your manager will see you as a backstabber. If you had friendly relations with the head and the manager was just some recent hire from outside the company it wouldn't be quite so bad.

What makes you think any comments would be taken as a harsh personal attack? Do you ever get performance reviews from either the owner or the manager? I'm guessing as a freelancer the answer is 'no'.

One option for you is to just 'tough it out'. It sounds like you are not happy with the situation though. It sounds like the money is good so you'd still like to stay if nothing changed, but you would miss the times when you were more satisfied with your work. But you are dissatisfied enough that you want to do something to try and regain your lost happiness.

You could try to talk to your manager. If you do, try to make things about you and not her. Use phrases like "I feel ..." and not "You make me feel ...". You mention they probably under-pay their employees. I think your new manager probably knows how much you make and if it's not more than they're currently making, it's probably more than she made before her promotion. This will make it seem to her like she was/is not being treated fairly and that you are getting preferential treatment. As a manager she should look at the numbers and see that you cost X, make the company Y, and Y > X so you are an asset. Those calculations don't always happen when someone feels like they are getting the short end themselves.

Another option of course is to cut down or stop doing the freelance work. Maybe you could just do this temporarily and hope the management changes: "I'm really busy in my personal life now and need to cut back on my workload for a while".

If you had been 'going the extra mile' and you just stop, this can backfire. Sure it's not all your fault because you just don't feel like doing that anymore, but the decrease in your productivity will be noticed. This will feed into your manager's feelings that you had been given preferential treatment and aren't worth the money. Yes she is setting you up to fail, knowingly or unknowingly.


Unfortunately, there is no way to fix this problem because the manager has higher priority than you. Unless there is a coordinated revolt, the manager will not be moved because one subordinate complained.

Your options are to put up with it or quit. My advice would be to look for a different position. When things like this happen, it is an omen that it is time for a change.

  • I don't feel like a subordinates, atleast with previous managers. And I don't think my only options are to quit or put up with it. I do have some influence, either be it directly with the manager (which isn't the case), but I do with the relations I have with them and how i shape them. And it's not that bad, we are not hostile. At times she tries to please me, but does so incorrectly actually offending me without knowing.
    – Gerben
    Apr 28, 2021 at 23:59
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    @Gerben Well, I am speaking generically. In general, contractors have less weight than their employer managers, and if there is a personal relationship involved, then it is even more of a problem. If you try to maneuver around her, it will just create bad blood which will be difficult to fix. You don't want to try to fight a political battle from a losing position.
    – Socrates
    Apr 29, 2021 at 0:37
  • True. I know. But I felt as if I had nothing to lose because it seemed like i've nothing to gain at this point. But I can keep the relations, albeit much colder and less coperative, and focus more on being a contractor. Previously being a contractor was a means of freedom, but it could also offer new challanges.
    – Gerben
    Apr 29, 2021 at 0:49
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    @Gerben, fine, if you push through it, no problem. However, the voice of experience reminds you that when political problems begin to mount up, it's a bad omen. You may want to re-evaluate your career path and look for new avenues in life.
    – Socrates
    Apr 29, 2021 at 1:38

It is often said on this list

  • "It's not high school."

1, Do the work asked, 2, Work exactly N.00.00 hours where N is the hours you are paid for, 3, go home happy.

Regarding the annoying person, every job anyone ever works at has one or more annoying people.

End of story.

I can not even remember the full name of someone we are working for presently - that's the attitude. You work to live: work is not life.

"Hey I've worked with your company for 2 years, and with great pleassure. I felt appricated and went along well with previous managers, however the current one is a bit of a hassle, and is therefor reducing my work pleassure. I don't know how to give her the feedback direct, just so you know, goodluck with it".

This would be so bizarre, the person would either just delete the email, or, email you back with a chuckle saying "Please get back to work!"

Regarding the annoying person, every job anyone ever works at has one or more annoying people. End of story.

It sounds like you have a great situation - enjoy!

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    Yeah this is not how I work. I'd consider working free if people had fun jobs (I actually consider sending solicitation, with this tone). I made with this job more then enough money while I barely needed any. I don't spend that much, yet I can live as a king. And whatever will happen I will most likely make much more in the future. Payment is not the real concern other then that it's a token of appriciation and skill. It's fun to make it, but it's not the focus for me. I work from home, I work in my "free time" and weekends. I do not care, because I like working.
    – Gerben
    Apr 28, 2021 at 14:37
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    If somebody said "Go back to work" I'd not take that well. it's belittling. Especially because I am working for myself. But regardless I am and most people that work should be perfectly capable to know when and when not to work. If you had to tell them to "get back to work" then you shouldn't have hired them unless they are unmotivated to work. Then the work spirit is missing and it's a work enviroment where i'd indeed rather run back home.
    – Gerben
    Apr 28, 2021 at 14:45
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    hi @Gerben ! I can only answer for let us say "normal" or "conventional" people who need to work to buy nappies and pay the electric bill. I urge you to put in an answer with your viewpoint!
    – Fattie
    Apr 28, 2021 at 15:23
  • In the real world, item 2 often results in item 3 meaning "go home happy in the knowledge that you will never, ever, get a promotion or a pay rise beyond the bare legal minimum". But it's your choice, of course.
    – alephzero
    Apr 28, 2021 at 21:42
  • @alephzero hmm; I haven't found that to be the case (at least in modern times); but sure! One issue, I "assume" that (as usual on this site) this is software related industry. Software is sort of exceptional due to the insane, "historic," demand. So, I see the OP has not really clarified this.
    – Fattie
    Apr 28, 2021 at 22:14

Ask for a meeting regarding renegotiating the contracts between your business and that of this company with a manager empowered to do so.

So, you're not an employee, you're a freelancer. You have a business of your own, and this is ultimately a side gig for you, rather than your primary source of income. That gives you bargaining power that ordinary employees do not have.

As a result, you could simply ask a manager who would be empowered to renegotiate your contract for a meeting regarding doing so, since the current business arrangement between your businesses has become non-viable, and you would like to renegotiate the terms of the agreement.

During this meeting, lay out the facts: you're not an employee, you're a freelancer, and you feel no loyalty to the company. You're working with them as a side-gig, you're not reliant on their wages, and if your enjoyment of the work drops below a certain threshold, you can and will terminate your business contract with them (or, perhaps, simply decline to renew it upon its expiry). This manager's behavior is impacting your enjoyment of this work, and you would like to renegotiate your contract to report to someone else in the business structure.

It's very likely that this will harm your relationship with this person, but you don't want to work with them anyway, so this is basically irrelevant. It's also possible that the business will "call your bluff" and decide not to make any of the requested changes, at which point you can demonstrate that you aren't bluffing by terminating (or not renewing) your contract with them, and if you wish to continue working this side-gig, I would encourage you to begin the process of finding other clients.

Remember, however, don't use the words "quit" or "resign" during this conversation, because those are things employees do, and you're not an employee. You're an independent business negotiating the terms of its relationship with another business, on a business-to-business level.

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