I know it sounds simple, but I'm finding it quite awkward to tell my boss I am leaving for another job. The main reasons for this are:

  • My boss is currently looking for more developers due to heavy workload.
  • He has took on a couple of "apprentices"in the past few days - and wants the business to grow with me helping it
  • A lot of urgent and specific work relies on me - I am the only one with the knowledge of the frameworks, etc, which will leave the company in a tricky situation
  • The company is literally next door. My boss has also approached the company asking if they have any spare developers - leading to more awkwardness.
  • My company has been quite lenient and good to me, despite me having some bad times which under other circumstances would probably be sack-able.
  • I have given no indication I want to leave / am unhappy

I'm not leaving even for a big increase. I just find my work stale, and the environment and jobs are uninspiring. There's no attempt to team build and even the simplest things like christmas parties don't exist. I could've asked for a change in this - but then I feel like it's only because I requested it, and this companies mentality and ways of working are incompatible with mine, which in turn is hindering my growth as a developer. The only problem now I see is it will be my 3rd job in 4 years - if it goes wrong at my new job, won't this cause a problem when looking for a new one.

I just really can't find an appropriate time to pull my boss aside and tell him I'm leaving, and why. I'm scared he will counteract and offer pay increases etc - any tips?

  • 1
    ... how many times have you tried to change the things you are finally frustrated enough to leave about? It sounds like never.
    – enderland
    Commented Jan 22, 2013 at 15:11
  • 2
    I've never sat my boss down and asked him to try to change it. However I've put forward ideas to change it that he's agreed are good, however never applies them. The quickest solution is always chosen, not the best solution.
    – rickyduck
    Commented Jan 22, 2013 at 15:40
  • 1
    I don't know your local culture, so I can't answer the question. I will mention that in HR circles it's common practice to give bad news on Friday afternoon. The reason is to give the recipient a weekend to think things over and calm down before he or she runs to a lawyer. Commented Jan 22, 2013 at 15:46
  • 18
    I went to my first boss and said I was leaving for another job. They were a little unhappy and asked for a resignation letter. I wrote "Dear Earl, I quit. Love, Bill".
    – Bill K
    Commented Jan 22, 2013 at 20:34
  • 2
    Would your employer hold on to you if they ran short on money or fire you? Essentially same question viewed from another angle. Commented Jun 24, 2013 at 15:58

5 Answers 5


Don't burden yourself with burdens not of your own creation

You're certainly not the only one (I do it too!), but realize that really only 1 or 2 of the reasons for your guilt are under your control. You could have been better during your times of personal crisis (perhaps), and you could have been clearer about your dissatisfaction about your company. The rest of this is coming from a business state that is not of your creation, so don't assume responsibility that isn't yours. Particularly if, as they were making these plans that centered around you, you were never consulted.

Caveat: This doesn't hold if you had a conversation along the lines of: BOSS: "We're planning a major strategy in which you are a pivotal part, does that sound good to you?" YOU: "Rock on! I'll be here forever, you guys are awesome!" - if you have recently had a conversation where you reaffirmed your intent to hang around for a good long time, then maybe you want to reconsider because you really are turning your back on the company with little to no notice, and not even giving them a chance to change things.

The Exit: Short and Sweet

There's no good way - leaving a company is hard. I go for short and sweet:

  1. Have a prepared resignation letter that is short and sweet and contains your end date
  2. Book a half hour of your boss' time, if possible, be aware of major, earth-shaking meetings, but timeliness is more important.
  3. Give your notice - "I have to give you my two week notice" is fine. You can be honest if you want and say you appreciate them standing by you in times of crisis, or just go with a quick good-bye. Be sure to state your end date and know any big wrap up tasks.
  4. Answer questions honestly - most decent bosses may want to ask "why" - be as honest but judgement free as you can. But don't own the blame and don't blame others - "working here isn't what I want" is fine. "working for you isn't want I want" - isn't going to win you any fans. "I can't figure out how to be happy working here" - takes on a lot of blame.

Counter Offers

If you are tempted - take a day and reconsider. Rarely will it work out if it's about money - you've just mentioned corporate culture issues that can't be fixed by salary. But if they offer you the ability to fix areas that have caused dissatisfaction - you may wish to think about it. Take a day, and give feedback the next day.

If you are not tempted - don't mess around with a 24 hour lag. Say you are flattered but say no.

Realize that if you really do want to take a counter offer, it is far better to tell the other job "no" before you work there (when they've spent little to no money on you!), then 1 month after you get there and find yourself unhappy. It is possible you'll burn a bridge, but not necessarily and there are other companies if you decide in the future to return to the hunt.

3 Jobs over 4 Years

Yep, in non-contract software development, that's a bit rough - it means no company has ever really suited you long enough for you get deeply involved in their code. It makes me think you may want to consider two things:

  • What's making you dissatisfied? is it following you from job to job? Even if the circumstances of you leaving have been different each time, is there any trend that marks these changes? Any warning signs? At the very least, any knowledge of "ideal" or "awful" working conditions you can apply to finding the next job?

  • Have you considered contracting? When I talk to many contractors, they speak of an interest in moving on after a year or so - it's just a drive to try new things, meet new people, have new challenges. It's a basic temperament difference from a full time employee and it isn't wrong. If you think that's you then maybe it's time to consider a different way of working?

  • ` But if they offer you the ability to fix areas that have caused dissatisfaction - you may wish to think about it.` I've thought about that. But it's a forced change... fundamentally, the workings of the company and upper management aren't right for me... surely that on its own is enough to dismiss it?
    – rickyduck
    Commented Jan 22, 2013 at 17:12
  • 1
    It's totally your call. Only you can really judge this one, so I left the two options out there. You really don't know what they will come up with as a counter-offer, so leave yourself the option that if you ARE truly tempted, no matter waht, you'll wait a day and make sure it's not just a spur of the moment decision. Commented Jan 22, 2013 at 18:59
  • Re: number of jobs - I don't know if the UK (where rickyduck is from) got hit the same way the US did in 2008, but if that's the case (or for the readers in the US in the same situation), 3 jobs in 4 years isn't as bad right now as it may be in other time frames, especially for people in agency-type jobs (doing work for client companies).
    – Shauna
    Commented Jan 22, 2013 at 20:39
  • @RhysW but at the moment there is absolutely nothing I like. While the appearance of job B, I already like most of what they offer.
    – rickyduck
    Commented Jan 24, 2013 at 16:14
  • It think it's only 2 jobs over 4 years at the moment (and will be the 3rd after resignation). Which is not too uncommon nowadays and usually time enough to get comfortable with the job, and often time enough to get deeply evolved.
    – phresnel
    Commented Mar 17, 2016 at 11:44

I just really can't find an appropriate time to pull my boss aside and tell him I'm leaving, and why.

Setup a private meeting with your boss - half an hour or an hour of their time. Email them, set it up in their calendar or whatever is appropriate in your work place. You don't have to indicate exactly what this is about, but even something to the line of "my future in the company" should do.

Have an agenda - think about what you want to say and how you want to say it.

This does have to happen - it would be irresponsible of you to not give enough notice to let your boss make some arrangements for your leaving and the time beforehand (to arrange handoffs, documentation etc...).

I'm scared he will counteract and offer pay increases etc - any tips?

Even if your boss gives a counter offer, you don't have to accept. Should this happen, you can always ask for a few days to consider it, instead of flat out refusing.

It is your decision, nor you boss's decision - don't confuse yourself with that.


I generally find it awkward to tell someone I'm leaving but my advice would be:

  1. Do it in person
  2. Do it near the start of the day
  3. Give them time to digest and agree to sleep on it.

As for your bosses resourcing issues, ultimately that's not really your concern but I appreciate you don't want to leave him in the lurch - all you can do in this situation is be professional.

As for counter offers, deal with them as they arrive, be courteous but be concious of the fact that you're claiming not to be moving for more money so I'd question the wisdom of accepting more money. The one thing I'd say about office "culture" is that it is driven by employees more than by management so the old - be the change you want to see is paramount here.

3 jobs in 4 years isn't great, I'd say the next one will need to last 2-3 years for it not to be detrimental in future so I'd definitely consider the risk of that before moving.

  • 2
    +1 for "be the change you want to see". You can't always wait and rely on others to make things happen. Especially if you're at the point where you are very senior and/or instrumental in the company. Then it's even expected of you.
    – pap
    Commented Jan 22, 2013 at 14:21
  • I agree pap and michael. This is my sole intention to move.
    – rickyduck
    Commented Jan 22, 2013 at 17:15

Your boss may feel that you are letting him down, or he may not. There really is nothing you can do to change that either way. In the general case, resigning does not have to be a terribly dramatic affair. Certainly in the software-industry, people move around and switch jobs - it's part of the game. Anyone who's been around long enough to be in management knows this and you're a good manager, you also know that holding grudges is costly.

However, the way you are describing the situation, it does sound like there might be at least an implied agreement that you're going to take more responsibility (leading junior apprentices) and actions have been taking (apprentices hired) based on this assumption. Based on that, your boss might very well feel that you have been leading him on. You're going to have to take this into account and try to anticipate what reaction you are going to get. And then decide if you can live with that and if it's worth it. Like I started out saying, there is really no way to sugar-coat a resignation and your boss is going to react the way he'll react regardless. Still, you can't have everybody like you all the time so maybe it's worth it for you, only you can answer that question.

Another thing, before you set up a conversation like this, be very clear on what your goal is. Is your goal to leave the company, or are you negotiating for better terms? If you are thinking about leaving, is there anything that would make you stay and if so, what? For sure, if your manager still wants you around, he's going to ask you. But he's not going to up and give you a counter-offer when you are in the meeting. He'll ask you "is there anything I can do to make you reconsider?" and/or "is there anything in your current situation that prompted this, and if we changed that, would you still stay?".

At that point, you need to be prepared because that is the opening of a negotiation. If you are set on leaving, you should say so immediately. While it's nice to get your ego stroked by being "courted" with offers, your manager is going to recent you more if you lead him on in a negotiation when you have no intention of accepting anyway.

If, on the other hand, this is a negotiation and you are willing to stay under the correct circumstances, know what those are. So when he asks, you can give an outline to what would make you reconsider.

Be warned though, initiating a salary-negotiation by threatening to resign is a pretty dramatic way and should be a last resort only. It will also have long-lasting effects on your relationship with your manager and his trust for you. For that reason, many managers will not even engage in discussion when someone resigns, they don't want to work with people who negotiate by ultimatums and threats, so be prepared to back your threat of quitting up since there is no turning back if it doesn't work out. My advice is to explore all other negotiating avenues before threatening to resign.

  • Hi pap, thanks for your answer. I am not doing this to force his hand... and even if I did see an offer, it would be too late? I've been here 2 years with no reviews / bonuses / pay increase and no promise of one any time soon. However, whatever my ulterior motive is, the most important thing is money - I have 2 children and am only 20 myself, and need as much as possible to live.
    – rickyduck
    Commented Jan 22, 2013 at 15:42
  • 2 years with no review? I think it's safe to move on - the 3 jobs in 4 years made it seem like you'd only been at this last job for a very short period of time which is why moving could be considered risky.
    – Michael
    Commented Jan 22, 2013 at 15:57
  • @Michael ... exactly. The new job will be the 3rd, so even if it's only 2 years there, it will be 3 jobs in 6 years
    – rickyduck
    Commented Jan 22, 2013 at 16:10
  • @rickyduck Have you been working in the software industry since you were 14? Somehow, I don't think that the fact that you had a couple of short-term jobs in your early teens will have much detrimental effect on your future career.
    – pap
    Commented Jan 23, 2013 at 7:24
  • @pap yes I have, however only full time since 16. I probably agree especially as they are all startups
    – rickyduck
    Commented Jan 23, 2013 at 9:04

Stress the opportunity at the new place

When I give notice I always stress that it is the opportunity I am traveling to but I regret having to leave the position I am in. I let them know that I am willing to help make the transition smooth and help out in what ever capacity they need.

This is the its not you its me speech of business. It leaves the relationship as strong as possible under the circumstances. Not everyone will be happy you are leaving but hopefully they will be happy for you.

Thank your manager and your team for the experience

You are not just leaving the business you are leaving the people behind. Letting them know that you value the experience you have gained there while working with them.

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