To quit or not to quit… and how to do it

In my life, I have resigned 7 times from companies and, over time, I have evolved and improved my approach to a point where I think it’s worth sharing with you, especially if you have never done it and are thinking of doing it.
You may find something valuable in my approach, but please do ask questions and make comments on Twitter and Facebook!

There are 2 main factors to consider:
1- The WHY. Why are you thinking of quitting, what is not working now that makes you want to resign?
2- The HOW. How are you going to actually tell your boss you are going to leave and what is going to happen between now and your actual last day of employment.

In my book “Office of Cards” I describe quite in depth both points, the WHY in Chapter 3 and the HOW in the Office Extras Section, but here’s a high level summary of the main points.

“You should never quit without giving your boss the chance to fix whatever you think is not working”. This is the sentence I was told my my boss, mentor and friend Paolo when I resigned to him, from eBay, in 2010.
At that point I was fed up, I was tired of my job, tired of living in Switzerland and commuting back to Italy every week, I felt undervalued, underpaid, under-utilised. To me, not even a promotion would have been a solution so I thought I would resign. That is how I saw things, there was no way out of those feelings if I stayed, so leaving was the only option. #PerceptionIsReality.
But was it? Was I really considering all options?
Of course, I was not 🙂
In fact, my boss came up with awesome ideas to keep me onboard but I stubbornly rejected them because I had already decided I would join another company, a startup. I had decided that was a lot better (it was my perception of that vs the feeling of what I had – I was not comparing facts, just feelings), I would have finally had the power to make decisions, to run my own Business Unit, to make things happen! And then 2 years later, I left this company, of course.
And, 4 years later, I came back to eBay, of course!!!

The reason why I started this section with that story and quote is because, in the majority of the cases I have seen, even people I managed directly, when people decide to quit usually they are not lucid in assessing what they have vs other potential alternatives. Which is why I have devised the Job Compass described in Office of Cards.
The point I want to stress here is:
1- IF you are as good as you think you are;
2- and IF people around you (especially your boss) think that the company or the team is better with you than without you;
3- THEN when you think about resigning you have negotiation power and you should leverage it. I am not talking about extortion, nor I mean you should threaten to quit every 6 months for a small pay-bump.

What I mean here is: if you use the Job Compass to understand what is not working and what you don’t like about your current job, you should give your company a chance to fix that issue before you actually decide to quit.

By trying to fix the problems (you think) you have, you are:
1- Showing a lot of professional maturity in that you don’t flee from a problem but you actually recognise there is one and actively and passionately surface it with the genuine intent to fix it.
2- Putting yourself in a position of strength in case issues are fixed as you will be perceived as “the guy who wanted to stay and had the courage to say what did not work and the will to help fixing it”.
3- Setting yourself up for resigning if things are not fixed because you’ll always be able to say “we tried, failed, so I hope you understand why I need to go”.

There is also a benefit in having an open conversation with your boss about the parts of your job that you think don’t work as that ensures he is aware and may see things coming before it’s too late (i.e. someone else, less mature than you, resigning for the same reason you would have). This will also make you appear as a sort of “second in command”, some ally the boss has in the troop ranks to help them get a sense of the team morale, a head-start on motivation issues etc.

So, you see, out of a potential situation that may lead you to leave, you may end up strengthening your position by staying.

Therefore, my advice is to reflect deeply on the reasons why(#GoOneLevelDeeper), accept you may not be seeing the full picture, have an open conversation about those issues, ideas to solve them, with your boss and then keep an open mind on the options that you may be presented with. #PlayTheLongGame

Clearly, you need to be smart about it and be aware that sharing too early, or in the wrong way, may lead to possible issues in relationships with your managers as not everyone appreciates honesty and transparency, so make sure you have a plan B if things go south (that is, have some possible job opportunities lined up before you talk to your boss).

As always, this is based on you being honest with yourself and knowing that, if things do get fixed, you need to stay with your employer for some time without complaining. The tactic of complaining every 6 months may work 2 or 3 times, but it won’t last and you’ll end up in a very sour place.

Even with the best intentions, all the transparency and honesty in looking at possible solutions to your problems with your boss, sometimes you end up deciding that leaving is necessary. It may be a personal reason, or some issue that practically cannot be addressed and so it’s best for everyone if you leave.

My top tips if you end up there are:
1- NEVER badmouth your company, no sour feelings, no complaints. Not even after you left. The world is much smaller than you think and there’s nothing to gain from gossiping (ever). You decided to go, good for you, take the high road, make sure you thank everyone and move on #PlayTheLongGame
The guy you may be complaining about could become your boss in another company, or could be asked for references on you. Or, like me, you may end up deciding to come back to the company so, #MakeNoEnemies when you leave.
2- Leave things in order. If you are a people manager, make sure you create a document you share with your boss (and they will share with your successor) to detail the main accomplishment of each individual, their issues, your plans for their careers. Make sure each team member has developed a Career Plan and you have an updated version of it to share with your boss or the person taking your place. Make sure there’s clarity on who should get promoted, improvement needs, people at flight risk etc. You owe it to your people to make sure that their contribution does not get lost simply because you leave.
If you are an individual contributor, prepare a doc with your codes, your files, a key to your folders. Share your work on GitHub, Shared drives or whatever form your company uses, and spend time creating a map of where your things are. Make sure you also highlight who your main stakeholders were and what they usually asked. Any tip that made you effective in what you do is fair game for sharing.
3- Make sure you give everything you need to your boss. For this to happen, spend time proactively doing all the things mentioned above, share them with your boss and ask if there’s something else they expect you to do. Make sure you provide them with updated org charts, a full list of who’s who of every person you interacted with, and highlight all the open projects, with a full status update, and all the things to watch out for.
4- Talk to your people (both direct reports and peers, bosses too if you are in great terms with them) and make sure you leave them with a path, a clear feedback on their areas of improvement, what to watch out for, skills they should develop, people to connect with. It should be similar to a performance evaluation discussion.

Of course, all these things are indeed a lot of work, but it’s not that much if you do them in small chunks over time, rather than a full immersion of a few days.

Simply put: do the best you can until the very last day, and leave with a smile… This is how winners leave the arena. In the end, you want to be missed, not for people to thank God you left.

And whatever you decide to do, whether you quit or you stay, if you have done a thorough analysis and have made a data-based decision, do not look back. Things may get emotional during notice periods, you need to remain objective and stand by your resolve, whatever that is. It’s ok to assess new data (although you should have done it in the first place) but it’s not ok to start treating emotions like data, they are not.

Best of luck with your next career move!