How to quit like a boss

On December 15th, 2021, I will leave Spring – the company I have been with for almost seven years.

Along the way, I've seen quite a few people quit, fired a few people, and made some pretty big mis-steps when planning my own departure.

The goal of this post is to summarise some patterns and anti-patterns, so that in the future you or I can leave our roles in the most professional and positive way possible.

This was written with an audience in mind of employees in good standing at tech companies¹. It would apply to other people working in high-demand industries, with functional relationships with their manager.

Your reasons for leaving shouldn't be a surprise to your boss

By convention, when people are uninspired by their role or unsure about their next career move, most hold this back from their manager. They feel a sense of duty to be invested in the organisation and to be appreciative of the opportunities they have. Perhaps they're concerned that if they "out" themselves as a weak link, their manager will be let down or even seize the initiative to exit them first.

As a general rule, your manager being at all surprised by your leaving is a sign of communication failures and something to be avoided. There are exceptions to this general rule – for example if you don't have high job security, or are in the country on a H-1B visa tied to a particular role. However, for most people in the audience of this post:

• Do have regular, clear, frank conversations about your career with your direct manager. After you, they are the person that has the greatest impact on the direction and speed of your career progression.
• Do tell your manager clearly if there's something you're looking for in your career which your current role isn't providing.
• Don't withhold concerns or aspirations from your manager. You are just robbing them of the opportunity to be your advocate, to mentor you, or – if it comes to it – to work through your departure plan with you.

Recommended reading: Radical Candor, The Alliance.

What's the worst that can happen?

The reason I can recommend adopting these patterns is that I know that this kind of candid conversation is the sustenance required to grow and maintain a professional relationship.

If you open an honest dialogue with your manager, there are three possibilities:

The only unhappy outcome is the red one. But if you have a crap manager it's better to find that out clearly, and early, so that a more functional organisation can benefit from your work.

Match your notice period to the handover period

A very short notice period will often leave a company in disarray, and leave the ex-employee with a lingering guilt for having abandoned their teammates.

What to hand over?

At a minimum, independent of your tenure and level of seniority, you need to consider:

1. Handing over access to key services and systems.
2. Knowledge transfers, documentation, and training on key technology, processes, or systems.
3. Helping hire your replacement, if required.
4. Wrapping up or handing over any work in flight.
5. Helping communicate your departure to the wider team.

It is very difficult to complete these points if you give a week's notice after a decade at a company.

However, as I found out when leaving Spring, it's also possible to give too much notice.

Avoid giving too much notice

I let my boss know I was leaving in February, so my commitment to see things through to the end of the year was effectively a 10-month notice period. I did this with the best intentions, but such a long notice period meant:

1. We didn't jump immediately into hiring mode for my replacement. This isn't necessarily a bad thing, but when you don't have to start something straight away, it's easy to let it slip until it's too late.
2. I forced myself and a couple of trusted colleagues to maintain double-think for nearly a year. We didn't want to tell the entire team back in February, but that meant we had to give very different answers to seemingly simple questions, depending on who we were talking to. This can be quite draining.
3. I didn't perform as well as I would like for my last few months. Honestly, knowing that you're leaving a role in a few months makes it hard to do the right thing: to make difficult decisions, to think long-term.
4. An unexplained power vacuum. I was stealthily delegating and divesting more and more responsibilities to my team over the course of several months, but because I hadn't told them I was leaving (see #2), what actually emerged was a lack of clarity. Some things which I should have decided, owned, championed, or changed, I instead deferred to the team. I wanted for people to magically step up into these new responsibilities, but couldn't make that expectation as clear as I would have liked.
5. I ended up leaving the company at one of the worst times in the year. Lingering like a wraith while annual planning happened around me, and forcing team changes in the holiday period (the busiest time of year for Spring).

Derive your notice period from the handover tasks

Overall, my recommendation here would be to think through the steps required for a smooth exit (the bullet points above are one place to start), work with your boss to figure out how long those steps will take, and make that length of time your notice period.

Your new role, if you have one arranged, should respect your decision to be professional about your handover period. They'll wait, don't worry.

Set the team up to flourish without you

Doing a good job of communication with your boss and being professional about your notice period – as described above – will go a long way to ensure that your soon-to-be-ex colleagues will emerge even stronger after your exit. However, there are other things you can do to maximise the chances that your departure will be seen as a temporarily-sad but eventually-beneficial change.

Don't sabotage, it's a dick move

Why would I want for the team to do better without me? Doesn't that reflect badly on me?

No, no, NO!

Sadly, I have seen people take this perspective. Perhaps due to some perceived slight, perhaps because of an over-reliance on external validation: some people want their teammates to fail after they leave. On the extreme end, people have committed full-blown crimes, but simple things like smearing other people's reputations or deliberately withholding information can set the team back too.

Although it should be obvious, here are some reasons why it's a bad idea to take this approach:

• Your team trusted you and depended on you. It's unethical to screw them over because they're no longer paying you.
• You might have stock options in the company, which will be worthless if the company fails.
• Your resume will be bolstered if the place at which you used to work is known as a high-performing organisation.
• People remember betrayal, and be less likely to help you in the future.
• Again, it's unethical!

Your leaving means other people can take on larger roles

Whether your role is backfilled or not, losing an experienced teammate means that the people who remain need to step up into more responsibility.

This could be simple things like being the subject matter expert on something, owning some part of the team's process, or even stepping up to be the backfill.

Actively identify the gaps you will leave: they become opportunities for career progression for everyone around you.

Perhaps some fresh thinking would be a good thing anyway

All but the absolute best managers become stuck in their ways after a while. Processes, practices, culture, and tooling become ossified and unexamined.

Perhaps you were so comfortable in your role that you lost a bit of the hunger to find better ways to do things, to bring new ideas into the team?

Admit – to yourself and to the team – that someone with new ideas and a different perspective is probably going to be a breath of fresh air.

Not only will your learning be accelerated once again in a new role, the team you're leaving will gain new insights by questioning the cows which became sacred during your tenure.