on leaving well

While it was certainly different for our parents and grandparents the truth is that most of us won't stay with one job, one company or even one career for the majority of our adult lives.

Leaving well is a core skill to build, but I found that there's little good advice as to how to do it. Below my takeaways from having left and seeing people leave.

1. Companies aren't emotional - but people are

Circumstances matter. A lot. Level, tenure, current and historic company trajectory, team, pre-existing relationships, or on-going projects all will impact how your departure goes. Do people feel like you are abandoning them on a sinking ship? Are people going to understand you wanting to take on a new challenge or an increased role in an exciting new venture? It. All. Matters.

Companies will usually treat you according to a set of standardized rules, policies and processes - few of which will be personalized to you. That's just how it is - don't be upset.
People, on the other hand, will have their own, personal views on your departure - influenced by their backgrounds, experiences, and feelings. While you might be most inclined to focus your departure on doing right by the "company", try to do right by the people first. By taking care of the people you usually also take care of the business side.

This is especially critical if you are a manager of people and/or owner of products, processes or projects. People you have hired (especially if recently) may feel mistreated or left alone, people staffed to your projects may feel like you are putting their success at risk. Simply don't. Try not only to have candid conversations with them, but also to work hard to make sure as much as possible gets done before you leave. Making sure everything is handed off is tablestakes.

2. Leave on your terms - and be stern

It should be common sense, but once you've made your decision, first talk to your manager - in person or if you are a remote company at least on video. They should see your face and hear it from you directly, not through office gossip or by email. It’s simply about showing respect and decency. Then, loop in the other important folks at the company - your close peers, direct reports, mentors, or anyone who's been a big part of your journey at this company.

Be ready for the 'please stay / let's find a way to get you excited again' talk, especially if you're very good at what you do and very important to the company's plans. But if you're set on leaving, be clear about it from the get go. Don't beat around the bush or give mixed signals. It avoids resentment down the road and allows the team to move on and plan for the future.

Let them know why you're out! You don’t have to spill all the beans - and you absolutely shouldn't make this the day of reckoning - but a bit of context helps. It's good for closure, allows the company to improve, and in many cases: it allows everyone to be excited for you - you are talking to other humans you have built a relationship with. Most of the team will want to see you happy and succeed in your career.

Now, don't just drop your work and vanish. Plan your exit. Tell them what you'll wrap up and who could take over your stuff. But remember - they may disagree and that's their prerogative, you are done making decisions and you need to be ok with that. Seriously, if they assign responsibilities differently from how you would have done it, you don't get to complain, and especially not publicly criticize their decisions.

Basically, quitting is a bit like firing someone. You've got to be honest, clear, and straight-up about it. It makes things smoother for everyone and leaves a good last impression. Plus, you get to walk out with your head held high, knowing you did it right.

3. Don't burn bridges - your industry is a village

The most frequently given advice when exiting any job: Don't burn bridges on the way out - and I have realized for once conventional wisdom is spot on. The world, especially as seen from the lens of a specific industry, is much smaller than one thinks, and the way you leave a job can echo throughout your career.

You'll be surprised how often paths cross in industries like tech, automotive, or finance. They might seem huge, but they're more like tight-knit communities once you look under the hood. Today's colleague could be tomorrow's boss, client, or business partner. The tech world, in particular, is notorious for this – new teams are often just old teams in a new constellation going after a novel idea.

There are two mistakes people often make when leaving: (a) when they know they're leaving they slack off or (b) they start turning into gossip machines. Avoid both at all costs. I repeat: avoid both at all costs!!!
Your last impression is what will stick with many of your colleagues most - it's not just good for them, it's good business for you as well to make those last weeks count. Work hard until the clock runs out and be kind and professional to everyone, including those co-workers you may not have gotten along with well. You no longer have a horse in the race and while it's never good to gossip, it's particularly stupid to do so, when you are about to leave. There is literally zero upside here.

And lastly, let's talk about references. They're not just the ones you handpick for your resume. People talk, and your reputation is built on every interaction – not just the ones you think count. The colleague you didn't think twice about could end up at a company you want to work for or a key customer you want to win - their goodwill may well become critical to you.

4. Don't rush - take YOUR time

The best decision I made while leaving Pipe was to give myself time. Now granted, not everyone will have this luxury, but more often than not a company will afford a long-term team member some say in designing their exit timeline and strategy. Obviously there is also a financial component to this, but even delaying your next job by an incremental two weeks may allow you to ensure a solid hand-off and/or to catch a breather. Trust me, it will be well worth the cost - both for you and your next project or employer.

From the moment I told our CEO I was leaving to the moment I started with my new project took over 6 months. I understand that the path I chose would not be for everyone - plenty of smart peers have told me as much. But it was perfect for me.
I chose to give myself time and in that had ample opportunity to not only wind-down my responsibilities and ensure the team was in a good place but also time to start easing into what's next without having to go 100 mph right away.

What did I do specifically? I spent a couple of quarters helping ramp up my successor, handing over responsibilities, making sure my team was in a good place and, to be honest, coming to grips with the fact that the company was thriving without me. I did this all while serving as a utility player for legacy projects with a similar expiration date as myself and as resident company historian. It felt right and in the end that's all that matters.
I then spent a month reading, seeing friends and traveling. I did this even though I already knew what was next. As eager as I was to dive in, I knew i owed it to myself and the project to get some rest. The more weird taking this extra time off sounds to you, the more likely you would benefit from doing it.

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Leaving is always difficult, but that doesn't mean it can't be done well. It is well worth the effort to try. For me it has meant that with the initial stress gone and my mind reset, what remains are the fond memories and enduring relationships. And what has come back is the excitement to start anew.

Let's build,
LW