How to leave a job

Saying your goodbyes with grace

Mar 24, 2023

Today was my last day as Head of UX at Drest! So I’ve been thinking a lot about how to leave a job in a healthy way.

In the modern working environment, the ‘job for life’ is a distant dream. If you are driven to build your happiest life, I think you can expect at best 3 to 5 years in one role before you end up moving.

There are exceptions to this rule (I’d love to hear them in the comments!)- but I do think you should get as good at leaving jobs as starting them- you’re likely to be doing it a lot!

Here’s my personal advice for leaving a job (without fucking over your team.)

Communicate your plan.

Within a week of resigning, I create an offboarding plan with the key tasks and responsibilities I aim to accomplish in my notice period.

I’ve found being proactive (like with making 306090 plans) gives others more confidence in your departure (and likely makes your last few days less stressful!)

Building this plan yourself, and checking back in on it with your manager at a regular cadence, makes your leaving less of a shock to others, and avoids those last minute requests that can make leaving such a chore.

A snippet of my most recent offboarding document

Consider…

Meetings to handover
Processes to document
Work to finish
Transition plan for direct reports
Accounts and admin to transfer
GET ALL YOUR PAY SLIPS!

Craft your messaging.

I believe in honesty- but some reasons for leaving a job leave a negative energy with your former team and employer, or leave people gossiping and discontented.

We all leave because we want something better. There are ways to say that without being an ass.

“I’m exploring a new industry and growing my craft” aka the mobile games industry release cycle burnt me out.
“I’m moving back to my home country to be closer to family” aka the business wouldn’t let me work remotely to support my family.
“I need time to explore my options” aka this role is no longer supporting my career goals.

Figure out how you can frame your exit in the positive, and it’ll be easier to talk about with coworkers as you leave, and in your next job interview!

Tell people at the right time.

In senior leadership, your decision to leave a business may rock the boat (or even cause a headline or two!)

I’ve been in too many business with sloppy comms plans, where either people know way too much (the reasons for your departure, the time and date, what you negotiated, the ensuing chaos) or far too little (people disappearing without warning.)

Find the middle ground. You are not beholden to tell anyone your reasons. But having a digestible message will make those goodbyes easier.

As a design leader, I would recommend

Tell your direct team as soon as you have your exit plan so you can build with them what the future of the team will look like. Use it as a chance to discuss their career path and goals, and how they will fit in the team going forward. The longer you can support them in the transition, the more comfortable they will be with it.
Tell your project team one month before, so your work can be accommodated for.
Tell the wider company/discipline 1-2 weeks before, if appropriate, with an open invite for people to grab you for coffee if there’s anything they need to catch up with you on (they rarely do, but it’s good to offer)
Send your goodbye email/message on the morning of leaving. Keep it short and sweet. Add your socials. This is not the time to air your dirty laundry- stick to your comms plan.

PS- We all hate the agonising, drawn out goodbyes of a Zoom leaving meeting. Avoid them wherever possible. Meet people one on one, and bow out with grace.

Thursday was my last day with Drest! An amazing few years with so many learnings for me about leadership, and space for me to grow. I’ll truly miss my team. But it was time for something new. Here comes unemployment!