Less-obvious advice for going on leave


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Life happens and work needs to take a backseat for a while.

Because I’ve done this twice recently, I figured I’d write out some of the advice I’ve gotten.

Did I follow all of it? Nope. Should I have? Hell yeah.

Get your paperwork in order

There’s the paperwork your company and their leave administrator (if they have one) will need you to fill out. Where will your paychecks come from? How much should those checks be? This math can be messy – do it while you’re logged into all your employee systems and not focused on your personal life.

Is there any additional paperwork you’ll need to file? Try to find folks who have done this before and are equally grumpy about the process. For gestating humans, a lot of Slacks have hidden #pregnant channels that can help you navigate this. Ask around to see if there is one and if you can get invited.

Get your career in order

Help your boss and your company manage you while you’re away.

  • Share with your manager (and potentially skip-level in case that manager heads out during your leave) what you want to know about and how to contact you. In general, larger companies really do train managers to respect leave boundaries by not reaching out. Would you like to be updated about:
    • Reorgs
    • Project canceled/new team direction
    • Team members leaving
    • Manager leaving
    • Off-site coming up around when you’ll be returning from leave
    • Team goodies and swag
    • Holiday parties, team member farewell gatherings, etc. Some things may not be something your manager is allowed to share, but a teammate might be able to drop a stray address or Zoom link.
    • Compensation and bonus changes
  • Consider scheduling a chat for a month or a few weeks before your return.
  • Get your next performance review in order. Unless you’re heading out during a review season, you probably have stuff you’ve recently accomplished that should go in your next review. Write it down.
  • Have a final chat about career goals. What are you looking for when you come back?

Consider Slack notification settings

Especially for parental leave, I didn’t want to log out of work slack. Parents groups helped me navigate working with our leave administrators, understanding our changes benefits and just generally adjust to being a new parent.

Instead I muted a bunch of channels, which worked wonderfully for me. Other things to do:

  • Set your Slack emoji status to something obvious. At GitHub, ⛔️ is common. It’s red. It’s loud. Folks get the message.
  • Set yourself as “away”. I forgot to do this, so it showed me as logged in every time I popped on. Whoops. Don’t forget this.
  • Consider deleting Slack from your phone or logging out. Potentially stay logged in on a work computer, if you think that division would be helpful.

Make yourself some breadcrumbs

When you go out on leave and come back, it can feel like you traveled through a wormhole. Things that just recently happened for you are ages and ages ago for your co-workers. Consider writing yourself some breadcrumbs, either before you return or just as you come back. It might look like this:

As I was heading out, we had just hired on a new CTO. Jane and Fatih had just joined the team and we were kicking off planning around Project Rocket.

Use your breadcrumbs when you get back to open every 1:1, to remind folks what they need to catch you up on and frame why you might have questions about things that were decided months ago.

Treat it like a new job

Be open to the idea that you may be coming back to a new job. Maybe enough things have stayed the same, and you slide right back in. But folks have been functioning without you for a bit now.

Watch how the team is functioning without you. Think about the role your team now needs. Is that the same as the one you left? You might find yourself asking yourself if this is a role you want. Using the breadcrumbs you wrote above can help broach this conversation if you think there’s no longer a fit.

Hopefully, you’re excited about the new (or old!) challenges your role is facing. It may still be helpful to talk through a clear onboarding plan, even if the on ramp is as short as a week or two. Going from 0-60 is going to be hard: even if everything feels familiar, there’s still likely a few things you’ve lost access to or a few security updates to apply on your work computer.