How to prepare your team for when you're going out of office

As the sole holder of most information and perhaps the one who keeps the train on the tracks, preparing your team for when you’re about to go out of office is key to keeping things running smoothly while you’re out. I’m not saying “I’m sick today” or “I’m taking a long weekend” - I’m referring to a longer trip of at least one week.

As I sit here at the airport about to take off for my flight to Florence, I figured this would be a perfect topic as I just went through my OOO prep.

Here’s my checklist:

What projects are in flight, and who will need to be unblocked while I’m out? I create an OOO document on Notion for the dates I’m going to be out and go project by project - what’s the current status as I leave, what do I expect the team to work on while I’m away, and what potential blockers may exist. My manager was actually out of office this week so the “here’s where we’re at” on each project is actually quite useful.

Since I manage two teams (engineering and IT), my document needs to cover both teams’ projects, which frankly takes up most of the document’s content.

What do I specifically need from my manager while I’m out?

This is typically a list of personal asks - review my expense reports, review some of my work, etc. Right now this consists of some SOC2 and policy items, checking in with a couple folks, and keeping an eye on some prospects who may have follow-up questions on some questionnaires I filled out this week.

What do I need from my PM(s) while I’m out?

Making a clear list of what you’ll need your PM to take over or unblock for one of your engineers is super helpful. You’re typically in sync anyway and they will likely know what they need to do, but it’s a good gut check for yourself as well.

What does my direct team need while I’m out?

I intentionally make sure I’m communicating with my team early that I’ll be out of office so they can book some time with me before I head out. I’m assuming you’d like to fully disconnect, so try to tie up as many loose ends as you can, and for what you can’t, make sure your team knows who they should go to in your stead should they have additional questions.

What do I need to get done before I go?

Seems obvious, but I have to make a very clear checklist of all the projects I have in flight that I personally need to get done. This for me included finishing up editing our policies, writing the OOO document, completing performance reviews for my onsite team, and getting through an engineering vision. (I only got through like 10% of the vision I’m working on, but I think I communicated it with my team enough times this week that they should know what’s going on.)

Set your Slack status, turn off notifications, and turn on your vacation message on your calendar. That’s it! I find it very helpful to make a clear checklist this this every time I’m going to be heading out on a trip because the days leading up to your vacation tend to be chaotic.

Now you can fully enjoy your vacation!