How we fully unplug on vacation at TestBox

Spoiler: It takes way more than just telling people "you should unplug." Here's the step-by-step of how we've made this possible at our growing startup.

Something that drives me crazy is when people constantly check emails and Slack while on vacation.

I understand that there are some jobs that demand this kind of responsiveness… But I also believe that in the majority of white collar roles, this doesn’t have to be the reality. I think in most roles, it should be possible to have fully unplugged vacations.

Before I go any further – let me define what I mean when I say “fully unplugged.” I mean that the individual could literally go to a remote island without any internet access for the duration of their vacation, and things at work would proceed on as normal without any hiccups, blockers, or other large challenges. Often when I’ve talked about this with others, they tend to put this possibility on a pedestal and think that the unplugged vacation is an unattainable ideal.

I would challenge anyone who reads this and immediately also thinks, “Well, that would be nice but it seems impossible” to take some time and reflect on what that also implies for a given company’s culture. If your team can’t make do without one team member for a week or two, are you knowledge transferring enough? Are you collaborating effectively across the team? Are you creating enough documentation? Do you have the right structure for making critical decisions that doesn’t just rely on one person with ultimate authority? On the flip side: Are you letting one person take on too much responsibility and not asking enough of the others on the team? Is there someone who is too unwilling to relinquish their power?

I’d also take this opportunity to point out that if you’re worried about someone being out on vacation and unreachable for one or two weeks, then what happens if this person suddenly quits one day? Or, in an alternate scenario, we can think about the bus factor: what happens if an individual on the team gets hit by a bus and can’t come to work all of a sudden?

Aside from all of these considerations, being fully checked out on vacation means that you actually get the chance to recharge and focus entirely on other domains of your life (family, friends, hobbies, new places you’re visiting, etc.). This allows your brain to recover from the challenges and questions that you might be bringing home with you every night after the work day ends, even if you’re not actively working after hours. I know for a fact that even if I’m only in front of my computer from 9-6 or whatever it is on a given day, there are often little tidbits floating around in my brain while I’m making dinner, eating dinner, or going for a post dinner stroll. Even on the weekends, it usually takes until after Friday dinner to shut down my “work brain” and get into weekend mode. And it all starts to creep back again on Sunday afternoon. Going on vacation and actually having a mental reset requires an even longer ramp down time that can be ruined in seconds if I were still seeing Slack or email notifications.  

As we’ve built the TestBox team over the past few years, we’ve made it a top priority to make sure that everyone gets a chance to unplug and recharge on a regular basis. At a high level, we started with providing unlimited time off with an enforced minimum (15 days per year). In practice, this means that every quarter, I tally up how many days each person on the team has taken off so far. For anyone who isn’t on track to take 15 days off over the course of the full year, I reach out either to them directly or to their managers to make sure they’re aware of our minimum and making plans to take time off. (We don’t reach out to anyone who’s already on track or above the minimum!)

However, a few months into my own time at TestBox, I was coming up to my first week-long vacation and trying to figure out how I could be fully unplugged. I realized quickly that there were so many things I wanted to keep an eye on, along with pieces of work where I was worried about losing momentum while being out for a week. As I thought more and more about my own concerns and discussed them with my boss/our CEO, I came up with a strategy that we’ve since trained the team on and continue to encourage everyone to use.

In the lead up to any long-ish vacation (typically a week or more time off), we ask the person going on vacation to fill out an “Out of Office template.” I encourage everyone to actually set aside a few hours a few days before their vacation to fill out the template and share it with their direct teammates. This avoids leaving it to the last minute, when there’s often a pileup of deadlines or a lot of momentum to try and get things done before going out on vacation. 

The template is broken up into a few sections:

1. Handover 

2. Things on pause

3. Things to pick back up on

The handover section is for anything that’s mission critical that must happen while you’re out.

This could be for customer-facing tasks, where the clock keeps ticking and can’t be paused. It could also be for projects with deadlines that can’t be moved, though I will note that this shouldn’t happen if your team is planning well – longer vacations typically come with more heads up and therefore your goals should be set with headcount limitations in mind. If someone’s out on vacation for a week of next month, you should only be scoping 75% of their usual work for that month’s projects. 

As part of the handover section, each task that needs to be handed over is documented in detail so that anyone can theoretically pick up the task and self-serve. Any necessary links, context, or other resources have to also be included in the documentation.

Additionally, this section is where I also include questions that I often field or areas where I anticipate the team needing my input. I put in notes about what I commonly answer for others on the team and make sure they know my guiding principles for any major decisions that may need to be made in my absence. I’ll also note any specific decisions that I would like the team not to make in my absence. Usually that latter part of the list is fairly short.

If there is anything coming up that may be time sensitive, I add it to a subsection called “things you may text me about while I’m on vacation.” 

Next, the “Things on pause” section is my personal favourite. This is where you get to say, “We’re going to be okay if this doesn’t happen this week. We’re going to just hit pause.”

And sometimes, this can even apply to customer-facing tasks depending on the context. This is a section where we encourage team members to collaborate closely with their managers on, as there are certain judgment calls to be made that may also depend on the length of the vacation. If I’m out for a week, there’s more leniency to put tasks on pause than if I’m out for two weeks. When I went on vacation earlier this year, I was out for a week and a half and we decided that it would be okay to put pause on invoice payments and reimbursement approvals given I’d do a round of them right before leaving and right after coming back. We had to communicate this to our vendors and it was included in my vacation auto reply. I also reminded everyone on the team who owns a vendor relationship so they could communicate this to them as well. 

The last section was inspired by my own experience coming back from vacation in the past. I’d always feel very overwhelmed on the first morning back from time off, because I couldn’t remember exactly what I’d worked on before leaving and where I’d left off.

The final section is where I leave myself detailed notes on what to do when I return.

I usually leave myself not just notes, but also links to resources, documents, and specific email/Slack threads so that I can pick up seamlessly on my first day back, after I’ve sifted through Slack messages and emails. It’s made it a lot easier to hit the ground running as soon as I’m back from vacation, and it’s also taken away a lot of the “Sunday scaries” that I used to get on the last night of my holidays. Now I know that I’ve left myself a dumbed down guide on how to get started for Monday morning and I don’t need to use too many brain cells as I ease back into things.

All in all, I get really frustrated when I hear about people who have to check their emails and/or Slacks while they’re on vacation. I really believe that it’s possible to set a full team up for unplugged vacations without compromising on how smoothly things can run.

I know that I’m fortunate to be at a company where we’ve made fully unplugged vacations a norm for our team. If you happen to be someone who’s not in a position to set this norm for your team, I hope at least the out of office template I’ve outlined can make it easier to prepare for and return from vacation, even if it’s not fully unplugged. For anyone who is in a position to set the culture for your team, think about taking some of these practices and giving them a try. I’d be curious to hear how it goes and what sorts of results you see. 

Tl;dr

It’s not enough to just preach a culture where you can “fully unplug on vacation.” In order to actually make that possible, you have to build a culture of preparing for vacation. If you’re someone who doesn’t subscribe to fully unplugged vacations, I’d challenge you to think about what being this dependent on each member of your team implies for your company culture.

P.S. A final bonus thought:

Sam (TestBox CEO) just went on a 3.5 week fully unplugged vacation this month to get married and go on his honeymoon. Even he prepared one of these documents using my template and we’ve only had to reach out to him once so far about something that was absolutely mission critical.