This blog post was inspired by a recent live YouTube discussion, “Out of Office”, from 9 Out of 10 Testers.

Go on, admit it. When you’re getting ready to leave work for a vacation, what are the words that you type into your Out of Office message / Slack status / team communication channel? Despite the geographical boundaries asserted in the tweet below, chances are it’s more like the latter than the former.

European out-of-offices: “I’m away camping for the summer. Email again in September”

American out-of-offices: “I have left the office for two hours to undergo kidney surgery but you can reach me on my cell anytime”

— Samuel Pollen (@samuel_pollen) April 30, 2021

The truth is, as remote working and flexible working hours become more common, the boundaries between work and home life are becoming increasingly blurred. This is especially true for those of us who work in the tech industry, where the expectation is that we are always available, always on, always connected. It’s not uncommon to see people working on their laptops in coffee shops, on trains, in airports, even on the beach.

So it’s unsurprising that, when it comes to taking time off, we sometimes struggle to disconnect. We frantically add clauses into our status messages: “I’m away all week, but I’ll check Slack a couple of times each day, and in an emergency you can reach me on my mobile.”

What drives us to do this? In part perhaps, in overworked times, it’s the guilt that we perceive when we’re taking time off while our colleagues are continuing to put their noses to the grindstone. We want to be seen as “one of the team”, that we can be “there for them” if they truly need us. But it’s a frightening fact that most teams can survive without a particular member of staff for a week or two. If they can’t, then there’s a bigger problem that needs to be addressed, before that person decides to leave or gets hit by a bus. (Worse, what if they can survive without you; have you holidayed yourself out of a job…?)

In part, perhaps we’re also trying to protect ourselves so that we don’t return to an overflowing inbox on our return. I’m especially guilty of putting in a couple of hours on the Sunday evening before returning to work on a Monday morning, so that I can effectively hit the ground running when I’m back at my desk. But this again speaks to the same problem: what’s happening which is preventing work from being allocated to others in our absence?

In the busy summer holiday season, there are obviously more holidays and therefore teams are working with fewer resources. Yet it’s rarely the absence of any one individual which causes a problem. In my experience, the challenges occur when the lines of delegation break down. Picture this scenario:

• Jo is away on holiday. They write on their auto-responder: “I’m out of office next week. Please contact Tony in my absence.”
• Tony is away sick one day. They leave a message on Slack: “Sorry I’m off today. Please redirect enquiries to Emma.”
• If you have a query which requires Jo’s assistance, you find yourself having to contact Emma. However, Emma doesn’t have knowledge of Jo’s day-to-day role, nor access to the same systems required for their job.

And that’s with only a couple of loops in the chain - and also without any recursive loops (I’ve certainly seen situations where, in the scenario above, Tony says “I’m sick, talk to Jo” when Jo’s on holiday). As with any sufficiently large team structure, the more nodes you add, the more the complexity increases, and the likelier it is that something will go wrong.

As with a lot of the Mojovational posts, the secret is acceptance. These situations are commonplace; you’re not doing anything especially wrong. And with acceptance comes a level of comfort. That’s why the Simpsons GIF at the top of this post (from the episode Homer Goes to College) is so surprisingly zen:

Professor: “If anyone would like to stay, I’m going to hold a comprehensive review session after every class.”
Homer: “Do we have to?”
Professor: “No.”
Homer: “Then kiss my curvy butt goodbye!” * runs outside to chase squirrels *

While the episode is making an important point about Homer’s lack of academic rigour, he’s doing a better job than us of having an authentic Out of Office experience. He doesn’t say “Kiss my curvy butt goodbye… but if something important comes up tonight, send me an email and I’ll pick it up.”

I’m not saying that we should all go out and start chasing squirrels, but the secret to a successful Out of Office experience is as simple as Homer makes it appear:

• When you’re off, be off. That’s it. Delegate whatever is necessary in order for you to feel comfortable with doing this. If you spot yourself saying “But I can’t take time off, because….” then address whatever the “because” is.
• Equally, upon return from holiday, try to normalise the idea that the first day back is going to be at a slower pace than usual as you get back up-to-speed. When talking about team workloads or velocities, try to factor in the time taken for people to catch up after a holiday. It’s also why some of the most successful sprint teams that I’ve seen will run a Wednesday to Tuesday sprint, rather than Monday to Friday: it’s hard enough to start a sprint planning session on a Monday morning when everyone’s had the weekend off, without also accounting for those who could be returning from holidays.
• If you’re holding yourself back from taking holiday in case it negatively affects your team’s experience: don’t. When you don’t allow yourself to take time off, you’re increasing your risk of stress and burnout; and when your colleagues see you avoiding holiday, it makes them feel guilty about taking time off for themselves. Be a trend-setter. Take the time off that you’re entitled to, and encourage others to do the same.

With these few pieces of advice, hopefully holidays will begin to feel more like actual holidays again!

Key takeaways 📝

• Don’t avoid holiday because you worry about the affect that it will have on others.
• Do do some due diligence before you leave, to minimise the impact that your absence will have on others.
• Do ensure that managers lead by example (especially if you’re that manager).