How to take vacation as a remote lead

Can you go on vacation when you are leading a remote team?

This summer I took two consecutive weeks of vacation to spend time with my kids. The reality is, I did not really have an alternative. Kindergartens are closed all of August where we live, and I split the responsibility with the father. I decided to use the situation as an experiment: could I leave my team for two entire weeks?

Two weeks without reviewing customer interactions for quality control. Two weeks without checking in with my team members. Two weeks without being on top of slack/email requests. Two weeks that I was adamant to enjoy without feeling guilty for my absence.

When going on vacation, what are you afraid of?

Officially I was afraid of my team not living up to our own expectations. I was worried they would forget about some crucial activities. What if I came back to utter chaos? Though to be honest, I was just as afraid (or even more) about things just going smoothly – showing that I was absolutely unnecessary for my team’s success.

Deep down, this is a prime reason as to why many leaders never (or rarely) take off more than a day or two. Yes, you might miss out on some crucial information. But more importantly, you might miss out on an opportunity to show how important and indispensable you are – running the risk to feel unworthy of your own position.

Being aware of how this veiled version of the imposter syndrome tries to backstab me at every step, I decided to invest time into two areas before leaving on vacation: mindset hacking and process definition. The latter can also be used as a training opportunity for team members interested in leadership themselves.

Mindset hacking: who, what, and why

I decided to frame my absence as an opportunity for other people to step in temporarily and hone skills that they are interested in developing. Yes, it still means I might be replaceable. It also means I am not stuck in my position – and it ensures that my team does not remind stagnant easier. This means I had to define who can take over which parts of my responsibilities and coach/prepare them accordingly. To make this a real learning experience, it’s not enough to just assign tasks. I had to take the time to define each task, explain why I am doing is the way I do, and allow enough leeway for the new person to adjust those processes to their style.

Side note: you don’t need to clone yourself, handing over all your responsibilities to just one person. Some projects can be paused for 2-3 weeks, some responsibilities can be distributed to different people to avoid overburdening any individual team member.

Process definition: documentation for everything

In parallel, I updated and created lots of documentation in our knowledge base, explaining exactly how and why I do things. This also included a list of “things expected of team members”, which would help the interim lead to know which results and numbers to check during my absence (weekly reports, signup deadlines for weekend work, team responsibilites per months, etc). Putting all this knowledge and behind-the-scenes work into words and numbers also served as a helpful tool to prepare my “back-from-holiday” checklist to make those first days pre-vacation less stressful.
What is holding you back from taking the time you need to recharge? What are you afraid of?

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