Virtual Whisperer 8 — Can I Go on Vacation?

By the time you read this, we’ll be ending our eighth week of sheltering in place and heading into our ninth. We’ll be staring down the barrel of Memorial Day weekend, the traditional start of the summer season here in the states. But will we be vacationing while sheltering in place? And how do you go on vacation when much or all of the team is working virtually, a phenomenon that won’t go away and may actually gain traction because of the experience of the past two months at home?

I wasn’t really thinking about this until one of my colleagues asked me the other day if he could take a vacation. I took it to mean “take days off,” and the answer, of course, was “yes.” We’ve always worked virtually at Outsell. Why wouldn’t we take vacations now? Yet, we’ve all been so focused on being productive in this new environment while our weeks have blurred between Monday and Friday into a straight line that the thought of vacay seems a little oxymoronic. Where could we even go?

The truth of the matter is vacations are important whether they are “tapas holidays” in the form of short breaks or dream trips to miracle destinations. The latter are off the table right now, but time off is still a must, so here’s how to take a vacation, especially while working virtually, both during COVID-19 and also when some semblance of getting out of the house is possible.

Be Clear That Vacations Are Not Just Okay but Expected

When things are strained, the economy is tight, or there’s a rough patch at the office, no one wants to come across as a slacker or risk being viewed as one. Frankly, it hadn’t dawned on me that taking time off was a question in our company, but it was for an important colleague, and odds are that if it was for him, it is for others. So make sure the expectation is clear that it’s okay to take time off during these wild times. In fact, I’d argue that it’s essential right now given the craziness of an entire family under one roof — working, cleaning, schooling, and dining together 24x7 for two straight months. Make it not only ok but encourage people to take a break.

Consider Saying Goodbye to Accrued Time Off

Most information businesses are running professional shops and aren’t unionized or dealing with external constraints. Give up the accruals and give people the flexibility they need to run their lives both professionally and personally. The slackers will really show up when you stop measuring, and the culture will weed them out. Meanwhile, free up energy, accounting time, and cultural goodwill, and let people take the time they need. I’ve done this for over 20 years and have yet to have an individual take advantage of our protocols. Where government regulations are involved, such as in the UK or France, then so be it, but flexibility is still the order of the day even within these regions.

Plan Your Time Off

Whether it’s two days or two weeks, announce the plan and let stakeholders you both serve and manage know that you’ll be out. Nothing wreaks havoc in a virtual environment more than seeing an “out of office” notice for a key person and discovering that someone who relies on the individual wasn’t informed. Nobody wants to find out that a colleague is on vacation right at the time that they need that person to advance something important. So, get the okay for time off, and then inform, inform, inform.

Make Sure Key Responsibilities Are Covered

In our virtual world, the work is never done. At Outsell, the amount of coverage we could provide is theoretically infinite but practically limited by our capacity to crowdsource or leverage the gig economy — which we do. But while the job is never done, vacations must go on. The trick is to wrap up key projects so they are done before you go. Not only can you then leave with a sense of accomplishment, but you’ll know that commitments have been delivered and others can be reviewing the work while you’re out. And if something doesn’t get done before you go, BE ACCOUNTABLE, folks! Either negotiate a new deadline, postpone vacation a day or two to wrap up and extend it on the other end, or find a win-win way of making sure this isn’t posing a problem.

Arrange Backup

It’s really important for every company to have succession planning in place and functions cross-trained. Even in our small company, we try to make sure that every function can be done by at least two people. Vacations are a great time to test this backup system — it’s the vehicle to ensuring that systems and processes are replicated while letting team members take essential time off. If there are prospects expecting follow-up, make sure to designate a fellow salesperson to agree to take them on in your absence and make sure your colleagues have the essential background that is also in the CRM. If you need to cover for client services, make sure someone is there to do it while you’re out. Every function can have a designated backup — if one doesn’t, then accept the fact that it will stop for a few days or a week or two. Even invoicing doesn’t have to be done every second of the day.

Unplug

Many of you will have seen my posts about unplugging and my strong belief that it is ESSENTIAL to model that behavior as a leader and insist on it from your team. A vacation is not a vacation if you’re on-call, being asked to answer email, or having to deal with “emergencies.” If you are a CEO or C-suite exec, name the very rare circumstances under which you may be called — such as a key person quitting or getting injured or worse, or your biggest client firing you. But I would argue that even that last one could be handled by someone else in your absence, and you can catch up upon return.

Boundaries matter, and giving your head and family some white space does too. Leaders who stay tethered to the office send the message that their team isn’t capable, which comes across as overcontrolling. Give the staff important freedom — unplug, people, unplug!!!

If you choose to keep Instagram current, fine, but keep your nose out of a screen and your face firmly planted on whatever cultures you’re blessed to be visiting. Of course, right now destinations are very limited. So take a local hike, step away to the beach. Take a drive through a state park if it is open and you can socially distance.

Do the “staycation” along with all the steps above. Remodel the house, bring the indoors outdoors, and ready the home for summer and BBQs. Paint some rooms if it gives you creative inspiration, or simply curl up with good books and have the kids curl up with theirs. Summer is a time for time off, and as school season ends, keep the kids off screens and outdoors — safely, of course. One colleague created an agility course for her dog in their backyard, with the entire family involved. There are lots of ways to staycay this year, and we’ll have to improvise even more.

Do take time off — it’s more important now than ever.