This Summer, Every Employee Will Want a Vacation. Here’s How to Not Lose Momentum

This Summer, Every Employee Will Want a Vacation. Here’s How to Not Lose Momentum

Avoiding the post-pandemic summer slump may be one of the toughest leadership challenges you will face this year.


Earlier this week, I sat down outside a restaurant in San Francisco. Within earshot, a group of 20- and 30-somethings gathered for an outdoor brunch. Their animation and excitement were palpable. The topic of their conversation? Where should we go on vacation now that the world is opening back up? Two girls shouted “Maui” in unison while others rattled off suggestions for weekend trips to Vegas, Joshua Tree, and Tahoe.

As I sat listening, it was hard not to get excited about the world reopening and the thought of going back to a wanderlust life. The past 12 months have been a grind for many, both emotionally and physically. We have been told to be good citizens–that we need to stay home and stay put. And as those restrictions are lifting, almost everyone is eager to pack their bags.

It’s also becoming apparent that this eagerness to travel will affect the early-stage tech economy. At Shasta Ventures, we focus on early-stage enterprise startups, and the firm has never seen such growth and velocity as during what is now being coined the “Great Pause.” Companies of all sizes picked up their knees and sprinted toward goals and milestones, often with leaner teams. Staying at home became the norm, and the boundaries between work and personal life became increasingly blurred.

We felt like we were on a mission to do as best as we could given what the world threw at us. We found ourselves poring over our work, grappling with burnout, and many startups also felt the sheer exhilaration of exceeding most people’s expectations of what could be accomplished during this great pause. With the light shining brighter at the end of the tunnel, and shots being placed in the arms of adults of all ages, the effects of toeing the line of burnout feel more potent than ever.

Summer of Stagnation

The world is ready to go on vacation, and that might lead to a summer of stagnation. Most founders have not thought about the fact that people are itching to travel, because for the past four quarters, their goals have morphed from survival to scaling to avoiding burnout. Now, everyone is ready to actually cash in their PTO for some well-deserved time off, and managers need to have an action plan to handle the onslaught of requests.

One of the first things we are starting to tell founders is to be proactive. Summer Fridays should make a comeback. Give your team a half-day on Fridays to be able to get out of town and enjoy some fresh air and sunshine. Founders should encourage everyone to take time off from Slack and avoid any Friday meetings late in the day. A company mandate helps ensure that the team actual uncouples from the workweek grind.

The second piece of advice is to preempt the conversation with your team and build a detailed schedule for when team members are out of the office. Approvals matter here, because you’re trying to avoid your entire CS team on break during the same week. Departmental approvals can ensure that even though there may be a higher percentage of team members out at once, at least departments have coverage. This is especially critical in a world where many startups offer “unlimited PTO.”

Third, look at your road map and try to tackle some of the smaller, less complex projects that have been piling up. Often these take less collaboration, so even during weeks when your team might be light, you can still be making progress.

As the world opens back up, your team is going to want to travel. Communication, planning, and understanding will be more important than ever for a manager. Make sure your team knows that it’s not only OK, but encouraged to unwind and explore this summer. Be realistic in your planning process to ensure that your startup doesn’t lose too much momentum and can finish 2021 stronger than ever.

MAY 5, 2021