A Productive Summer Your Team Will Fondly Remember
There is a version of summer that happens to organizations.
And there is a version that organizations design.
Most land in the first category by default. Not because leaders don’t care. But because workforce planning rarely includes a line item for delight, and by the time June arrives, the calendar is already full of everything else.
This is the part where I tell you it’s probably too late to restructure your summer staffing plan. If you were going to implement Summer Fridays, redesign schedules, or build a formal seasonal flexibility program, that conversation needed to happen in Q3 of last year. Workforce planning — real workforce planning — requires lead time, manager alignment, coverage modeling, and budget. You can’t bolt it on in June and call it a strategy.
But here’s what I also want to say: it’s not too late to do something. And something, done with intention, matters more than you think.
Why this is worth your attention.
Let me give you the backdrop, because the data is not subtle.
And here is the part that should make every senior leader pause: the same report shows manager engagement has dropped nine points since 2022 — the steepest decline of any worker category.
The people closest to your teams are checking out. And when managers disengage, their teams follow.
Summer is not the cause of disengagement. But it is a window into it.
If your organization is already seeing high absenteeism, elevated callout volume, or that particular brand of collective fatigue where people are physically present but mentally somewhere on a beach, summer will amplify it. Anyone who has managed a call center or a retail operation knows exactly what I’m describing. Coverage gets thin. Callouts run high. Customers feel it.
The question is not whether your people want to enjoy their summer. They do. The question is whether your organization is going to acknowledge that or pretend it isn’t happening and wonder why engagement and NPS scores keep sliding.
A note on the return-to-office conversation.
If your organization is among those mandating that employees come back to the office this year, I’ll say this plainly: the office and your leadership has to be worth coming back to.
I’ll write a full piece on work location strategy another time, because it deserves a real conversation. It’s a philosophy and a workforce design decision, not a control mechanism. But for now, the relevant point is this: as larger organizations move away from flexibility, smaller and mid-sized organizations have a real opportunity to differentiate by offering meaningful seasonal perks. If you are asking people to show up, meet them there with something that makes showing up feel worthwhile.
What you can still do this summer, with what you have.
You may not be able to restructure your entire operating calendar. But you can still shape how this season feels for your team. Here are some of the most effective, and frankly, most memorable, things I’ve seen leaders do.
Protect time off like it’s a business priority. Because it is.
Have the honest conversation with your managers: how do we make sure everyone on this team gets to actually use their PTO this summer?
Not just accrue it. Use it. That requires proactive coverage planning, team-level conversations, and managers who are empowered, and expected, to approve time off rather than quietly discourage it.
This is not soft. This is retention strategy.
Bring the summer to them.
One of my favorite memories from a leadership role I held was the summer luncheon we hosted for our team. We had access to a barbecue grill on-site, and we used it. We cooked. We ate outside. We brought the feel of summer right into the middle of a regular workday and it cost almost nothing except intention and a little planning.
Other organizations I’ve seen do this well: ice cream cart days, where a cart rolls through the floors on a Thursday afternoon with a bell ringing like the trucks from childhood. Cupcake trucks parked outside the building. Food trucks on the campus. A cafeteria team lunch with ice cream sundaes and life-sized Jenga in the courtyard.
I watched other departments press their faces to the glass wondering what was happening in our courtyard. That is the energy you want. And it spreads.
Let managers lead something fun for their own teams.
You do not have to wait for an enterprise-wide initiative. If you lead a team, whether that’s a team of five or fifty, you have more latitude than you may be using.
A team lunch. A walking meeting in the park. An afternoon offsite that isn’t about deliverables. A summer reading challenge. An end-of-day team happy hour on a Friday in July. These are not grand gestures. They are small, human ones. And they add up.
The leaders who do this consistently tend to have teams that talk about it. The ones who don’t often wonder why their engagement data tells a story they didn’t expect.
Start planning now for next summer.
If there’s a broader takeaway here, it’s this: the best summer cultures don’t happen in June. They get intentionally designed in advance.
If you are looking at your engagement, customer service, and NPS data right now and not loving what you see — if your absenteeism is climbing, your team energy feels flat, or your people seem like they are going through the motions — let’s connect to discuss your workforce planning strategy with your HR, operations, and finance leaders. These are complicated efforts, but not unssolvable, and the returns on investment make it worthwhile.
Your people are going to experience summer one way or another. The only question is whether your organization will be part of what makes it good or the reason they callout or leave to find it somewhere else.
Design the season. Your team will remember it. And honestly? So will you.
Cassandra Shepard is the founder of Shepherd + CO, where she helps leaders and organizations find strategic clarity at the intersection of business, leadership, and a life well lived. Learn more at cassandrashepard.com.