When the last boats are stacked, the trails are covered with powder, or the lodges lock up for winter, many people assume outdoor outfitters slip into hibernation. But anyone in this industry knows the truth: the off-season isn’t downtime, it’s your only real chance to sharpen your systems, develop your team, and prepare for a smoother, more profitable next season.
And the teams that use this window with intention? They’re the ones who open the spring calmer, stronger, and more connected.
At Flybook, we talk with outfitters year-round, and the highest-performing operators share one thing in common: they treat the off-season as a strategic advantage. Below are the most effective ways we’ve seen outfitters keep their teams engaged and why it matters more than ever.
Many seasonal operators wrestle with the same challenge: how do you keep talented guides, instructors, and seasonal employees coming back year after year?
The answer starts with engagement.
Studies across hospitality, tourism, and outdoor education industries show that staff who feel invested in, trained, and connected to their team return at much higher rates (MDPI). And return rates matter. Hiring and retraining new staff each year drains time, money, and culture. (Staff Connect)
Engagement doesn’t mean endless meetings or “busywork.” It means giving your team purpose, growth, and visibility into what’s ahead.
The off-season is the ideal time to do that.
Skill maintenance is critical in any guide-driven operation. But training doesn’t have to be a multi-day or even all-day commitment to make an impact.
Here are high-impact training ideas outfitters use effectively:
When your crew understands how everything fits together, not just their piece, opening day suddenly feels a whole lot smoother.
Certifications aren’t just credentials; they’re confidence builders. When guides invest the time to refresh their WFR training, update their swiftwater rescue skills, or expand into a new discipline, they walk into next season with a stronger sense of readiness and professional pride. That confidence is contagious; guests feel safer, team members trust each other more, and leaders can delegate with less stress.
Consider offering (or subsidizing):
These deepen professionalism and give guides pride in their work. Some outfitters also create internal certifications, such as “Lead Guide Certification,” “Kids Program Specialist,” or “Advanced Trip Leader.” Those internal distinctions not only help with scheduling, but they also give your team something to strive for.
Your staff doesn’t want a trust fall. They want a connection.
Here are team-building ideas that outdoor people actually enjoy:
With team adventures on the mind, check out this fun story Jessica Ary, Flybook’s Business Analyst, shares in our Flybook Adventures Series.
Your team wants meaningful work...not time fillers. Give them projects that improve operations AND sharpen skills:
Using last season’s patterns to fuel next season’s strategy is one of the most powerful off-season habits you can build and with today’s AI tools, it’s easier than ever to execute. AI allows your team to create solid, thoughtful drafts you can refine and approve, speeding up progress without sacrificing accuracy or oversight. The result is a more empowered staff, faster iterations, and greater confidence in your team’s ability to drive meaningful improvements that might have once lived solely on your plate.
Your systems are the backbone of your operation. The off-season is your chance to optimize them without disrupting daily tours.
Here’s a checklist many Flybook users work through each year:
These updates eliminate headaches in April and May when the rush starts back up again.
While updating your systems, don’t miss Flybook’s latest Google integration update. Your team can now manage their work schedules directly from their calendar apps; simple, seamless, done.
Engagement isn’t only about training; it’s about belonging. Skills make someone capable, but connection makes them committed. When staff feel like they’re part of a community, they invest more of themselves in the job. Belonging creates pride in the brand, loyalty to the team, and a shared sense of purpose that carries through the toughest days of the season.
A few low-lift ways to keep the spark alive:
People tend to stick with organizations they feel a connection to, not just the ones they work for.
Your team doesn’t need busywork. They need development, purpose, connection, and a clear picture of the future.
When you offer that, the off-season becomes:
Investing in your team now doesn’t just prepare you for next season; it sets the stage for long-term success and a business that thrives year-round.