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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.
Table of Contents
- Reframe the Off-Season: It’s Not a Pause, It’s an Advantage
- Skill-Building and Training That Gets Results
- Certifications That Level Up Your Guides
- Team-Building Activities That Aren’t Cringey
- Off-Season Projects That Drive Revenue
- Use the Off-Season to Upgrade Your Systems
- Keep Your Culture Alive All Winter Long
1. Reframe the Off-Season: It’s Not a Pause, It’s an Advantage
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.
2. Skill-Building and Meaningful Training
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:
- Swiftwater rescue refreshers
- Even your veteran guides benefit from muscle memory practice.
- CPR + First Aid practice sessions
- Keep certifications current and confidence high.
- Guest experience micro-trainings
Short, 30–45 min sessions on topics like:- De-escalation
- Storytelling on the trail/river
- Inclusive guiding practices
- Communication with nervous guests
- Cross-training across departments
This is where your systems and processes will play a crucial role. Teach team members how different operational parts flow together:- Rentals ↔ Ticketing
- Activities ↔ Lodging
- Inventory ↔ Passes & memberships
- Guide assignments ↔ Capacity management
When your crew understands how everything fits together, not just their piece, opening day suddenly feels a whole lot smoother.
3. Certifications That Level Up Your Guides
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):
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Wilderness First Responder (WFR)
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Swiftwater Rescue Technician (SRT)
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Avalanche Awareness
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Leave No Trace certification
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Rope systems or technical rescue courses
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Bike maintenance and repair certificates
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ACA, AMGA, or other discipline-specific certifications
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.
4. Team-Building Activities That Aren’t Cringey
Your staff doesn’t want a trust fall. They want a connection.
Here are team-building ideas that outdoor people actually enjoy:
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Adventure-based team days
- Ski day, group paddle, a mellow climbing session, or a bike skills clinic.
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Volunteering in the local community
- Trail cleanups, river stewardship days, wildlife habitat projects. These reinforce purpose and local partnerships.
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Story-sharing sessions
- Ask team members to share their best guest moment, toughest challenge, and biggest win. This builds empathy and reminds everyone why they love this work.
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Leadership handoffs
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Have seasoned guides teach sessions to newer staff. It boosts confidence on both sides.
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With team adventures on the mind, check out this fun story Jessica Ary, Flybook’s Business Analyst, shares in our Flybook Adventures Series.
5. Off-Season Projects That Drive Revenue
Your team wants meaningful work...not time fillers. Give them projects that improve operations AND sharpen skills:
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Create new experiences to launch next year
- A new sunset tour.
- A winter add-on.
- A multi-day version of a popular trip.
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Review your booking data
- Which trips sold out fastest
- Which days had unused capacity
- Where pricing might need adjustments
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Update guest communications inside your booking platform or email manager.
- Polish your:
- Confirmation emails
- Pre-trip reminders
- Post-trip review requests
- Automated texts
- Clearer communication → fewer guest questions → smoother operations.
- Polish your:
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Refresh waivers, SOPs, and safety policies
- A great off-season task for senior guides and managers.
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.
6. Use the Off-Season to Upgrade Your Systems
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:
Off-Season Audit Ideas
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Ensure pricing tiers & taxes are updated
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Refresh waivers or add multi-lingual versions
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Revisit activity descriptions and photos
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Build out capacity forecasting and guide scheduling
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Clean up tags, guest segments, and email templates
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Check rental inventory counts
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Review permission levels and user roles
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Add new passes, memberships, or season-long products
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.
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7. Keep Your Culture Alive All Winter Long
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:
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Seasonal staff advisory panel
- Invite a handful of guides and team members to give feedback on next year’s changes.
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Monthly check-ins
- Quick 10–15 minute conversations keep relationships warm.
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Transparent communication
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Share what’s happening in the business, what’s changing, and what’s ahead.
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People tend to stick with organizations they feel a connection to, not just the ones they work for.
In Summary, The Off-Season Is Where Great Teams Are Built
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:
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A retention tool
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A revenue-growth engine
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A culture builder
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A training ground for smoother operations
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A competitive advantage most outfitters don’t leverage
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.
Want support with system upgrades, staff management tools, or system optimization ideas? We’d love to help.
