"They'll Figure It Out" Is Not a Training Strategy: What Seasonal Employers Get Wrong About Onboarding
Let's be honest about something.
A lot of seasonal operations — outdoor guiding companies, adventure tourism outfitters, resorts, ranches — still run on a training philosophy that sounds something like this:
"That's how I learned. They'll figure it out."
And yes. People do figure it out.
But figuring it out on your own, in a high-pressure environment, in front of guests, on a river or a trail or a mountainside — that's not resilience building. That's just expensive inefficiency with a safety risk attached.
The Reality of Your Incoming Workforce
Your seasonal hires are not blank slates.
They're coming in with:
Prior guiding, hospitality, or outdoor experience
Real expectations based on how other operations are run
Opinions — formed from working across multiple companies — about what works and what doesn't
They are quietly evaluating your operation against every other place they've worked. And the gap between "this place has its act together" and "we're just winging it here" shows up fast.
Within the first week.
What "Figure It Out" Actually Produces
The myth of sink-or-swim training is that it produces tough, self-sufficient employees.
In practice, vague or inconsistent onboarding produces:
Hesitation in the field when confidence is needed
Fear of asking questions — because questions weren't welcomed early on
Preventable mistakes that erode guest experience
Hidden frustration that drives turnover
Silence — and in outdoor operations especially, silence in the field is where real problems start
This isn't about coddling your staff. It's about building confidence before pressure arrives.
Because pressure will arrive.
What Strong Seasonal Training Actually Looks Like
Good training doesn't remove challenge. It doesn't protect people from difficulty. What it does is ensure people enter difficulty with enough foundation to handle it well.
At minimum, that means:
Clear expectations. What does "doing this job well" actually look like? What are the non-negotiables on day one? What gets addressed in week one versus month one? Don't make people guess.
Structured reps, not just shadowing. Watching someone else do the job is not the same as doing the job. Build in low-stakes practice before people are operating independently. Give people a chance to make small mistakes before the stakes are high.
Psychological safety during onboarding. If your training period is when questions are most punished, you've inverted the entire point of a training period. Early questions are cheap. Late questions — after someone's been too afraid to ask for three weeks — are expensive.
Intentional selection of who trains. Your best guide is not automatically your best trainer. Teaching is a skill. Whoever leads training should be modeling how to learn, not just how to perform. Being selective about who trains your incoming staff is one of the highest-leverage decisions you make all season.
The Resource You're Probably Ignoring
Here's something most operators miss:
Your incoming seasonal staff has likely worked at multiple operations. Some of them have seen systems that work better than yours. Some of them have seen things that would genuinely improve your guest experience, your team morale, or your operational efficiency.
If you create space for it — real space, not performative "open door" space — they can tell you:
What scheduling practices felt fair and which created resentment
What training structures actually built confidence
What recognition or debrief cultures made teams stronger
What made them stay at one company versus leave another
That's free organizational research. Most operators leave it completely on the table.
The Cultural Shift That Actually Needs to Happen
There's a 20-year veteran guide at a lot of seasonal operations who says, "I had to struggle through it and figure things out on my own. They should too."
That experience is real. That guide earned what they know.
But the logic — that struggle without support is the best way to develop people — doesn't hold up.
We're at a point in the outdoor industry where we know: yelling at someone for asking a question doesn't create excellence. It creates silence. And silence in the field is where real accidents happen.
At Guide Theory, we reject the "figure it out" culture wholesale. That's actually why we created the Shoulder Season Series — because there's a massive amount of collective knowledge in this industry, held by people who've worked in it for decades. Leaving training and culture up to chance when that knowledge exists is, frankly, a choice to underperform.
Where to Start
You don't need a perfect system. You need a better default.
Start with:
Normalizing questions during your training window — explicitly, out loud, repeatedly
Asking new hires (after a few weeks) what they've seen work well elsewhere and what surprised them about how things run here
Being deliberate about who you put in charge of training, and what you're asking them to model
Replacing "they'll figure it out" with "let's set them up well"
None of this is complicated. But leaving it to chance costs you more than you think — in turnover, in guest experience, in the culture your veteran staff is passing down to new hires.
The Question Worth Asking Yourself Before This Season Starts
If someone new walked in the door today — no prior context, just their experience from other operations — would they feel set up to succeed? Or would they feel thrown in?
The difference between those two experiences shows up everywhere: in guest reviews, in staff retention, in the way your team talks about working for you when they're somewhere else.
Build the foundation. The rest gets easier.
Guide Theory helps seasonal workers and the operations that employ them build better systems for this lifestyle. Learn more about the Shoulder Season Series.