How guiding trips prepared me for operations: lessons from the road that helped me thrive behind the scenes.
It’s a cold fall morning in Southwest France. My colleague, Laurent, and I have been up since before dawn, wearing all the layers we could rummage from our summer-season suitcases. We’re prepping equipment, food, and bikes for the third day of our cycling trip from Dordogne to Bordeaux. As we remind each other to ditch the headlamps, I’m furiously racing to top up the tire pressure that has dipped from the previous day’s excursion. Dom, more experienced, coaches me in a thick French accent, “Doucement Charles. Review your cultural talks. Catch your breath. You can finish the tires when the guests arrive. After all, if they don’t see you refilling the air, how will they know to appreciate how smooth their bikes are rolling?”
Leading luxury hotel-hopping bike trips across the world is a dream job filled with unforgettable experiences at a discount. Oui, oui, bien sûr! But behind the curtain of French châteaux, Patagonian vistas, and other world wonders lies a training ground of logistics, direct customer experience management, and problem-solving.
After eight years working in the field, I transitioned to back-office operations. Part of it was about wanting a change—a new challenge and a chance to put down roots in one place. Having firsthand experience on the road gave me a different perspective on what it takes to run tours smoothly behind the scenes. And surprisingly, many of the same principles that helped me thrive as a guide were key skills for navigating the office environment. Here are the five lessons from guiding that became my greatest strengths in the office.
Lesson 1 - Make Your Work Count (and Take the Credit!)
It’s important that your work always adds value, and as Laurent taught me in the field, that means ensuring the customer sees and feels that value. In the field, you are constantly getting direct feedback. I would personally read comments (often brutally honest) from the week’s guests. That kind of feedback loop taught me that doing great work isn’t enough—you need to ensure that others recognize and benefit from it.
Doing great work isn’t enough—you need to ensure that others recognise and benefit from it.
In the office, this translates to documenting and showcasing your contributions. If you optimize a process, launch a successful initiative, or enhance the guest experience, make sure that your efforts are visible to your team and leadership. Otherwise, it’s like refilling the air in the tires when no one is watching—people will assume the ride was always smooth.
Lesson 2 - Adaptability is Key
No matter how much planning goes into a trip, something unexpected will always happen. Whether it’s a sudden thunderstorm, a mechanical failure, or a guest who needs special accommodations, a guide’s job is to adapt quickly and seamlessly. The best tour leaders don’t just react to change; they anticipate it and embrace it, knowing that the unexpected is only highlighting the added value they bring to the product.
In our volatile world, the months of work behind an itinerary can go up in smoke at any moment. The trip-ops office can quickly become a race to re-book, re-design, and make hard decisions while phones are ringing off the hook. When you’ve tackled these moments alongside guests, your empathy and stoicism from the field are like super-powers allowing you to focus on the tasks directly in front of you.
Industries shift, projects evolve, and priorities change. Instead of resisting, the most successful professionals are those who stay flexible, pivot when needed, and see challenges as opportunities rather than obstacles.
Lesson 3 - Details Matter
Luxury travel guests expect seamless perfection—and they notice when something is off. That means ensuring their luggage is in their room before they arrive, curating cultural experiences that feel effortless, and knowing that a wedge of local cheese is a far better post-ride snack than a can of Pringles. Small details aren’t just nice extras; they’re the moments that make an experience unforgettable.
The same principle applies in any workplace. People often say, “I’m not a details person,” but details are what set top professionals apart. It’s the extra hour spent refining a presentation so it looks polished, the well-timed follow-up that keeps a tour on track, or the careful wording of an email that prevents unnecessary back-and-forth. These small efforts signal care, competence, and reliability—qualities that don’t go unnoticed.
These small efforts signal care, competence, and reliability—qualities that don’t go unnoticed.
Lesson 4 - Leadership at All Levels
Leading luxury tours, it’s daunting when high-powered guests—CEOs, investors, and executives—rely on you for leadership. People with immense authority in their day-to-day lives are looking to you to guide them and sometimes even make a decision for them when at odds with their spouse.
I learned that even when you’re not the official leader in a meeting or workplace, you can still contribute meaningfully by synthesizing the thoughts of others, recognizing good ideas, and adding your expertise. A great way to do this? Reflect different opinions back into the room while adding your perspective. Even a simple statement like, “I agree with X person, and additionally, there is a bonus factor to consider,“ can showcase your critical thinking and leadership.
Lesson 5 - Trust and Empower Your Colleagues
No tour guide can do it alone. The best trips happen when team members operate in sync, playing to each other’s strengths and distributing the workload strategically. Trust is the foundation—trusting your co-guide to handle a mechanical issue while you lead a hike, trusting the logistics team to get luggage where it needs to be, and trusting that stepping back in one moment can elevate the experience as a whole. My highest-rated tours weren’t the ones where I controlled every detail, but the ones where I focused on adding value in the right places. Handing off a favorite cultural talk to a junior colleague while I handled a behind-the-scenes fix might seem like giving up the spotlight, but in reality, it made the entire team shine.
The strongest leaders recognise when to step in, when to step back, and when to trust their colleagues to take ownership.
The same principle applies in any workplace. Micromanagement stifles creativity, efficiency, and morale, while true collaboration empowers teams to perform at their best. The strongest leaders recognize when to step in, when to step back, and when to trust their colleagues to take ownership. Before redoing someone’s work just to match your own style, ask yourself: is perfection more valuable than progress? Whether you’re leading a project or contributing to one, fostering trust and shared ownership creates better outcomes for everyone.
Final Thoughts
Tour leading might sound like an unconventional career training ground for desk jobs, but the skills it cultivates are invaluable. Adaptability, attention to detail, initiative, and teamwork aren’t just for the road—they’re essential for success in any field. So whether you’re planning a cycling trip through Bordeaux or navigating a complex project at work, remember: smooth rides don’t just happen. They’re built, one thoughtful decision at a time.
