When The Office Meets The Crew

It’s not every day that your job description shifts from “Office Manager” to “Cycling Through Italy with the Crew.” But here I am, trading spreadsheets for spokes, heading out on the Viva Italia Tour to get a first-hand look at how things work beyond the four walls of HQ.

If you’re like me, the thought of joining the team on the road sounds equal parts thrilling and slightly terrifying. I mean, I know how to answer emails like a pro and organize registrations with my eyes closed, but pedalling up a hill in Tuscany? That’s a different story.

Olha with Assistant Tour Leader Balazs

Here’s the thing though – this kind of experience isn’t just good for me; it’s crucial for everyone involved. Getting out from behind the desk and onto the saddle (well, mostly the tour van for me, let’s be honest) is an eye-opener. It’s a chance to understand what it really takes to make one of our tours run smoothly from start to finish – and trust me, there’s a lot that goes on behind the scenes.

From the very first day in Rome, I’ve had a front-row seat to witness how our crew transforms a complex operation into something that looks effortless. And as much as I’ve prided myself on being organized, there’s a whole other level of coordination when you’re on the road. You’ve got cyclists to manage, food to prepare, bikes to fix – all while moving to a new location every day. I thought handling rooming lists was intense… until I saw crew members juggle flat tires, snack requests, and route changes all in the span of 10 minutes.

On the flip side, the crew learned a bit more about what happens back at HQ. Sure, they’re the rockstars on the road, but a lot of magic happens behind the scenes to make sure everything runs like clockwork. From organizing all the registrations, and checking all the forms to ordering the jerseys and race plates, the office plays its part too.

Dealing with dishes instead of spreadsheets

There’s something to be said about both sides understanding what the other goes through. It makes communication smoother, processes more efficient, and honestly, it gives everyone a little more empathy. After all, when you’ve spent the day cycling in these steep Italian hills, you might think twice about grumbling over that 11 a.m. Tuesday meeting.

One of the coolest parts of this whole experience? Meeting the riders I’d only ever known through emails and form submissions. It’s like seeing characters from a book come to life! I’ve spent months sorting through registrations and insurance forms imagining what these cyclists were like in person. So, when I finally got to put faces to names, it was a bit surreal. And let me tell you, meeting them in person was even better than I expected! Hearing their stories of past tours, travel adventures, and what brought them to tackle Viva Italia added a whole new dimension to the work we do. It reminded me that behind every form, there’s a passionate person, ready for the ride of a lifetime.

So, here’s my takeaway: when the office meets the crew, everyone benefits. Whether you’re an office newbie or an assistant of the tour leader, having a foot in both worlds creates a stronger, more connected team. Will I trade in my office chair for a bike seat full-time? Probably not. But having experienced the Viva Italia tour from the inside, I will head back to Toronto with a new appreciation for what it takes to make these adventures happen – and maybe, just maybe, a few more muscles than I had before.

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