5 Habits Ryan Leak Says Will Separate Good Travel Advisors From Great Ones

Make intentionality your operating system.

Leak’s most useful point wasn’t about mindset; it was about how you work. “Excellence is never random. It’s never, oops. I’m amazing,” he explained. 

What makes service memorable isn’t luck—it’s doing the homework early and being ready with the right details at the right moment. His hotel anecdote—the team that placed a framed family photo on his nightstand—wasn’t about budget; it was about noticing.

Try this: Build a 10-minute “intentionality huddle” into daily workflow. One question per client or partner on deck: What’s the one specific thing we can do today that would make this feel designed, not default? Then log it. If it’s not documented, it’s not scalable.

Ask “How are you?”—then ask it again.

Most relationships in travel and hospitality live at the surface: “How’s it going?” “Good.” Leak’s challenge: ask twice and leave room for the real answer.

When stakes are high, whether it’s due to FAA snarls, weather, or shifting entry rules, the first response is often a shield. The second opens the door to the information you actually need to anticipate problems, set expectations, or triage.

Try this: Bake a two-step welfare check into client and team touchpoints during disruption windows (irregular ops days or major holiday periods, for example). Begin with the basics—what’s going on—then make space for how they’re doing with it. Track the client’s mood so you can then tailor your tone, pace, and communication style appropriately.

Build self-awareness into service reviews.

Leak’s framing question—“What’s it like to be on the other side of me?”—is a leadership diagnostic disguised as a posture check. With so many delays and supplier hiccups this year, the way leaders communicate (how clear they are, how quickly they respond, and the tone they use) shapes how their teams and clients react.

Try this: Perform a quarterly “other side” audit. Pull a random sample of your last 20 emails and 10 call notes. Score for clarity (did you name the decision and the next action?), latency (how long between client nudge and your reply?), and temperature (does the language reduce or amplify anxiety?). Share your own scores first in team stand-ups—then invite peer feedback. 

Mentor on purpose, not by osmosis.

Leak’s story about the people who helped him along the way is tied directly to a real issue in the travel industry: developing the next generation. New advisors don’t learn luxury service just by being nearby—they also need structured training and hands-on practice.

Try this: Instead of hoping new advisors “pick things up,” give them a set period of guided practice—shadowing calls, trying one client interaction with coaching, and learning a few core service habits. Judge progress by performance, not seniority.

Bet on consistency over charisma.

“Momentum does not belong to the most talented it belongs to the most committed,” Leak emphasized. The brands and agencies that win next year will likely be the ones that close loops faster, reconfirm more often, and communicate with fewer surprises.

Try this: Make it a rule that clients never go a full day without hearing from you on active trips or problems you’re working on. Even if nothing has changed, send a quick update, tell them when you’ll check in again, and explain what you’re doing behind the scenes. Consistent communication builds trust; silence breaks it.