10 Questions Boards Must Ask When Hiring Travel, Hospitality, and Leisure Executives

The hardest part of an executive search isn’t finding candidates. It’s evaluating them. 

Résumés tell you what someone has done. References tell you how they did it. But neither tells you whether someone can do work they’ve never done before. That matters more now because the work itself keeps changing. 

Most boards ask similar questions in executive interviews. They’re good questions. They’ve worked for decades. But they test for excellence in running existing operations, not for capability in building new ones. When the role requires both, boards need additional questions that probe different territory. 

The ten questions below test for things traditional interviews miss. They reveal whether someone has built new business models or just improved existing ones. Whether they think in partnerships or transactions. Whether they can make good decisions with incomplete information. Whether they can explain change to people who made their careers in the old model. 

None of these questions has a perfect answer. That’s intentional. They’re designed to surface how someone thinks, not what they know. 

Question 1: Can This Executive Explain Platform Economics in Simple Terms? 

Start here because it reveals whether someone genuinely understands the business model you’re building or just uses the vocabulary. Ask a candidate: “Explain to me how a hotel becomes a platform business and why that matters financially.” 

The wrong answer sounds like consulting jargon. “We leverage our data assets to drive synergies across the value chain.” That tells you nothing. 

A good answer sounds specific and grounded: “Right now we earn $150 per room per night. If we capture guest preference data and connect it with airline partners and local experience providers, we can orchestrate a complete journey. That guest might spend $800 total, and we coordinate all of it. We don’t own the flight or the restaurant, but we own the relationship. The margin on orchestration is better than the margin on rooms.” 

MIT CISR research found that only 26% of company boards are digitally and AI savvy when measured against updated criteria that account for newer technologies. The other 74% struggle to evaluate whether executives actually understand what they’re talking about or just repeat phrases they’ve heard. This question cuts through that. Someone who understands platform economics can explain it clearly. Someone who doesn’t will hide behind buzzwords. 

Question 2: How Have They Built Something That Didn’t Exist Before? 

Traditional career progression in travel, hospitality, and leisure follows a predictable path. You join operations, master efficiency, expand scope, take on bigger properties or routes or networks. That path builds competence in running what exists. It doesn’t necessarily build competence in creating what doesn’t exist yet. 

Ask: “Tell me about a time you built something new rather than improved something existing. What was it? Why did you do it? How did you know if it worked?” 

Listen for specifics. Did they launch a new service line? Build a data product? Create a partnership model that didn’t exist in their industry before? The details matter less than whether they’ve actually done it. Creating new business models requires comfort with ambiguity, tolerance for experimentation, and judgment about when to persist and when to stop. You can’t evaluate those capabilities if someone has never built anything new. 

Question 3: Do They Think in Ecosystems or in Transactions? 

Here’s a test. Present a candidate with a scenario: “An airline approaches us about bundling flight bookings with our hotels. They want to share guest data. What do you think about that?” 

Someone who thinks in transactions will ask: “What’s our fee per booking?” That’s not wrong. Revenue matters. But it’s incomplete. 

Someone who thinks in ecosystems will ask different questions: “What data do they share with us? Can we use it to personalize the hotel experience? Do we get access to their loyalty program members? Can we offer our guests flight upgrades? What does this partnership enable that neither of us could do separately?” 

The second person sees opportunity in connection. The first person sees a deal term to negotiate. Both matter, but the second mindset is what builds platform businesses. 

Question 4: Can They Translate Between Two Worlds? 

Every executive search in travel, hospitality, and leisure now involves tension between domain expertise and platform thinking. You need both. The question is whether this person can bridge them. 

Ask about a time they had to explain a new approach to people deeply invested in the old one. How did they make the case? What resistance did they face? How did they handle it? 

We’ve seen CFOs succeed when they can speak both languages. Someone who spent years in traditional hotel finance followed by time at a cloud software company could explain to real estate-focused board members why platform revenue was more valuable despite lower margins. They could also explain to software teams why hotel operations couldn’t move as fast as SaaS product cycles. That translation ability mattered more than pure expertise in either domain. 

PwC’s research shows that only 35% of executives rate their board’s performance as excellent or good, partly because boards and management often aren’t aligned on priorities. An executive who can translate between traditional business thinking and platform thinking helps close that distance. 

Question 5: How Fast Can They Learn? 

Industries change faster than careers prepare people for change. Ask: “What have you had to learn in the last two years that you didn’t know before? How did you learn it? How do you know you actually understand it rather than just recognizing the terminology?” 

The specifics of what they learned matter less than how they learned it and how they tested their understanding. Someone who took an online course on machine learning because their company was implementing AI, then spent three months in weekly meetings with the data science team asking questions until they could explain model performance metrics in their own words, demonstrates learning capacity. 

Someone who says they “stayed current by reading industry publications” might be knowledgeable, but you can’t evaluate whether they can learn genuinely new things when their role demands it. 

Research from the Corporate Governance Institute found that boards increasingly need “deeper knowledge and expertise” around digital capabilities, especially AI, rather than just general awareness. The same applies to executives. The learning requirement isn’t one-time. It’s permanent. 

Question 6: How Do They Evaluate Technology Investment? 

Don’t ask about specific technologies. Technologies change too quickly for that question to stay relevant. Instead, ask how they think about technology investment decisions generally. 

Present a scenario: “Your CDO proposes spending $50 million over three years to rebuild our booking system and create APIs so third parties can integrate with our platform. How do you evaluate whether that’s a good investment?” 

Someone whose background is purely operational might frame this as a cost question: “Can we reduce the cost? Can we phase it? What’s the payback period?” 

Someone who understands platform economics will ask different questions: “What new business models does this enable? What data do we capture that we don’t capture now? What partnerships become possible with these APIs? How does this change what we can charge for?” 

Both sets of questions matter. But the second set reveals whether someone sees technology as infrastructure that enables new business or as an expense that requires justification. 

Question 7: Can They Make Good Decisions With Incomplete Information? 

The playbook for running airlines, hotels, and logistics networks is well-established. Decades of best practices. Clear metrics. Proven approaches. The playbook for becoming a platform business that happens to own planes, properties, or trucks? That doesn’t exist yet. 

Ask about decisions they’ve made when they couldn’t know if they were right. How did they decide? What information did they gather? What did they do when the data ran out? How did they know when to proceed and when to wait? 

Someone who needs certainty before moving will struggle in this environment. Someone who can make reasoned bets with partial information, set up ways to test whether those bets were right, and adjust quickly when they learn more, has better odds of succeeding. 

Board Intelligence research found that 83% of directors don’t believe their board is set up to harness AI opportunities, despite widespread acknowledgement of AI’s importance. Part of that gap comes from waiting for perfect information that never arrives. The executives who succeed will be the ones who can move forward despite uncertainty. 

Question 8: How Do They Think About Talent That Doesn’t Fit Traditional Categories? 

Your next CHRO search will force you to answer a question boards often avoid: Do we value someone who knows hospitality HR, or someone who has integrated technology talent with operations talent in another industry? 

Ask candidates: “You need to hire a head of data science. The compensation band is $350K. Your VP of Operations says that’s more than they make after 20 years with the company and it sends the wrong message about what we value. How do you handle that?” 

There’s no perfect answer, but the response reveals whether someone can balance fairness to existing talent with the need to attract new capabilities. Someone who says “We pay market rates for important roles” without acknowledging the tension probably hasn’t thought carefully about culture and change management. Someone who says “We structure it carefully, ensure the VP understands why, and create a plan so operations leaders can develop the skills that command those compensation levels” understands you’re managing both the hire and the organization’s response to it. 

Question 9: What Do They Actually Want To Build? 

This question sounds soft, but it’s not. Ask: “If you took this role and succeeded, what would this company look like in five years that it doesn’t look like now? Be specific.” 

Listen for whether they describe running a better version of what exists or creating something different. Someone who says “We’d have higher occupancy rates, better margins, more properties, and improved guest satisfaction scores” might be a great operator. But they’re not describing what you need if you’re trying to build a platform business. 

Someone who says “We’d own the complete travel relationship for our loyalty members. They’d book flights, hotels, ground transport, and local experiences through us. We’d earn money by orchestrating that journey efficiently rather than by owning all the pieces. Our data would be so valuable that airlines and experience providers pay us for access to our insights” is describing a different business. 

The first answer isn’t wrong. It’s just solving a different problem. Make sure you’re clear which problem you’re hiring someone to solve. 

Question 10: Can They Explain Why Change Matters Without Dismissing The People Who Made The Company Successful? 

This might be the hardest one to evaluate, but it’s perhaps the most important. Change management failures kill more strategies than bad strategies do. 

Ask: “You’re going to stand in front of 200 hotel general managers who have spent their careers perfecting operational excellence. You need to explain why the company is betting its future on becoming a technology platform. What do you say?” 

The wrong answer sounds dismissive: “The old model is dead. We need to think differently now.” That alienates the people you need to execute the new strategy. 

A better answer sounds respectful and clear: “Everything we’ve done to become excellent operators creates the foundation for what comes next. We know how to deliver exceptional guest experiences. Now we’re using technology to deliver that excellence across a broader journey. Your operational expertise becomes more valuable, not less, because we can now extend it beyond the four walls of your property. But it does require learning new capabilities alongside your current ones.” 

Someone who can deliver that message honestly while maintaining credibility with people invested in the old model is rare. But that’s exactly what the role requires. 

MIT research shows that 74% of directors believe their boards should spend more time on high-level vision, but 80% think their boards are stuck in operational details. An executive who can help both the board and the organization focus on the right level of abstraction creates enormous value. 

Using These Questions in Practice 

These ten questions won’t eliminate hiring risk. No interview process can. But they change the conversation from credentials to capabilities. From what someone has done to how they think about work they haven’t done yet. 

Most boards discover something when they start using questions like these: the candidate who looked safest on paper often gives the weakest answers. The person with 25 years in the industry struggles to explain platform economics in simple terms or describe a time they built something new. Meanwhile, someone with eight years in travel and five in a marketplace company can articulate exactly how they’d approach the role. 

That doesn’t mean you should always hire the outsider. Sometimes the industry veteran gives brilliant answers because they’ve been thinking about these questions for years. The questions just reveal who has and who hasn’t. 

At Stanton Chase, we help boards with executive search for these roles because we know exactly how to assess candidates to find out what kind of problems they can solve. We’ve spent three decades placing executives in travel, hospitality, and leisure. We know what traditional excellence looks like in these industries. We also know what newer capabilities look like because we’ve been placing executives who bring them. If your board is preparing for an executive search, we’d welcome the conversation. 

About the Author

Toon Balm is a Partner at Stanton Chase Amsterdam, specializing in executive search across consumer products and services, with particular expertise in the travel, hospitality, and leisure sectors. Toon previously held strategic leadership roles at Air France KLM across Nigeria, Iran, Italy, China, and the Netherlands, where he was part of the KLM Management Group. In this capacity, he led commercial strategy, transformation initiatives, and regional operations, developing deep expertise in both traditional business models and the platform-era thinking now reshaping the sector. His unique background—combining aviation industry leadership, executive search expertise, and a tenure with the Special Forces Division of the Royal Dutch Army—positions him to identify leaders who can navigate the complex convergence of technology, operations, and customer experience.