The Art of the Upsell: Sell the Dream First

We speak with Jack Ezon and Anne Scully of Embark Beyond and learn that once you determine what’s truly special to a client, you’ll free them to make travel choices that truly speak to their desires.

Ruthanne Terrero: It’s great to see you both! Today, what we want to talk about is the luxury landscape and the art of selling up. I know you both have a very particular view on how to interact with clients to assess what would be the best trip for them and what they really need from you.

Anne, I know that you are a big believer in selling the dream trip first. So, if you don’t mind, I’ll just leave you with that very wide-open question. Can you talk about selling the dream and what that entails? 

Anne Scully: You know, Ruthanne, a lot of what I learn is when I have clients in front of me. When something happens or I have an opportunity to engage with a client, I can learn a lesson from it. 

Several years ago, a couple came in from New York City. They had just retired. They were from the Bronx. I was born there and lived there for my first four years. They were as adorable as they could be, and the gentleman was just so charming. They sat down and said they’d retired, they’d worked hard their whole lives, and now they wanted to travel. So, the husband suggested that the wife say what she wanted to do, and she talked a little bit about Paris, and maybe doing a little cruise in that area, and suggested several other things on her list. She went on about 15 minutes. 

I said, “You know, before we go any further, I think rather than looking at what you want, let’s really get to know each other a little bit better. Tell me more about yourself and why this particular trip.” We always talk about the why and the meaning of a trip. Again, they wanted to relax. They wanted to enjoy it, and they thought maybe this was a good step in the water. 

So, I turned to the husband, who had been very quiet. I said, “I’d love to hear what you’re thinking about. What’s on your list?” 

He said, “You know, one day, I’d like to go to Australia and New Zealand. It’s my dream,” he said. “But maybe later.” 

As you know, I work with advisors. At the time, I had Beth Jenkins next to me. I said, “Beth, go get that Oceania brochure.” I told them, “I want to show you something.” 

Actually, I could tell you how many years ago: It was 2009. It was at a time with the economy not being so great, there was incredible value out there. 

So, Oceania had free business class from L.A. — of course, we’re on the East Coast — and they had a two-for-one rate on staterooms. So, I just presented it to them. They both got very excited. At the end of that day, they walked out with a 35-day cruise to Australia and New Zealand. They had children in L.A., so it also gave them an opportunity to start from there, from their children’s home. 

They took nine Oceania cruises after that in several regions. 

I always like to sit back after I’ve done something that really works. I realized you should talk to a client, engage with them, and find out what that dream trip is because several wonderful things happen when you focus on the dream first. 

Number one, we’ve just come out of — and we’re not out of — COVID yet, but at least people are now traveling. The thing about working with a client on a dream, they talk to you more. They will tell you more about things that really matter to them so you can create an itinerary that’s suitable to them. 

I always say a great advisor doesn’t design a trip that a thousand other people take. The trip should totally be about that particular client. 

The other thing about selling the dream, they will travel longer because the trip means more. They are willing to pay more because when it’s your dream, it’s like, “Oh, we’re just going to go do it.” 

The best result of selling the dream trip first is no one has just one dream. I just said they did nine cruises since that particular trip and have done countless other travels. The thing is, we exposed them to a part of the world they weren’t sure that they could have. Remember, they were retired. When they went on that cruise, they walked across the bridge in Sydney, Australia, and it was so wonderful. It changed the way our relationship developed. They still work with Beth very closely. 

So, it’s a lesson I learned just from engaging a little bit more and not being an order-taker. We talk about that all the time. You don’t want to sit there and write down what a client wants, especially when you don’t know them, and you don’t know the why, and you don’t know what other possibilities are. So, it’s a lesson I’ve learned, and it’s one I’ve used ever since. 

Sydney, Australia (Getty Images)

Ruthanne Terrero: When you ask them about the dream, you’re not asking them where do they want to go. Because when you say, “Where do you want to go?” one’s mind starts trying to figure out, “How will I get there? How much is that going to cost?” In your mind, you put up all these barriers and you narrow down your options. When you ask, “What is your dream?” you’re not really challenging the client that way. 

Jack Ezon: I think it’s even more than that. Anne and I do a lot of training together, and we say this all the time. “Don’t ask about deliverables. Ask for the ingredients. Sell by aspiration and not destination.” 

If somebody says they want to go to Paris — like Anne was saying, ask “Why?” Once you learn that "why," and you understand that, you can sell them 10 other places that deliver on that "why."

So, what we like to really say is to upsell is to really specialize in that client and know the world, because once you know what’s meaningful to that person and understand what drives that person, you can equate value to anything that’s aligned with that person’s priorities. That will unlock unlimited spending potential for that client with you. 

Ruthanne Terrero: That’s a great tip. You also earn their trust. Right? 

Jack Ezon: And loyalty. 

So, Anne and I, so many times, we’ll be on trainings and we say, “Ask why, not where. Know me. Understand me, and we’ll build this future together for you.” 

Anne, I’m going to steal your line now. Anne says, “As travel advisors, we’re really like biographers. We’re writing each chapter of their life through their travels, and travel is a platform.” I mean, you say it much better than I do, Anne. You should say it, not me! That’s your line! 

Anne Scully: But, you know, we’re talking about upselling. If an advisor wants any tips on working with a new client, start with the dream. You’re upselling instantly. The reality is clients realize that travel is a lifestyle. They fall in love with it. Every time I take a trip, when I come home, the first thing I’m thinking about is, “Where am I going to go next?”

We have a lot of senior citizens (baby boomers) who haven’t been able to travel for two years. They haven’t spent money in two years on travel, and they’re ready to go everywhere. If anyone isn’t focusing on the dream right now, they’re making a mistake. 

Jack Ezon: So true. The key to understanding that dream is not just listening to what the client says the dream is. What Anne was saying is understanding what’s behind what they’re saying.

So, you need to listen. Listen, listen, and ask open-ended questions. You may find out things such as, “Space is very important. My husband snores; I always need another place for him to sleep.” You might be able to understand priorities. 

We once had a family, and the matriarch of the family was telling us that they were getting older, and their goal was to keep their grandchildren together. They wanted to travel where they were all going to be under one roof. So, where they were going originally, they were going to take just general rooms in a hotel and probably spend about $6,000 a night. We were able to upsell them to a gorgeous estate on Jumby Bay for like $30,000 a night. The reason is we tied that to their legacy. We tied that to, “You want everybody under the same roof, to wake up in their pajamas, and have breakfast together, and not have to worry about who’s in what room.  You want them to bunk together and be at the pool together. This is what you want for your legacy.” Nobody puts a price on that if they can afford it. 

Think about people who can’t afford sometimes to buy dinner for themselves; they will save up for that Gucci wallet or that bag. Not because they can necessarily afford it, but it’s important to them. So, find out what’s important to your clients and you’ll have unlimited upselling potential. 

Bridge of Alexandre III, Paris, France
Bridge of Alexandre III, Paris, France (Getty Images)

Ruthanne Terrero: When you’re training new advisors — they might be new to the industry one way or the other, either just out of school or coming from another career — if somebody doesn’t have the confidence or is nervous to speak to a client in such a way, are there any tips that you can provide? Because there’s a fine line, too, between asking too much. Do you find that new advisors have some kind of trepidation in terms of speaking with candor and courage to a client? 

Anne Scully: The reality is, some have no problem talking to people because they’ve come from other industries, and they really enjoy it. We have a lot of people who have been in the airline industry, they’ve been teachers, they were event planners. We have lawyers. We have all kinds of people. Everybody’s rethinking their lives right now since COVID. Do they want to work behind a desk from nine to six? Did they want a boss over their shoulders? 

That’s why independent contractors are becoming so important to our industry. They can adjust their time. They can live the life they want. They can travel. They have the ability to use those skills they had before. 

But we have people who are very new to the industry. That’s why Jack and I just spent 60 hours doing training, and that doesn’t exist, I think, anywhere else. We role-play with them. 

Jack, I’m going to turn it over to you, now, because Jack’s wonderful at that. But we really give our advisors homework, and we put them on the spot a little bit because we want to see if they have passion. 

Jack Ezon: Anne, what you’re saying is absolutely true. There is an art to building a relationship and to understanding a client. If you make them feel like you’re robotically interrogating them or filling out a survey, it will never work. 

We do a lot of role play. There are people that are new to the business, like Anne said, that are great at it because they may come from fashion, or luxury retail, or real estate where that was natural. They could be people that have been in the business for 10 years but were historically order takers, and it’s not natural for them. They may be even 20-year veterans, and there’s trepidation when they have to have a conversation with a client about their personal life. 

So, you know, there’s an art to understanding how to speak to someone at their level and speak respectfully, but to speak at the same level and to create a trusted relationship. A lot of that also starts with understanding who that client is and the world they come from. 

So, if you’re working in the luxury space, for example, you need to know the difference between a Kelly bag and a Birkin bag. You need to know the difference between someone who drives a Ferrari or a BMW, and what class of Mercedes they may have. You need to understand fashion. You have to understand a little bit of art. 

We also train for that, to be able to speak holistically to a client and have them open up their life to someone who they feel will understand them. 

Ruthanne Terrero: Holistically, I know you’ve spoken about that before. It’s about trying to find out where they are in their lives, what matters to them, what brands they like, and what means luxury to them, too. 

How about the old adage, “Don’t sell with your own pocketbook”? Someone could come in and want to do XYZ trip, and the advisor is like, “Well, there goes my mortgage for an entire year,” in some cases. 

How do you get people past that, as well? To get them to feel comfortable with some of the numbers that they could potentially be dealing with. 

Jack Ezon: I think the key to that is to make sure — and this is a one-on-one — that you are not selling what you want, you’re selling what your client wants and you’re listening. People ask me all the time, “Where would you stay if you were going to Paris?” for example. My answer is, “This is not my vacation. This is yours. My job is to listen to you, and to hear what’s important to you, and tell you what the best place is for you,” and to make it about them and not me. If you keep training yourself to think about what’s good for somebody else and not me, you’ll be successful at upselling. 

Anne Scully: I would add to that, Jack, that even the wealthiest person wants value. It’s not about the price point; it’s not. It’s about the value of the experience.     Here’s an example of “value:” We all know there are some issues out there with suppliers with lack of staff. One of the things that would cost them no money is to train staff to make a guest feel valued.

Here’s a recent example of why a client just left one hotel for another. The first hotel welcomed them, gave them that warm hug on arrival, and said their name. When they went to the next hotel — this was in the Amalfi coast — and as beautiful as that hotel was, they weren’t welcomed. Two people who were standing outside for luggage never even looked at them. When they went inside, the person was polite, registered them, but no welcome. They wanted to know about dinner but were given no real information. They had to walk into the restaurant on their own. 

Hotels may have less staff, but the staff you have need to learn the welcome. We have to do that with our clients. We say their name. We train people and remind them when you’re talking to somebody, everybody wants to hear their name. They want you to repeat what they said because they want to know you actually listened to them. Even if it’s not good, you just want to repeat it because they may have had bad experiences before. You have to listen to those objections, and they shouldn’t scare you. 

But then, you have to step in and say, “Let me show you what we can do for you. This is what we have.” 

For example, when someone has a concern about going from hotel to hotel in Europe, I talk about a cruise, and I talk about seeing the world on the U.S. dollar. There are people that will buy the finest suite on a ship, as you know, because cruises are now back. But they don’t want to be moving around on trains and cars and getting on planes. They are happy with the cruise. 

Again, you wouldn’t know that unless you really opened up a conversation with a client about how best to see the world? 

No matter how much money someone has; a good advisor shows their value. Even if it’s $10,000 a night, it could be the fourth night free. You want to highlight that! If you get the upgrade, you want to show them the value of an upgrade. 

A Jet Boat in Shotover River, New Zealand
A jet boat in Shotover River, New Zealand (Getty Images)

Jack Ezon: Anne, what you’re saying is so important. If you want to be able to sell someone or upsell them, it’s trust. Building that trust. Because if you tell someone, “Listen, you don’t want to show up and have FOMO that you’re not in the right space. Listen to me. I’m giving you my advice because you trust me. This is what you really want to do.” You can say that with conviction and convincingly if they trust you, and you’ve already established a relationship, and you know what to say that’s going to align with what’s meaningful to them. That only comes from listening and understanding. 

As Anne said, there are billionaires that will spend $20,000 a night on a suite, but they’ll fly coach or vice versa because it’s not important to them. 

So, you don’t want to sell them something that is not important to them. You need to speak their language each time and speak out of that cornerstone and trust and goodwill that you’re here to advocate for them, no matter how much money they have. Because billionaires especially — and millionaires — they feel like they have a sign that says “schmuck” on the top of their forehead, and they are sometimes paranoid of people taking advantage of them. For others, it comes from cultures.

Then, there are also cultures. Indian cultures, Middle East, Persian, there’s a lot of them. Part of their ego and integrity is feeling like they were given concessions. It doesn’t matter how much they’re spending; that’s just part of the culture, and you need to respect that, too. 

Ruthanne Terrero: Say a relatively new advisor is sitting with a client. The client is booking a hotel. Now, the advisor wants to upsell them because you should always offer the client something more. Not for the sake of upselling and making more money, necessarily, but you want to show them everything that’s possible. How do you paint the picture? How do you open up that conversation to say, “Well, you know, you booked a king-size room. May I suggest a suite with a balcony?” How does the advisor make that jump to the suite with the balcony, to paint the picture, to create the experience that they’ll have? It could be an awkward moment for the advisor, or it could be a home run if they do it right. 

Jack Ezon: I think the key is you can’t be apologetic about it. You have to feel like you’re doing the client a favor. You’re their hero and their advocate, and the way you approach it is all about them and what’s valuable to them. Say, “Listen, for just $200 more a night or $500 a night, we can get you this, this, and this. It may make sense for you — and I’m just thinking why — because you mentioned that you hate that your husband snores, or you wake up early in the morning and you want to do work. Imagine how much more bliss you would have in your relationship because you have this private space,” whatever that may be. 

Again, you turn it back on them and how it benefits them, and you’re not selling, like, “Please, I’m trying to sell you more because it’s my job,” but, “I am thinking about you, and I’m helping you get a better value.” 

Another great thing is if there really is trust, discuss what they’re getting from a business and transparent situation. For example, talk about supply and demand. You want to go to Paris in May? It’s peak season. You know, yes, you’re entitled to a beautiful upgrade on arrival because we’re a Virtuoso member, but it’s peak season, the hotel is going to probably be very full. This is the time I recommend you really buy the room that you think you want because there’s so much compression in the marketplace. Because we’re lucky enough to get you this room, because, because…”

Be very transparent. Once they understand that, again, you build more trust, and they’ll follow your lead. 

Ruthanne Terrero: That’s very interesting. That’s a good point. 

Anne Scully: You know, Ruthanne, when I did training on cruises, for example, I would show them what the top outside cabin looked like on a cruise ship, and then showed them what the next cabin category with a veranda would be. Sometimes it was $20 per person per day, and they went from an outside to a veranda. 

An advisor should look at what’s above and what the additional square footage is; that’s the benefit of using an advisor. That’s the whole thing. You want to teach features and benefits of that upsell because then they understand — and I don’t want to repeat what Jack said because he said it so perfectly. But it really does matter that when you’re talking to a client, you explain what the advantage would be if they went one step more. It could be an anniversary. It could be a celebration, if you knew the why, they’re happy to pay more. Again, if it’s a dream, it’s an easy upsell. 

Jack Ezon: What you’re saying, Anne, is you took a price, and you broke it down into something that seemed reasonable. It’s just $20 a person a day. It might be a 20-day cruise. Look what you’re getting! It may be a family that you’re going to upsell into a club-level, but when you speak about it, you would say, “Your kids are going to want to get sodas every day from the minibar and spend $10 on each drink. If that’s 10 drinks, you’re already spending major money, so why not consider the club lounge.” 

So, you’re putting it into perspective of what’s meaningful to them, and what’s important, but also managing the nuggets of the price points. I loved how you said that. 

Ruthanne Terrero: I love it. This is a great conversation and these are some great takeaways. Thank you both. I have learned a lot. I feel so fortunate that we were able to present two of the top experts on this topic. So, thank you both for taking the time out to be with us. I appreciate it. 

Anne Scully: It’s our pleasure.

Jack Ezon: Thank you!

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