Eric Bailey on purposeful travel, transparency, and trust

Justin Schuster: Welcome to the Travel Is a Human Emotion Podcast. My name is Justin Schuster. I’m very excited to share that my guest today is Eric Bailey. He is the owner and managing director of a consultancy called Purposeful Travel Solutions, and prior to that, he was responsible for managing the travel program at Microsoft for nearly 20 years.

Welcome, Eric. We’re very excited that you’re here.

Eric Bailey: Glad to be here. It’ll be fun.

Justin Schuster: Eric, just to kick things off, let me ask: when you led the travel program at Microsoft, it reached over a billion dollars in spend at one point. And yet, despite having such a large program to manage, I always think of you as somebody who was not only focused on that responsibility, but thinking in a bigger-picture context about how you could contribute back to the industry as a whole.

Among the ways that you did this was pulling together leaders from across the industry, other travel buyers, and travel suppliers, and you created two foundational documents over a series of years. One was called the Corporate Travel Innovation Manifesto, and the other was called the Corporate Travel with Purpose Platform.

Looking back on this, I just wanted to ask: what did you hope to achieve with the documents, and what do you feel the impact actually was?

Eric Bailey: Well, I think everybody who’s been around this industry long enough knows that there’s sort of a slow inertia, that we just keep going the same way. I knew that we couldn’t build all this stuff ourselves.

So I think the best way to do it is to discuss it in a larger group, make these things public, make these conversations open. That way, we could figure out what it is that’s going to work. We could also tell suppliers and buyers, these are things that we kind of agree on. Let’s not just ignore these or make everybody reinvent them.

Let’s try to document them. And in fact, some of the stuff, I look back to 2018 and the manifesto, and some of it is really… I’m glad we documented it, because it hasn’t happened in eight years. But part of it was to set kind of a baseline too, and have these conversations and not just…

Sometimes we’ll have the travel conversations with one supplier or just with a group of buyers. This was a way to bring all of those together and to try to get that open conversation and say, where do we need to go? Let’s set that roadmap and let’s put a stake in the ground so we know where to go from here.

Justin Schuster: One of the themes that you raised in the manifesto was the need for greater transparency. I certainly have heard quite a bit about this from buyers over the past year at The Beat Live, at the Garner Family Meeting, and reading about this in news coverage. What do you think are the core challenges with transparency in corporate travel?

Eric Bailey: Well, by transparency, we really often mean just show us the money. Show us where the money is flowing. That means that people then have to sort of give up what their business plan is, so I understand there’s some resistance to that. But understanding where the data goes, where the money goes, is key to this.

In fact, every time I had a new manager or a new executive that we had to explain how the travel program works to, I always showed them two documents. Here’s how the money flows, and I showed them how this rebate goes here, and this money goes back here, and there’s a commission that goes here and here. And also where the data goes.

Some of these things we used to take for granted, and I think we’re starting not to anymore. But a passport number that you put in the online booking tool might go to a foreign government somewhere, and we don’t know which foreign government. We don’t know who’s controlling that.

So transparency, part of it is that dollar side, part of it is the data side, but I think all of it is just being able to see how we are in business together and what we are doing together. I think the concerns that have come up recently are when we see that 60, 70, 75% of revenues for some agencies are coming in from commissions and from suppliers.

Well, from the buyer perspective, that was our business. We’d rather get a discount up front than have this money go somewhere in the background. So there’s always going to be that tension, that conflict between, would I rather get 2% off, or would I rather have 2% go to my agency?

I’d rather have those lower fares. So there’s always going to be a tension there, but the more open, the more honest about it, I think the better.

Justin Schuster: Well, the TMCs are not making huge profits either. They need to stay in business, and I know that there’s appreciation and a desire for that to occur. So what can be done to increase transparency and still also let the TMCs adhere to the confidentiality clauses in the agreements that they sign?

Eric Bailey: Some of it may be just better understanding of what the costs are. Because when we looked at it, we know how many transactions an agent can do, we know about how much each person makes, and we can sort of put all this together. We could look at that and say, “This is what we would think a profit margin would be there.”

And then you tell me that’s only covering one-third, or definitely under a half, of the cost. Where is all of that other cost? Now, if technology is costing you an extra $100 million that nobody ever anticipated, if we know that, if we can see some of that, I think that’s just going to be better for the relationship.

Because, once again, nobody says we don’t want our supplier to be making money. Of course, that’s an absolute necessity. Nobody’s going to be servicing without making money. I almost said airlines in there, but I think they’re actually making money now. But we understand that there needs to be a fair profit and a fair amount in there. We don’t want that to be undue profits, unrealistic expectations, and we need to look at those things.

I’m talking from the buyer hat still, sorry.

Justin Schuster: Of course, yes.

Eric Bailey: I still sometimes go back to the “we.” But we still need to look at those things, because we need to explain them to our management. The travel manager needs to get budgets approved, and those are not easy to get. We also need to demonstrate savings.

So all of those things kind of balance together, and in a model where it looks like somebody should be making money and they’re not, well, that’s where the transparency is needed.

Justin Schuster: That makes a lot of sense. As we talked about, the manifesto came out in 2018.

Eric Bailey: Yep.

Justin Schuster: It talked about a number of topics, including challenges with legacy infrastructure, AI, consumer-grade experiences, blockchain payments, and other things as well.

Where do you feel the travel industry has made good progress on the ideas that you outlined?

Eric Bailey: That’s going to take me a second. I think that we’re getting better, that the technology has caught up now. So we had sort of blockchain, and all the bits of technology were there. I think we’re getting to the part where all of the technology really is there now. Personalization is something that I’ve been a big proponent of for many, many years, because I think that we’ve spent too long creating systems that show travelers what they’re not really going to book.

We’ve created what I would call a buying tool. The traveler goes in and they already know what they’re going to buy, because they’ve already gone to their airline. They already know what their preferences are. And if we’re not showing them what they really are going to be looking for, we’re not doing a lot of good for them.

We need to understand, if a traveler is going to fly on Alaska for a particular flight 90% of the time, why do we bury that down and have 20 other choices before that, that the passenger is never going to fly, and it saves them $2? I mean, just simple things. These aren’t even AI.

But humans do very well: $300 is less than $301. But not really, from a decision-making perspective. Those are the same. Actually, probably $310, maybe $320, maybe $330. All those numbers are basically the same, and yet we rank them in a way to say, “Oh, look at this terrible routing that I’m going to give you to save $20.”

I think that makes both the travel management and the travel managers kind of look like they don’t know what they’re doing, because the traveler knows what they’re looking for. And how do we make sense? Because the most important thing is that the traveler gets the work done if they’re going on the trip.

Now, other things I think that haven’t been done there: we don’t have the transparency. I think the payment has moved forward, I’ll give you that, and I think that the personalization is moving forward, but it is still in silos. So my flight is becoming more personalized, but that is not changing my hotel experience necessarily.

And when I land, I’m still not being given a ground transportation option. So some of these things that are really simple that everybody does — often when you’re leaving a conference, “Hey, who else is going to the airport? What time are you going? Let’s share a ride together. Hey, we’ll get some more time together. We’ll have a smaller carbon footprint. We’ll save some money.” All of those triple-win things, we don’t have any technology really doing those things well yet. So those are where the frustrations are, I think, for me. You’re seeing the personalization at a single level, but those silos really aren’t talking to each other yet.

Justin Schuster: There really is still so much area of opportunity for improvement. And you’re right, I feel like the technology is there now. Just with the personalization and the offer recommendations, I think AI plays a good role in bringing that to the surface, so that we’re starting to see conversational user interfaces that no longer require me to look through 200 options in order to find the flight that I already knew that I wanted.

Instead, hopefully, the recommendations are good enough where in a list of three or four, there it is. And that’s the challenge that needs to keep being addressed: how do we get to the point where that’s the case? There’s still so much area of opportunity just to do better and to tie all the pieces of a trip together.

Eric Bailey: Yeah. We did some research, and this is 10 years ago, but it’s still pretty accurate, I think. People flying Seattle to DC were flying 75% on Alaska. People DC to Seattle, 75% on United.

Justin Schuster: Amazing.

Eric Bailey: So we have blatant statistics like that, and yet we still haven’t been using them, I think. And I think that’s where you’re right. I think we’re starting to get into understanding who is somebody really going to fly on this, and maybe we don’t need to show one that there’s only a 10% chance they’re going to fly, to save that $1.

Justin Schuster: So there were two summits. The first one focused on the travel manifesto. The second one was focused on purposeful travel. And I don’t know if you remember this, but I was actually an attendee of this. I had joined Spotnana a little before that, and in that sense, I really had no right to be there in this room of amazing luminary travel industry veterans.

But I was lucky to get a ticket. Steve Singh was gracious enough to bring me along. And for me, it was such a transformative opportunity to be in that room and to hear all the ideas flowing, and to just have a seat at the table to contribute my own thoughts. It really opened my eyes to the exciting potential that exists in the travel industry and the impact that we can have together.

I would love to spend a minute talking about purposeful travel in particular. You’ve been a big advocate for this for a long time. How do you explain the concept of purposeful travel to people who are new to the idea?

Eric Bailey: Well, yeah, I do remember you being there. That was a fun day. That was super interesting, and I’m still super appreciative of Steve for hosting that. When I look at purposeful travel, I think it’s looking beyond just the logistics of it. People don’t travel… Corporate travel is not about getting onto a plane or going to a hotel, or even planning a meeting.

It’s about the connections that you make when you’re there. And I feel that we underestimate those, and that’s one of the reasons why I started pulling together some people to put that together. It’s really looking at the whole experience of the trip. And if we look at the sustainability, I think that’s still a big… We need to look at the impact. I know it’s maybe been downplayed a little bit lately. The accessibility of the trip: how do we have people participate? With that, I mean, I think that it is both having people participate in person. How do we make it, if they have physical disabilities or whatever else, to get there? How do we make that as easy as possible?

But also have virtual solutions, so the people that don’t have the time, the dollars, or the ability to leave work for a week might be able to still attend a conference or get the content out of it. Looking at the experience, I know, is one thing that I’ve always found really important.

If you’re traveling halfway around the world and then you go and sit in your room and do email and then fly back the next day, I feel like you’re missing out on a lot of it. You’ve really kind of lost the value of that trip. And then just overall, the productivity. How do we look at making those people more productive when they’re there?

And I remember that one of the areas that kind of spawned this is we were looking at what a digital meeting was like, because we had to. It was the pandemic and all this other stuff. What you found, though, is that you had these different sorts of conversations, because you saw everybody in the room.

You could have a chat with them. “Hey, did you hear what so-and-so just said about that?” Which you couldn’t do in real life. And so as we looked at that, it’s like, think of all the times you go to a conference and you’re sitting in a room. The person that you should be talking to more than anybody else is two rows in front of you, but you don’t know it.

Or the person that you really want to be talking to is across the room, and you don’t see them. So as we look at all of those together, I mean, you could kind of say we’re trying to figure out the ROI of travel. We know what the I is. We know how much it costs. That we’ve known for years and years.

But the return on it, what are the different things that we can get back, and how do we maximize that return? That’s really what I’ve focused on with purposeful travel.

Justin Schuster: Do you feel that there’s a calculator that can be built that quantifies this in a way that drives decision-making? Or is it more about a mindset, where if you’re thinking about how do I maximize that social capital gain that I’m going to get, it drives you to be more thoughtful about the choices that you’re making and to make the most of the time that you have?

Eric Bailey: I mean, calculator sounds simple, but, I mean, try to go into it… I guess it’s probably a little bit like how a self-driving car is a calculator. It’s just taking in a whole bunch of different things. I think that’s probably what we’re closer to. And by the way, this should be easier than a self-driving car, and we have those. So I think that part of it is looking at, if I think of some of the metrics you could measure, how many contacts did I make? How many new contacts did I make? Then you could actually follow that up with things like, okay, how many of those people did I reach out to after the conference? How many of those people… Or meeting, or whatever it was. Did I achieve those goals that we set out to?

Normally, whether it’s a team meeting or whatever, there are certain objectives that you have. Measuring those objectives and looking at a PowerPoint presentation that was your output six months later, that’s not super technology to do that. You just have to look at it, and you have to pay attention and not just get drowned by your email. So I think there are a lot of things like that that you need to look at maybe a little bit deeper and to say, “What is it that…” I can’t measure trust exactly, but maybe I could survey on trust.

Hey, I have greater trust in my team after this. I can’t measure, like, sales. I know some people say, “Oh, did you go and close a deal?” Well, in a lot of big companies, closing a deal takes two or three years, and it’s 100 people. You can’t say that that trip did it. But can you say that from that trip, there were 10 new relationships built, of which five of those are followed up with monthly on email or a phone call?

That’s actually measurable. So I think we’ll start to be able to get to some of that, and I think that’s what people do. That’s what your people that are paying attention to their trips really do. They make sure they’re spending for the right reasons: both time, money, environment, all those things. They’re spending for the right reasons.

Justin Schuster: That makes a lot of sense. I think for me, one of the reflections was just a real encouragement to be introspective and to ask myself, “Am I getting the most out of this trip?” Or when I’m agreeing to send people on a trip in my team, how am I guiding them to really make the most of it? Or should I spend that one extra day, because that one extra day allows me to get so much more interactivity with other people, that it’s worth the investment? It’s worth the cost.

Eric Bailey: Right. Right. Well, and remember that in that too, the cost is not just the cost to the company. It’s the cost to you. If you have a newborn or a parent that you’re caring for at home, that extra day might be really valuable. If the kids are all grown and out of college, or you don’t need to worry about a dog sitter or something like that, maybe taking an extra three days is a great investment.

And I think understanding how to balance those things — and nobody will… There’s no policy that’ll ever tell us how to balance those things. It’s always, at some point, going to be leaving that up to the judgment of the employee, the traveler, and then ideally their manager will have some sort of requirements on that.

Justin Schuster: One of the things that I thought was fascinating at that summit, and just sort of reflecting on your experience at Microsoft, is that you had the chance to look at these questions not only through the lens of managing one of the world’s largest corporate travel programs, but also by working at one of the companies that provides the most widely adopted technology for communication and collaboration.

How did that inform some of the ways that you made decisions, or influence some of the things that you decided to explore?

Eric Bailey: One statistic that hit me early in the pandemic was an event that was supposed to be in Seattle that was going to be 5,000 people in person. It was all programmers, so you’re going to tend to have people that are fairly upper-middle class, upper class, well-paid, lots of flexibility, a lot of US-based people, and stuff like that.

Well, that had to be canceled because of the pandemic, so instead it went online. You know how many attendees? 197,000 attendees. So instead of 5,000 people, now 197,000. Now, I’m assuming that they were learning something from it. This was not just a propaganda sort of thing.

This was actually where, hey, we’re trying to teach you how to use these tools. So now you have 40 times as many people who can attend. You can now attend off hours and things like that. You could attend from Egypt, you could attend from New Zealand, wherever.

It doesn’t matter if you have a newborn at home or you have to take care of your dog, whatever else it is. We’re allowing a lot more people to attend. And I think fundamentally, when I heard that statistic and you’re able to see this, it’s like, maybe we’re not trying to be exclusionary in corporate travel, but I think we kind of are.

When we say the only way you get this content is by coming here, is that really the best way to do it? And I think we’ve seen now there is a lot more, even with events that are in person, there’s a lot more willingness to say, “Hey, let’s have somebody present virtually. Let’s have this content available later. Let’s have another level of engagement that might not be the same as taking a week off, flying halfway around the world, and spending thousands of dollars to go to this event.”

Justin Schuster: Makes a lot of sense. I remember one of the topics at the Purposeful Travel Summit was sustainability. We spent a good amount of time talking about that and had some great ideas that came through that. How did you drive buy-in for sustainable travel at Microsoft? I feel like you had a wonderful program for that there, and I’m curious to see how you felt about it and what it took to get it started.

Eric Bailey: I started working… I think I put it on my card, because I just could. Environmental was one of the… I think it was reporting, environmental, and strategy, or something like that. But that was about 2008. So the focus was pretty strong, and the company, I think, was carbon neutral by 2011 or 2012.

Justin Schuster: Oh, fantastic.

Eric Bailey: So those sorts of goals help a lot, that you can say, “We’re doing this and we’re doing it for the right reasons.” Obviously the data center boom has changed that a lot.

Travel used to be one-third of the carbon footprint. This is all public stuff if you look at CDP and things like that. It was one-third of the carbon footprint. I think it’s now probably 0.2% or something like that. But at a lot of companies, it still is a pretty big part of that footprint. And I think that, if nothing else, you’re looking at where the opportunities are.

You’re understanding what the footprint is. I think it ties into… I mean, your footprint is also the impact that you have on your employees, on the families of your employees. It’s just another element in there. I also found that you could almost directly associate carbon footprint with budget, too.

The carbon footprint of a business class flight is almost exactly three times, as the cost is exactly three times, if you look at cost per mile of a coach ticket. So having that direct correlation isn’t bad, because if you say you want to cut carbon… If you cut budget, you cut carbon almost the exact same amount.

So it was another lever that we could use, but it was also a way that we could bring that awareness. There was a lot of early investment in SAF and some things like that. And there is some impact, but as we know, with SAF there’s only so much. Maybe you get 1% impact, just because of the supply.

But it still is not bad to show, no, companies are willing to pay a premium for this. Companies are willing to do the right thing. We need a long-term solution, and so we’re willing to invest in it. We’re willing to understand it. We’re willing to look at the best ways to do this. And I think that all the…

If you look at the AI boom now, all of the companies, they’re just trying to find the power. If we look at shortages of oil now, all these things… One of them was just sort of maybe what people would’ve thought of as an idealistic solution, but now you’ve actually got a logistical solution. We need to have more forms of energy. We need to have better ones, and ideally the new ones that we get are going to be more sustainable, not less.

Justin Schuster: That’s an interesting lens, that sustainability in some ways could become more of a necessity, because there just isn’t an infinite supply for us to take advantage of. We have to be more conservative and thoughtful in the choices we make, just to make sure that access is available.

Eric Bailey: I’ve heard people say that maybe rebuilding the infrastructure in the Middle East that is diminished at this point, maybe we don’t do that, but why don’t we just build new infrastructure? Why would we rebuild dying infrastructure when we could build forward-looking infrastructure?

Justin Schuster: Sustainability seems to have fallen out of the conversation somewhat in the travel industry. I’m curious as to your thoughts about why, and what would it take to get travel managers to prioritize putting more thought into sustainability?

Eric Bailey: I think part of it is the difference between the gestures and the impact. So the gestures is our 1%. If you remember, in the Purposeful Travel Summit, we did talk about what are the different things you could do. One of them is air traffic control. You could streamline that. Now, I think the problem is, right now we’d actually just like air traffic control to work, and streamlining…

I think that some of those priorities, like first you have to have it working perfectly before you say we’re going to streamline. Because I think we were saying five, six, 7% of emissions could be reduced by better air traffic control routing and things like that. That gets zero attention until air traffic control is working.

Justin Schuster: Yeah, we need to get that on modern infrastructure before we can optimize it.

Eric Bailey: Exactly. Yeah, we need to invest in that before we can improve it. I think one area where you have seen at least some companies change is just saying, “If we cut budgets, we cut emissions, we cut costs, we cut all these things.”

I always thought it was good to have multiple levers in there, as opposed to just saying, “Just slash the budget, cut the trips.” But we do know if you want to have a more sustainable trip, the easiest way is to not have the same number of trips. Now, I’ll give you one thing, though. Technology probably will add into that too.

Do you need 10 people going to a conference that don’t know each other? Maybe you could have had five people from the same company if you just coordinated that better. I think we’re getting to the point of data sharing and things like that, where hopefully that’ll become more apparent: “Hey, I see all of these people going to the same conference.”

It appears to be the same conference, and in fact, I’ve read their email or their credit card statements that say that they registered for that conference. Maybe we should have a smarter way of looking at that and saying, instead of 10 people, we could have five people go.

Justin Schuster: That’s a good example. I remember another topic that came up at the Purposeful Travel Summit was the idea of creating more enjoyment and fulfillment for travelers through things like blended travel or bleisure, whatever your preferred term is.

Eric Bailey: Nobody’s preferred term is bleisure, I don’t think.

Justin Schuster: Yeah. Or pleasure. Yeah.

Eric Bailey: Yeah, yeah. Exactly.

Justin Schuster: Why do you feel employee enjoyment should be a tenet of purposeful travel?

Eric Bailey: I mean, we look at employee stress as a negative potential of travel, so why don’t we look at employee enjoyment as a positive of travel? I think it’s that same investment, and I’ll give you a great example. One of my last business trips was going to Nice, and I was like, “You know, I think I’ll take an extra day,” and just managed to have this really nice day afterwards. I went canyoning up in the gorges behind. I went to a small hill town and did a hike up out of there.

As I was driving to get cash for the canyoning thing, I drove by a karting thing, and if you’ve ever done karting in Europe, it’s super fun. They do like 50 miles an hour, which was a blast. But it was sort of a one-day kind of mini vacation that I was able to take at relatively low cost.

One night’s hotel cost was about it, but it was a great experience to have. So why not have those sorts of things? Why not have those things where people are able to work from somewhere else for a few days? Why not, if you’re going and you’re staying at your parents’ house or your cousin’s house, work a couple of days and get the weekend, have a beach weekend afterwards?

I don’t see any reason to control those or to stop those. Now, we don’t want people primarily taking trips to do that, and anybody who’s seen a lot of traveler behavior knows there will be some bad traveler behavior. There once was a traveler, somebody looked up and they saw that they were some sort of a musician, and their business trips were matched exactly with the gigs that they were playing.

Now, it’s tough to tell if the gig was posted first, or if they had the business trip planned and then they posted the gigs. So there are some controls that you need to put in there, but I still think, in general, most people, if they’re working and have a good job, don’t want to be fired over a $500 plane ticket or one night of hotel or something like that.

So I like to think that most people are going to do the right thing, and that, as I said, the encouragement we have for you to do the right thing is you get a paycheck. Now, everybody isn’t going to be like that, so different companies have different levels of how they control that, too.

Justin Schuster: Why do you feel blended travel has been a tough problem to solve, technologically, or from a policy perspective, or operationally?

Eric Bailey: People worry that they’re traveling for personal reasons, right? Which…

Justin Schuster: Those are…

Eric Bailey: So there’s context. Yeah, I never wanted to incentivize people and say, “Hey, if you go coach when you could’ve gone business, we’ll give you $1,000.” Because I’d have a lot of reason to fly on places where I was going to get $1,000 of income every trip I took. So I think that’s part of it, and I think that it depends on how you’re… Like, I would see all that as back to a budget control thing. If you don’t even have people expecting to ask for frivolous trips because you control your budget well, then you don’t need to worry about that so much.

And also when we look at the ROI, when we look at the manager looking at the expense reports, there are controls in place. There were times where we were talking about, maybe instead of an expense report, we really need a success report. If you show me that you went on a trip and these are the things that you delivered when you went on that trip, maybe I don’t care if you stayed an extra day and visited with your family, or whatever it was, because you’ve proven to me that you delivered success from that expense.

So why don’t we just look at that? And we have to trust the traveler, because if we don’t trust the traveler, you have a much worse problem. If you don’t trust your employees to do the right thing… In a lot of companies, your employees are dealing with thousands or millions of dollars of revenue and all these other things. So if you can’t trust them to make a $3,000 trip decision, I think you have worse problems.

Justin Schuster: Makes a lot of sense. It’s interesting seeing the wide range of philosophies and perspectives around policy in the industry. In tech companies there might be one view, and at other companies it might be different, depending on the profile of talent that they’re bringing on board.

But it does seem as though trust is fundamental, and you should be able to trust employees. So how strict do we have to really even get, or how elaborate should these policies be, if that’s the foundation that they’re built upon?

Eric Bailey: I was about to say don’t get me started on policy, but no. Before we start on policy, it depends on what sort of traveler you’re looking at.

If you’re looking at travelers where you say, “I need you to go out to repair a windmill. I need you to go to Quincy, Washington, for one day and do this, and here’s where you stay, here’s how you get there.” There’s not a lot of ins and… That person can’t say, “Oh, I don’t really want to do it,” or, “Hey, could you just do it via video call or something like that?”

They have to go. And for that type of travel, there is a lot of control that you want to have, because you’re looking at the costs and there isn’t a lot of flexibility in where that person goes or how they’re meeting or what they’re delivering. It’s very measurable: you need to be at this place for eight hours to do this job, and then you need to come home.

Then you’ve got the next sort, the knowledge worker side of things, which I would say is where there is a fair amount of flexibility. You do know that there is a lot of loyalty with different programs, whether that’s for carrier flights or a hotel or whatever else. So you’ve got a lot of those decisions.

And then you’ve got maybe the super high-end, super picky, maybe in the entertainment space or something like that, where you hear about people having these different policies and things like that. I still think that all of those, to some extent, have to be based on trust.

Unless you are just… I won’t use the word bribing people, but you’re just paying them to be happy. Nope, I don’t care what it costs, because if this person’s ticket is $1,000 or $7,000, it doesn’t matter to us, because they’re generating a million dollars of revenue. It’s a concert. They’re making a million dollars that day, or whatever it is. But when I look at the knowledge worker space, it’s about trying to balance all of that. I saw something today about just having these long policies, which are just worthless. At Microsoft, we had a two-page policy for 120 countries, and it basically says, “Use the agency, use the card, fly business class only if you have this approval.”

We don’t even have an approval process. So look, if you thought you had approval and you didn’t, that’s your problem, not ours.

Justin Schuster: How fascinating.

Eric Bailey: You couldn’t use the word “should” in a policy. So I know, and I looked at, over time, advance purchase and things like that. In my experience — I know other people are different — you can say, “Everybody book 14 days in advance.”

Well, that doesn’t change the needs of how you need to get there and when you need to get there and when you can plan your trip and things like that. I never found somebody intentionally just waiting till the last day so that we had a full Y class ticket. And once again, if you had that, that’s not a travel policy problem. If your employee is trying to maximize their spend so they can get anything they can out of the company, that’s an employee problem, not a travel problem or a policy problem.

So I think that simple is always going to be better. I would always rather have a policy that says, “Do the best thing for the company with the money.” Then, if it is very easy for somebody to buy a $2,000 hotel room and say, “No, it was within policy. It was a preferred. It was within this range of where I needed to go, and I needed to be here at this time,” it would be very difficult to argue that that is a good decision for the company and that you shouldn’t have stayed a block away for a quarter of the cost. So I still think that in trying to make a policy so clear that you make it perfect, you inherently make it imperfect and easier to game.

And I would challenge… I will look at anybody’s policy, like, for free. That’s a fun thing for me to do, to look at somebody’s policy and say, “Okay, let’s see how this is really being implemented. Let’s see if you’ve really got people in Atlanta flying on somebody other than Delta.”

And if you show me anybody who can get 20% of people in Atlanta flying on Delta and everybody else on somebody else, I’ll hand the torch over to them. But I do not think that’s going to happen.

Justin Schuster: I loved that you brought up that invitation, and it’s a great segue to my next question, which is to say, now that you’ve moved on from Microsoft, what are the things that you’re excited to be working on? What’s the focus of the company that you’re currently leading?

Eric Bailey: So a lot of what I’ve been doing is working with startups, trying to better, hopefully, facilitate their movement in the industry and try to figure out what are the things that I can help them do better.

I’ve seen all the resistances that corporate travel can put up, both on the ecosystem side but also on the buyer side. How do you get this past IT? The gates of IT are difficult. The privacy people to work with, to get through there, is difficult. So how do we create this in a way that is palatable?

How do we minimize those risks? What are the real risks that people are looking at there? Because the risks that we see in corporate travel are not always real. They’re sometimes one-in-a-billion risks, but they are acted on as if they’re real. So I’ve been working with them. I do some work with advisory boards, so better understanding how do we bring together these supplier-customer conversations, because I’ve been a little bit of both of those. Those are fun to facilitate. And just mentoring. A lot of stuff that I do, and a lot of it’s for free, is mentoring startups.

Just saying, “Hey, you should look at this. Don’t look at this. That’s a terrible direction to go.” That’s my favorite one to go. It’s easiest to say. And then actually there’s one more super fun one that I’m working on, and this is totally different. My daughter, who is a printmaker and graduated from college, has been doing a bunch of work in creating prints, and now we’re actually doing some prints for different events.

So think of taking the old TWA or Pan Am posters. Anybody who’s seen my phone knows that I love the old TWA stuff. Sort of creating some of these old-time posters that kind of create that nostalgia for travel, and creating those around business travel experiences. So doing them for a particular destination or a particular event or something like that. And I get to work with my daughter, so that’s super fun too. It’s creative, it’s fun, it’s interesting, and it’s so not AI. She has to make every poster all by hand with ink, and I love the tangible side of that. So it’s really fun.

Justin Schuster: I’m hopeful that this world of AI is going to bring back more of an appreciation for human-crafted art and products. I think that’s wonderful that you’re getting to spend that time with your daughter. There’s a great intersection there of travel, where you’re passionate, and print, where she’s passionate, and ways that you can make that consumable in the world together.

Eric Bailey: Well, and that tangible, touchable side of travel, that’s what we all understand. We all know it. We all understand it. We haven’t been able to always measure it. And so the measuring part maybe gets into kind of this wonky, technical side of how we’re going to do it, but we all know that there are advantages to it, and then how do we take those and how do we maximize? How do we maximize that in-person experience, that in-person conversation, that is different than one that’s a virtual conversation?

Justin Schuster: Well, that brings me to my last question, which I ask every guest. Since this is the Travel Is a Human Emotion Podcast, what do you see as the importance of that connection between travel and human emotions? What resonates for you when you think about that connection?

Eric Bailey: So another thing that I’m doing that is sort of interesting is a little bit of academic research on the impact of travel. One of the things on the business side of it is the uniqueness of venue: does that drive a different experience? Not just by being in a different venue, but by creating different memories. And so on just travel in general, I’ve always been a big believer that getting out of your comfort zone actually cements in memories much better. A lot of people, if you ask them, “Tell me the first meal on the first international trip that you ever remember taking, as either a teenager or as a young adult,” most people can tell you what they ate on that day. And then if you’d say, “What did you eat last Thursday?” Nobody can tell you what they ate last Thursday.

And so how do we take these things and say, by creating unique experiences, by creating experiences that aren’t always easy… We don’t want them to be easy, because easy isn’t memorable. Club Med is not… You’re not going to go to Club Med because it’s the most memorable trip ever. You just want to relax and do nothing, maybe. But if you want to go to Istanbul or Cairo or something like that and go to a night market, you want to do that because it’s different. It’s going to push your brain in a different way.

So I see that tying together on both the leisure and corporate side. Taking us out of our comfortable zone, putting us into something else, is going to create more value. We’re going to remember those conversations more. We’re going to be more creative. We’re going to create better bonds with people.

We’re going to trust each other more, because we weren’t just sitting in some suburban conference room that looks the same as every other suburban conference room. We were somewhere that was a little bit unique.

Justin Schuster: Eric, thank you so much. It’s such a pleasure spending time with you. I feel like I would love to spend all day just picking your brain and hearing your thoughts on different topics related to travel and life. I’m grateful for the chance to spend this time with you. Thank you.

Eric Bailey: Absolutely. No, it’s fun. I kind of do it for fun now. No, it’s been a great, a real pleasure. Thanks, Justin.