How to Use AI for Strategic Planning in Your Travel Business

In this episode of the AI Compass podcast, Jason Halberstadt and Jason Elkins dive into how travel businesses can use AI for strategic planning. They explore how to go beyond gut decisions and create your own AI-powered advisory board using a powerful prompt framework: CRIT (Context, Role, Interview, Task).
 
 💡 Learn how to simulate real-world scenarios — like conflict in a travel region — and gain insights from virtual experts, such as airline CEOs, tourism ministers, or financial analysts.
 
 Discover how using AI strategically can illuminate problems in your business you didn’t know you had — and help you take proactive steps instead of just reacting.
 
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🔗 Check the strategies here: https://mytrip.ai/strategic-use-of-ai-for-travvel-companies/

Book a FREE AI strategy call with host Jason Halberstadt at MyTrip.AI.

Transcript

Jason Halberstadt (00:00)
Welcome to the AI Compass podcast for travel leaders. I'm Jason Halberstadt.

Jason Elkins (00:04)
Jason Elkins.

Jason Halberstadt (00:05)
And we're going to talk today about how to use AI for strategic planning and purposes in a travel.

Jason Elkins (00:14)
Cool, Jason. So good to see you again. Excited to jump into this topic. So for our listeners, when you say we're gonna, what did you say we're gonna talk about?

Jason Halberstadt (00:24)
how to use AI for strategic planning, and how to use AI strategically in your travel company.

Jason Elkins (00:32)
All right, very cool.

And why is that important, Jason, to our listeners?

Jason Halberstadt (00:37)
⁓ Well, because actually making the right decisions as the owner of a travel company ⁓ is really important. many of us are, actually all of us, we kind of have our own biases and our own perspectives that, ⁓ yeah, sometimes we make decisions based upon our previous history and our experience.

And I'm going to show you some techniques today of how you can use AI to get perspectives from multiple different virtual people and put them together as your own AI advisory board.

Jason Elkins (01:27)
I think when we had this conversation before we pushed the record button, it occurred to me that okay, strategizing about the future, it's not always one of my best subjects. And I think a lot of people that work in tourism, sometimes we get pretty, maybe a little bit more reactive than we do proactive. So strategy is really kind of taking us, you know, I bet there's people listening to the show that have really not spent that much time.

Jason Halberstadt (01:46)
Mm-hmm.

Jason Elkins (01:53)
They kind of look and say, well, this tour sold really well last year, so we're going to do that one again. So that's their strategy is keep, you know, kind of keep doing the things that work and the things that don't work, change them up a little bit, but to actually sit down and think about, what is our business potentially look like a year from now or two years from now? That's a tough, that's a tough thing that kind of feels like AI makes it a little bit easier. Remove some of those barriers to doing it, right?

Jason Halberstadt (02:20)
Yeah, yeah, absolutely. We can actually kind of go through a process here of how to approach, how did you say it? the, reactive as opposed to proactive. Okay, and so yeah, we as humans, tend to like react to our environment. We've done that since we were infants.

Jason Elkins (02:33)
Reactive as opposed to proactive? Yeah, yeah.

Jason Halberstadt (02:50)
But yeah, the next level is to be able to proactively plan out how we're going to react to potential challenges in the road, know, holes in the road that we haven't seen yet. And so I thought maybe to demonstrate this, we could actually use a case that's unfortunately very timely right now. ⁓ Let's go through kind of the role playing of us being

a ⁓ tour company that's in the Middle East right now. ⁓ yeah, unfortunately, over the last weeks, there's kind of been a war that's broken out between Iran and Israel, now the US. And so, yeah, for all of the companies in that region, they kind of need to have strategic plans of how they're going to deal with conflicts. And then...

⁓ specific techniques of how we can deal like reactively to a situation that actually happens. And so, yeah, let's pose as Dubai Adventure Inc. Okay, so we have a, ⁓ say like a parachuting company in Dubai and obviously ⁓ right now, know, the...

We have some serious challenges because the airports were just closed in Dubai. There's lots of delays and you can't even get to Dubai from certain places. so yeah, there's definitely going to be a major impact on our business over the coming months.

Jason Elkins (04:32)
Okay, so we're gonna pretend

that you are the president, founder of Skydive Dubai or whatever. Maybe there's a company out there with that name. There probably is, ⁓ but this is just a role play. So am I getting that right? You're gonna kind of role play like that's your position and what are you gonna do now?

Jason Halberstadt (04:48)
Yeah.

Yeah, we're actually going to have another role play inside of our role play. Yeah. Okay. And so what we're going to do is, yeah, we're role playing as the, yeah, the CEO of ⁓ Adventure Dubai, Inc. And we're, we're going to put together a strategic advisory board. Yeah. That's going to go out and do research on the current situation. ⁓

Jason Elkins (04:56)
Okay?

Jason Halberstadt (05:21)
And ⁓ actually what we're going to do is we're going to use this prompting framework for strategic prompting. And then you can remember it by the acronym CRIT, C-R-I-T. Context, the context of the situation is war just broke out. We're an adventure company that does skydiving. ⁓ We need to analyze the future.

projections of how many people are going to be coming. So we can kind of project how many clients we're going to have next month and several months down the road so that we can make decisions about staffing and marketing and all these different aspects of the business that this crisis is going to impact.

Jason Elkins (06:13)
So what we're talking about, Jason, right now is we're going to write a prompt that is going to help us figure out all this stuff. So what tool are we talking about? Because there's so many different AI tools and so many things. So when you say we're going to write a prompt and we're going to use this, you said, what was the acronym?

Jason Halberstadt (06:18)
Yeah.

C-R-I-T, context, context, interview task.

Jason Elkins (06:34)
Okay, so you're gonna, we're gonna use,

okay, now I interrupted you, I'm sorry, tell me one more time.

Jason Halberstadt (06:42)
context, role, interviews, task. Yeah, and so we're going to use a reasoning model from ChatGPT. In this particular one, I'll use ChatGPT 03. Yeah, and so actually, is a model that uses actually relatively important, not necessarily if it's OpenAI, ChatGPT or Google, but that it's a reasoning model that can

Jason Elkins (06:46)
All right, very cool.

Jason Halberstadt (07:10)
analyze very complex situations and reason about those and actually sits there and it will actually start thinking for several seconds. And so we're gonna walk through this. ⁓ first we set the context. Context, yeah, we're this company in Dubai, war is broken out. ⁓ And I'm going to give you different roles of different people. We're actually going to like name our

our all-star team. Like if we could have the world's best executives to advise us on how to deal with the situation, we're gonna, you first we can actually go to, actually say, this is my problem, help me find my dream team of advisors. Who would they be? And you can actually name them. So that's the role. And so let's start off with this first role. yeah, go ahead.

Jason Elkins (08:03)
when you

say when you say name them I'm thinking so do you tell chat GPT ⁓ like bring me is it Mark Cuban or you know other characters out there Tony Robbins or or whoever or are these some completely hypothetical I'm just curious about that

Jason Halberstadt (08:22)
It could be both, but you want to choose somebody that's a true, like the world's best expert in certain, in the theme that you're talking about. So in this case, we're gonna have your first role on ⁓ our first member advisory team as the CEO of Emirates. Yeah, they're, yeah, our national airline.

And it says, are skilled at doing comprehensive research about the current aviation and tourism situation and are skilled at taking diverse information and compiling it into future projections of passenger volumes and different markets. Okay? So that's your role. and then the next step. So we've gone context, role. The next step is I is interview. And so it's simply, going to prompt, say, ask me any questions that you need.

Jason Elkins (09:02)
Cool.

Jason Halberstadt (09:17)
in order to accomplish the task that I lay out below. Yeah, so this is actually really, really important. So because in order to give the AI like a complete context, it's really hard to do it, predict what every, all the information that's going to need in order to, you know, compose this task. So, and then we're gonna go on to give it the task, the T of CRIT.

So create a report of estimated tourism levels to Dubai month by month over the next year. Take into consideration my main markets of travelers from the UK, India, Saudi Arabia, Russia, US, and Israel.

Jason Elkins (10:00)
So in this example, whatever response you get back, hypothetically, theoretically, whatever, is the response of that one person on your board. So this is like the first, or do you add, how does that work?

Jason Halberstadt (10:17)
Almost. Yeah, actually, we're going to first do the interview. so I asked him, I asked the AI to ask me questions to clarify the context. Yeah.

Jason Elkins (10:29)
Right, but is the AI, right,

is the AI behaving as though Heishi Et is the president CEO of Air Emirates, correct? In this scenario? Okay, okay, gotcha, all right.

Jason Halberstadt (10:42)
Yes, yes,

But first we're gonna, yeah, it's gonna ask us questions and then it's going to take the answers to all the questions and then go out and do research and then act like the CEO of Emirates and then give back a report. Yeah, and so I've got, yeah.

Jason Elkins (10:58)
Okay, so that's one board member. we're just, we're basically

having a conversation with one board member who right now is the president CEO of Air Emirates. And then do you, because you mentioned earlier, like having your own board. So you could go do this and create different, ⁓ I don't know, personas ⁓ and then combine that. that where we're going with this? Very cool, okay.

Jason Halberstadt (11:20)
Yeah.

Absolutely. Yes. Yeah.

Yeah. And so, we could say, you know, what other people would be on our dream team advisory board to help us make decisions about the situation. So, it could be, I don't know, the Ministry of Tourism, UAE, the... Could it be the president? Because it's very much, you know, a political situation. So, yeah. You probably want to... The perspective of... Maybe you want a military advisor.

on your dream team, in this case, since it's a war. So yeah, so we think of, know, how can we see this problem from many different perspectives? And then.

Jason Elkins (12:04)
kind of sounds

like fantasy football. Do you remember that? don't I think people still do that, right?

Jason Halberstadt (12:06)
Absolutely. Absolutely. This is totally, it's like

it's building your own, your all-star team. Yeah. And the game is ⁓ your business's survival and thriving in the future. So yeah, we're very much.

Jason Elkins (12:15)
Cool.

And this

is an example that is relevant to everybody. So anybody listening to this, well, I'm not in Dubai, so this isn't helping me. But what I'm getting from this is, I'm thinking when we're done with this conversation, I need to go do that for my own, for my business and for, and it's pretty cool.

Jason Halberstadt (12:44)
Yeah, yeah, absolutely. This is very much focused on how to build your dream advisory board about one specific problem, a war in the Middle East. But actually, we just recently published on our blog. If you go to mytrip.a slash blog, you'll see there is a link to an article about the 50 largest challenges that travel companies have in 2025.

And so there we find all kinds of it. Yeah, from that list of 50, you'll probably find some of your largest problems as operator of a travel company there. have things such as inflation, ⁓ commission pressure from OTAs, ⁓ staffing issues, all the major challenges. So I'd actually recommend going and actually take a look at that article because that gives you a good perspective. OK.

My current strategic situation is I have these problems. Yeah, and I may have these problems.

Jason Elkins (13:48)
Right, yeah, not necessarily

what's going on with air traffic in Dubai, but maybe it's something else. So if you don't know what your problems are, you can go to that list, pick them out, and decide which one to play around with the first. Yeah.

Jason Halberstadt (14:04)
Yes, from that list,

there's 50, and it's like 50 pages, almost like a small book of current challenges that travel companies have.

Jason Elkins (14:13)
And you'll probably see every item on that list, you'll see us having a conversation in a podcast episode. So there's our next 50 episodes right there, I think. So anyway.

Jason Halberstadt (14:22)
There you go. Yes, they are actually

ranked at how ⁓ well AI potentially, ⁓ how it could help to resolve those strategic problems. So that's a great place to start. What is my strategic environment? You have to understand what your challenges are and then build your dream team.

Jason Elkins (14:48)
Okay, very cool.

Jason Halberstadt (14:51)
In this case, it was a war situation. But in most situations, we would want an expert CEO. So we pick out, say, a travel industry CEO. If you pick out a ⁓ CEO of a small company, LGBT, they may not really know who they are. So you may want to pick out somebody ⁓ famous or, like I did here with the example of Emirates.

the current CEO of the company.

Jason Elkins (15:23)
because he's probably, he's

probably said and done some things that have been posted that is able to be evaluated. So, okay, so we've got this scenario. You're having a conversation. If I was sitting here looking over your shoulder, you're in front of your computer screen, you're having this conversation with the chairman of Air Emirates and he or she, don't.

I don't know, let's just keep it neutral, is interviewing you now. So maybe give us just kind of an idea of what the interview looks like. If someone were to imagine themselves having conversation with ChatGPD, what kind of questions is ChatGPD going to ask you?

Jason Halberstadt (16:06)
Yeah, OK. So yeah, here we've got, I've got this on the screen here at the GGBT. It says, from the CEO of Emirates to shape an accurate 12-month tourism forecast in Dubai. It says, historical benchmarks. ⁓ What are your traditional ⁓ guest volumes for each of your five markets for the last 24 months broken out by month? Yeah.

Obviously something you need. You need the historical data. Number two, customer segments and price points. How are your travelers distributed across segments like budget, ⁓ premium? And also, think another important factor in this particular case is the psychographic profile. Okay, so people are going to jump out of an airplane, probably have a higher risk tolerance.

than somebody that wants to go shopping in Dubai. So that's another thing to take into consideration. Number three, we've got marketing and distribution plans. Do you anticipate any major changes in marketing span sales channels? ⁓ Yeah, hopefully actually the AI would tell us, eventually was going to give us the answer for that. So we could say with this one, give me your recommendations of what should I do for.

if you don't know the answer. ⁓ Number four, we've got operating capacity and costs. ⁓ Here it says, will you retire aircraft, lay off instructors? What is your fixed and your variable costs of your business, the different variables? ⁓ Risk tolerance and scenario planning. Yeah, actually we already mentioned that. ⁓ Maybe Israeli skydivers are probably more risk tolerant than say,

Yeah, shoppers. ⁓ actually, so we've got 10 here. Let me just name it off really quickly or this is going to take forever. ⁓ Competitive landscape, ⁓ regulatory and visa assumptions. are certain nationalities prohibited or are their airports closed, et cetera? Financial planning horizon, ⁓ data access.

And then it's asking me, what format would you like me to present all these findings to with your virtual board? And yeah, and so we kind of have a bit of a back and forth here. And so the AI now, after having all these questions, hopefully also after doing research about current events, will then have enough information to go and create the report for us.

Jason Elkins (18:57)
Here's the question that I think anybody listening to this, not anybody, but some people listening to this might want to ask you, okay, Jason, you're the expert. When I sit down and have a conversation with ChatGPT, if I remember to say, please interview me, which is a really important step, ⁓ sometimes ChatGPT comes and asks me stuff that I'm like, my gosh, I don't know that, I don't have that, and. ⁓

Maybe somebody's listening to this like, well, geez, I gotta provide all this information or I'm not gonna get anything. So what do you advise to people? Because there's obviously a garbage in, garbage out scenario. The more of this information you can provide, the better. But at the same time, I think both you and I have seen when chatGPD asks questions that you're like, yeah, that's, I'm.

Jason Halberstadt (19:33)
Mm-hmm.

Jason Elkins (19:47)
I don't have that. not going to go spend the next hour trying to get my, you know, my marketing plan from three years ago, whatever, whatever, whatever. So what do you say to that?

Jason Halberstadt (19:55)
Yeah, think, ⁓ OK, so one of the questions they asked was about your marketing budget and your marketing plans. ⁓ You could definitely just say, I don't know, because that depends on the outcome of this analysis. And so you can say, actually, make recommendations to me.

Jason Elkins (20:18)
And some people might,

I mean, there might be some people sitting in some markets and you ask them that and they don't, they just legitimately don't know anyway. You know, well, it depends on how many tours I sell next week. My marketing plan and budget is an evolving type of thing. So I'd hate for anybody to, you know, but you could be honest, right? You could just tell ChatGPT that. I don't know. Okay, all right.

Jason Halberstadt (20:33)
That's right.

Oh, absolutely, yeah. Yeah, absolutely.

Yeah, and just ask for their recommendation if you don't have the good answer. That happens all the time in this technique. But I think this interview part is actually, is very, important when you want to get insights from really complex situations like this, you know, because AI is...

it can be really bad, you know, if you just say, ⁓ there's a war, what do I do?

Jason Elkins (21:22)
Well, but you know,

it's interesting because it's the same thing in human to human interactions. If you go to your psychotherapist, I don't know why I'm thinking about that. But if you go to your therapist and say, you know, my partner is a bad person, treats me poorly, what should I do?

Jason Halberstadt (21:27)
Absolutely. Yep.

Yeah.

Ha ha

Jason Elkins (21:43)
and you're hoping your therapist is gonna ask you a few more questions, but help me understand what that means before providing a suggestion, or your doctor. My side hurts, on my left side, what should I do? And your doctor's, well, here, you need surgery. Wait a minute. Right?

Jason Halberstadt (21:48)
Yeah. No, absolutely.

Absolutely.

No, I think that's a really good point. You need to treat AI like it's somebody you just met. Or a lot of times we say like a new employee. A new employee comes in as a salesperson. Maybe they don't know much of anything about your company. They have their past experience. So you have to give them orientation in the context.

Jason Elkins (22:23)
Maybe they're afraid to

ask questions because they're new and they don't want to ask questions. So you almost need to give them permission. Here's the job. If you have any questions, please let me know. If there's anything else you need to know to make this easier, please let me know. So you're kind of giving chat GPT permission to ask questions, right? Yeah, that's cool.

Jason Halberstadt (22:32)
Yeah.

Yep.

Yeah, no,

absolutely. Yeah, no, I think it's like starting a conversation with somebody you haven't met before. Like for your new virtual advisory board director who doesn't know you, you need to give them the context, then they ask the questions, and then you, yeah, give them the task of what they need to accomplish.

Jason Elkins (23:09)
So the acronym CRIT is really not, I mean, I think that acronym came out because of AI, but that's the same, that would be a great acronym and just in life in general, right?

Jason Halberstadt (23:22)
Yeah, you see that in AI

all the time, these parallels of human interactions. ⁓

Jason Elkins (23:29)
Yeah, All

right, so I know we were discussing putting this board together. We've kind of gone through one board person, but let's tie that all together for our listeners.

Jason Halberstadt (23:35)
Yeah. Yeah. Yeah.

Yeah. And so then you basically kind of repeat this process for, say, your political advisor, your military advisor. You're not going to have military advisors in most travel company boards, but in this one, it makes sense. ⁓ And so you ⁓ basically, you ask each one of them to give you a

strategically important piece of information such as ⁓ to the military advisor when do you predict the war would be over or do you predict that the airspace over Dubai will be open this week, next week, etc. And so then you can repeat this process with as many different board members as you'd like and then at the end you actually you want to do this all in like one

Chat to be T or one in Gemini session.

Jason Elkins (24:33)
That was what I was going to ask. You saw the look

on my face, didn't you? was like, so you're not starting a new session. It's one session. OK.

Jason Halberstadt (24:40)
Yes. Exactly.

Yeah, you want to have the memory of the entire conversation so you have really all these different perspectives. ⁓ And then at the end, ⁓ actually one thing you may want to do at the end is use the absolute most powerful AI that you have access to. Just recently the 03 Pro came out for for ChatGBT, but I think only on the paid versions. And so I would say ⁓

GPT-03 Pro ⁓ helped me make my strategic plan for the next 12 months to optimize for revenue and continuity of the business, for example. And with that, hopefully you get ⁓ a summary of all the different perspectives and some insight that will help you make the best decision.

Jason Elkins (25:39)
think what you just said right there was important to me and a lot of our listeners is it's not necessarily you will know what to do, but you will have some ideas and you use the word insight to help you make decisions. Right? Because I think this is always important and I think that let's.

Let's chat about that for a minute about using this AI information that you get to just follow it blindly because it's AI, it's smarter than I am, or what are we using this for really?

Jason Halberstadt (26:14)
Well, I think if you would have a human board of advisors, ⁓ you would want to take everything that people say with a grand sale to be critical, think critically about it. ⁓ And yeah, by actually having this board of many different perspectives, you get quite a bit of that happening during the Chepji conversation. ⁓

just by nature of you hashing through all these different perspectives and solutions to problems.

Jason Elkins (26:50)
could something could come out of it that you didn't even realize. Like we were using the example of, what's my marketing budget? I have no idea. So now you realize, okay, that might be an area that a board of advisors would advise me to get under control, whether there's a war going on or not. ⁓ So you might come away from that. You might think you're going in to talk about, ⁓ you know,

Jason Halberstadt (26:59)
You

Jason Elkins (27:17)
commissions or whatever with OTAs, you think that that's the problem you're trying to solve, but then your board of directors come back and says, you got a bigger problem. You're pricing on your tours, you don't have any money for commission. We don't need to talk about that. You need to raise your rates, you need to do this, you need to do that. So, and that can just kind of illuminate, we use that word here on the podcast, illuminate things, right?

Jason Halberstadt (27:26)
Yeah.

Yeah, no, and I think that's a good place to wrap up that we as humans, we have limited perspective. And we go out and we build advisory boards in the real world in order to get different perspectives, to be able to, it's hard to read the label of the box from inside of the box as a leader of any organization. And so yeah, this is a...

cheap, easy, relatively fast way of ⁓ getting a lot of different perspectives that are really, really focused on your problem and hopefully gonna help you make better decisions.

Jason Elkins (28:29)
Very, very cool. And for anybody that's listening, Jason, before we pushed record, you mentioned we're gonna have a link in the show notes that'll go to where you've got a kind of a recap of this conversation and along with maybe some prompt examples that we discussed today, is that right?

Jason Halberstadt (28:45)
Yep.

Yeah, absolutely. Yeah, so take a look in the show notes, and those will be on our website.

Jason Elkins (28:53)
Very cool. So as soon as we jet out of here, I'm going to go play around with ChatGPT ⁓ and actually exercise this and do this. That's very cool. Great, great advice. Thanks, Jason. Appreciate it.

Jason Halberstadt (29:06)
You're welcome. Have a good one.

Jason Elkins (29:08)
All right, everybody, see you next time. Come back to the AI Compass podcast for travel leaders. see you again next time. Bye.