Why Comms is a Two-Way Street

Leslie Cafferty: No matter how good your intentions are as an organization, you have to understand that good intentions are not enough to ensure that perception of your decision is going to be aligned with what the actual intention was. So you think, you know, “Well, if you’re a bad company doing bad things and there’s a big public backlash, well, that makes sense. But if you’re a good company doing good things, there can’t possibly be major public backlash.” There can.

Shahar Silbershatz: Hello everyone. I am Shahar Silbershatz in Copenhagen, and this is Always On, the podcast about brand, reputation, and data-driven communications. Today I have a special guest, Leslie Cafferty, the CCO of Booking Holdings, the parent company of travel and leisure brands like Booking.com, KAYAK, Priceline, and OpenTable, reaching millions of travelers worldwide. Welcome to Always On, Leslie.

Leslie Cafferty: Thank you for having me. Happy Friday. It’s great to be here.

Shahar Silbershatz: It’s great to have you. Now, let’s start from the very beginning for those listeners who don’t know you very well. Tell us a little bit about who is Leslie Cafferty? How do you describe yourself at a cocktail party?

Leslie Cafferty: How would I describe myself at a cocktail party? I’m probably the person at a cocktail party you would see kind of sitting in a one-on-one conversation versus fluttering around the room. I am actually quite an introvert by nature, in a setting like that, but I really do love good conversation. So in an environment like that, I’m probably more hopefully I found a really interesting person to have a good conversation with, sitting maybe in the corner somewhere. That would probably be me at a cocktail party.

Shahar Silbershatz: So you’re the introverted communicator?

Leslie Cafferty: Yes, yes. Which is funny sometimes in our world, in the world of brand and communications, people tend to, and I don’t know why, assume sort of an extrovert personality. But yeah, no, I’m the introverted communicator.

Shahar Silbershatz: So, you’ve had a long career and we want to talk a little bit more about the journey that you’ve been through. Why don’t you tell us first, what inspired you at the very beginning to get into communications?

Leslie Cafferty: Yeah, I had no idea this is what I would end up doing whatsoever. Interestingly, my sort of connection is, my father and his father worked in the media business, but on the journalist side, which is very different. But I had no aspirations to get into journalism. I really didn’t know what I wanted to do when I went to school. I was always very interested in the world, what was happening outside of history. And so when I went to college, I studied international relations, which I really enjoyed for years, but I left at the end of it going, well, what exactly am I going to do with this? I thought about going to law school, doing international law.

So that was sort of the path I was on. But I needed a job in the meantime. So I worked at a company — I got a job just as an executive assistant to pay the bills — at a company called IAC in New York, which was a really fascinating company. Big internet conglomerate. Owns a ton of internet companies — actually Expedia at the time, which is funny now in my world of online travel. And I started to get to see the world of business, and I was just fascinated. It was a really fast-moving company, and it was a company that was always in the spotlight. And so I got to actually see and understand what a communications team did, and it was really, really interesting to me.

So I spent my time there and I waited, and there was a very junior entry-level opening in communications at the company that came up that I applied for and didn’t get — because they said, well, you know, it’s great that you’re interested in this, but you have absolutely zero experience, you’ve studied nothing on it. Well, six months later when they still hadn’t found it, they came back and I raised my hand again and they gave me a shot. So that’s sort of how I ended up here. So it wasn’t part of the plans, but I’ve enjoyed every minute of the 20 years I’ve been doing it since.

Shahar Silbershatz: So you’re both the introverted and accidental communicator.

Leslie Cafferty: Yes, yes. I’ll put that… change my LinkedIn title.

Shahar Silbershatz: So tell me, how do you see — I mean, obviously the field of communications has changed a lot over the years and also over the years of your career. What do you see as the main changes?

Leslie Cafferty: It’s far more complex. I mean, at the end of the day, if you look at it at a macro level, it’s quite simple. There’s something, there’s a message of some sort, that needs to be delivered. The formalities of it used to be quite different. The channels that you used were different. So you had sort of time and space to think about what you would put in a press release. You had a choice about when exactly you wanted to issue it. Of course, there were time pressures and constraints and lots of other things dictating it. Our world has never been fully relaxed in that sense.

But the world is very different now. You don’t have the luxury. The channels are so much more — I mean, press releases, we use every now and again for very formal purposes and mostly Reg FD purposes, but that is hardly a channel that we use anymore. So you have social media, you have real-time media, right? The deadlines of journalists are different. It’s no longer a daily or weekly paper. They’re pumping news second by second. So the speed at which we have to operate, the speed at which we have to make decisions and the channels across that we have to operate and monitor and make sure we’re responding to, it’s so much more complex than it was when I started. So I think that keeps it interesting, but makes it really challenging. It’s never been more 24/7.

Shahar Silbershatz: So the pace has changed, but that is a result of the channels and the media changing, and all of that is also connected to technology evolving and actually changing the infrastructure that we use. And let’s talk a little bit about technology, because you’re also very active on that side within your organization. I know that you are leading an AI and comms steering committee, right, across all the brands of Booking Holdings? Can you tell us a little bit about that? Also, how you — I mean, it’s a diverse family of brands — how do you ensure there’s consistency and innovation in AI communications across this diversity of brands?

Leslie Cafferty: Yes. So we definitely, we operate different brands and they all actually have their own communication strategy, their own marketing strategies, right? And that’s how they have to thrive and compete in their world of business. But when it comes to something like technology, I’ve been — our team has been — very open talking about the prospects and opportunities that technology bring. There’s of course a fear of technology is going to take, and because you can produce content with the likes of generative AI, in our world, people are terrified. You know, is this…? Are we all…? And that’s not the case and that’s not how we see it at all. Technology provides immense opportunities to be better, to be faster.

So what we’re doing is all of our teams are thinking about this technology, not just within marketing and communications, right, but across the spectrum of business. But we’re looking at it, but we want to make sure we’re not duplicating efforts. We’re not investing money in the same opportunities or the same testing grounds of things. So we have a steering committee across all the brands, representation from all of our comms teams across the brands that come together to say, what are you interested in? What do you think you’re doing? What have you learned? And so the learnings and the positive, rather than having five brands all test a new technology or a new platform, you test it. What did you find? What worked, what didn’t? Here’s what we tested.

So we’re trying to be really fast, really efficient, really smart with it, and bring those learnings back to say, this is what worked, this is what didn’t, here’s the results. You guys can take it if you want to try it for a different reason. So just making sure that we’re really smart about it and so that we have used all of our bodies and people and monetary resources as effectively as possible.

Shahar Silbershatz: So in a sense, you’re scanning the market for the new tools and the new applications and how they can be used within the organization and doing it on a cross-brand basis to become more efficient. And the regulation that’s also increasingly coming into the fore, how is that affecting things? I mean, we have the AI Act in the EU and other regulatory initiatives happening. Is that having any impact on that work?

Leslie Cafferty: I think in our work, very specifically, not so much yet. That’s a different access to certain tools, varies based on geographies, and of course regulation has to be looked at very carefully. I think for what we are doing, specifically within our teams, not so much yet. But I would say the bigger picture, and just in terms of the business, yes. One of the hardest parts about being a global company is that you have regulation that is different in every part of the world and have to comply with that is really quite challenging. So I think in general, the more coordination we can have with respect to regulating or looking at AI across regions, across governments and the private sector, the more consistency, the easier it will be for people to use this technology in a smart way and use it within the bounds of what requirements are going to be set up by law. But it’s definitely challenging when you have different perspectives and different rules in place for different regions. But definitely something we have to be very mindful of. And we stay very close to our legal teams to make sure that they sign off on the tools we want to test, the data we want to input in it. And that would be — so we definitely have a very close, aligned relationship with our legal teams on that front.

Shahar Silbershatz: Right. And within this work around AI and comms, are you also looking at the risk side of AI? Because obviously, it’s also introducing risk to our world, and especially within comms where we need to be aware of that, whether it’s misinformation and different malgorithms and stuff like that. Is that also part of your remit or are you only looking at the opportunity side and how you use it?

Leslie Cafferty: No, we definitely have to be very careful on the risk side of things. I think I mentioned data a minute ago — that is one piece of it. We have to be very careful. As a big global company, we sit on a lot of data, and making sure anything that we input into a tool or system — knowing where that goes, where that doesn’t go, how protected is that — so that is a huge risk for us because we have to make sure we are just compliant from that perspective.

Also with customer privacy concerns, right? So the data we input is one huge risk that I think about. In terms of misinformation — absolutely. We tend to think of our job as communicators as: our job is to communicate, right? But communication is a two-way street. For as much as we need to communicate, we need to be listening, we need to be observing. So we need to be watching everything out there that is being said, where it’s coming through, and making sure that we have the means and ability to fact-check that, flag inaccuracies, and make sure we have an ability to course-correct in instances like that, if they come up.

Shahar Silbershatz: Yeah. So on balance, it sounds like you’re seeing AI more as a friend than a foe. I mean, it’s got risk, it’s got opportunities?

Leslie Cafferty: Definitely. And I don’t think it’s — we’re not at the point where it’s wildly changing the game or changing our day-to-day operations on a massive scale right now. But it definitely — the benefits and the opportunities are definitely there. It’s definitely quite exciting. I think we just have to do it in a smart way. But I think that’s with AI or really any technology. You know, technology innovation that sticks, you have to look at it and say, okay, if this is here to stay, clearly it’s bringing some kind of value. How do we find that value? And finding that value is really important too. Technology for the sake of technology is not great, right? So just to start saying, oh, Gen AI is going to write all of our content now and it’s going to be — there’s some things that it’s actually not great at, and then there’s some things that it’s better at. So finding where there’s real value for what you do, your function, your needs as a business, is really important. But I’m very excited for it. And we have a great team that really has a learner-first mindset when it comes to technology. And so I think if we can — if we know how to use it well, that’s where there’s opportunity, and that’s where you move away from the fear-mongering of, you know, AI is going to take my job. It’s the people that really know how to use it are going to be — they’re going to be assets.

Shahar Silbershatz: Sure. And you’ve also been on the forefront of using new media formats. So, for example, the expansion to TikTok — if you can talk to us about that. You’ve done a pretty good job at that. It’ll be interesting for us to hear, and the listeners, what prompted that expansion. How did you go about it?

Leslie Cafferty: Yes. I think at the end of the day, sometimes there’s — I don’t know. There’s social media fatigue for sure. There’s a new channel — Instagram launched this new format — and so you have to be … as communicators, one — there’s just a responsibility to be up to speed, right? But it can be overwhelming. And how do you think about making sure — but clearly TikTok, we were seeing quite early on — this wasn’t going anywhere, right? This was a format that people wanted and used. And at the end of the day, as a communicator or as a brand, you have to be where your audience is, right?

And so if you are traditionally a marketer, we grew up and built our business a lot on Google, and that’s where our audience was at the time when the internet started booming and we were building our company out. And then we migrated — in places, there are regions and geos where TV is still a big media — but you have to go where your audience is going. And as a communicator, as a marketer, it can be intimidating, because if you’ve built your experience communicating on a certain channel or platform, and then another one emerges that’s wildly different, and you say, well, this is the Wild West — but if your customers are there, if your audience is there, you have to be there.

And so we started looking very early on. We are a very data-driven company. So we do a lot of — our mindset is test and learn, not to assume, here’s the message we need to deliver and we delivered it on that channel and it worked really well and people got it and understood it. And then taking that and saying, okay, let’s put it on this channel — we certainly tried that. But then when you say, hmm, it doesn’t seem to be being received, right, we’re not getting the reaction — so you have to look at, okay, what if we tailor it this way? What if we shorten it? What if we do it in a video format? What if we modify it this way?

So we really needed to look at our content and we test different formats and structures and watch how that resonates. And so what you end up with — how we communicate on TikTok is very different than other channels. But that audience — there’s a certain expectation for what content and a message looks like on that platform. So I think the biggest lesson for us — whether it’s TikTok or whatever the next channel will be that emerges tomorrow — is really paying attention to not what you think will work because that’s worked elsewhere, but really looking at how did your audience respond to that. And if you don’t know — if they didn’t respond well and you don’t know — test. Iterative testing of things — different fonts sometimes, you’d be surprised, will have an impact on how a message is received. So the level of things that we test to make sure that it’s working is a constant iterative and ongoing process.

Shahar Silbershatz: So it sounds to me more than an attitude about technology, this is a mindset of experimentation that you have in the organization.

Leslie Cafferty: Yes. And it’s very much embedded across Booking.com in particular, which is our biggest business. The business was built on experimentation. So at any given time, our website is running like a thousand different experiments. Things like, when you click on a hotel listing and what you see — do you see written content? Do you see images, right? And we watch what people respond to. But we’ve really picked up on that culture within our comms organization. And so we test everything to see what works. A lot of experimentation. Because there’s again that mindset of, I know what resonates with me and how I like to receive a message. But you have to remember, right, that that’s not the way everyone else is. So the more in tune you can be with data and the facts and watching that, I think the better and smarter we can be as communicators.

Shahar Silbershatz: That’s very interesting, because it’s a way that the comms side of the business can learn from the commercial side in terms of the mindset and the culture, just adapted in a different way. So let’s also talk about the data side that you mentioned. What kind of data points do you use in comms to show the value of your work or to prove the effectiveness of your activities? What is the tech stack that you use for that? What are the data points that you use?

Leslie Cafferty: It depends on what we’re actually looking to measure, right? So in communications, there’s the external and the internal. On the external side of things, I think it really — again, it varies per platform, right? On platforms, it’s really hard to tell on the more traditional side of media, right? Success is: you have a message, you want to get it out, and you hit the media targets that you want that are reaching your audience — that’s success. It’s very hard to measure: did people understand that message? How many people actually read it, right?

So that’s a channel that’s a bit more difficult. When you’re looking on TikTok though, for example, when you put a message out, you can actually measure how many people engaged with that, right? If it’s a video format, how many people actually watched the entirety of the video? So we take those pieces as signals of resonance, right, and engagement. Of course it’s not as great as asking the user, did you understand that message? Did you like that message? And are you taking an action from that message? But we can get a little bit more granular on a platform like that than we can with more traditional media.

So the more we see people engaged with our content in places where we can measure that, that certainly. And the same — that applies also a bit I talked about internally. We’re looking at — we use, when we communicate with our employees, maybe — we have 22,000 employees all over the world, right? So we use a lot of video format, a lot of live-streaming format. And different technologies will allow you to measure different thing. Of course: viewership — we can measure length of stay, right? When do people drop off of a video so we can understand where our content started losing our audience. Engagement with the content — so we have options for people to engage, for people to like, for people to leave comments. So obviously we look at that from a qualitative perspective and a quantitative perspective. How many people engaged, and was the engagement positive or negative? So it depends on the platform and who you’re communicating to again, and what those capabilities are. But I really — our team, we try to focus on — sometimes, these technologies and platforms will throw a lot of metrics at you. We try to really think through: does this metric mean anything?

So to give an example, impressions is something that a lot of different platforms can give you — here are your impressions. When I look at that — we capture it, yes — but I don’t know what that — that doesn’t tend to tell me too much, right? Engagement will tell me more — if people heart something or like something, that’s a little bit clearer about, did my message have an impact or get toward the way I want, rather than something. So we try to just be really — we have a lot of conversations about it. We kind of nerd out a little bit sometimes on the data front.

Also an area where the culture of the business has kind of embedded our function — but really to talk about like, are we gleaning any insights from this actual data point or not? And we try to then focus on the ones that we think we can get some tangible impact or advice from.

Shahar Silbershatz: Exactly. And that’s really where I’m getting at, because a lot of people are struggling to measure the ROI of communications because, as you said, we have impressions, we have engagement, we have media mentions, we have a lot of these things that are maybe kind of helping us understand the output of our messages, but not so much the connection to the business value and the impact on the business. Do you have some kind of a dashboard that tries to work it all up to business impact? I don’t know if you’re looking at trust or looking at other things that you think are kind of an overarching, “Here’s our ROI of communications”?

Leslie Cafferty: Yes. So we do look at a lot of things like that. We look at trust in the brand. We look at brand recall and overall awareness, top-of-mind awareness in a market. What becomes difficult is — so many factors also contribute to those macro metrics, right? So we definitely look at that. But was that top-of-mind awareness that grew in market X over the period of Q1 — was that just communications? Was that the TV brand advertising we ran?

So it’s hard to also — but I think there is an intrinsic belief that when you are putting a message out about your brand, about your products, what you want people to think, and they are positively engaging, there’s some belief there that that has impact. Can I prove how many bookings we got on Booking.com? No, we’re not quite there. I don’t know when and where we will be. But one of the things we also look at ourselves as a team: when we spend our budget to achieve our objectives that we set for the year, can we do more, more efficiently? So that’s something we look at a lot. If we’re putting out a consumer communications campaign tied to a new product launch — I’m just making up an example — what is the investment we’re going to spend on that campaign? What are the results? How many earned media hits did we get? How many people did we reach on social media? How many people engaged with it on social media? And then to say, okay, we spent that, this is what we got.

The next time we launch a campaign, we say, can we achieve that with either less budget or, with that same budget, achieve more? And we’ll apply different tactics to different campaigns. So we sort of look at that as a bit of an efficiency ROI metric. And in a certain campaign, if we say, wow, that one tactic helped us achieve far more, and it was so — then we have campaigns sometimes where we say, well, we spent the same amount, we got a fraction of what we got there. So what didn’t work so well?

So we try to take insights also about how to achieve our objectives effectively — which again, these are things that we can measure, so we do. But it’s not necessarily to your question, how did this drive the business? But there are things that we can do to measure driving the business, but also things to make sure that we’re doing it in a way that is increasing with effectiveness and efficiency.

Shahar Silbershatz: Right, right. And doing internal benchmarking, of course, is a good way to do that. So let’s talk a little bit about the communication landscape today. It’s obviously becoming a lot faster, a lot more complex. Things happen very, very quickly, and this is why we call this Always On — because we find that as communicators, we’re forced to be always on. How do you see yourself and the team being always on at Booking Holdings?

Leslie Cafferty: Yeah, it is always on. If you’re a global business, you have to equip yourself with a few things. One, we are a global business, so no human being can be awake 24 hours a day, seven days a week. So we have people —

Shahar Silbershatz: Some of us might want to —

Leslie Cafferty: Yeah. Yeah, it would be nice. We don’t have buttons yet that can just hit the button and go. But we have people all over the world, right? We have monitoring services in place all over the world. So we have social media monitoring happening 24/7 and we use different partners and technology that will flag things. We have different agencies in place. So we definitely have a system that is equipped to — has monitoring happening 24/7 and alerts get raised and ideally someone somewhere in the world is always awake and available to be responsive to that, to see what’s happening. And we have a very tight ecosystem just in terms of a global team, our touchpoints, our ways that we can get in touch with each other. So if things need to be escalated in time. But I think the monitoring piece of it is very real. You don’t have to respond to everything instantly, but the monitoring allows you — if something really important is bubbling — to learn about it as early as possible, to give yourself as much opportunity to think about how you need to respond.

Shahar Silbershatz: Do you have a good system whereby the brands in your portfolio are interacting with the mothership, so to speak, so that there’s a good interaction — so some things are dealt with locally, some things are elevated, so that you can make sure that things are covered well?

Leslie Cafferty: Definitely. And it’s that balance of autonomy, right? The brands and teams need to be able to run themselves without being hindered by the handcuffs of the big mothership, but also making sure that there’s a system and process in place. So we have various touchpoints with the brands all the time. But I think our job is to make sure that there’s a very clear understanding of what needs to be escalated and why, right? So people understand — it’s not just, you have to do this for the sake of we need to know that, but why do we need to know that? Is it — would it get us into a compliance issue? Is it a reporting Reg FD issue? So we’re very clear with the teams and we’re in constant communication around these types of things — anything you see that has to be escalated. So I think what helps make that effective is making sure there’s very clear understanding between everyone about what would need to be brought up and what’s okay to be dealt with locally and shared maybe as an FYI.

Shahar Silbershatz: Do you find that your approach to crisis preparation is changing these days? I mean, there’s obviously some newer risk — we mentioned disinformation before. There’s a lot of, for example, geopolitical events, social controversies. I mean, are you finding that you are developing new ways to work or to have your team work so that things are responded to quickly and in a cohesive way?

Leslie Cafferty: Yes. And I think we think about this a lot. When it comes to crises, where you can prepare well is in the systems and processes that you have in place, right? So like I said, that’s more of the tactical: crisis issue spotted — what’s the immediate action steps? We have playbooks for who needs to be involved, when, how to reach them, etc.

So getting your process right is really, really important. What’s harder is, when I’m asked by the business every year, “What’s our crisis plan?” Well, my first response is, well, for what crisis? And the crisis that we don’t know that’s coming? So the crisis that we then can’t prepare for. There are certain scenarios that we try to look at, and you should look at our industry and say — so we’re an internet company, so things like data and privacy — so big internet companies can have a data breach.

So that’s something that could be a situation. Rather than, we don’t have physical stores, so damage to a physical store — they’re different. You have to look at your business and say, what could be a higher-likelihood type of crisis? And then we sort of work through broad-level plans for, in an instance of, say, a data breach, here are some things we would need to think about. But what you can’t predict is, every crisis is completely different, right? And there’s no one-size-fits-all approach. So having the process in place and some basic understanding of the types of materials you would need and those playbooks and templates ready to go — but then that’s where the human brain needs to come in, right? And so then we know how to get the process in place, and we have to come together quickly to look at the actual facts.

But that’s where it’s also really important to have connection between communications and your security teams, your legal teams, right? And so we keep touchpoints all the time with these groups of people because you’re going to inevitably need to work across a lot of functions in some of the big crisis moments.

Shahar Silbershatz: And have you found recently that these playbooks and these trainings, the processes, have had to undergo a lot of adjustments because there are new risks that are coming to the fore?

Leslie Cafferty: Yes. We definitely — we take a once-a-year look at our playbooks and processes, and we dust them off every year if there’s a need to do it more. I think we used to do it on a maybe every third year basis, but now we look at it every year because we look at the spectrum of things that are emerging and bubbling to just say, do we feel these are in a good place? Do we feel like there are newer things that we need to — and for example, when you have changing geopolitical winds, that could change the types of crises you think you might have, or something different is happening in your business and you think about, okay, now it could be — so you definitely need to look at it every year and you need to say, does this still feel most relevant for where we could be today?

Shahar Silbershatz: I heard you talk before about — there was a backlash that Booking.com went through for accepting Dutch government aid during the pandemic, and you described it as one of your toughest lessons. Can you tell us a little bit about how that experience changed your approach to understanding public perceptions and local sensitivities?

Leslie Cafferty: Yeah. So we did — during the pandemic, travel came to a screeching halt, and our business pretty much came to a screeching halt. So it was not good very quickly. And so we were trying to think about what we needed to do. It became clear quickly — I mean, you saw the headlines and layoffs in the travel industry — it’s really hard to support a business when there’s no revenue coming in. Booking.com is based in the Netherlands and there was an option for government aid, and so we decided to take government aid to preserve jobs as long as possible. And other companies were taking it, and we thought, we didn’t want to let go of employees, so if we could hang on, anything we could sort of take.

So the business made a decision through a lens of truly believing what was right. The backlash was like nothing I had ever experienced in my career and we didn’t anticipate it at all. It was not well received that we were taking government money. And I think the lessons that I learned were — no matter how good your intentions are as an organization, you have to understand that good intentions are not enough to ensure that perception of your decision is going to be aligned with what the actual intention was. So you think, you know, well, if you’re a bad company doing bad things and there’s big public backlash, well, that makes sense. But if you’re a good company doing good things, there can’t possibly be major public backlash. There can. And that was the first time we saw that.

So there was just a disconnect between what we were trying to do and how that was perceived. So a really big lesson for me. Now I think through that lens a little bit more, because I didn’t necessarily think when the business made the decision that we were going to have to have a big public relations campaign ready to explain why, because it was intuitive for us. And that wasn’t the case.
So a really big learning now, to always say, we think we might know how this might be received, but let’s plan for the opposite of what we think and just, you know, looking through things like that through that lens.

Shahar Silbershatz: Let’s talk a little bit about internal communications, which is also an area that you talk a lot about. So today, employees are a lot more vocal within the company about what happens in the company, what happens in the world around them, world events that are also influencing people’s opinions. How do you foster open lines of communication? How do you build trust within the organization in today’s world?

Leslie Cafferty: Yeah. It’s an ongoing — I don’t think there’s a right answer for it, and I think it’s a continuous journey for us. I think a culture of open communication is very important to us, and so we try to foster that.
At the same time, we try to foster a culture of respect of different points of view, right? So the minute you say you create a culture of open communication, you’re allowing 22,000 employees to voice an opinion on the decisions you make, on what your company’s doing, on the state of the world, the state of politics — you name it. Inherently, you’re going to have differing points of view. So making sure that striking the balance of allowing openness for points of view and opinion, but also respecting points of view and opinion, is something that balance — it doesn’t happen perfectly, but that’s what we strive for. And those are the sort of principles with which we try to operate internally.
But creating trust also means when those opinions surface to the forefront, you have to, as a business and as leaders, you have to be ready to respond also. But you have to do that carefully, because it’s not our job as a business to speak on things that are not related to our business or industry. So if something happens that’s related to our employees, to our customers, our partners — then yes.

But for the sake of coming out and speaking on political issues that don’t necessarily impact the day-to-day or don’t directly impact the day-to-day — but our employees have strong points of view on — you need to create that trust, you need to be responsive back, but you also have to help find that balance and that focus on where the dialogue is productive and respectful, versus going into a place that’s not either respectful or productive to what the business is trying to achieve.  But it’s a very hard balance.

Shahar Silbershatz: Yeah, it is, because that balance is very hard to hit. And I’m wondering if you can share any examples of how that dialogue — that openness — within Booking Holdings has helped you navigate difficult conversations internally?

Leslie Cafferty: We’ve had leaders sit down with our ERGs internally to say, okay, you know what, this is a topic our employees — insert a topic — our employees are really passionate about, opinionated about, we need to have a point of view. How do we help?
And we’ve had our leaders sit down with our different ERGs — employee resource groups — to just understand different perspectives. Just listen. Just hear different perspectives. So that helps inform how you have a dialogue. Everybody has their own personal perspective, right? But how do you think about listening to make sure you’re hearing different points of view and perspectives to make sure that can help facilitate productive conversations?
I think that’s something we do in times, making sure that we’re all informed about the different opinions and perspectives that exist within our organization, whether we agree or not. I think being informed helps give a perspective to shape how and when we engage in dialogue.

Shahar Silbershatz: Right, so even if you don’t adopt a specific stance or something as people might expect. at least to involve the leaders in listening, so that there is an understanding within the company that leaders are listening?

Leslie Cafferty: Yes.

Shahar Silbershatz: Even if the outcome is not the outcome that people are expecting.

Leslie Cafferty: Yes.

Shahar Silbershatz: Because it’s very hard to satisfy everybody. There’s diversity of opinions in a company, especially on —

Leslie Cafferty: You’ll never satisfy everybody, and you have to accept that as well, right? And that’s another point — even in places where we listen and then the business does say we have a point of view and this is the point of view — you have to approach that with conviction. You have to say, if that is the business’s point of view, here it is and here’s why.
And you have to accept that not everybody will be on board. You will never please everybody. But it’s also important to say when there is a point of view — that the business is transparent back to employees to say, this is our position and here’s why. And you have to be ready for people to not like it. And that’s okay.
And I think the more we also train our leaders to understand that there will always be different points of view — even if you are on board with a decision, not everybody will be — and that’s okay.

Shahar Silbershatz: Right. Now, as a CCO, you work very closely with your CEO, and you serve as a strategic advisor to him and also collaborate a lot with your peers across the C-suite. What are the tactics that you found effective for that collaboration over the years?

Leslie Cafferty: I think the most important thing is, especially in a function like ours, you have to really know the business. You have to really know and understand the business at a very granular level. That’s how we as communications add value back to the business.
If you really understand the business, you can help the business risk assess. You can help the business understand different scenarios — for how business and commercial decisions will impact perception, reputation, etc.
And so when you can establish that trust with your leaders because you know the business and you’re giving good counsel, that’s where it creates a really great relationship that goes both ways. When the business learns to understand that we do know the business and we can help on these fronts, it creates a really healthy, productive relationship with the leaders across the organization.

Shahar Silbershatz: That’s pretty simple actually. So really understanding the business side helps you gain trust as a communicator from the other.

Leslie Cafferty: That’s my biggest piece of advice to anybody.

Shahar Silbershatz: I’ve heard you in the past talk about how in the past companies used to speak out only during earnings calls — that actually they didn’t really speak out much otherwise. And today, of course, that’s not really possible. There’s a lot of pressure on CEOs to have a voice on major societal issues. How do you decide within your company when it’s appropriate for leaders to speak out and when it’s better not to?

Leslie Cafferty: It’s a great question. At a high level, I think it depends on your company and your culture to a degree, right? Some companies have different — and it just might be the DNA of their company. So you have to kind of first assess, where is the appetite in our organization? Culturally, where are we? Historically, where have we been?
Yes, we were a very heads-down, workforce-type of company for a long time. But the world has changed and you can’t be that way anymore.
We have a lot of pressure from the outside world and from our employees to speak out on a lot of issues — political issues, societal issues. We try to put a few principles in place: Does the issue or topic impact our employees, first and foremost — if it does, then that is relevant to us. Does it impact our partners? Is it related to our industry — be that travel technology, travel in general? Is the issue in a region where we have a presence? Do we have offices there? Do we have people there? Is this connected to us and our business and our people? Then yes, there’s probably an area of opportunity.
Amd then we say speak, if we decide yes, this touches us in some capacity, there is an element of: are we speaking just to our employees? Are we addressing the topic internally or are we addressing it externally? But also knowing you cannot control that. So even if you intend to say, “We’re just going to address this with our employees,” and we’re going to keep this conversation here, you have to, of course, be prepared for that conversation to be taken outside.
That’s a little bit of how we think about it and you have to apply that lens. But it’s not perfectly black or white in every scenario. That’s where you come together and really think through — who is it impacting, how much is that, and then do we need to speak? Mostly to protect our employees and our company.

Shahar Silbershatz: And do you have a structured process around that, where if an issue pops up, then there is a certain process that you go through to kind of put some evaluations, assessment or ratings, and come with a recommendation to the CEO?

Leslie Cafferty: Yes and no. Sometimes it will fall within the threshold of a bit more of a crisis, right? So I talked about that — in those moments, if it’s an earthquake, a crisis that happened, and people want to understand, or a major event like an election coming — okay, so then you have a process in place.
But what an issue is, is subjective to the person, to where you are, to your perspective on the world. So there are a lot of things that sort of arise that maybe won’t hit that official threshold, but it will be flagged. We’re watching the news. We’re saying — do we need to have a point of view on this? Should we be prepared for questions on this?
Things will surface. Or employees will ask a question directly. Or we’ll get a question from the media on a topic that didn’t hit that threshold for process.
You have to be very eyes and ears, listening on the ground, understanding the conversations happening about your business, and then being as prepared as possible. And we as a communications team, we meet every week — more if needed — to look at exactly that. Is there something happening out there that we might be asked for a point of view on, that we’re not thinking about yet? So we try to get ahead of it as much as possible.

Shahar Silbershatz: And I guess it also is connected to the relationship that you have with the CEO. Because a lot of these things probably also touch on personal perspectives of the CEO and when he or she feels comfortable talking. I guess being trusted by the CEO is probably also an important element. I think you mentioned somewhere that you argue in a good way with the CEO every day, so probably, I imagine that’s part of those conversations — about do we or do we not talk about this issue?

Leslie Cafferty: Yep. And certainly our CEO, he will come sometimes and ask, “Do we have a point of view on this? Am I going to be expected to have a point of view on this?” But then it’s also — I see very much my job and my team’s job to make sure he’s aware. Right? “You may be asked about this. Make sure this is on your radar.”
And also having a sense for — you can kind of have a sense: is that something he might want to address or might not? But the job is, first and foremost, to make sure he’s aware — these are things you need to be prepared for. And then we can have a point of view on it. It’s always a challenging conversation. Those are the relationships with anyone I work with that I love.
He’ll challenge everything. If we have a point of view on something or a recommendation on something, he’ll challenge it. And that’s great because it makes us think through — even if it’s — we’re guaranteed this is the right approach, we always have to think through: what if it’s not?
So challenging that — and our thinking — really puts as much of a stress test as possible on recommendations that we bring forward on any front.

Shahar Silbershatz:  All right, so let’s wrap up with a more personal question. So, we talked about being always on — but how do you switch off?

Leslie Cafferty: How do I switch off? I love to cook. I don’t have time to do it as much as I used to, but sometimes on a workday when I’m not traveling, I’m here — because I don’t cook when I’m traveling — but when I end a workday, I find that to be a nice transition. To slowly get my brain out of the thousand things that I need to think about for the next day, into something — and I enjoy it.
And it takes a lot of — I think to cook well, it takes a lot of time, effort, and energy. So I find that to be my nice transition window. But otherwise, I try, once or twice a year, really to take — and they say Americans are not great about taking vacation — but really try to switch off a few times a year, where you say, “You can reach me if you really need to”, but the world survives without any one person.”
I have a phenomenal team. And the business can live. So really trying to understand that and take that time to actually shut off. If I can shut off for a good chunk of time — that’s my battery recharge for another six months. And then I hit that point again and say, “I need to just turn off for a week or two.” But yeah.

Shahar Silbershatz: That’s great. Leslie, thank you so much for all your insights. We loved having you here, so thanks a lot.

Leslie Cafferty: I very much enjoyed the conversation. Thanks for having me.

Shahar Silbershatz: Many thanks for listening to this episode of Always On. If you haven’t done so already, check out some of the other episodes — they’re packed with unique insights from seasoned experts at leading companies. Oh, and if you have any comments or questions about anything you’ve heard on the pod, we’d love to hear from you. Just drop us a line at [email protected]. Thanks again for listening. Till next time, take care.