Radical Innovators #19 leading with experimentation: fostering innovation & simplicity with Booking Holdings’ Paulo Pisano

In this episode of the Radical Innovators podcast, host Frank Congiu welcomes Paulo Pisano, EVP and CHRO at Booking Holdings, to discuss his career journey and how his background in operations and finance influences his approach to leadership.

Throughout the conversation, Paulo shares his thoughts on the importance of organizational clarity, the role of a leader in consciously shaping culture and the necessity of doing "fewer things better" to drive business outcomes. He also explores the unique challenges of operating a multi-brand tech and travel marketplace and how Booking Holdings is currently embracing experimentation through generative AI.

Additional takeaways include:

• simplicity and prioritization: why HR leaders should be removing low-value activities and "must-dos" from the system to reduce complexity
• culture as a deliberate choice: leaders are always shaping culture, whether consciously or not; therefore, it’s critical to align cultural levers to support business strategy
• encouraging innovation through scarcity: creating boundaries and limitations can actually engender more creative and interesting solutions than having unlimited resources
• AI as an engagement tool: how Booking Holdings uses "marketing-style" awareness campaigns and meeting check-ins to drive broad employee engagement and experimentation with generative AI
• the evolving CHRO role: why the CHRO will increasingly serve as a "chief simplifier," helping organizations navigate massive global and regulatory complexity

Transcript

SPEAKER_00 0:00

Welcome back to the Radical Innovators Podcast. I'm your host, Frank Hanju. And for this episode, I sit down with Paolo Paisano, EVP and CHRO at Booking Holdings. Throughout our conversation, he discusses his company's culture of experimentation, why he prioritizes the idea of doing fewer things better, and how he sees the role of the CHR evolving to be one of driving simplicity and focusing on what matters most. So let's dive in with Paolo Paisano. Paolo, great to see you. Welcome to Radical Innovators.

SPEAKER_01 0:34

Great to see you as well, Frank.

SPEAKER_00 0:36

I've been looking forward to this for a long time, and I'll get into that into one of the questions in a little bit. But we were at a dinner, and I think about a CHRO who asked a question, and it was very policy-driven in nature. And your reaction immediately caught my attention because you stopped abruptly and said, Why are we asking these questions? Do these policies actually help the business in any way? And then as HR leaders, do we sometimes just get in our own ways? And without even knowing your background, I immediately was able to kind of pick up on, okay, this is clear, right? And this is where the question comes from is that, you know, you spent some of your early years in management consulting and then you moved into HR. And those, and it's those moments in the room where it becomes readily obvious. And I'm sure the people in the organization feel and see this. But I'm curious what led to you pivoting from those operational and financial roles and then into ultimately into human resources?

SPEAKER_01 1:30

I love the space of consulting and advisory, right? So I have nothing against it. I think it gives you the opportunity to work across a lot of variety. I they tend to be very uh, you know, kind of strong, you know, talent-rich or strong talent density organizations. So they're great academies and I think they can be great partners for businesses. The thing about it for me back in the day was because I was working in management consulting already more and more focused in the organizational side. What got me really curious was you come to your client with some amazing ideas or at least some good ideas on things that can really make a difference for their business. But unless they implement it and they implement it well, your idea is not really worth much. And we often came across with the issues of implementation. Yeah, people get the concept, they agree it's a good idea, but they don't know how to do it because it often means them changing the way they do things, changing the way they view the world, changing talent they have or the way they structure their teams or whatever. So that early on was catching my interest. And eventually I found in the AGR field a place from which I could make much more of an impact from within organizations, right? Where you have much more depth if you are inside the organization. You have more breadth, you can touch more levers than you can do as a consultant. And then you have time, you have cycles, right? Some of these changes they don't happen in months or even in a year. Some of them you need to live through two or three cycles before the organization starts embodying new ways of working. So this is for me, this was the um the road from from consulting and advisory into inside the business.

SPEAKER_00 3:23

And tell me what it feels like sometimes in terms of being in that. So you you come with this bit of a different background than I think some of the CHRs who've been on the podcast, who have been career-long journeys, started in HR and 25 years in that role. What does that look like and felt like for you? And how does that help you implement and drive those ideas that you previously maybe couldn't get over the line sometimes?

SPEAKER_01 3:43

In fairness, Frank, I've been in HR now for the vast majority of my career, right? So although I started in the consulting space, now I I can no longer use the uh the excuse of, you know, I'm new in the space and ask those questions. I think that the challenge first, and this is something I think you and I talked about in maybe in that dinner, the challenge in HR is that folks in HR usually get exposed to very senior people pretty early in their career, right? If you think about someone doing an HR business partnering role, they'll often be supporting or partnering with someone who's no two, three, or four layers above them in the organization. What I found that that tends to do is it tends to motivate you to know your stuff, to know your answers, to know how to answer things well and how to be perceived as an expert as quickly as possible. There's nothing wrong with that. It's how you build trust at that level, at that layer in the organization. But as time goes by and you become more senior in the organization, the more senior you become, the less the problems you are engaged with are going to be yes and no questions or black and white problems. They're gonna be complex things for which actually it's more important for you to know how to ask great questions and how to be a thinking partner and how to explore than actually to come up with here's the framework or here is the answer for that. But there's nothing natural. Some people will have it, but in general, there's nothing natural that's gonna help you move into that space. Um, and I think that's one of the challenges, right? When you are in this role, is how to help the HR organization to move more into the space of questions and quality of the decision making and connecting the dots, and less on the business of just uh delivering product to the business.

SPEAKER_00 5:47

So maybe less focused on moving within the different roles and then into HR and the functions, but a question around working in different sectors and industries because you've worked in publishing, high-tech travel now, right? And then energy between those two roles. With your cross-industry experience, what's the common thread you found that that helps to make sure you've got a strong culture and you're driving uh key engagement all in service of while you're, of course, doing what's most important driving business outcomes?

SPEAKER_01 6:15

First is more, I think, in common across sectors than there is difference, right? People always want to feel they're very different and very unique in their sectors. And I think there's, you know, probably 80, 90% of the challenge you may have as an organization that is similar, regardless of the sector you're at. When you talk about engagement and drive and building culture, I think the first thing that's critical, and that's that's been true for every company I've been in, is clarity on your vision as a business. What is it you're aiming to do, and how that translates into a strategy, into something concrete. Because if you don't have a lot of clarity around that, it's very difficult for you to hang everything else, like your operating model, your talent strategy to support that, your ways of working, the culture, you need to support that strategy. So whenever I've had an instance where we were able to clarify that and to work on communicating that to people and engaging people on that, I think we had an easier road to building culture and to engaging our people. And when that wasn't very clear, or there was misalignment uh across the leadership, lo and behold, it was harder to get kind of high engagement in the organization. It was harder to lend on which culture you need because you look, well, what is this culture going to serve? And you're not clear on that, and you spent a lot more time. So I'd say the main thing starts there. The second thing, I think, for culture, more specifically, is investing uh time and energy in supporting your leaders or sometimes teaching your leaders on the notion of shaping culture, right? On the notion that you like it or not, as a leader, you're always shaping culture. Now, there's ways in which you can consciously shape culture in a particular direction, thinking about some of the levers, right? Like you know, the symbols you use, the systems, the behaviors, et cetera. The more you invest in aligning people on that, or sometimes educating them on that, the more effective you are on building uh culture in a in a very uh conscious, in a very deliberate way, uh, and in a way that's easy for people to understand. So that'd be my my other angle there on culture, which has been very similar across different sectors.

SPEAKER_00 8:50

Is there any one book or or thought leader or or maybe even an organization that you've leveraged as inspiration as you thought about how you strive this here at Bookings?

SPEAKER_01 9:00

There are many authors and researchers that have done good work on this. A couple that come to mind. Carolyn Taylor, uh, walking to talk, very simple book, but very spot on, I think, when you talk about shaping culture. Fred Kaufman, Conscious Business, he draws from Carolyn's work on the culture side, but he talks about a number of other areas which we do work on here at Booking, and I've I've done some of that work elsewhere. I'd say those two come to mind as useful sources. And they're both like most good things, derivative of other authors and other people, which they honor also in their in their publication. So it's quite nice.

SPEAKER_00 9:39

And then in your current organization, um, you sit in the bit of the uh the intersection of technology and travel. So is there anything, any nuance there where you'd say in this fast-paced tech world and then this customer-facing travel industry, where you need to be thinking about sort of two different potentially uh personas in that culture? Or I'm curious, like how that looks like in the in the current organization.

SPEAKER_01 10:02

Yeah, it is interesting, right? We are in the intersection of tech and travel, which is which is quite, I'd say, good from a talent standpoint. It is a very desirable spot to be. We are first and foremost, uh, I think a tech company whose mission is to make it easier for everyone to experience the world, right? So we work as a marketplace, connecting partners and and and travelers right around the world. If you think about that, there are a number of challenges. If one of which, for example, that comes to mind is from a technology standpoint, you are looking at speed of innovation, right? You're trying to provide new features and trying to remove friction from the process of booking travel, or you know, we have open table as well, booking restaurants, and uh we have some B2B businesses that most people might not know, but support small kind of or smaller entrepreneurs and in providing experiences to travelers. So you're trying to move at speed and to innovate. And we've been great at innovation and A-B testing over the years, now iterating and experimenting, and we have a lot of processes to do that. On the other hand, if you think from a traveler standpoint, you're looking for stability as well and for reliability, right? You want to engage with an organization that's you're gonna trust and it's gonna provide you something that's predictable. And it's not always, but sometimes those things can follow somewhat different dynamics. So to uh operate and support a workforce that can do both things well and see how those things actually intertwine and don't necessarily compete with one another as much as people might think, is part of a challenge, right? The other part of the challenge, which is not as much about the intersection of tech and travel, but about our operating model, is we are a holding company with a number of operating companies underneath, different brands, like Priceline or Booking.com or Agoda or Kayak. And historically, we've managed those brands independently for speed, for agility. And there were a lot of really good things about that. But as our ambitions uh you know became larger in the sense of providing a real kind of connected experience to travelers, um, it became evident that we are leaving value on the table if we don't build a little bit more connection and alignment or collaboration between those various parts of the organization. So then the other dilemma or challenge that we have is how to navigate the balance between autonomy and agility with interdependency and reliability on one another, right? And that's not not always easy. I'd say more often than not, it's more art and science, but that is a constant challenge as well, how to balance those two things. So it's often about balancing elements that are seemingly contradictory, and they're not necessarily always so, but it it means you have to support scalability on the one hand, and that means doing things in the same way everywhere, but also I need to understand in which instances we need to allow for different ways of doing things, because that really makes sense in this in this case, and it's gonna create more value for our customer.

SPEAKER_00 13:27

It's a balance, right? Because you want to continue to drive that innovation, and those are going to come from those different pockets. But at the same time, you do need to be able to figure out how to scale these across the different businesses. And given that this is the radical innovators podcast, one of the things we're always looking to do are pull out some of the innovations. Um, I think I shared this with you, but the podcast was actually born out of the idea of what are some of the world's leading organizations doing to improve the lives of their employees while improving the lives or improving the business. Thinking about that, I mean, you've talked about how you're removing or integrating low-value activities. I'm curious what some of those processes have been that you've eliminated. And as a result, you've seen some positive impact.

SPEAKER_01 14:07

I'll take an angle here. Let me see if I can answer your question, but I might go a little bit on a on a tangent for for for second year. Because yes, we've done what many organizations do, like, you know, pick up areas that you can simplify and remove things like, you know, more manager self-service. So AGR can focus on higher, you know, kind of uh value add activities, et cetera. We're doing some of those things. But I want to take it a maybe a level further up because for me, before almost like before the innovation itself, uh you need to focus on the on the mindset that's going to enable that innovation, right? So for us, for example, we we come from an experimentation culture, uh, which is great, but it also means that there's a tendency for people to want to do lots of different things. And I know myself, I have that characteristic as well. You know, someone from my team brings an idea, it's interesting, I'm excited about it. I'm like, why not? Let's try it out. The the challenge with that for us, and I think for many organizations, is that you end up adding more and more stuff to the system. And the more stuff you add to the system in an already complex system, it means you're probably gonna add more people to the system over time. And if those people are good people, they're gonna want to do a good job and justify their jobs and create values. So everything becomes more in quantity and more in complexity. For us, I would, you know, I don't know if I'd call it an innovation, but the the biggest thing we've done in that space has been more broadly becoming better as a business uh on prioritizing and making trade-offs and making choices. And this has been a multi-year process where there was a point in time where we were realizing in our planning that we are adding things and we're great at adding new things to do, but we're horrible at removing things from the system. And there's only so many hours in the day, and there's only so many people we can hire at a given time. So we went through a process of actually reducing the number of things we're doing. And my team is tired of hearing me say, you know, fewer things better. How can we simplify? I remember, I think, in my first um planning for booking.com specifically, we had, I think, 180 initiatives from one year to another one. I'm like, my God, you know, and you'd look at any of them, and they all had a reason. You know, some of them were more compelling, some of them were less so, but still interesting or exciting, or experimenting, or we're we're tinkering with something. But that generated enormous complexity and lack of focus. So just through the process of reducing the number of things and spending time on the criteria, what are we going to use to guide us on that? Right. So we came as a business to a number of priorities that are strategic priorities, a number of must-do's that they are elements that are related to uh regulatory requirements or infrastructure or you know, things that are foundational for us and keep the lights on. Things that look, these things you have to protect. You might not innovate or drive something very different, but they gotta be there humming kind of in a regular cycle. That made an impact for us. We're not there yet, we're improving on that, but I'd say the the process and the mindset to to be much more relentless on focus and priority and simplification and just removing stuff has been, I'd argue, more impactful for us than any one individual initiative I could tell you that is helping.

SPEAKER_00 17:57

And it's a tricky process to navigate, right? Because I think you don't want to reduce people's energy around innovating. At the same time, not all of these things are created equal. And it kind of reminds me of Will Gadera's book, Unreasonable Hospitality, as he encourages the entire staff to go through every element of which a customer is touched. And he says, look, we can't work, we can't focus on all of these. So what's one of the most meaningful moments? And it's when they get the check, right? And so it's for you. When when do people get the check? And what is that, what are those few that you can key in on while still managing the idea of we do still want to have people with an innovative mindset and helping think about how to prove the business. So I'm sure this is a tricky exercise to go through. I look forward to hearing and seeing more as it progresses.

SPEAKER_01 18:40

100%. 100%. But again, it's even for innovation, I think that there's something around the notion of if you build boundaries and you you build scarcity in a way, it contrary to what some people might think, it will engender innovation, right? When when when you have everything available, arguably, you don't have to think too much. I've trailed a parallel career in the third sector with NGOs for for the last 20-something years. And something I've learned constantly from them, and I've I've used it in many of my internal conversations and companies I've worked in, is that while some of my colleagues in big multinational successful companies were complaining about, you know, I don't have enough resource or budget or what have you to get some things done. And you're talking about millions and millions, and that was not enough. I had uh, you know, I was living an experience at the same time in one of the NGOs I'd be working with, where folks had, you know, a rounding error of that, and they were coming up with creative, interesting solutions, et cetera. And this notion of create some limitations, and that might actually force you to think differently about things. I don't think the two things are necessarily in um in conflict with one another, but but I agree it is a very delicate kind of road to uh to match.

SPEAKER_00 20:04

I know you had to expect this was coming at some point with an with a question on AI. I'm curious if if you think about innovation and how you're encouraging champions of AI experimentation, how are you balancing the need for these deep specialized AI engineered talent versus cultivating just more general awareness and getting people to adopt the different um tools and resources that you're deploying?

SPEAKER_01 20:27

We have been in the in the machine learning and AI space for for a very long time. So it's not new new to us in a way. I mean, of course, Gen AI, the way we're seeing it today, is new to to everyone or almost everyone. But at least it's something we had some uh familiarity with over over over time. But we are not a hyperscaler, we're not a you know, a large language model producer. So I'd argue on the one hand, we you know, we do have and we need highly specialized individuals for for those areas, but we're not gonna need them, you know, in the thousands or or tens of thousands of some other organizations might need. So I'd argue in that space, we are consistent in the work we're doing. We're investing, we're growing, uh, we're we're we're doing what we've done for years. More broadly across the organization is where the novelty is for us. And we are investing in almost like a classic marketing campaign with awareness, and then you know, get people engaged and interested in it, and then start providing the basics and then offer different tracks for going deeper or or less deep on that. And we've been doing that across the organization with a very high level of engagement. Uh, a lot of it is around our leaders being obsessed with the topic in town halls, in general communications, in meetings. We start some meetings by people just going around as you do uh normal. Normal uh check-in you do with certain sour people do with different things. And sometimes we do that, but sometimes it's like, okay, one thing you've been playing with or learning or done differently through generative AI in the last week. So we we try to play with it from lots of different perspectives. And I think where we've got to is uh a high level of uh engagement, awareness and engagement. Uh it helps that because we have a culture of experimentation, you do have a lot of people doing a lot of experiments. And I put that in two levels. We have hundreds of experiments happening on a product level. Uh, so that's more attached to our culture of building kind of new functionalities and products for customers. Uh, but now we have a number of people in uh other areas and other functions, including HR, finance, uh legal, et cetera, playing with uh ways to use a generative AI to improve uh productivity, uh to improve their learning, et cetera. So it's hard to measure the results of that from a productivity and impact standpoint. But if you measure it from an engagement standpoint and just number of experiments and things that are going, we're pretty pleased with that. So luckily, yeah, it hasn't meant we had to sacrifice one for the other. We still have, I'd say, a pretty stable kind of growth trajectory on the specialized AI people. But uh, but yeah, we have now, you know, thousands of people uh playing with with the new new toys.

SPEAKER_00 23:35

I love that idea of I mean, because you know, we talk about this in the dinners. It's yes, we want to make sure that people get a chance to know each other, but then the other part of those dinners are around specifically exchanging best practices or conversely putting out things that you're struggling with and leveraging the people around the room. And it feels like you're building in both of those, which are great because as I think about that, that's a practice I want to take and figure out what are my own colleagues doing around. What are the one thing that they learned this week that they're leveraging that I can pull in and make my own? I want to bring you back to culture because you've spoken on the topic a lot. And I know you've all got a strong stance on culture. I think uh if I've got it right, it's high execution, low ego. And if I think about that, how that must exist in terms of the service of strategy. How do you continuously measure and reinforce um that in a that complex culture that you spoke about and a global organization to really ensure you're hitting the strategic objectives?

SPEAKER_01 24:30

The high execution, low ego, I'd say, is a feature of booking that has been here way, way before me, right? And that's great. It's a it's a great starting ground for us because it means that people are really focused on getting things done and they don't spend a lot of energy on politics and uh territory grabbing and whatever. Look, I'm not saying it's unexistent. Anytime you have you know two or three or more people working together, you're gonna have a level of uh politics or complexity. But compared to other organizations I've been in or I've seen, it's it's it's it's got that advantage, right? That most of the energy of the business is focused on just creating value for customers and creating value for our stakeholders and our shareholders in general. The work we we started more deeply in culture was around looking at the ambitions of the organization and looking at our strategy and how the strategy evolved and asking yourselves do we have the culture that we need to support that? And in those dialogues, in those conversations, realizing that there were, as any organization, certain things that were aligned and certain things that were getting in the way. And then we started the process of touching on levers in a more uh deliberate way to see if we could move us closer to that. And we build a few ways to measure how we're doing that. Some of it is embedded in our so-called engagement surveys, and we we measure a few elements of culture and ask people, hey, you know, do we have the culture we need to help the business succeed? Or there are elements of culture, such as being uh, you know, in a in a learning mindset or being more of a protagonist and a victim, or teamwork and being one team versus a collection of teams. There are a number of characteristics that we then try to measure as well and ask people how how do we feel? So we look at the sentiment of that. And then we are in the process of tying that to uh other business metrics that will link to you know to productivity or to business results. So I'd say it's an imperfect process, but it's it's it's almost a bit like that quote that the plan is not important, planning is important, planning is everything, plan is not what matters. And I'd I'd borrow from that, or the sentiment from that, in that the process of uh engaging the organization, how do you track and measure progress sometimes is more important than the absolute precision of those metrics that you're gonna use. Because, quite frankly, in our in our space, there's many of these areas are very difficult to measure precisely in the short term. You can measure it over longer periods of time or in hindsight, but while you're doing it is harder. But if you push the organization to constantly be in the lookout for how we're gonna measure it, how will we know, et cetera, then you find many ways in which you can imperfectly uh look at how you're evolving. But for us, you know, engagement surveys, uh goals and uh and you know, kind of business results in some areas, that's how we we keep it tied to uh to our strategy.

SPEAKER_00 27:33

And I thought the quote you were searching for there for a second was uh Drucker and Culture Eat Strategy for Breakfast. So I'm glad I didn't jump in and try to help you there.

SPEAKER_01 27:41

That quote, I must say, I'm not a big fan of that quote. Uh I I like it because again, the I don't get me wrong. I mean, it's my meat and potatoes, you know, cult culture for all of us in this space. But if your strategy is not sound, no matter how good your culture is, it's it's not going to work out, right? So you need strategy, and then you need culture to support. So you need both. It's not one versus the other. That might two cents on that one, which which I I hear a lot of quotations of that.

SPEAKER_00 28:09

Yeah, that certainly does get used often. Five years from now, what's the one major trend, particularly given in travel technology, that you think will fundamentally redefine the tra the role of the CHRO?

SPEAKER_01 28:21

I I would not tie it to tech and travel in particular. I mean, I will tie it to tech in general, but but also just more broadly. I think that the chief AGR as a chief simplifier, I think we'll hear more in that direction. You know, the level of complexity that we have around us in organizations, right? If you look at how organizations are becoming more complex, the level of interdependency of things, it's massive. Then you have government regulations coming from every direction, and you have a bit of a breakup from blocks, and not say a full breakup of the EU, but you have a um a movement towards more independence rather than more togetherness in many ways, which will probably generate even more complexity in the business environment. You have more volatility in the markets, uh, it's things are more unpredictable, more shifts. So if you pull that all together, you have a massive drive towards more complexity. And I think because of the place we work from in organizations, it gives us a very broad view and perspective of everything that's going on in the organization. And you have almost an alibi or an excuse to get engaged in many different things. I think we are uniquely positioned to play more of a role in that space of simplifying and focusing the organization on what matters the most. We do it also by the way we engage with the executives in an organization and we challenge them and we seek clarity because we need clarity for our agenda. We sometimes, through our need, we force clarity into the organization. So I think there's something along those lines that I I expect and I hope we'll see more and more of in the next five years for the Chief HR.

SPEAKER_00 30:15

Now I'm gonna hit you with a couple quick hard questions. Given we're uh we we're talking to someone who leads a travel organization, ski trip or beach vacation?

SPEAKER_01 30:23

Ski trip because of uh recency bias.

SPEAKER_00 30:27

Okay.

SPEAKER_01 30:28

But I I ski trip it's just the mix of exercise, focus, and uh nature, it's such a uh amazing combination.

SPEAKER_00 30:39

Netflix and chill or out to the theater?

SPEAKER_01 30:42

Netflix these days, yeah.

SPEAKER_00 30:44

Red wine or a Heineken?

SPEAKER_01 30:48

Red wine. Okay.

SPEAKER_00 30:49

Where's the the the best place you went to most recently? Or or best place that you're look you're excited to go to?

SPEAKER_01 30:55

Yeah, look, very recently, most recently, I was in Andorra uh skiing, and it was a great uh it was a great experience. It's uh easy to get to nearby. We got good snow, uh, service is good. Everything was easy about it, and that's what you want in travel, right? That's what we talk about at booking, is how to you know make travel easier, which is damn hard, right? All the things that can go wrong on a trip, we we all know that. Looking forward to um uh going back to Japan, been there before uh with my kids, they loved it. Uh, and we're heading back there at some point soon. So that's that I'm excited about in the near future.

SPEAKER_00 31:30

Awesome. Well, hey, thank you so much for today. And I look forward to the next time we catch up in person, and hopefully it's before you go to that Japan trip. But if not, I look forward to hearing how that that trip went.

SPEAKER_01 31:40

Thanks, Fran. I appreciate it. And I hope to uh see you in person very soon.