Unfiltered: #ChooseToChallenge with Tina Weyand

Welcome, everybody. I'm really excited today to be here with Tina Weyand, and she is the Senior Vice President of Multiple Product Engagement. I think you have said you are an SVP and GM, which doesn't really encompass all the things that you do, and I just want to walk through your bio just for a second so people have an idea of the scope of what you do and your influence at Expedia, because you have been enormously impactful to me when I worked there, but you continue to be that every day. So I wanted to walk through that first. And then we're going to go through a series of questions about your insight and your experience and what that's meant for you throughout your career. All right. As Senior Vice President of Multi Product Engagement, Tina leads both product and technology teams for a travel portfolio that includes six global brands, including Expedia, Orbitz, and Travelocity. Tina is currently focused on designing, developing, and delivering engaging multi-product trip experiences that travelers love. She also sits on the Expedia Group Inclusion and Diversity Advisory Council, and is the Executive Sponsor for EG Well, a global initiative to empower and support women towards leadership roles at Expedia Group. Prior to her current role, Tina has held a variety of product leadership positions, including Chief Product Officer at Vrbo. Before her time with Expedia Group, Tina graduated from UCLA, go Bruins, and has since held a variety of leadership roles at Yahoo, Ask.com, Demand Media, IAC Publishing Labs, and more. She's an avid runner, adventure seeker, and an art lover. When not at work, her favorite places are on mountaintops in Tokyo and Iceland. So welcome, Tina. I am super excited to have you here. Let's get started first with telling the audience a little bit about how you've made the transition. You've worked in startups and you've worked in large corporate environments. What are the skills or the qualities that you think you have that allowed you to make that transition back and forth? Thanks, Tracy, and thanks for having me. I'm so excited to be here. You know, I gave this some thought, and actually the skills are roughly the same. And I feel like every day I'm calling upon myself to remember those skills, and they're really basic. It's grit. It's having a point of view, having the tenacity to stick with it. It's taking initiative, and initiative is hugely important, and important in many different ways, both in terms of pushing yourself to learn and take risks, but also in moving teams forward. And then I would say something that has always been a part of me growing up is puzzles. It's critical thinking. You know, it's not just curiosity, but it's actually a little bit deeper than that, just constantly trying to peel back why things work the way they do, which is probably why I ended up in product. So yeah, I think those have stuck with me all the way through. Yeah, I could see how that would come out in all of the different types of roles that you've had. So just kind of a follow-up question, you know, I don't want to assume that you've encountered barriers due to gender or any other kind of innate characteristic, but if you did, what form did that take, and how did you handle it? Yeah. Interestingly, early in my career, it took the form of both being young and female, and therefore dismissed. And how I overcame that, you know, part of it is trying to really stay grounded in what we were going after is in terms of building a product and building the business, and just ignoring, kind of trying to ignore those signals, and just getting to the work. Finally, though, when I needed to, just speaking up, and I think as I got older, the speaking up part starts happening earlier. I'd say in my early in my career, I let it go to a point at which it was, it had reached like a climax of, like, I'm willing to walk out the door like right now, like it's too stressful, I'm banging my head against the wall, and, you know, maybe I'm in an unhealthy place, and I, you know, can't kind of can't win. And there's got to be something, you know, better out there. I think as you get older and wiser, you realize there are other things out there. And you don't need to reach that critical piece. And you also realize that when you do speak up for things that are important, both whether it's like, you know, what is at the core of the customer pain point, what is going to drive business results. Typically, you've put a lot of thought into it, and you're often right, and others will appear out of the ether and support, you know, support you. So sometimes I think that, you know, we encounter those barriers, and we let it, we let ourselves think that there must be something wrong. Yeah, you know, it's interesting that you said that, because in the mentoring that I've been doing, most of the young women are coming about precisely that. I feel like this is happening, or this person is discounting me, or this is happening, and I don't think, I think I deserve this raise, or whatever it is, and they are afraid to speak up, and how do I navigate that, and how do I handle that. And it is usually at that critical juncture where they're ready to quit. How do you think, what made you shift to where you felt confident enough to know you had choices, and could walk, and that you had some leverage in that conversation? Um, I think, you know, reaching that, that point, and just what it cost me to get there, and then what was really a wake up point for me was when the team that I was working with also kind of came forward and just said, you know, how critical they felt the situation was, and I, and I felt that sense of responsibility really that I carried with me going forward of, it's important to speak up. It's like, again, whether it's things that are happening that shouldn't, don't meet your, meet the values of the company of spouses, or, or you just believe that, and a certain approach to build a product, or drive business results, you know, are critical. You just have to have that confidence, and I think that when you take that step, just learn from it, don't forget it, and you will find that as you reflect on it, it gets easier the next time, and the next time. That's so true. Yeah. Is there anything you had to do differently, you think, than your male counterparts in your career? Yeah, so interestingly, this came up both just in terms of experience, but also some advice that I've been given, and it came in kind of two forms, and I think it's, I think it's, I think it's partially gender related, and I think it's partially, we all have, you know, ways that we are, and that, that can sometimes create misunderstandings. So what I was told early on, I'm a fairly serious minded, pragmatic person, and I, and I'm a thinker, so I'm not someone, I can't do what you do, Tracy, which is your external boss for the moment, yeah, I'm like, I got to think about it sometimes, but because I do that, I give the impression that I have an agenda. And so, you know, and so people may not always trust, like, where I'm coming from. And so I've actually tried to name it. I've, I've tried to say, hey, I need to think about that. And whereas I saw it as a sign of weakness, and frankly, the perception was that it was weakness, and that's where I had to overcome getting more comfortable being, you know, like, fly by the seat of my pants, or it felt like to me, I was flying by the seat of my pants. You know, that introspection is really valuable, especially to someone like me, for example, who is kind of externally processing and just kind of saying what comes to mind. Yeah. That's the balance that I think is sometimes missing in a group when you don't have a leader who's saying, have you thought through all of these different things. And I mean, I was lucky in that someone, a few people actually just pulled me aside and just gave almost SBI type feedback like this was harder for you than it probably needed to be because, you know, this was the perception of the people around you and it's like, oh, okay. Yeah, we all have to work on these things. Yeah, because, um, yeah, that's really interesting to me because I feel like that balance is very much needed between like the off the cuff and really kind of the deliberation that goes into planning for a larger initiative or larger programmatic kind of offering which is, which is the kind of work that you do so balancing all those personalities could be, could be quite a, quite a challenge. So, can you share with me some of the principles that guide your career. Yeah, and I think, um, I think they sort of change just depending on what you're kind of what's going on in your life at the time. I, you know, I think the life is too short to work in an environment that's toxic. I agree. And it seems easy to say but I think if you accidentally find yourself in that environment and I, and I have found myself in that environment before, and so my. So it's not as if I had a principle going out the gate it's more of like I, it's a learned principle that I have not forgotten and it guides decisions about how I want to spend my time and where you know where I want to work. And it's just so it's so critical. You know, they say sometimes you can learn a lot from, you know, poor leaders or like you learn what mistakes you know not to make but I think that only takes you so far. I think the more quickly you can recognize it and and and have that commitment to yourself that you're not going to put up with a toxic situation. No, I love that. Um, because I think we all have been in those situations and tried to figure out how do I avoid it ever again. Yeah. And I was gonna add one more thing is to ask for help. And I still have to tell myself that, even though it's like, maybe that's why it's kind of a principle. And I think when you find yourselves in difficult situations, you know, getting outside perspectives and asking for help gets you through it a lot faster. I agree. I, it's hard to ask for help, especially if you feel like you're still ramping you're still learning you're, you're kind of almost automatically thinking, what are they going to what is everyone going to think if I fess up and say I have no idea what you're talking about. I know this already. Yeah. Um, so kind of in that vein, what do you do or how do you foster kind of equity and gender in your career because I also think sometimes what can create that toxic atmosphere is the lack thereof. So, as a leader, how do you foster that. Um, yeah, equity and equality. So, um, the way that I'm able to do it now, and partially because the position I have is especially around equity so for example, we, we want to make sure that we're bringing in all different diverse backgrounds for in terms of hiring and opportunity and recruitment and frankly promotion and all of those cool projects, things like that. The equity part really comes into play if you think about recruitment. Yeah. Others areas too but recruitment is a really clear cut example where you need to, you need to be more patient. And you need to be willing to have that recruitment process take longer, maybe even three times longer because it's harder and harder to find candidates, um, you, you need to I think actually take more time in terms of making sure that you have a interview panel that is diverse, which means you have schedulers to come through, you know, to juggle, but it's my commitment as a leader of, like, holding my team accountable to doing that and doing it myself I just went through this, as well as then also just signing up for goals and cascading those down. And the last thing I would say is participation. So participating and things like what you know what you guys are doing participating showing up at events and giving time like all of this and amazing signals and set an example. I could not agree more. One of my favorite memories, actually when I worked with you in the past was when we went to Houston Tillotson, and attended that award ceremony. And I thought that was a great example of meeting people where they are, making sure that you feel that they know that you want to be a part of their community as much as you want them to be a part of yours and I think that was really critical and making me feel like, you know what, they do believe in diversity, it is important to them because it's not always easy being the only one or the only one of few in the room, and being willing to go into a community and be that shows that you know what the other person is kind of experiencing so I thought that was really an important and kind of impactful thing to do. And so yeah showing up is a big deal for me and I'm sure a lot of other people it makes such a difference. So, you know, how have you just pivoting for a second, how have you managed or taken risk during your career. Yeah, um, I think it's seizing those opportunities where you don't feel like you're ready. Like I know it sounds, but like the my current role. There is so much that I'm learning, and I'm managing engineering teams and product teams and getting deep in architecture and tech staffs in an area that I'm less familiar with, which is the front end experiences area. And I made the decision and it was a scary one because I was actually in a fairly comfortable space of what I was managing before, but I really felt it was important to take the step to learn and grow and just see, you know, see what I could do. So, um, so I think that that's probably to me like really risky I think other risks are the example I mentioned earlier is when you see something that's not right. And you stand up, and you say something, and you, and you, you do it in order to affect change. Yeah, no, I, I could scare I could totally see that. And have you had to make any trade offs in your career. I, I have and they're they take a few sort of related dimensions one is time. And, you know, in particular, I reached a point at which I was, I was doing nothing but working, like, literally, literally nothing I don't know what movies are happening. And it cost me, you know, some relation close relationships that could have been closer, and even some that are, you know, irretrievable. And then I would say the other dimension but related was not taking care of myself so not taking on just letting my, my health actually come to a point that it was, you know, I needed, I actually needed to stop. And that is, those are trade offs that are way too costly too much and so now those are those your non negotiables now. Absolutely. Yeah, yeah, sleep, sleep, and it's not because it's a fad now, but no sleep and an exercise, because I find that exercise gives you it gets rid of some of that self doubt and it makes you feel like physically stronger and I think no matter what the shape of exercise takes just getting out and do it you never regret it afterwards, like you always feel good afterwards, even if you have to get up in the dark, pure honesty that it was the thing that suffered the most during the pandemic when I thought, Oh, I'll have plenty of time now, it was the thing that suffered the most. Yeah, I'm now remembering we've had these conversations before. One of the things that we give up. Yeah, but the exercises pure stressfully for me brings so much clarity for me and I solve problems. And during that, yeah. And so, you know, you actually answered my next question about what might be the non negotiables you have, but what does it look like to foster inclusivity at Expedia slightly different from what I asked before, but, um, how do you, how do you foster inclusivity and, and, and encourage people to feel like they belong. Yeah, it's, it's so important. And, um, you know, I've been somewhat intentional about it in the sense that it actually is what will make our products more successful. And there's lots, there's lots of data that shows that companies are more successful, whether you measure it through stock price or whatever. Um, but it's also super important in technology in general, which is, um, you, you have to have diversity of ideas and ways of doing things like there isn't always one solution for, for every problem like whether it's an architecture decision or system design or a product design, like there's so many different ways of doing it. And the more ideas you have coming in and those ideas differ when there's different, when there's diverse backgrounds and people and experiences that are, that are throwing those ideas out there. And so in order to get those ideas and get people to be comfortable sharing, like you can try and you can get everyone at the table, but they may not speak because you haven't created that environment. And so, um, one of the most important aspects of cultivating inclusivity is having an environment of trust and, and basically rewarding creativity. Yeah. Yeah. And so, so I do try to make sure that the culture does, is not one of like, um, high, uh, it's learning from mistakes, but it's not punishing mistakes. It's not, it's, it's, it's creating, um, a safe environment to put your ideas out there and to get feedback. Um, and that's not easy, but it's so critical just, you know, to, to have, uh, I think a high functioning team loving to come to work and, and I think getting people to do better work actually. Yeah. You know, that's interesting because now that I think about it, that I, the places where I flourish the most, you have that kind of professional safety, um, for your ideas and for your contributions, or even for your critical feedback, like you could disagree and commit or just, you know, there was a lot of room for that. So, you know, um, yeah, I could, I could, I could absolutely see that. Yeah. And I think you'd have to have both sides of the coin, right. You'd have to have the people there and then you have to have like the environment. Yeah, for sure. And it has, the trust has to be both ways. Yeah. So, you know, what has been the most powerful leadership moment you've experienced? Um, I think that one of them was, there was a, there's probably been a couple, but one of them was, um, I was part of a core team and we were working night and day to get, unfortunately, literally like night and day to get something out. And basically we got to a point at which we either needed to move forward and hit a deadline, or we needed to do something different that we thought would be more impactful and delay it. And so critical point was, was basically me making the decision to delay, which meant upsetting a lot of people in some ways, upsetting the team, but at the end of the day, it was the right thing to do because we ended up with a much more impactful and successful outcome and everyone felt better afterwards. But going, making that decision and then going through it was some, was, was one of the more impactful leadership kind of moments where I could have almost taken the easier route. Um, but I felt I took the route that I thought was the most important for the, for the company. So just a follow up to that, then, do you felt like you had the safety to do that in the role? Um, you know, I think that was part of the, the impactful leadership point was I wasn't, I wasn't entirely sure. Although I knew that my, my manager had my back, I wasn't sure what was going to happen around that. And I was kind of worried about the team too. Yeah. And that's where the leadership part comes in. Like, are they, are they going to become so disenfranchised and frustrated? Like, are you going to lose momentum? Um, so it's like, I felt like it was a calculated risk, but like when I think of impactful leadership, that was one signal to me, which was, um, I did have, like, I did have the team on board and we carried through. That's awesome. Um, that's awesome. Cause I think that would also go to building your confidence later about making hard decisions like that. And, you know, um, there's a lot of conversation about imposter syndrome. And sometimes I think it's imposter syndrome and sometimes I think it's a little bit of microaggressions and, and we absorb it as imposter syndrome. But, um, that would go a long way to helping you feel more confident if you even suffered from that, um, in your decisions and taking risk and, um, standing by the hard decision that you made. Yeah. I love that. That's awesome. So, you know, if you, um, I'm trying to think like based on, you know, where you are in your career now. Um, what would you have told your younger self in retrospect, um, in terms of advice, what would you tell yourself? This is, you're not going to probably expect my answer. Um, I, I would have, I wanted to be a, an air force pilot. I didn't want to go shoot. But I wanted to like, I wanted to fly planes and, um, there was something about it that was super attractive to me. I think it was the precision of it and the technique. I don't know why I saw a movie. I don't remember, but I was like really intent on, and I loved, um, science fiction. Um, and I was told very early that I, I wasn't, uh, I couldn't be good enough at math. It was a bit of a girl thing. Yeah. Yeah. And I, I let it, I actually let it influence me in the sense that I never stopped science. I'm like, but I, but I, I felt like, yeah, I can't do that. Like that, that dream is not going to like happen. Like it's just, it's not attainable. And I think I would have to that. Yeah. Yeah. I would have told my younger self not to think like, not to think that way. Um, don't, I was just a little too like, oh, and 40 tells me that that's not true. And because you know, it's, it's funny that you said that about math. I was literally president of my high school engineering club. And, um, my first year of college, someone told me one of the professors told me I wasn't good enough at math and I quit that major like pivoted completely went to like history and economics. Right. So it's crazy how influential those voices are. When you're young, and, and the impact it has throughout your career. Um, but you know it's the pilot thing did surprise me, because I've always thought of you as kind of an artistic creative person. And I'm not sure where I got that from but that's how I viewed you as someone who's very artistic and very creative, and it. I didn't put the two and two together but are you artistic and creative. I, um, I am very much inspired by and appreciate art and creativity I mean that's what I see in the places that I go, like constantly go to art galleries. I like to buy. But I am not I mean, I think if I put more time into it, I would, and I probably would do this like, you know, 20 years from now, dabble in something I like sculpture, in particular so like form and function. Yeah, so we do spend a ton of time when we're able to travel like Berlin, or Tokyo, or even, you know, I lived in Austin I went to Dallas and there's amazing art galleries there. Yes, that's just, I, I find sort of peace and inspiration from it so yeah so I do have that, and I am doing some gardening and I do sculpture gardening. That's cool. Yeah, yeah, but no I don't have the gift. While you have a full because literally that's, I think of you as a very artistic person and maybe that comes out in the product too because you're creating things from scratch with your teams. But, um, so going back a little bit we talked about your most powerful kind of leadership moment. Is there another moment in your career that you thought was really pivotal for you as well. Um, I'm going to share. I'm going to share like a little story that I have carried with me, and it's something happened more recently and it goes back to this whole topic in some ways, which is, it goes back to, you know, fostering, you know inclusivity and in culture and your workplace, and, and I said like, you know, participating and showing up. And I can't emphasize enough how important it is especially for people in leadership to show up. And so, a little moment that like had a cry over as I was at the pride parade for Virgo in Austin, and I've been going like three years. And I've gone in lots of different cities but in in Virgo and Austin, there hadn't been an executive that had attended before. And I had two interns that show like that were there. So the pride parading is in August. And they came up to me and they these two women, and they just said, Oh my god. We can't believe you're here. This means so much to us we've been hiding. And now we see just our experience in our internship and the fact that like you, you know you support it and you're here and you're celebrating with us like we're not going to go back to hiding again and like I kind of got to it, it just reminds me like it's such a little thing. Um, but it matters. It matters so much, and it matters. And so to me what I just keep think when something's hard, or, you know, I just think of like that, you know, it matters and so you know showing up is, I think that's a pivotal, pivotal, it really is. Actually, I think that's probably a good note to end this on because I think that's, that sounds like the way you've chosen to challenge yourself every day. By showing up and being present and impactful to folks. That's also how I remember you, and because you showed up and everything it seems like so I can tell you take that to heart. But thank you very much for coming. I really appreciate you being here and it was awesome to see you. It was my privilege. Thank you for having me.