PM Pivots: Thriving in Startups, Global Companies, and the Unlikely Places In Between

Speaker A: Welcome back to Practical Product Management. This podcast is all about how theory is nice in product management, but uh, product management happens in context and it has to be practical. So today Marilyn and I are really excited to talk to Jay, um, who has 25 years of experience in product leadership, has worked at some really well known companies like Microsoft and Expedia and Exxon, and now is Chief Product Advisor. Best title. So Jay, tell us about yourself and uh, you know what, what do you want to talk about?

Speaker B: All right, well, thanks for having me, ladies. Um, yeah, just uh, a little bit of my journey. I, out of college, I was in, uh, I was at college and was part of a startup there, kind of backed my way into it. Really smart sophomore, had a great idea. Um, and my whole goal, my whole goal in college, dating myself was I really wanted to work at Microsoft. Microsoft was the dream company at the time, um, and I really wanted to be there. I tried interviewing, got, you know, few rounds deep, didn't, didn't get to the end and was, uh, had already, you know, signed an offer for another company. And I just kind of had this opportunity to work in this startup in the college town, uh, just for the summer before I was going to move on to another company. And that, that was an amazing experience. And one thing led to the other. Uh, my offer kind of fell through a little bit at the company I was going to go to, but I was ready to tell them that I was going to back out anyway. And that company ended up getting acquired by Microsoft. We had the right product at the right time, uh, during the Internet bubble phase. And one, uh, thing led to another and you know, they, they bought us and they, they wanted to make us part of the Hotmail group that they had bought the year before. And uh, so they moved us to the Silicon Valley office and I was like dying to get to the headquarters. But you know, I was fine. I was at Microsoft. It was a great thing. Um, so I did that. I ended up, you know, I was, I was into entrepreneurship in college. I knew I want to do something small business related. Um, but I also had this love for this huge company I hadn't worked at because it seemed like this very, you know, very small, fun thing. And uh, one thing led to another and I was at Microsoft for 15 years after getting acquired and everyone would laugh at me, including the CEO of the company that he sold to Microsoft. And he said, what are you doing? And I just said, I found a way to be an intrapreneur at this company. They keep tapping Me for day zero type projects. Um, every team I've been on has had a family feel to it. And at the time I was just like, man, I keep lucking out and keep picking these teams. And then I realized, no, I think I'm a part of, of that, like a small part. But I think I'm attracted to the same folks who like to make it feel like a family and make it, you know, make it more than work. Uh, so I did two stints at Microsoft. Halfway through I did a. I left and moved to the East Coast. I was based in Seattle. Um, went for personal reasons and decided I joined another startup. That one didn't do well during the 2008 recession. We had a good idea but ran out of money. And then I went back to what I knew was I did another seven years at Microsoft to total 15. Um, and then I didn't think I was ever going to leave. My friends didn't think I was ever going to leave. They're like, get out there, like, you know, use your skills elsewhere. And uh, I, you know, I, for the. I went to Expedia next as a VP of Product Management and Design. But that was another, like, backed my way into it. I was hanging out with a friend and she was telling me about roles she was looking into. And she kept talking about like, she had Expedia, Facebook, all these roles. And she said, she kept talking about this Expedia role. It was inside of the customer service world, inside of Expedia. Um, she had, they had a very large product and dev organization, which was not my experience at other companies like Microsoft. Like, they didn't really fund the support group at Microsoft with actual product and engineering talent. And she kept talking about it, but she kept talking about it as like, this is this very mundane job. Like, I like the person, I like the people, I like the leader. But I just, the content's not super interesting. And I just, I kept saying over drinks, I'm like, I think that's the one you should take. I think that one's got the most, the most growth and the most transformation opportunity. Um, and, uh, yeah, one thing led to another. I did five years there. Uh, and then I ended up moving on to a company called Axon that makes software and hardware like body cameras and tasers and evidence management software for law enforcement. I did that for two years and then now I'm doing my own thing. I'm trying to work with as many companies as possible.

Speaker A: So I think we all were at Expedia at the Same time then?

Speaker B: Yes.

Speaker A: Is that true?

Speaker B: Okay, yes.

Speaker A: I mean I sat back to back with Marilyn, so I know she was there.

Speaker C: You knew exactly where I sat.

Speaker A: Exactly where you were all the time.

Speaker C: Except for when I was putting glitter on your desk and then you didn't know where I was.

Speaker A: That's true. Um, good point, Jay.

Speaker C: You've had such a cool career, um, from actual building products, um, through to building teams and then leading large divisions and now you're, you're, you know, you're advising CEOs and founders and startups on what it means to sort of bring in and build a product practice and taking on a lot of those responsibilities for them or helping them with those responsibilities. Um, what, what do you think that people misunderstand the most about bringing product into ah, a company or a space where product hasn't been or hasn't been very strong?

Speaker B: That's a great question. I think the two things are one product that are not product folks are not just an under product. I lump design, product management, all creatives. You know, I think of it as lowercase product, lowercase P. Um, the misconception for folks that aren't, don't have product backgrounds that are hiring you is that you're the Rosetta stone that knows how to talk to developers. Like your job in life is to be put in the same area of the building as developers and you know how to talk to them, you know how to make things happen. Um, but that you are a counterpart to engineering only and that there are certain class of problems and opportunities and strategy that clearly map to you. But that, that's your lane. Uh, and that you know where I, where I've seen the best work happen is when one, you think of product more as an ethos. And I know this is a very practical podcast, but like product as a philosophy in that it's you know, it one no one the, the product leader doesn't own product for the organization. They just help steer it. They help bring the collaboration together. They bring the processes and just the just the thought process to product. But there are so many different types of problems that a product organization can help with that uh, first blush, don't feel like a product problem to the untrained eye or the person who hasn't been in there. So I was in an organization, Expedia, which was about managing customer service agents around the world 20,000 plus when I was there and there were many problems when I was and I sat on the slt, um with the, the guy who you know, managed Those agents around the world and procuring them and training them and working with outsourced companies and. And I was. I was kind of expected to be quiet during those conversations during the slt. Um, and these were all people that would love to take me out for a beer. We all got along really well. But when it came to, you walk into that SLT and you put on your hat, like, they thought I only owned a product hat. And they thought that was only like, okay, when we come to you to see how are we doing with the website or the new app. That was my role and the reason my SVP brought me in. And he said, I don't. I don't. I was looking for someone with. I didn't want someone who was a classic telephony call center person. I got tons of those resumes. I needed someone who thought differently, started with the customer first, and didn't have a particular solution in mind. And I love watching you in those meetings because you're hearing stuff for the first time that we've been talking about for years, and you're like, have you tried this? Have we thought about this? And doing it in a way where you're not disrespectful, like, know it all, like, oh, duh, like, why don't you do this? And your. Your colleagues aren't realizing that, you know, you bring more to the table. And it's not just you. The product discipline brings more to the table.

Speaker A: You.

Speaker B: We could pull a couple people in your organization right now, move them over to that area, and they would bring a fresh perspective and solutions. It's like, why you go to a company like IDO to help you design things. Like, they're not just, you know, in a particular lane. They'll help you redesign the. How you walk through the grocery store, and then they'll also redesign the gadgets that are on the shelves. Like, they're. The breadth of what they can do. And I think that's the biggest misconception is that product is something that you. You have to put in one lane, and it's not somewhere. We, uh, as product folks, we love to swim upstream, and we want to hear it all raw. Just give me all the problems. And maybe the only thing I build for you is the most simple web page from 20 years ago, because that's all you need. I don't need to bring you AI necessarily, but I need to hear the problem.

Speaker C: Yeah.

Speaker B: And you know, that, that's. That, I think, has been the. The biggest. And that was the biggest growth Opportunity at Expedia, both for me, growth and then helping that organization. They were the, probably one of the last organizations at Expedia that wasn't product first mentality. And so it's, you know, it was one of the hardest. But my favorite part, um, of my career was, was that opportunity.

Speaker C: Yeah, I love that I'm smiling at Leah, uh, because I feel like you've been, uh, we have also, uh, experienced places where product was not expected to have any strategic influence.

Speaker B: Yeah.

Speaker A: Yeah, for sure. Yeah. I think, I mean, uh, I think what you said really resonates with me because I think there are, there are so many times you bring in this person who has this ability to think in this way and see all of the different pieces and parts, and you say, like, go sit in that chair and only sit in that chair and don't move out of your chair.

Speaker C: Yep.

Speaker A: Right. Meanwhile, I'm like, what, what do you. What's the problem in finance? What's happening in the finance team? Right. Could I, Could I ask a question about hr? Right. You're just like, in there sort of picking at things, and when you start to say, like, what if we apply this mindset to that? You can get these sort of grumpy faces, but sometimes they're like, okay, what? Say more.

Speaker C: Right.

Speaker A: And, and I think that that's, like, for me, you know, I was at a startup where they were like, we're going to hire. On my, like on my first day, I had started a cpo and they said, um, we're going to hire a chief customer officer. And I was like, no, you're not. You're not going to hire a chief customer officer because that's my job. Don't hire that role until we know. Till you know what you have in me. And we can define what it is like if we decide later to hire one. Great. But let me, let me in here before we go hire some other person whose job doesn't make sense to me. Right.

Speaker B: And how do you, and how do you do that? Oh, I'm sorry.

Speaker A: No, uh, no, go ahead.

Speaker B: How do you do that without. Because I live this there at Expedia. Like, how do you do that without coming off as full of yourself as, you know, we used to say at, uh, Microsoft? Like a cookie licker, someone who goes and licks all cookies that say, like, this is my emp, this is my empire. When you're just like, no, like, just give, give us a crack at it and that. That might save you a hire. It's not that I want to a title that CPO/, CCO/ Like I'm just telling you, like, let's figure out what we need first. And, and, and the challenge with Expedia was I walked into a fully baked org that worked a certain way for 20 years. So those roles were already filled. And some of those were um, they weren't odd at the time. Like I don't if I was there as the, the leader back in the day when that organization was designed, there was needs. For what? For these, for how these folks were laid out. And they were all smart people. And I would, I used to say to my boss, I'm like, I think you should take all of our titles, put them back in a hat and then shake them up and redistribute them or change them. It's not like I don't think I can work with that person. It's just like this is an archaic way to think about things. And you like everyone. I went through the interview loop. It was great. That's why I was like, I love these people. I can't wait to work with them. The boss tells me the day he announced that I accepted the offer, he's like, everyone just applauded. They were all great. And then I got there and it was like within a month I was just like, maybe I should leave. I feel like a fish out of water. Like I, I have caused disruption just by showing up. People who think I have a great personality are like, I, we, we had this our first off site and we had to do a secret survey of each organization. Like how well does product work with finance? How well does product work with this org that was created to work with the Expedia.com brand? And I got voted like least likely to collaborate. And all of my numbers were like in the toilet. And I was just like, I don't know if you know Shawshank Redemption, but it's like my favorite movie of all time. And there's a great line in there where they're like, you know, what did you do? Why are you in here? And he's like, I had to come to Shawshank to be a criminal. Like I wasn't a criminal. That's why I felt at Expedia I was like, I had to come to Expedia to be a non collaborator. Like the things that were at the top of my reviews at Microsoft Collaboration great to work with doesn't bring his idea and say my way or the highway. I was getting the exact opposite feedback. And I just said, Dude, I'll go. It's easier if I leave and go back to Microsoft or somewhere else than to change the mindset here. He's just like, I'll lose half that SLT if I need to. You're not going anywhere.

Speaker A: So that's must have been so hard for you. That must have been so hard for you. That never happened to anyone else in that situation.

Speaker C: I like, I like both Lee and I are laughing because like uh, literally have had the same experience. Experience. And I think this is about people not understanding what they're hiring. I mean that, that product is the translation layer to engineering and that's all you do. Your, your sole purpose is to make the engineers build software. Like that's not product management. Um, and like, I mean I like I, I, I've had one terrible review in my life. One usually it's like, you know, know, knows the customer. Like you know, understands the problem, thinks about the big picture and to the same, to the same thing. Like you're a terrible collaborator. I, uh, like it's so surprising that in this day and age with this breadth of information, um, the companies don't understand what they're purchasing.

Speaker A: Right. Right. Well, I mean, I mean I would just say like even very similar. And I'm not trying to bag on Expedia, but even between Marilyn and I, they hired me as a director of strategy. She was hired into the product team at the same, in the same org. And within 60 days I was like, you don't need me because you have her.

Speaker B: Mhm.

Speaker A: Like you, she does strategy. She doesn't need me to build her a strategy. That would be, that's ridiculous. Right?

Speaker B: Same conversation in reverse. I just, I was like this, one of us needs, one of us isn't needed. You should repurpose us because.

Speaker A: Well that's why I was like, find me something else to do.

Speaker C: Right.

Speaker A: She doesn't, I can follow her around, but that's not really useful. Right. For her. But yeah, yeah, yeah.

Speaker B: And I just, I just chose to hug, I just chose to hug the strategy person, which is what you guys probably did. Which is like, let's just be thick as thieves because you know, and that person recognizes it as well and we're friends to this day because it was like, you know, like there is no, there aren't two strategies. Not a product strategy and a uh, organization strategy. And, and, and the, the org. And I, I don't, I now have seen enough, especially moving on to other companies that it wasn't like Expedia was The anomaly here. So it's not. I'm not bagging on Expedia either. And my number one takeaway of the whole thing was, what could I have done better? I should have gone in and done product 101.

Speaker C: Yeah.

Speaker B: I just came in assuming it looked like every environment I'd ever been in, where the product leader, like, at some places was almost like a prima donna, and that's not what I was wanted, but that it was at least understood that, like, hey, this person. This person, you know, gets to hear all the problems and gets to help, you know, form strategy. So I just assumed. Good. I assumed everyone knew. So then I started. I did things like I did a reorg early on about after 90 days. And I was just trying to get my house in order because I feel like my number one job as a product leader is to create the best house for creatives to work in where I would want to go and play. That's my job, and it's not about other people. And I announced my reorg, and I made two people in a sister organization cry and go into their leader's office. And these were amazing people because they felt I had defined one of the roles in my org as a replacement for her. Uh, but I just said this. This is an example. I didn't even know there was overlap with her. And I sent out my reorg mail for everyone to review it, and no one flagged, like, hey, so and so on, my org is gonna want to know why she's not in your org or why. Why this isn't a duplicate of hers. No one said it to me. And I caused two people to cry. I had. I caused arguments. And I was like. I literally was just cleaning up my house, which I thought was a mess. I didn't. It was nothing about you guys. Like, you know, later on we can talk about an overall reorg. But, you know, and it's just, uh, it was one thing after the other, and it was some of the most tiring, stressful work I've ever done in the first 90 days when I got this great book sent to me by the Expedia execs. Maybe you got it the first 90 days?

Speaker C: Yes.

Speaker B: Did they send you the book? I love that book. And it was like, make sure don't come in guns a blazing. Like, sit back and listen. Try to find a colleague that you can help with. You know, show your skills by helping them with one of their problems first before you start making. And I'm doing all that. I'm like, And I am just getting lambasted for. I leave a meeting, and. And, folks, I would. I would. You know, you have that spidey sense. Uh, you know, in a meeting where you're like, I lost that person around minute 49. Like, I could just tell they kind of would, like, rolled their eyes. So you stay back after the meeting, you're like, hey, Like, I don't. I don't think. I think I said something crazy about, you know, about 10 minutes left in the meeting while. What was it? And folks would be like, oh, no, you killed it. That was great. And then that same person would escalate an hour later to my manager and be like, he comes. When Jay comes to a meeting, it's his way or the highway. And I'm like, I can't win here. Like, I'm just gonna go. Like, this is. I see so many opportunities where I can help, but, like, you brought me in to disrupt, and I'm doing it, and it doesn't feel good to me, and I know it's not feeling good to my colleagues, so why don't I just go, would you.

Speaker A: You know, when you, uh, you said, like, okay, that's an opportunity for me to think about what I would do differently. That you would have done differently.

Speaker B: Yeah, I totally would have spent time under, like, what is. But doing in a way where it's like, let me understand your role deeply. Like, can I. Can I shadow. Like, so it doesn't feel like, let me come in and tell you what product is. Right? It was just. But do it in a reciprocal way where it's like, at the same time, can we just assume. None of us. We just all got here yesterday, and we have to explain each other's roles and departments to each other and, you know, put any misconception, preconceived notions aside, um, so I could have. Create a more fertile environment for my folks to play, because I got my folks so spun up on. Like, oh, my God, this guy talks differently. We haven't had someone who.

Speaker C: Who.

Speaker B: Who starts with the customer first and, you know, uh, all these things. And they got so spun up and so excited that they would run through brick walls for me, but for the. For the new mission, because they were. They felt like order takers. They. I just, you know, changed the culture within my group, but I didn't have as much respect for change management. That sounded like a very stuffy HR term to me. But, like, there's pieces of it. There's still some aspects of it that I think can Be overkill. But there's pieces of it as like I got to own this. I was an executive, new executive. This was a place where I learned how to be an exec. So I made a lot of mistakes myself but I really should have just said like does everyone like you know like forget, forget that you like that you hired me. Like do you know why you hired me? Like can I show you some of my previous work that we didn't get to in the interviews? Just so like you know I, and, and let's be honest, like if anything, if anything sets off. But I didn't even know what I didn't know. I didn't know that I was going to set off all these trip wires. Um, but yeah I paid for it. And then, and you know it took. Luckily I had a leader who was just like behind me pushing me and he was just like go, go go disrupt, disrupt, disrupt. Like I'll let you know if you ever go too far. And even across the company I was just like how many, no how many tough escalations can you handle from a president across the company? If I have to say no to something. Because my organization just like your uh, organization Expedia, we were a shared service to the company. We were a half a billion dollar cost uh center customer service. Because what folks might not know is with all the brands that Expedia bought over the years, all the consumer know direct to consumer brands like Travelocity, Hotels, Expedia etc plus um vacation rentals plus they had a little known uh which was their Most successful business, B2B uh, uh B2B offering where they would relicense the inventory for hotels and flights etc to third parties. So Chase had their rewards program based on top of uh Expedia. So we, we, we would what part of the services we offered as a company and our organization offered was we'll answer the travel customer service phones as Chase for you Chase. Because travel is a very complicated customer service scenario and we can do that for you because you, you know how to handle credit cards, you don't know how to handle travel. So we had to be a chameleon behind the scenes and be like you know we our tools needed to know oh this call is coming in for Chase. So the right, the right tool need to pop on the desktop. So it was a very complicated space. And uh, yeah I just, I feel like I could have done a way better job of you know just mapping out the world and then you know some things you're just going to walk into and you deal with on the fly. But I just like I'm not a drinker and I was, I was ready to drink. Like my first three months were so pain, so exciting when I talked to my team, so painful when I, when I went to the SLT meeting every week and all the emails afterwards and

Speaker C: all the escalations and how um, I think that's very. So I think there are what I will call um, I don't want to call it tech native. Um, but there are companies that, that grew up around technology and were founded after a certain, after a certain year. Um, and those seem to have a better feel for what like. And I'll tell you, it's like you can, you can tell kind of immediately if tech is on the P, on the L side of the P and L, like if it's it in the corner, you know, you're entering a company where like uh, it's going to be a hard slog to actually get to uh, um, a mental mindset that enables product management. But there are whole industries um, that are now wanting to move to these capabilities. Banking is one of them. Right? These are 200 year old companies that grew up with paper processes. Um, there are other industries that all of us have worked in that do not understand technology. They see it as a T. And again that language, that language is very telling. They're now hiring product teams that are experiencing exactly what you talked about, Jay. And there needs to be a broader conversation about um, what you're bringing in. Because I see this kind of time and time again where they'll hire in a leader or a set of leaders, um, it causes the disruption you just talked about. Um, because humans, humans are uh, you know, we're all reactive. And when it's like your livelihood, right? Like people are like, oh you're taking my job, AI is going to take my job. Um, which we all know is uh, it's probably not as real of a fear as you should about. You now have to advise these companies on how to sort of affect change management. I understand what you would be doing differently in that moment. But like as someone who may be trapped in a situation like that or as a leader who is experiencing that in the organization, what advice would you give either the leader or the person besides just like you're in a shitty job bail, um, do you need to transform organizations to be able to work uh, a little more optimally? Because you will lose product market fit if you do not. You will.

Speaker B: I think that's why there's a number One, there's a, there's a key opportunity for this consulting angle as well, is that. Plus I, I've been the type of technologist where I'm not in love with the technology that's under the hood. Um, I totally understand it. You know, I stay on top of it. But if all, if all an organization needs is for me to build a scooter, I just want to build a scooter. I don't want to always build a Ferrari. Like, I don't care about the engine under the hood. Like, I'm not running around trying to bring AI everywhere. You know, I will. When it's needed and when it can have a major impact, which it can. It's an amazing technology. Um, I do that. So I think there's an opportunity for me, like if my next 10 clients are all companies that are moving from a paper process to digital or, um, just need help getting over turning this corner that you're talking about. Like, I'm excited by that. That Expedia role is still the most fulfilling role I've ever had, despite some of the painful PTSD I have about the early days. Um, so my recommendation is the number one thing a product person can do when they get there. One, I think establish and try to educate on what product does in the most respectful way. But you can show it. So the things that were working well from the beginning was like, we're working well in terms of how do I turn the organization from being an order taker wherever their orders are coming from. And I use that lovingly. Like, some organizations need to be sales led from the beginning just to help get the first three customers. Like, we're doing these features because this customer needs it, uh, so we can land that deal. But you do. Everyone needs to turn that corner eventually where you're more strategy, roadmap, you know, driven. And really it's how do you come in and if there is an order taker mentality or if the processes are set up where the product and tech team are at the bottom of the totem pole and everything flows downward. And you can read into what I mean by everything like that. That was the number one problem to attack because I had morale issues. Like I talked to all the engineers and product managers and had some creative people and people had done some great things in their past and they were limited to being project managers on a set of things that were demanded from other folks in the organization. And, and all they, you know, they, they were leveraged for their execution skills that they knew how to turn requirements into, into something, but they didn't love what they did. And that's why I came in and said, you know, you, you don't need a product leader if you want to continue to run this way. Like, I'm, um, you're, I'm overpaid, you're paying me. And we, we should probably extract about five plus product managers from the organization, give the money back because you just need project managers. If you don't want someone to go and listen to the end user and come up with what needs to be done, um, in concert with the stakeholder that's requesting it, then let's get project managers that have a really great skill set of managing schedules and everything else and product managers. It's a skill we need to have, but it's not necessarily the number one thing we love to do. Like so really coming in and saying, I used to say to the group like, you guys are running a diner and you're all short order cooks and you're like, oh, you want to bacon an egg sandwich, you want a sausage and egg sandwich, you want pancakes? Like, you know, and it was just like this chaotic. Like, you know, just take the ticket as is and doing it. And like I was like, I'm touchy feely, but I think we want to be running a gourmet restaurant where just like, oh, do you have any allergies? Oh, you don't like mushrooms? Okay, you're going to love what I, what I've listened to everything you've said and you're going to love this meal that we've been working on in the back. And people thought I was crazy. Especially in my org. They're like this, this is decades of this, how we're looked at in the food chain, in the company. And there's no way you're going to make this change. Um, but breaking through there and showing enough people. My colleagues on the SLT were the last to embrace it because they were losing stuff. They went from having the ability to tell the product and tech team, I need this tool that does this with these drop downs to I turned off the intake. We had an intake form M you can go to, you go to a website, you could type in what you want, like an IT ticket and then it was expected to get done. And I'm like, we have hundreds of tickets that we've never gotten to. You're complaining. You've been waiting for something for five years and unfortunately I'm going to tell you if it's up to me we're never going to do the thing you asked because it's not on strategy. And you're ready to kill me because I'm saying no to something. I was just like, uh, but I got enough people that saw the benefit of like I said, I turn off the intake form. If you want something you have to talk to a product manager and then they have to present at an intake meeting to me. And I normally wasn't that process oriented for product planning, but I had to do it for that organization. And as soon as I raised the bar that okay, I have to be one of the approvers and then the SLT have to approve it, the, the requests coming in were, you know, were higher quality because they couldn't just slip it in because they had a favorite product manager who would, who would make it happen. Um, so the number one thing is try to, try to, there's always an order taker mentality in, in each of these organizations that are struggling with what is true product. And you, you, I think you go for that and you try to double click and pick at that and, and try to solve that in a way where hold hopefully the majority of folks, including the leaders see value. And then you can say you should see what I, uh, my organization and I can do with a bigger funnel of problems brought our way. But this is what we did. We turned around. You know, I got rid of the POS system. You can't, you can't send tickets to the kitchen and now look at some of the dishes that came out of the kitchen. Now we have more customer self service. They don't have to take, they don't have to call an agent. Like that's because we said no. And you know, and I would go to brand leaders in the company that they were the main generators of requests to GCO to, to the customer service org. And I just said product leader to product leader. Like look like they're like, we're so glad you're here. They've needed product leader for a while. And I'm like, I was like, I foresee saying no to you a lot in the next three to nine months. What's that going to do? And they're like we've been waiting for you guys to say no. Like I was like, well back at the organization they, they're scared of, you know, saying no to you guys. And you're like no. Just that's product management. Say no to stuff because you then tell us the stuff you're going to say yes to. And we know you'll blow us away by like, you can raise more boats if you let us do this. If we just keep doing this, you're just going to get like point solutions. So sorry, that was a ramble, but

Speaker C: it was awesome and I'm going to. Now, I know, Leah, that I'm not supposed to ask you questions, but I'm about to ask you a question because I feel like you have experienced the exact same thing, except for your telling founders know, you're telling boards know. But, but it's that like that same misunderstanding of product, um. And what would you do differently? Because I know that you've sort of had that same arc with, with the

Speaker A: founders, with a couple of great founders.

Speaker C: Yeah.

Speaker A: Um, yeah, it's interesting because as you were talking, I was thinking one. I think one of the best things you can do as a product leader, certainly if you're going into a store startup, is say what, what you said at the beginning, Jay. Like, I'm not sure I'm what you need. You need to decide. So what happens a lot and what's happened to me a lot and what I see happen to others in kind of what I've done in the startup world is founders want the shiny thing that product managers can do. M. And they want to be like those guys. They want to be digital, they want to be whatever they want. They're like, I want to be like that. And you're. And when. But then when you bring it in and start having the conversation and they realize that I'm going to tell them they're part of the problem, then suddenly I'm not shiny, I'm not interesting, I'm pain in the ass, I'm all these things. Right. And I'm like, who do you want to be when you decide who you want to be, we can have a conversation about whether you need me or some project managers. Mhm. Right. Because I'm not, I'm not for everyone. Right. Like, it's not what I do isn't for every company.

Speaker B: Right?

Speaker A: Right. And. But if you want me, I am going to disrupt things. I am going to push for everyone to have a product mindset. I am going to talk about strategy everywhere in the company. I am going to ask questions everywhere. Right. But uh, that's because you're saying you want to be like that guy. You want to have a company like we, uh, want to be like Amazon. We want to be like Microsoft. We want to be like, no you don't. If, if what you want me to do is sit in My chair. Go back and sit in my chair and be in my chair, then that's not what you want. And so I think those conversations are hard, but they're so important. And I think it is a testimony to our bravery as product people when we say, I'm not convinced you need me.

Speaker B: Mhm.

Speaker A: So let's have that conversation. Like, you shouldn't pay me this much if you don't really want me to do what I'm good at.

Speaker B: Hm.

Speaker A: Right. I mean, I think, I mean, I had that conversation at Expedia. Why are you paying me? What are you paying me to do? Right. Because you have Maryland. You don't need to pay me for this. You have Maryland. Right. Um, but I think that that's a. To your, to your point, Marilyn? I think there is a conversation. It's it for me, some of the things I would have done differently. Um, and I learned this along the way. Like there is this concept of first team, second team. Right. The first team is the team you're on. It's the team you are a part of. Often we, as leaders and especially in product, we view our first team as the team we're leading. Who am I? You know, if you're a product manager, it's this set of engineers and these designers. This is my first team. If you're a, uh, product head of products, you're thinking it's the product managers. You, you know, that you lead them. But your first team is the team you're on and you have to win their hearts and minds. You have to convince them. And if that isn't a startup and it's you and the rest of the C suite, you've got to get that CEO and the CMO and the CFO and all these people, you've got to win their hearts and minds. I can win my team's hearts and minds all day long because they're product managers and engineers and designers and they love what we do.

Speaker B: Yeah, right.

Speaker A: But I need to win the hearts and minds of the people that are my peers. And that takes a different set of humility and listening skills. And, you know, you need to come in ready to say, I want to know you and you need to know me so we can decide if this is what we want to do together.

Speaker C: And I do think, but. Yes, yes, yes. Um, but I do think if you go back to Jay's lived experience and Leah, clearly your and my lived experience, when someone doesn't understand the role or the value it brings, when you enter into a space and probably for the first, I don't know, year. Uh, you are misunderstood and you're, you're seen as a jerk. Someone that doesn't listen. Someone like that because you ask a question question or because you want to know stuff outside of your seat, right? As translator of, to engineers that will do exactly what they're told to do. Um, you're perceived as a, as a, as a terrible person. And I do think that, uh, I do think that actually wears on your soul. And I wonder, um, I wonder because I, like, listen, you guys are both very strong, talented people. There's a lot of people that want to be you guys, right? They want to be the product leader that comes in and changes an industry, but it is freaking exhausting. So what advice would both of you give to someone that wants to be you? Walking into a space that's going to hurt for a long time because sometimes it feels like it's not worth it, Right?

Speaker A: Yeah.

Speaker C: Yeah.

Speaker A: Jd, you want to go first?

Speaker B: Yeah, I would just say, uh, you know, breathe through it, right? Like, you just, you have, have confidence in the, the process, the discipline, the approach. Have some hubris about yourself as well, because you need that. You, it's a, it can be a soul crushing time. Like, so you need that a little bit. Being like, no, I'm, you know, I've made all the mistakes in my career. I continue to grow, so I'm far from perfect. But I, like, my intuition here is right, so. But play the long game. So, you know, do I regret going back to the leader and saying, hey, dude, like, I'm the fish out of water. Let me leave. I don't. Because I think I needed to know early on that he was like, no, I got you. Like, you're like, you know, like, I will let you know if you make you do something that I'm not, I don't approve of, but like, keep going, keep disrupting. So I needed to know that. And then I just took a breath and then like, I think I had a six month stretch where it was like, all right, I'm just going to go, go, go. And I wasn't feeling that. And then had another kind of setback, you know, But I think it's really just breathe through it. Take a medium to long term view. Like, change doesn't happen overnight. Um, embrace the principles of change management and the spirit of it. Um, without maybe all of the process. If you're a larger company and they want to have like 57 meetings just to roll out the change, it's just like, you know, but. But really just, you know, take. Take the long view and, you know, believe in. Believe in the outcomes, and you're going to get some things wrong, but it's also, you need. I needed to understand from the leader, how much room for experimentation do I have here? Like, there's one thing for you to say, I got you go. But do. Doesn't. Do. Does my team and I need to stick every landing. Like, we're not going to. Like, I'm gonna make one of my hunches is going to be wrong. One of their, you know, they're gonna. They're going to have an execution challenge. There's going to be miscommunication between me and my group. Like, Like, I need to know that I don't need to be perfect. Now, you've said, uh, uh, you've given me guardrails. I got you. I'm giving you air cover, but I need you behind me the first time we fail and just be like, hey, like, we tried that. That didn't work. Like, let's get all behind. Get. Get behind Jay's team again and, you know, for the next one. So, yeah, I think Longview is the best. Best thing I can say.

Speaker A: Yeah, I agree with that. I think what comes to my mind is that two things you need to have. And this is true. I'm telling you, like, I'm, um. I, um, coach people all day long. You have to have people, your people. And when you're walking into a new company, know who your people are outside of all of that that you can lean on and say, I'm in. I'm in the shit, and I need someone to talk to about it. Right. I need. You have to stay still, have your circle of friends and people and colleagues and people often who have worked with you are great for that. I mean, Marilyn has been that for me in the past, and I think I do that for her, where she can call me and be like, I'm in the. I'm in a bit of shit. Can we talk about it? Right? And we. And I understand her and the way she works. And so there is this support structure that sits outside of. Yeah, the. The pot of stew you're in being boiled in today. You do have to have somewhat thick skin to do what we do. Right. You product managers that don't have thick skin should do something else.

Speaker C: Yeah.

Speaker A: Like, it is not a job for the faint of heart. Like, it is just not. I tell product managers all the time, you are going to get your feelings hurt. People are going to accuse you of things that are. That are not true in your core. And you have to be able to go, oh, that's not who I am.

Speaker B: Yeah.

Speaker A: Like, you have to say, like, that's a misunderstanding. We can have another conversation. But I am not who you just described me as.

Speaker C: Right.

Speaker A: So that's key. And then I think what has saved me time and time again across my entire career is the ability to bring lightness to the conversation. Can you do it with a bit of humor? Can you do it with a little self deprecation? Can you do it in a way that says, listen, I know I sound like a know it all, but. Right. Could I ask one more know it all question?

Speaker B: Right, right, right.

Speaker A: And having that ability to be light. And I tell clients this a lot when I'm. When I'm coaching, um, you know, executives and new leaders. I'll say you can say almost anything if you can swing it with a little bit of humor and a bit of lightness. People will take almost anything you say if you're like. So I was thinking, right. And it's a little. There's a little angle there. And I've done that so much in my career that I can land some pretty hard truths. And people are like, I can't tell if we're supposed to laugh or cry. Right. Not sure what the reaction is supposed to be here. And for me, that has saved me time and time again. When you're in that long stretch, right, where you're just like, this hurts, how much fun and humor and a little bit of lightness can you bring? Because again, most of what we're all doing is not, like, it's not going to kill people. Right?

Speaker B: Yeah.

Speaker A: How much lightness can you bring? And sometimes. But. But. And then how can you make sure that you have a support structure around you that keeps you from just wearing down to the bone?

Speaker C: I love both of those tips. I think that the other. The other piece of advice I would give to anybody listening, um, is you need to find your source, like, your source of joy. So, Jay, you talked a little bit about, you know, your team being super happy. Aliyah, I know you've experienced that. One of my favorite parts of leadership are building these, like, super productive, happy teams where joy can happen. Like, listen, work is serious, but it doesn't. You can have fun while you do serious work. Um, and so recognizing the goodness that you build, um, and almost soaking yourself in that pool of support is restorative to me.

Speaker A: Yeah.

Speaker C: But. But yes to everything. Both of you guys said, like, long game. Get your support system in line. Like, this is it. This is a rough job. There's a reason not everybody wants to do this job.

Speaker B: Yeah.

Speaker A: There's also. It's also part of the reason why it's so misunderstood. Yeah, right. It's a. It's a difficult job. It's this weird, like, I got to do all of this and all of this and all of this and all these different pieces. It's part of the reason it's misunderstood. So as hard as it is for. For us as individuals, when we have product management jobs, whether that's on a team or as a leader, I think if we can look at that and say, man, this job's hard. Oh, no wonder people don't understand it.

Speaker C: Yeah.

Speaker B: It's a great way to put it.

Speaker A: Of course they don't. They don't do it.

Speaker B: Yeah, no, it's a great way to put it.

Speaker A: Yeah.

Speaker B: I think the key. Just. Just mixing everything you guys said together and humor, like, to me, it's not a good day if I haven't made someone laugh or someone hasn't made me laugh. Um, and self deprecation or being vulnerable is. Is, you know, it's in my toolbox. I've had people say, you know, be careful about using it too much as an exec. And I'm like, no, I can only be. I can only be one way. And, you know, you get deep, deep connections from people within your org and hopefully outside of your org, where, you know, like, they'll surprise you with a present and you didn't even, like, know that you had that kind of impact on them or. Or like, I got a go big or go home hat someone gave me because they're like, you say this all the time and you live this every day. Like, you know, just. I was. I love the way you described it, Marilyn, of like, sitting in that restorative pool because I would literally call an off site with my team and, like, the worst moment where they were feeling beat up, we'd have a lot of fun. And then I would go to an SLT meeting. And it was just like, I had to manage those. Those mood changes and everything else, but it gave me the energy to then go to that meeting and be like, hey, how can I help here? Because like you said earlier, I think there's a great book, like, the 55 dysfunctions of a Team or something like that where, like, your first team is really the team of your colleagues that you're on as fun. It is as it is. And you want to think it's the team that you spend the most time with. Like, you really should be spending equal or more time with your first team. And, like, how could I help you? Person outside of my discipline? Um, but, yeah, you need. You need that restorative energy and the person, you know, getting someone on the outside. I randomly found someone I'd worked with at Microsoft. We reconnected. I found out he was running customer product inside customer service at Airbnb. And I was just like, oh, my God, we have to have lunch. And it was literally like we were like doppelgangers talking about the challenges we were having and the, you know, where. Where customer service stood in the food chain for the overall company. So, yeah, I couldn't agree more with what you guys said.

Speaker A: Yeah, so what we. One of the questions we like to ask when we're sort of wrapping up is, what are you excited about right now, Jay?

Speaker B: Right now, for me, I'm really early on in this consulting, uh, world. Uh, I had folks telling me for years to do it. The idea of consulting. I always had this classic, like, you worked for, uh, Accenture back in the day, and you left on a plane on a Sunday night, and you came back on a Thursday and travel, travel, travel. And, like. And it just never sounded interesting to me. And also, I had this, like, I had this, uh, snobbery around, like, how could I possibly go from being a Craftsman product leader where, like, where I'm responsible for, you know, my team and I are responsible for our products. How could I possibly go and find passion? Because I'm a passion first person. Like, you know, I will. I will run into things that I shouldn't run into because of passion. And it was just like, how could I possibly get re. Uh, energized every day if it's not our thing? And, uh, I had a friend come to me and just say, look, like, you seem. You seem burnt out on the corporate stuff. I started my own consulting company with a few others eight years ago. And he's like, I'll tell you, especially post pandemic, where remote is more, you know, is more accepted, obviously. Um, so a lot less on the travel side. Maybe zero travel with some clients. Um, and, you know, he's like, I. I know you have wisdom from your 25 years that you will get energized by helping someone else with a piece of it and going and recalling and saying, oh, this reminds me of the thing I did here. He's like, you're not going to lose that passion. And he said it will be restorative and you'll love the variety of clients. Like every day will be a different business or industry you're talking about. So he said like if you, if you want to try it, I'll, I'll throw, throw a project your way. A couple projects. And I literally I, I um, created an LLC on a Monday by Thursday because we had, we were having some conversations. I was in a full time contract with one of his clients that you know, he, he just went to them and said, you need uh, we, we're known for dev and architecture consulting. Do you need any product help? And they're like, oh, glad you asked. And so I'm early on. I've been on that contract for 16 months. I've had some other clients I've done on the side but I'm really early on. So I'm super excited about you know, just continuing to varying the industries, the businesses, the types of leaders I work with. Um, analog products versus digital products. I've got a, a doctor that wants me to help bring their teas online. They have some, you know, restorative and medicinal teas. So like I, you know, I, I've got to learn the e commerce world. I've got to learn the, you know, the non where, where I'm not the creator of the product or helping someone create the product per se. So yeah, I'm just really excited about, you know, getting, continuing to grow that business and getting exposure to so many clients.

Speaker C: That sounds like fun. I uh, want to like one of my throwaway phrases is it's like we don't make dog food. Without technology, we don't exist. But in your case, you're making m something physical which is going to be super fun.

Speaker A: Maybe you'll make some dog food.

Speaker B: Yeah, maybe. My dog is right here on the couch.

Speaker A: Right.

Speaker B: See a little Yorkie.

Speaker A: Yeah. Cute.

Speaker C: Cute.

Speaker A: Well, Jay, thanks for coming and talking to us. It was really fun to just kind of talk shop a bit about how this all works. Um, I hope it was fun for you.

Speaker B: Wow, it's a lot of fun.

Speaker C: Awesome.

Speaker A: Um,