Let People Think

Tim, welcome to the powerful interview podcast. It is so great to have you. You’re a very busy person, thanks for taking the time. Anything for you, man. We know each other. We go back. I don’t want to count how many years, probably 13 at least. Yeah. He’s going to count. I’ve actually had a couple of other people on the podcast from this, from Yes, Mail. They’re really great people that we worked with at the time. You are my first manager. I was just starting on this leadership journey for myself. You were super supportive and encouraged me. You are a serial chief product officer, engineering and product leader. Serial, it sounds so heavy. Wow. Wow. Yeah, of the chief. Heads. I really wanted to have you on the powerful interview podcast because I think you really represent what someone who, maybe if you don’t identify as an introvert, you’ve tested as an introvert. Just what people are capable of. I’ll just want to say a few, reminiscent about you. So you’re a very inspirational leader. You’re the type of person engineers have followed from job to job to job. So people are very loyal to you. And there’s good reasons for that. As a leader, you’re very caring. You’re very direct. You hold people accountable for things. But you create a very supportive and motivating environment. And things that were just kind of blew my mind at the time going back. You’re just emotionally vulnerable. Like sometimes something moves you. You’re not afraid to show that, which is really cool. So my question for you is like, what made you like this? So I mean, wow, where to start? I would say if I just tackled the leadership, but he’s talked about being vulnerable, right? People will appreciate both the vulnerability, but also the authenticity. Plus, I just, I suck at faking. Like you said, be very direct. So you know exactly where I stand. And so I just always had enough confidence to say, I’m just going to be who I am. People can take it or leave it. The reason why I got into leadership, literally, was I remember I was still developing. Now I was trying to decide architecture, technology, or leadership. And I asked myself a question, why don’t you yourself for the next month or so? And wherever your mind wanders, like just implicitly, that’s what I should be doing. And I found myself driving to work or when I was just relaxing. I was thinking about like, how do I help this person or how can I help this person or, what could I do to make this team better? And I just realized that where my interest really lied is, yes, the technical stuff, but really more importantly, was like working with people like you and saying, how do we bring out the talents of Greg? Right? How do we tap into who he is and his strengths? Because him, confident and authentic and empowered makes all of us better. And so I just felt like that was what’s motivating me. It’s like, how do I really get other people to just lean into their strengths? Because I think everybody is special in a lot of ways. You just have to have the courage to be who you are. Yeah, that’s great. It’s definitely something that I felt and that I saw. Where were you when you had that realization that that’s that’s what interested you and that’s what you wanted to do? It’s third grade. I would just say this far back as I can remember. I’ve always tried to not lead for the sake of power, but rally for the sake of like, hey, the collective is greater. And so even in middle schools, I tried to organize community events and in high school. I was doing leadership. So I think it’s just always been something I’ve wanted to do is from a social perspective, how the bigger impact by connecting with people and seeing if the collective can be greater. So it seems like it came quite natural to you. Yeah. Interesting. And like a lot of us, some of our patterns come out of early family dynamics. So did you play a similar role in your family? That’s a great question. I am from a big family. And I was kind of a, was I say a lock key child or a… That’s key. The Lodge key child, something like that. Yeah, that probably has a lot to do with it, just that upbringing. I couldn’t tell you the specific events that we created it. But even right now, I was just doing a personality test for somebody else who wanted to kind of like understand a little bit of like, hey, what’s your personality type? These personality tests, they all have different ways to frame characters. And I’m like, oh, you’re a social performer. So like, oh, you see something in the world that you want to change. And so that becomes your, like, your soul focus. But it almost always has something to do with social impact. So I think once you get into your leadership, it’s very much the same thing. It’s like, hey, we are a team sport. Collectively, we cannot build great products and serve people without us really working together. And so I think my drive is how do I eliminate all friction, all coordination, all attention? So everybody is always in the flow. And it’s almost always about interpersonal skills and about how and bringing the best out of individuals. All right. Well, that’s a great segue. Maybe we can talk a little bit about the roles of these tests. And obviously, I think this is an important topic, just because there’s kind of a stigma attached to it and that people get labeled by this, like it or not, for courtesy of Myers-Briggs and things like that. And people like, well, maybe I can’t be a leader if this here test or people are telling me that I’m quiet or I’m introverted. And so if that can help people kind of accept and understand these parts of themselves, so that’s a benefit. Maybe there are some limitations as well. But let’s first of all, like you’ve taken Myers-Briggs many times, you test as an introvert. Yeah. Yeah. And so what do you see as some of the limitations of maybe that test? Maybe there’s alternatives you prefer to look at? There’s so many of them. I think there’s something to learn from all of them. Like the INTJ, that’s great. And then you go look and you say, oh, that’s an INTP. But then you have some colors and then you have character pillars. And I think all of them, they’re just different ways to help you understand who you are. I was just telling my team, I wanted them to go take any personality test and then take a second one. And then walk away with three things that you learned about yourself. To me, that self-awareness is just so powerful that each one of these, there’s no one that’s great. They’re all just informative. And how they help me is they help me understand what triggers me. They help me understand when do I get emotional? What drives my stress? Why do I procrastinate? They’re all very interesting to help you be more self-aware. And that obviously makes you more aware of others. It creates better empathy. It just makes you a more informed person, but also a much better leader. Awesome. I think that’s a really great way to think about it for yourself. I’m curious, when you have your team get these test scores, do you have them share them with each other? Or is there a group disclosure kind of thing? Yeah, you can. It’s so funny. They put them on their profile. It’s like, oh, this is what you are. I don’t know that that’s very helpful, because that oversimplifies it. The high level categorization, that doesn’t do anything for me. It’s like, OK, great, you’re this. That doesn’t change anything. It’s more like, what stresses you out? My personality types, I’m quick on my feet. I can respond fast, kind of a fast thinker in the moment. And especially in America, in our society, that is conveyed as like, oh, that’s what you want in the leader, that type of stuff. As I can take it older, I actually think it’s the opposite. I’m actually pushing really hard to not be a fast thinker, to be a slow thinker. And I’m leaning into people that are naturally slow thinkers and saying embrace that. Right now, I don’t do things like, hey, let’s all brainstorm this. Don’t do it. It’s like, write it down, send it. Let people think. That’s good for me, and it’s good for you. That’s great that you’re doing that brainstorming technique, because I’ve written a piece on that, just how toxic, just the live reform brainstorming can be, or just not super effective. And I also heard, it looks like you’re searching for balance and your team and diversity of thinkers, making sure there’s thinkers of different speeds. Yeah, it’s, like I said, that thinkers of different speeds. As I’ve become a father, and you start to see, you know, if my daughter, she’s a very intelligent person, but she thinks differently. And when I see how she processes and comes up with ideas or identifies patterns in ways that I couldn’t done, it really highlights just how there’s so many different intelligences. And I don’t think we, as a society, are good at appreciating or recognizing that. Even when you talk about social norms or neurotypical or neurodivergent type stuff, you’re already classifying it. I think it’s just an appreciation that, like when I work with you Greg, one of the things that I really appreciate, when we go for walks, right, have a topic, I would ask you a question, and then I would wait, because you would want to think about it, and you would always give it back to me in a way that I hadn’t thought about it. And it’s just a different level of intelligence. And I don’t think that we, in the professional world, do a great job of appreciating that. So we have to be more intentional about it, because if you’re accidentally, you’re gonna fall into a life step to make a decision fast, because I’ve only got five minutes. So here’s what we’re gonna do. You really don’t need to. You can wait an hour and let someone get back to you. And who knows, you might be the right decision, but you, most often not. That’s great. And we’re talking about an environment where you’re kind of setting up the support of an environment that’s more inclusive. But you’re in other situations, like let’s say with your executive team and you’re dealing with working with type A personalities, and how do you address it in those situations? Oh, yeah, so that’s a great question, because it starts with hiring, right? Trying to appreciate the right type of person. And knowing like, hey, this is like we did the colors. This is a white, this is a yellow, this is a red, this is a blue. Because then you know, like, do we have diversity on the team? So from an executive team, the thing that I’ve been pushing in the last couple years is, you know, don’t meet us for status because then that’s just like talking to talk, right? Write the stuff down, share it. When you do meet for discussion, but make sure that you have material beforehand and or decision. And if it’s gonna be a discussion, then make sure that there’s clear topics that people keep your prayer before. So I think in that case, because it is hard from an executive, especially across marketing and sales, and the person that bubbles to the top, especially in those organizations, tend to be more of the, I wouldn’t say extravagant, but I would say like the alpha, right? However you wanted to frame the alpha. And I have worked with the last couple of years with a couple of leaders that were not the alpha, and it’s been amazing because they’re sitting here thinking, how do I get other people to share their thoughts so we can make the best decision together? But it’s a typical. So I think from an executive team, it’s putting a couple practices in place like you write stuff down, you prepare for the information beforehand. You give people a chance to process, and whoever is running the conversation, always looking around to see who hasn’t been providing input and see if you can pull them in. That’s great. So what I’m hearing is that in this situation, you’re one of a few executives. But you can frame the discussion that’s coming up by ensuring that people are preparing in advance and bringing their ideas becoming more prepared, then then also being actively looking around the room, making sure everybody else, everybody’s voice is being heard. Yeah, I’ll say it, and then I reflect back, even in the last couple of weeks, and I felt bad on my face a few times. There are moments when you have to move with urgency. There are moments where good right now is better than great tomorrow, right? And so usually the high-stress moments, they tend to reinforce everything I was just talking that we’re trying to build around, which is the quick decision making, the often the room decision maker, things like that. But all of the other moments, just like a good relationship, your relationship isn’t great because you bought something on Christmas and Valentine’s. It’s great because all the small moments, every day, every week that add up, I think that’s the same thing when it comes to appreciating all personality types, all talents on a team, is all the small, in minute moments, every day that you’re trying to foster this inclusivity. Yeah, that’s great. And of course, business culture is what it is. And it has been dominated by the alpha personality is quick decision making. And when things are stressful, you might fall on bad habits. But then there are those, truly, those situations, which were call for a lot of attention. What’s been your experience? Like you’re on the executive team. What’s been your experience on? Because obviously this is a topic near and dear to you. How did you navigate it? Certainly kind of pushing in the direction of inclusivity and that sort of thing. I think a lot of it is tone set by the CEO. There’s that. But as any executive, you have a lot of sway on how meetings go, any meeting that you attend, you can set the tone on. No, it’s a great point. You raised the CEO is so impactful with respects to the culture. It’s almost like what behaviors do you reward? Like from a team perspective, do you reward heroics or do you try to eliminate them? Do you celebrate the person that worked over the weekend? Or do you celebrate that the team rallied to get a release out, something like that? So those sorts of things reinforce the right or the wrong behaviors. And so as a leader, it’s creating the environment where you can reward results and not necessarily some of these behaviors that make it easy to reward. Because in a lot of ways, an alpha person, you’re kind of like rewarding just being the loudest voice in the room. Yeah. And some people will naturally be quieter. And you’ve achieved this level. So everybody in there is smart. Everyone there is experienced and accomplished. And so the good ideas are going to be evenly distributed in that team. And so if you’re just letting the loudest person speak, then you’re losing out. You’re not getting the best results for yourself or your company. Yeah. If I don’t watch it, it’s easier for me to be the loudest person in the room. It really is. I have to work really hard not to be. That’s why I like to work with persons like yourself, that compliments who I am and helps me remind me who I want to be. Awesome. So let’s dig into that part a little bit. Because I think that’s going to be something that’s a little unintuitive to people. In introvert, I guess in what sense is it more in the sense of the social battery? You’re in a social situation. Do you finally hit a limit? And then you go and need to go off and recharge? Or I guess where do you see more introverted aspects in your own personality? Oh, I almost never look forward to social gatherings. I mean, if I could stay home read a book, I would. Social events are always exhausting afterwards. Even my last company, the team knew it. And when I go to social event, they pop me into like a customer circle and walk off and laugh, because I knew that it was just going to suck all the energy out of me. But I think where I get really energized is in almost one-on-one conversations that are not superficial, but there’s real depth to them. That is just I could do that all night long. I could pull a little night or easy. We have a good topic. Let’s dig in. I love that. If I can find a corner in a social situation where there’s one person’s interesting to talk to you, oh, that’s what I’ll do. It’s so interesting, because I mean, just externally, just because you are not shy at all, you’re very open. And like you said, you’re like, oh, you’ve got to watch myself for talking. But it’s really clear that that’s such a really distinct trait from introversion. And it’s really about where you’re drawing your energy from. Yeah. Is there ever been part of you that’s wanted to be comfortable or is just there’s something that’s always been drawn to things that are pushing you maybe beyond your limits, but what you’ve done in the past. Ooh. Life is short. Who wants to put on your graves down? I made a lot of money. That’s, I mean, some people might. For me, it would be like, I want to look back and be really proud. Part of you, Commissioner, that is by the impact you have on other people. Part of it could be like some of your own achievements. I think right now I look back and saying, you know, how can I be the best father possible? How can I be the best provider? And what’s that next thing I want to do to grow? When I’m interviewing, the key thing I’m always looking for is how do you invest in yourself? How do you grow? Do you know how you invest in yourself? Or is it passive? If it’s active, then I want you. If it’s passive, then you’re going to ask me to push you. You know, people that have hobbies, lots of hobbies, they’re invested in life. You know, if they do music, if they do arts, if they volunteer, if, you know, I’ll ask him, like, hey, what book are you reading? I don’t care what book it is. I just want to know what you picked and why. And then what do you get out of it? It could be fiction, it could be non-fiction, it doesn’t matter. It’s like you’re investing yourself. Because if you can be passionate about one thing, I can make you passionate about something else. Right, are you someone who is passionate, who are curious about life? Yeah. Like my dad says, you can’t fix apathy. Right, so I can fix a lot of things. I cannot fix apathy. Right. And so you talked about motivated. It’s just like life is too short. It’s like, wake up. What am I going to do today? All right, awesome. You’re looking for people who are awake. Yeah. One other question. What advice would you have for, say, someone who is maybe quieter, but they’re interested in leadership. They want to make more of an impact maybe than they’re having right now. Well, I actually thought about this quite a bit. I would say one is, you want to find an advocate that appreciates you for who you are. Here’s a great example. When I was in college, there was one course that I flunked. A couple of you send to the course that I only drop out of this instance and go, well, I was like, no, I’m going to, I’m going to overcome it. Right. It was a mistake. It was just the wrong course to take. And it wasn’t because of the topics. It was because of the teacher. And the next semester I took it with a different teacher did totally fine with it. And I think that sometimes it’s like you need to, you don’t want to be in an abusive relationship where maybe your boss is going to try to force you to be somebody that you’re not. Have someone that wants to embrace who you are. But I don’t think that being quiet has anything to do with it. Because if you look at like teams, sometimes you have the quiet leaders that are the captains. And sometimes you have the person jumping up and down and running up and down the sideline. They’re both effective. They’re just different. The things that I would look for is like, why do you want to be a leader when they say it? They’re like, oh, because I have great ideas. That’s the wrong reason. Or I’m good at organizing things. Yeah, that’s probably the wrong reason too. I would say it’s like, because you’re a great listener. You’re really driven to have other people collectively get be better together. If you’re driven by helping others around you, like that servant leader type mentality, then find someone that will appreciate that and you’ll blossom. Awesome. I love all that. Yeah, I really, really agree. Finding someone, especially if you’re not sure, having someone who is valuing you for who you are, and not just blindly going along with this alpha ideal of what a leader looks like. Because there are other archetypes, other models out there. So is there anything that I haven’t asked you about that comes to mind that you would want to share on these topics? I’m really curious. Thanks to being an interesting topic. When you’re looking for, let’s say, a lieutenant, someone that you want to foster and grow. What is it that you’re looking for? Yeah, I’ve always thought of it as, I’m looking for signs of life. And I think it’s similar to what you were saying before. Are you inspired by life? And I am looking for things that are outside of just the role. To me, if I’m hiring a sense of humor is kind of non-negotiable. Nice. Because it’s such a path through stress and life is stressful. And so you need a way to have some distance on a situation and laugh about it. And this is all assuming that people are qualified. But I think beyond that, I’m looking for a level of kindness in people. The team I’m hiring, the way I try to organize is for things to be very collaborative. And there’s degrees of mutual respect. I’ve had to bring in the urgency and the need to make a decision more quickly than so these are things that I’ve added over the years and layered on. But those are my roots. Those are my people. That’s who I’m looking for. That’s cool. Yeah, I would align with that. And I remember some of my criteria were that, the empathy, the kindness. If you don’t get that on day in that first interview, moving on. And then past that, I like to find people that ask really good questions. That will challenge your assumptions. That shows how much of a critical thinker you are. Are you actually processing the information or you’re just going through the motion? Because I need to know if you’re making decisions that I don’t need to second guess them that you’ve thought about it. And that is such a great quality for a good leader as someone that doesn’t really have the answers. But really knows how to ask great questions. Yeah, I really like that. There’s always a bad sign when someone just leaps into the answer. And it’s like, what, wait a second. Are you sure you understood the question? Are you sure you understand the context? And that’s a can be a red flag. We kind of did a little bit of bashing on the alphas, right? And it’s not that. There’s nothing that’s the defend wonderful quality. The problem is, and this applies to everybody, is when you know enough to think you have the answer. And then after the fact you realize how much you didn’t know. Just being aware that there’s probably still a lot of unknowns. And so I like to have people that love to understand the nuances and the subtleties or the complexity. Because then at least you know that there are real trade-offs to be made. How many times have you backfired on a decision or a project or even a team because you oversimplified the problem? How do you make sure that people are willing to call Bullshitt for you and keep you honest? I don’t know that I’m, ooh, maybe I have had that problem. It’s hard, right? Because for yourself, you don’t look at being a leader or someone that has power. But that doesn’t mean that your team doesn’t look at you and look at you as someone with power. And so that dynamic makes it really hard for certain people to embrace this. You’re just a person. Give me the truth, right? And so then I think oftentimes it’s on us to look for people that are not being honest. Not because they’re deceitful. It’s because there is a power dynamic whether you see it or not. And you have to do your best to tear it down so you can get unvarnished truth, especially with situations that are tense or stressful for people because then most people clam up even more. Yeah, that’s a really good answer. Just the higher level of the leader you are, the more delivered you need to be to be sure that you’re getting people’s honest feedback. You’re fostering that environment too. Well, I would say a value. I don’t know how well I foster it, but I definitely value it. Right? But I think what you had just said there is because we can always get better. There’s always that balance of speed versus like inclusivity. You know, I was trying to find that balance when to apply one situation. But I think they’re going back to the very beginning. It kind of reinforces that as your influence gains, your level of inclusivity or self-awareness or empathy needs to gain. So it almost kind of reinforces the more introspective you are, the more likely you are to move up because that’s the quality that delivers the best results. Not the most vocal. That’s the quality that probably oftentimes does not deliver the best results. If it doesn’t go with self-awareness and thinking and critical thinking and humility and all that and kindness, if it doesn’t go with that too. That’s a great message because, you know, regardless of where you are self-awareness, inclusivity, these things are just inherently advantageous to you. Yeah. In your career. Yeah, exactly. Tim, this has been so cool. I really appreciate you’re taking the time and your inspirational leader. And I just love hearing your perspective on so many of these things. My pleasure. I’m sitting here going, oh, wow. I need to practice at this. I’m a gambler. Yeah, no, I appreciate you having me on. You are a fantastic guest. Stop beating yourself up. You said it before. You’re just authentically you. And that’s good enough, Tim, that I’m really glad to have you on. Yeah, I’m glad you’re doing this. This is great. I decided to see where this goes. The Bleacher Report app is your destination for sports. Right now, the NBA is heating up, March Bandit’s is here, and MLB is almost back. Every day there’s a new headline, a new highlight, a new moment you’ve got to see for yourself. That’s why I stay locked in with the Bleacher Report app. For me, it’s about staying connected to my sports. I could follow the teams I care about, get real-time scores, breaking news, and highlights all in one place. Download the Bleacher Report app today so you never miss a moment. The Pacific Northwest is a beautiful place, but with all our rain and steep slope, they can turn your beautiful yard into a muddy mess. That’s where we come in. Dick with the wall here in since 1985, our team has transformed the landscape around the Portland Metro area. 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