#11: Building Leadership Communities with Laura Thompson

Priyanka: [00:00:00] Hello everyone. Welcome to Unleash Your Leadership podcast. I'm really excited to have another special guest today on this podcast. Please welcome Laura Thompson. She's the founder and director of Execs On Deck, A fellowship that helps diverse leaders dramatically expand that impact across the startup Ecosystem. 

Laura has been a founder of VC and an operator in both Big Tech. As an early product lead at Google X, she launched delivery drones and smart contact lenses and at startups. She's also an angel investor and advisor to number of mission driven startups across EdTech, FinTech and pets. Laura splits her time between San Francisco and Puerto Rico and is an enthusiastic but thoroughly mediocre surfer in her own words. 

Hey, Laura, welcome to the podcast. 

Laura: Thanks so much for having me.  

Priyanka: Well tell us a little bit more about you and what you do for the world.  

Laura: [00:01:00] Yeah, so what I'm focused on right now is really execs on deck. And so as you mentioned, It's a curated community for leaders with 12 plus years of experience who are looking to build a big career in startups. 

And essentially we offer executive coaching plus basically an unparalleled peer community to help top leaders take the next big step in their careers, whether that's leveling up from VP to C-suite, or , even jumping from a bigger tech company into a startup.  

Priyanka: That's great. I definitely want to put in a word for Execs On Deck that that's how I came to know Laura. 

I joined Execs on Deck Deck earlier this year, and it has been one of the best communities that I have been part of, especially working by myself. I felt really connected to a lot of people in the community, even though it was all virtual. But I got opportunities to meet so many people one-on-one in real life as well as virtual. 

So yeah, I definitely recommend Execs On Deck to anybody who is [00:02:00] listening and is interested in having a community of like-minded thinkers. Tell us about your journey. How did you come about to be in your current.  

Laura: Yeah, so it's been an interesting journey. So I, first, I fell in love with startups and innovation really in college when I was at Brown, a few friends, and I started a company called rna, which was a clean energy drink company. 

Basically healthier ingredients and a strong social mission around creating local jobs in Amazon and Ecuador. And so, , had an incredible run for two years while we were still in school. Going to Ecuador, getting the company off the ground. We got some seed funding by winning a couple business plan competitions. 

And so just totally fell in love with it. And then after graduation, My friends continued to run the company and actually sold it a couple years ago, so you can still find it in shelves, which is quite fun. But I had come from very humble beginnings and needed to go get a full-time job that [00:03:00] paid for, , food and things like that. 

And so I ended up at Google and I spent almost a decade. Was an early, one of the first go-to-market leaders in Google X. And so as you mentioned at the start, got to launch self-driving cars and delivery drones and, , work on lots of robotics and it just really felt like Willy Wonka's chocolate factory, but with. 

Robots. So had an incredible time after that, spent a little bit of time in BC and then made the leap to startups and, , essentially I started execs on deck out of that experience of leaping from big tech to VP and C-suite level roles in startups because I found that I loved the. 

Mission and the culture and the pace and all of those things, but I really missed that peer community that you have when you're at a bigger company and the conversations that you can have around career development and learning from other people that are thinking about similar problems and you just don't [00:04:00] really have those peers when you're the COO of, , a series a company. 

So yeah, it's been a, it's been a meandering path, but I've definitely throughout have follow. Some pretty clear threads around doing, solving, really challenging problems on missions that I think are important in the world with, , people that are really smart and passionate. 

Priyanka: That's amazing. I didn't know about your college, so, so it looks like you've made so many interesting pivots along the way in your journey. Tell me a little bit more about, , every time you made a pivot, how did you go about doing it? How , because I'm sure there's a lot of energy required to do that and Yeah. 

And I'm sure it can be nerve-wracking sometimes. So tell us more about,  

Laura: Yeah, definitely. Actually, some friends always joke that I should write the Triple Pivot as my cheesy business book because I really do believe that, , I think the, the era of the linear career is. [00:05:00] Pretty much dead for most people at this point. 

And actually, if you look at any interesting career, there's not just, , a single sharp pivot in a different direction, but usually continuous course correction in these small or, , sometimes larger pivots to, to follow interesting opportunities and, and curiosities. 

But for me it was really, , I think every single time. That I moved to do something different. It came out of falling in love with a really interesting challenge and also finding people that I really was inspired by. And it's funny, I remember. , for me, I'm super motivated by working on hard problems with great people and the idea of clear career progression maybe isn't as important to me. 

And I remember when I was at Google, I was working on a promising new product launches, and I got the opportunity to join x and. Really, really admired, pulled me aside and was [00:06:00] like, please don't take this job. This is, you're leading a team right now. You're working on a globally important project X was at the time, was a playground of interesting things. 

I was gonna go back to being an individual contributor. There were no queer titles. And he was like, what are you doing? Don't do this. But I knew that I was just gonna be so excited. I looked at , what are the problems I would have to. If I went one path versus the other and I just knew that I was so excited about the opportunity at X, that I would more easily probably solve that set of problems, of lack of clarity and , different roles and all of those things. 

So for me, a lot of it has just been following excitement and leaders that I really believe in and , challenges that I'm excited.  

Priyanka: That's so great to hear. And I think it's really important to stress, your career is no longer just a straight line and it can meander and you can pivot. 

And, I feel like that creates so much of a diverse experience and versatility in terms of you as an individual. And it's great to see that , [00:07:00] you did that right? Having reports and having a team is not necessarily the pinnacle of a career success. You can go do other interesting and exciting things. I always wanna emphasize that for our listeners here as well.  

Laura: Yep. A hundred percent. .  

Priyanka: Well what did you wanna become when you were younger?  

Laura: That's a good question.. I loved math and solving puzzles, so probably something there, although I was always really curious about a huge range of things. 

Actually I have this amazing photo of a journal entry. I think I was seven or eight at the time. And I made a list of the things that I wanted to do when I grew up and the list is hilarious. The list is mathematician. Physicist zoo owner and circus performer, that was those I all saw as equivalently possible career options. 

And , looking back maybe that was a foreshadowing on what a mix my career was gonna be. But , honestly though, I think even in those [00:08:00] things again, you see it, those are very different career paths, but still those same threads of. Solving hard problems, interesting, unique people looking at the world a little bit differently. 

So I haven't yet necessarily done any of those things, but , I still have a ways to go in my career, so we'll see.  

Priyanka: Like you said, those do tell a lot about your interests and what might excite you. So you may not choose the exact job title in a certain area, but you still get to solve the same kind of problem. 

And so I think it, it's also interesting, what are the things that you can do as opposed to a title that you can stick to when you. I don't know, eight, 10 or 15 and, oh, this is what I want to be.  

Laura: , it's funny, I said that photo actually to a friend that I've worked on a couple of startups with when I , came across it going through stuff a year ago and they were like, , startups are not that, they're like, zoo circus thread is, , not that similar to, to the chaos of startups. 

So maybe that really was foreshadowing.  

Priyanka: [00:09:00] That's so funny. Yeah, I like. you mentioned that . Before you joined Google X, you had a team and you had, , you evolved into a leadership role as we think about leaders having teams. Tell me , what was something that surprised you as you started leading teams? 

Laura: Honestly, I was surprised that I loved building teams. , I think that early in my career I bought into the stereotype of, , I think you hear leaders are extroverts with answers, how leadership is portrayed. And I. That has also changed over the last decade and we have many more examples in media and out in the world of leaders that are female and come from non-traditional backgrounds and , are not white. 

And it's been amazing to see that change, but certainly I came in with that stereotype. And for me, , I am funny given that I now run a community and do so much public speaking as part of making a living. But I am very introverted and I was [00:10:00] like, I just don't know that this is gonna be for me. 

, I love having deep conversations. I'm terrible at small talk. And so I was really surprised to find that I loved building teams and I think, of course the reality is, Building a great team is a lot like the math and logic puzzles that I loved as a kid, and that you're fitting together the work that needs to be done, each team member's skills and interest, how to best create culture to really gel a team together. 

So yeah, , now when I coach first time managers or early managers, I feel like one of the things that I say first is , Basically, the faster you can give up the idea that you need to show up with an answer, the faster you'll add real value to your team. And I really think that is true.  

Priyanka: Yeah. 
 

You don't need all the answers or you don't need to know all the answers to be a leader and to inspire people. So that's so great to hear. You also mentioned moving back to an individual contributor role. Right. But [00:11:00] to me, Leadership doesn't necessarily mean always have reports. So how did your leadership evolve as you navigated these different titles where you had reports versus where you were individual contributors versus now you're a founder or even investing. . Which is a very different . Job function. Yeah.  

Laura: I think the thing that has changed the most for me over the years is just leaning into. A more authentic leadership style. So when I started at Google, I was in the AP M M program, which at the time was run by Marissa Mayer. And we got this ridiculous benefit where we each got, , as 22 or 23 year olds, a few sessions with the executive coach that worked. 

Larry Sergey and Eric Schmidt, the founders and c e o of Google at the time. And so it was, it, so it was this crazy experience to, to meet with her. But what was interesting about those few sessions was the focus at Google at the time was professionalizing. They had brought in [00:12:00] Eric Schmidt as the c e o to be adult supervision. 

And there was a lot of emphasis on growing up and growing out of being messy, chaotic, curly company. And so a lot of her advice was super tactical, , , leadership is about sitting next to the most powerful person in the room and make sure that your voice isn't too high and don't sit on one foot, don't nod too quickly. 

 She had a lot of, and it was clear that that was what she was working on. I mean, she said that was what she was working on with the leadership of Google at the time, and that was the advice that she gave these 22 and 23 year olds. And I feel. It was actually, it was good tactical advice for somebody starting in their career. 

But it's been interesting. I think I've , what's changed over the length of my career so far is just really leaning into what is more authentic for me. I love to be pretty informal, , I really like building high trust teams where everybody knows what everyone else is doing in their lives as well as at work. 

And, , I saw so many good examples of. Like [00:13:00] Google X was the opposite example of that for me. , super informal engineering driven culture. Lots of engineers, didn't wear shoes. Sergey showed up wearing Crocs every day. Often in spandex, biking outfits. It was just totally the opposite. 

But I think the culture, the leaders there, I think of Astro Teller who runs Google X or OB Felton who is my manager at x and is an incredible leader that I learned a ton from. , they really had this emphasis on they wanted a culture. The, the meat, the best idea one versus the best presentation. 

And I, I think that I've taken that. Into everything else that I've done. And , even at OnDeck, we, there's a joke. I never put together fancy PowerPoints for anything that I can avoid. , I love forcing people to put together really crisp docs that , where the idea is the star and not the presentation of it. 

So I think, , my leadership style probably is still evolving, but I think that, , being. [00:14:00] Comfortable with being more authentic and informal and really focusing on ideas and people first has been just so valuable to me over the last, , 10 plus years.  

Priyanka: . So ideas and people first, and presentations and PowerPoints later.  

Laura: Exactly.  

Priyanka: I think there's, Really important thing here, which is you become a leader, sometimes people might feel that you are unapproachable, especially if you don't come across as, authentic or that it feels too formal for relationships. 

And that is where I think it can also get difficult as a leader to then inspire your team or motivate your team. And I feel like authentic leadership goals a long way to even keep your team aligned. With your vision and your goals as well?  

Laura: Yeah, a hundred percent. Because especially as you work on bigger problems, , the team sees smaller and smaller parts of what everyone else is working on. 

And , I've seen this repeatedly in startups that go through hypergrowth of, , the [00:15:00] culture changes. As the team is growing really fast, each team member is working on a slightly smaller chunk of it. And, , I think culture can break down if you don't have that overcommunication culture where, where everybody feels like they are part of this inspiring bigger mission and that their work really fits into something meaningful. 

And , I think all of that comes from is right. Gets wrapped up in, in the same thing.  

Priyanka: Tell us a little bit more about the community you have your founders community, you have your execs on deck community as part of on deck. 

Yeah. You have multiple communities. How did you come about thinking about communities and where does it go from here? Because I'm sure you have your vision in terms of building a community as well. Tell us a little bit more about that.  

Laura: Yeah, it's funny. So , OnDeck, so I've been involved with OnDeck since before it was a company. 

It started as a group of us in San Francisco, in tech and startups getting dinners and quickly realizing actually [00:16:00] there was a ton of value in this cross. Pollination between different people interested in tech and startups. And so, , OnDeck has launched and, and, and canceled and wound down many, many different fellowships over the last couple of years and really tried a number of different things and. 

, I think where we've landed with the execs on Deck Fellowship and the Founder Fellowship is, is a return to the core of being able to really get to know people who have a lot in common and be able to really figure out how do we serve them and how do we make the right connections and. 

, what is the best way to build communities that really turn into this deep, meaningful web? And so, so honestly, I think we're still figuring out what's next. So much of execs on deck changes, , we bring in people in cohorts of 40 to 50 fellows at a time. And the reason, , to keep that those cohorts so small is that we. 

Everyone to really get the chance to know everybody else. But it, and it also means that we [00:17:00] really get to know each fellow and we hear, Hey, I really found X, Y, Z useful. Or , this was less useful for me, or, , whatever that feedback is. So it's been really fun to , iterate on it in, in real time and, and I think we'll continue doing that as we continue to expand. 

Priyanka: Is there a memory or an experience that comes up from one of these community engagements that you had that is really, , lasting effect on you? 

Laura: I think what, what is absolutely magical to me is the serendipity that happens when you bring together really, really smart people that are also really excited to give back. 

And so there was an example. We run mastermind groups in execs on deck where we have four to five fellows and a facilitator. Curated around a topic, whether that's AI or climate or whatever. And in one of the mastermind groups, somebody suggested a podcast to one of the other fellows was , oh, you're interested in, , x, y, Z [00:18:00] about climate. 

You should really check out this podcast this guest. It was really interesting and he went and listened to the podcast, loved it, reached out to the c e o and now works at that company. It's just , , that's the thing, we never could have engineered that as part of the execs and deck experience. 

It certainly wasn't in my OKRs for the quarter. But amazing to see when you bring together incredible people and create space and trust and all of those things that, that kind of magic happens. That's one of my favorite stories.  

Priyanka: That's a great story. I think it also tells us that your next opportunity is not necessary where you apply to a job description on a company website. 

It can happen to these connections that you make, and so I feel that's where the power of the community is amplified even more is you're not necessarily looking for a specific thing, but you don't know how the community will just come up with something for you. .  

Laura: A hundred percent. Yes, I agree. 

Priyanka: I love that. I think that [00:19:00] is really important and , I do encourage a lot of peoples, you form your communities, you never know what will come out of it.  

Laura: Yeah, yeah, a hundred percent. And they say, , I think there's research even that weak ties are where most people get their. Jobs from,, I feel sometimes when we talk to job seekers in execs on deck or outside that are banging their head against the wall, looking at startup job boards, I'm , okay, step away from the job board. 

 Go have 10 conversations with , interesting people that you think are doing cool things and then, , follow those threads. And it's, I think it's harder because it's a less structured path, but it's probably more ly to bear. 

Priyanka: You're right, it's harder and it requires more time of people, but that is where they might find something that really excites them and fulfills them for the longer term. In your journey, we talked about, there's so many different things you have done. So you are also doing startup advising and investing. Tell us, what does that look like.  

Laura: [00:20:00] Yeah, I do. So I do quite a bit of advising, investing, and , I think, I talk to a lot of folks that. Trying to get into advising and investing, and there's two things. 

Two pieces of advice I have, I guess one is starting really informally, and two is to just write stuff down as you think of it. And what I mean is, , I think the best advising relationships for me have grown organically. , I have, one of my favorite startups I advise is an EdTech startup called Wayfinder. 

And, , I know the founder from many, many years ago and originally was just keeping in the loop on what they were doing. Cause I thought it was really interesting and powerful and , slowly , started getting texts in the middle of the night around , Hey, I'm hiring this person. 

, how much equity do I to get? Give them , I just don't, you, , he knew a lot about the business, didn't know a lot about that side of it. And, , he knew that gradual. Expands when there's that natural synergy there. And so, , I think a lot of people come and they're , okay, I wanna start an advising [00:21:00] relationship. 

, what's the path? And I'm , actually I think, , the best ones are really informal and chemistry. And that's one thing. And then I think the other thing is, is the write stuff down. Which is weird advice, but I think that the best advisors are often bridges. And so, , you think about the example I just gave in that. 

I know a lot about equity because I worked in bc I do a lot of angel investing, spent many, many hours reading about it and, and , this founder really, really didn't. And so, , the ability to summarize and translate between two worlds I think is one of the things that great advisors is where most of the value comes from. 

And so, , I really encourage people , think about the things where you maybe. A language that, that a founder might not speak and, and start processing that, that knowledge. And you're on my, whether that's writing blog posts or LinkedIn posts or just taking some notes so that you are really well positioned to to share that [00:22:00] with a founder , and be able to add some value 

Priyanka: is start informally. So maybe advising doesn't even look like formal advising when you start. It's just conversation. , I guess that's, yeah, totally right. You're not necessarily thinking, oh, I'm going into this conversation with the intention of advising. So I think that is really great. 

 Then the second thing is writing it's stuff down. What you're talking about is writing down things publicly and sharing your thought leadership based on the expertise that you might bring for somebody out there who might benefit from it. There's a. Thought leadership that people are starting to share. And I feel like people have definitely realized that they can, they have some unique expertise and experiences that they can bring forth. And what you're telling them is , those are all great ways to get into advising. Or helping other people who may not know about the same things that you. 

Laura: Totally. And I have, I have rant about thought leadership. I hate the word thought leadership or the words thought leadership. And the reason why is [00:23:00] that I feel like I have so many conversations with, whether it's with exec on deck fellows or just other really impressive leaders where they're , okay, I feel like I should do. 

Thought leadership, how do I do that? And they feel totally overwhelmed by it. And it just seems impossible. And , you should have this packaged, , you're the best in the world and you're Mozart sharing, , your masterclass on composition or I, I don't know what it is, but that's definitely where all of the conversations start. 

And I think that in reality, the folks that are most useful and provide the most valuable quote unquote thought leadership, Tend to be folks that are one or two steps ahead of the reader in terms of what they know. So maybe you're , you've spent a couple years as a, an operator in startups and a bit about what that looks like and you are much better positioned to write a quick write up of , Hey, here are the five things that I've learned about this [00:24:00] by making all of these mistakes. 

Then someone who's. 20 or 30 years into their career and probably doesn't even remember what that's like. So , one of the things that I talk to our execs on Deck Fellows a lot about is this idea of , thought leadership doesn't have to be polished. And actually it's better if you learn in public. 

And I think, , so many of the folks that I follow on LinkedIn or Twitter or whatever, that are really interest. Are basically learning in public and they're one or two steps ahead of where I am and, and I think that that's hugely resonates and , is really.  

Priyanka: Thank you for saying that. 

, I think it's great to have that distinction because you're right. You can't be a thought leader before you start putting ideas out there, before you start writing. The thought leader comes afterwards .  

I have this story where , I joined this company and I was , really new there. And I met a very senior leader and they asked me , are you considered a thought leader? And at that time, I never know what that meant. I was , what? And [00:25:00] I didn't realize it until I started putting things out there on my own, not thinking about it as thought leadership, but then I realized, oh, maybe that's what they meant, leadership, because then I heard more about that term and I was , oh. 

, for everybody out there . You want to tell people what are your ideas? Come up with interesting points of views and share that with the world. I think that is the more important things. And then that's what gets you to be quote unquote a thought leader or express your leadership in that ways. 

Laura: Yeah, a hundred percent. Yeah, and honestly, and I think personally, I was just so uniquely lucky in some ways that when I was at. Google X there was this huge demand for people wanting to know, how, , is the really early days. It was still pretty mysterious and there were so many people that were reaching out saying, we really wanna understand how is Google X innovating and, and how do you think about. 

, these radical innovations and, and all of this stuff. And at the time we were still a pretty small team and [00:26:00] Sergey and the leadership didn't have time to do that stuff. And so they'd be like, Laura, can you go talk to the c e o of L'Oreal and explain how Google X is innovating? 

And it was totally ridiculous. I mean, I was definitely not qualified to be meeting with all of these CEOs of, , huge companies. And providing my thought literature on innovation, but because, , it was such interesting new content and there was just no other option. It really was a great forcing function for me personally to get, hone that muscle of , Okay, well what have we been learning and , what were some of the mistakes that we made recently that might be interesting to someone else in terms of culture or projects or whatever. 

And so it was this amazing trial by fire of being forced to think in real time about , okay, I, I am speaking to. , X, Y, z, c e o this afternoon. And I need to come up with a couple interesting things to say and , what are, what's, what's top of mind right now? And , thankfully the Google X brand is informal enough that they weren't expecting [00:27:00] something super polished and , but I just think it was , I almost wish everyone had that experience because I think it was just so useful to get in the habit. 

Thinking through in real time what we were learning and practicing explaining that to somebody else because of course then it also helps you get really clear on it. Yeah,  

Priyanka: no, that's, that's great. And it goes back to what you were saying, which is a leader doesn't need to necessarily have all the answers you can learn in real time. 

You, I think what a leader can do is to show up consistently.  

Laura: Yes. A hundred.  

Priyanka: Well, , any last words of advice for our listeners who are, , thinking about leadership or are rising leaders in their own organizations? ,  

Laura: I mean, I guess I'm a bit biased, but I really do. I just hugely believe to the core and the power of community, especially as you get further on in your journey because, , I am someone that was like a very, [00:28:00] I think, I think technically it's called a nerd, but I'm gonna say a very dedicated student when I was in school. 

And , I love the structured learning. And , even now I do online classes and all that kinda stuff. I just love that stuff. But the reality is as you get further along in your career, , there's just not enough of that content that's gonna get you there. It's gonna be, , the peer community and hearing how other people are thinking about it and getting pressure tested on how you're thinking about, , certain challenges. 

And, , there's no. Book or a Coursera course or , whatever, as you get into that level of intricacy. So , I think I, I just hugely believe in, in community and the power of continuing to seek out community as you progress. And I think it gets even more important over time. 

So, so yeah, I think that's, that's something obviously I spent a lot of time thinking about that. And, and I, I really do think it's, it's key.  

Priyanka: Well, I totally agree and I think. It is something that I ask Aspire to do as well is [00:29:00] have a community. I've always thrived off of a community, even when I was at a bigger company. 

And my whole goal of starting initially when I just started out my website as a blog was to just build out that community of people who just benefit from what I had to say. But it has evolved into so much more. And I still, there's such a bigger vision that I have in terms of having a community of people. 

And so this advice, not just for people who are listening to this, but even works for me. So thank you.  

Laura: Love it. Well, I love what you're building and yeah. Thank you so much for having me. This was so. .  

Priyanka: Well thank you again for coming to the podcast and sharing such wonderful thoughts about, , community pivots. 

What's next for you?  

Laura: Well we are furiously recruiting for the next cohort of exec on deck. We're about three quarters of the way full. And we will, we'll kick it off May 2nd, and so if anyone is interested, definitely folks are welcome to, to shoot me an email or reach out on LinkedIn. And , obviously very excited about [00:30:00] that community. 

And , I think personally, one of the things that was most personally meaningful for me is with all of the, the layoffs and the macroeconomics right now, and all of those things. I think it's. It's a really hard time to prioritize investing in yourself when all of that is happening. 

And so, , one of the things that we did that I felt really personally was important and meaningful was we raised a massive scholarship fund. And so for this next cohort specifically, we're covering, I think it's up to 75% of the fees for anyone who is. And, and interested in joining. It would benefit from some coaching and some community. 

And, , for me it was non-negotiable and I'm thrilled that we, we pulled it off. So yeah, very busy meeting with new people for recruiting for that. And we'll see what happens.  

Priyanka: I'm sure a lot of people would really benefit from the ex Exon deck, so I encourage everybody to take a look, reach out to Laura. 

You can find her on LinkedIn if you have questions about it. If you have questions, I'm happy to [00:31:00] answer those questions being part of the community as well. And it's indeed that you're offering people ways to reduce the friction and investing in themselves because I do believe that, yes, this is a tough time for a lot of people in tech. 

Whatever we can do to help, , will go a long way and I'm sure it'll come back and, and become a full circle. So yeah, , I definitely encourage people. Once again, I wanna do plugin having been through the experience for the Execs On Deck program and happy to answer questions. I'm sure Laura would be too. 

And I'm looking forward to, engaging with the future EOD community as well. So once again, Laura, thank you so much for being on the podcast. It means a lot to me and I wish you and the OnDeck team all the very best , and looking forward to continuing to be part of this community. 

Awesome. Thanks for having me.