Conversation with Laura Butler

Episode #217
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Chris Williams: Laura Butler is among the most passionate and intelligent people I’ve ever met. Just keeping pace with her lightning fast intellect makes a conversation with her a delightful form of exercise.

Laura is known for having been Microsoft’s first female technical fellow. That title is held by just a dozen or two in a company that numbers over 150,000. It’s reserved for the most brilliant and innovative in a company where those qualities are not just common, but often expected. She’s an unabashed geek who sprinkles her conversation with deep technical analogies, and sci fi references.

But Laura is so much more than that. A multi-year voyage of discovery mid career changed her perspective dramatically. She began our conversation with this observation:

Laura Butler: What are the scarcest things in this universe? They are time, freedom, quality of life, and happiness. There are not enough of them. They are not evenly distributed, maybe 100 million. Okay, at the outside extreme, maybe 500 million people on this planet, get to, in some way, do things they love, make a living from it, pursue their dreams. And even if it’s 500 million people that is not 10% of this planet, it’s not enough.

CW: This realization and a return to Microsoft turned Laura into a thoughtful and respected leader. In our conversation, we talked about her career, her thoughts on leadership, especially as a woman, and her latest expedition into investing. And that’s what this is all about.


This is Leading Smart, the show about managing in the brainpower age. It’s a field guide to the joys and challenges of leading and working in the modern workplace.

I’m Chris Williams, your guide to the stories and ideas that I hope will inspire you to be a better leader in the world of knowledge work.

In this episode, we talk with a premier woman leader in the technology world. This is Episode 217, my conversation with Laura Butler.


Chris Williams: Laura Butler’s story begins like several we’ve seen in this series: a kid whose pure intellect earned her a spot in the Ivy League where she found her passion. She took a leap of faith to dive headlong into the tech world and there became a star. But as I noted, she began by giving a most unexpected answer to my question. How did you get into tech?

Laura Butler: I think it depends on the definition of tech. I want to back up and and maybe we should talk a little bit about engineering and what it really is and not the scary thing. Engineering’s a contact sport. Okay. It is about getting your hands on things making things and using science and logic and creativity, hopefully good versions of those things, to make things that solve people problems and it is done by people.

And what are the problems that matter are what are the the scarcest things in this universe. They are time, freedom, quality of life and happiness. There are not enough of them. They are not evenly distributed. Right? on in this planet, maybe 100 million. Okay, at the outside extreme, maybe 500 million people on this planet, get to in some way, do things they love, make a living from it, pursue their dreams, they turn their ideas into things they get to 3D print their ideas, okay? And even if it’s 500 million people that is not 10% of this planet, it’s not enough.

Okay, so So that’s my bag. That I was always in into, like one part detective one part breaking things and touching them one part making things but I just didn’t know that that was tech. So when I went to college, I knew what I was going to do.

I graduated early and not because I was a genius but because I was a troublemaker. It is true that the nuns of St. Mary’s Cathedral, school in Superior, Wisconsin were like, “we could reprimand her or we could make her skip a grade and get her the heck outta catholic school.” Like we’re pretty clear. Which one of those two is less trouble as paperwork anyway, okay.

So I went to college, I was going to be an archaeologist, doctor, lawyer, not because I wanted to practice… but I had this image of me like standing picture this little girl like but you know bossy on a pulpit. Okay. And archaeologist because I was gonna like skip over all the unfun part of that like psycho linguist, historian detective, international spy. Model was not in my feet like or athlete, I knew those weren’t my future. And that’s what I in math with mathematical research, or on the side, that’s what I was going to do.

And it turns out that you can’t get a degree in that. And at Harvard, you have to declare your concentration from freshman year, so I couldn’t even afford to do it. And from that is how I fell into tech.

Computers like that was just this really annoying class with really annoying people that just tried to, I don’t know, patronize you. That’s how it felt when I was in college, in high school. No, I fell into it because Harvard requirement called the quantitative reasoning requirement. QRR, QRA might be now today. And there were a limited set of options to meet that requirement, many of which most of which I had no time or money for. And I could either take math for dummies, which was a total waste of my time and insulting, or I could take a real programming class. So I’m like, well, that one, and everyone tried to argue me out of it, because like everyone else has built their own like Trash 80. And, you know, they like have been making games and you’ve never done this. And I’m like, No, you don’t understand. Like, it’s the only thing that fits my schedule and, and gives me real credit towards what I think I really want to do, which is mathematics / archaeology / biomedicine, whatever.

And it was freaking hard. It was crazy hard. I’m like, I think I spent a week of I spent 48 hours in one week, to make a Pascal program that would print out a triangle, you would give it a depth, okay, you give it like one or two, okay. And it would print out a beautiful little like symmetrical triangle. And on the even ones, I just had this off by one error. And I was so close to quitting because I’m like, I can’t fail this class, like I mean, financially cannot afford to fail it. It’s not even the time investment.

And everyone else in this class. This is how they would waltz in about two hours. Because like, I think homework homework was due at like 3pm on a Friday, they would waltz in at 1pm in the computer center, and they would just type type type and it would work perfectly and I would have been there the whole week. One guy who was also became an intern at Microsoft, as I did, felt like he like patted me on the head, you need my help? This is what I heard. This is not what he did. But this is what I remember. Hey, Laura, you moron. Like if you ever need any help from a real person who knows what they’re doing, like, just ask, I was so angry. It was stubbornness.

And then somehow I got over the hump. And then the harder the topics. The more ethereal, either investigative debugging Sherlock Holmes-ian and they got, or the more theoretical weird mathematical things like recursion, oh, it’s just inductive proof, like the better I got at it. But it was pure stubbornness. And no other option that got me into tech.

CW: One of the things you said was that when you got to Microsoft, it felt like the Island of Misfit Toys and and a really homey place to be because there were a lot of people like you. Tell me about that.

LB: Yeah, that was my first real home. And I mean, home based off values and style and not physical locality. I mean, I had two homes, that didn’t feel like places I was wanted or belonged. Well, I needed to get a real job that paid real money instead of working in my town grocery store. So I got my act together, went to the Career Center in February of nine, teen 90 … 1989. And this person just who was a woman, it was Karen Hargrove, you might remember she was really the first head of Microsoft Research grabbed me in this room, and I just got asked these interesting questions. They weren’t stupid questions like, can you please make a 90-page, you know, Turing machine that I’m like, who cares about that? Or can you please solve this complex analysis problem? And then you’d ask the teacher questions like, well, it’s obvious meaning they didn’t know. These were like useful things. They were like, can you get yourself out of it? How would you get yourself out of a room with some popsicle sticks, dental floss, and perfume? And I’m like, I can think of at least eight ways, you know, I’m like, I know how to do these things. I’m a life hacker already.

And next thing, they’re like, Oh, great. You want to come to dinner with us? And I’m like, I don’t have any money. No, like, no, it’s free, you idiot. And I’m like, great. Where is it? They’re like Legal Seafood. So I’m allergic to shellfish. I don’t eat seafood. And I’m like, I’m in but I don’t have any money to get there.

And they made it so easy. Like, they this was a place that seemed to want me and they made it easy. They sent me a ticket. They told me where I was gonna be it wasn’t a Oh, Laura, you want a major mathematics? Well, that’s too bad because you’re not going to be a Nobel Prize winner. So we’re just not going to be around. You’re going have to forge a signature on a card and you have to pay a fine. That was just like every class at Harvard.

And I showed up was Memorial Day weekend. It was a Saturday that weekend 1989. And there was speaking Japanese and SeaTac airport and I take in Japanese. And I’m like, it was like going to a 24 hour grocery stores. I had to break my way in the building. And I’m like, this is a place that rewards like common sense. Like, I like this place. And it was wonderful.

And I think the other thing that maybe isn’t so obvious to younger people now was how diverse and creative it was. There was no like discipline, you could not go get a useful computer science degree, not one that would have you prepared to work on anything, that the Microsoft’s or the DECs, or the Texas Instruments, or the IBMs were doing it was like all a joke, right? So they’re like, we’re looking for creative problem solvers. People kind of hack and kind of have some social hacking skills. There were more women like Jody Greene was the head of Word for … DOS Word at the time. And it was really wonderful.

So I was there for the summer of 89 on Word for Windows, and then I was like, I just can’t imagine going back to school, I’m getting paid to do things I like and learn cool stuff and be treated like a grown up, or I could try going back to school, which is the … and I’m like, Okay, well I gotta defer this decision. So I actually took the year off without Microsoft tried to go back for my junior year in the fall, and I’m like, screw this. And then Brad Silverberg, called me, and he’s like, you should just come come to Microsoft, like, this is just … a Bachelor of Arts in computer science. It’s like just a waste of your time. And I’m like, so spot on. So then I ended up dropping out. And that was a hard conversation to have with my mom.

CW: I bet.

LW: Because she had dropped out of University of Wisconsin because she was working three jobs. And she had put herself back through school later, and it was hard. And she wanted so much more for me. I also didn’t realize she pretty much spent every penny she had to for those first two years. And I mean, and was almost destitute, can you imagine and I give her a tremendous amount of credit for supporting me in. And I guess I didn’t realize how selfish I was in my dreams. And we thought that we had any idea that Microsoft is going to be incredible. It was just that she understood that was my place.

And so I ended up in Windows, because nobody else wanted to go there. They were desperate. It was fun. And I had a pulse and I said, Yes. And I think that have has probably ruined me for the rest of my career, which is that showing up, saying yes, going to problems, not these beautiful things on a silver platter is where you can actually get a lot of fabulous opportunity. Now sometimes you could also be throwing yourself off a cliff like a lemming, right. But that contrary it is.


CW: Laura worked in Windows as an individual contributor finding and fixing bugs in some of the most complex code. And in ways that got her exposure across the company. I asked her if she remembered when she first managed people.

LB: Well, I remember in unofficial management, which is probably what leadership actually is, right? It’s not the authority of a gun. Okay. And that was after we shipped Windows 95. Accessibility was on the rise. And what is 95 broke at all, in the state of Massachusetts to just passed a law, the Americans with Disabilities Act, and was going to ban and then the federal guard was going to ban. So it started as this panic “crap, somebody who understands like windowing, and all this and who’s a little bit of a hacker”, and I went into a little bit arrogant. I mean, I was flattered. I’m like, Oh, I get to be the tech lead on this thing. “Well, thank God, they, you know, they contacted the person who’d be best at it.” And it was really an eye opener, like my partners Chuck Opperman, and then Peter, I want to say Peter Wong, who had vision issues. He was our tester, and also our best user.

And it went from being this disaster hero thing in my mind to being a this is really important. Like, wow, I didn’t, I mean, I didn’t realize like, This is tough. And how many of these things that these tools are doing like Dragon Voice Dictation are actually useful? So I had to be a little bit of a leader on that because no one would give us any cycles. So we had to kind of go reverse engineer, some of the toolkits that like Office and other things were using.

But after that, I kind of got stuck I got caught kind of got caught in this no person’s land. And I was just sitting in my office being I have nothing to do nobody wants me like what am I and this these two people Blake Irving and Kurt Smith show up in my office and Blake really got chartered with with me some apps for the internet. And then he went on later to go run Go Daddy, story for another time. And Yahoo was at Yahoo before that. said, Hey, we have this suite of tools that this is 1997-ish, right? are doing video conferencing and screen sharing and collaboration and meetings and messaging on the internet. And, like we were partnered with this company in the UK, but like, we cannot get this to work on Windows or NT, because I’m going to need to have a display driver to catch what was going on. And we need someone who knows this stuff, and we hear you’re free. And I’m like, I was just so happy to be wanted. And then they’re like, so come aboard. And then before I knew it, they’re like, well, we need someone to be a Dev Lead to the area.

And in this case, actually, I still think this approach is probably is the one most likely to succeed. It’s not the only path that anybody ever gets. And you shouldn’t hold out for it if you don’t have any other path. If you have another path, but I was the subject matter expert in the area. And I had built trust with the people on the team. And I knew my management already. So it was a supported a job. And in this case, I mean, I wasn’t really managing, I was pretty much doing what I was doing before as like the number one Dev, and then everything else I didn’t I didn’t understand what the role should be. I think at the time, it was a little bit more like Well, clearly, I’m the best, you know, a little bit arrogant, like the best person to be a lead on the team. And I just had really great, I was very fortunate that I had support side sponsorship, and I had a thing I understood and it was relatively stable for a couple of years anyway, like Microsoft was pretty clear, it needed to have something for the internet. So like that wasn’t gonna go away tomorrow.

I didn’t change my ways that at that time, I had to kind of leave Microsoft kind of realize how wrong I was about that job. Because it was all about me. I can look back, and I can’t believe that most of the people that I worked with still talk to me because I must have stressed them out. Okay, belittle them in some ways, and probably kept all the fun stuff for myself. Because it was these were actors in my play. That was not I was not a leader then.

CW: Right? You were a supervisor at best, right?

LB: Yeah, I was, you know, I was the number one I was the Alpha Dev. That’s what I was.

CW: You said you weren’t a leader, then. Do you remember becoming a leader? Do you remember the realization that came to your head that said, suddenly, I need to think about this differently?

LB: Yes, but it wasn’t like a moment in time. So I was doing that first thing. And by the way, just like as an IC, as well, individual contributor, you can kind of get it out until you get to staff engineer / principal. And then the things that are like, I’m just gonna work a little harder, a little longer, a little faster, they just fall over. So I’m going to take that example outside of management because it’s a little simpler, right? Where to become a to be a principal and be a good one means it’s more work than 168 hours of a very fast typist, it’s about having influence when you’re not there. And it’s about teaching. And a lot of folks that become principal, were like alpha Dev, right, and then they’re like, Okay, I’m just going to type even a little bit more. And they know, intellectually, that if they would, could just take the time to write something down, take 30 minutes and teach somebody else to do it, who might do it. Even if that person did it at two thirds as good. It would add up, but the feeling isn’t there. And you have to almost let people kind of get half into the weeds. Until they kind of realize that, hey, like the job is you’re building a civilization when you’re at that level or higher.

You can get away with a lot in a crisis situation. And it doesn’t mean that consciously you’re trying to although if you look at World circumstance, you know, it’s a classic sign of a petty dictator to manufacture crisis, because you can throw principles and longer term things and measurements out the window because it’s all something’s on fire. Who cares? You know about how many people in the building get burned if we save their lives kind of a thing. So I managed to get it out cuz it was on fire and the strategy and then I landed on the wrong side of reorg. And I went, screw you guys, these boots are made for walking. This isn’t what I signed up for. I could have told you what I had signed up for other than some stability and belonging.

You know, to be able to I can actually take my mom and travel overseas to places we only ever got to read about in books in the library. You know, it was a wonderful, those are wonderful moments, right? Like we can buy fresh squeezed orange juice. You know, money is a means to an end and it’s not linear. You have these moments of like, I don’t have to sit there living in stress, trying to squeeze pennies.

And anyway, as a total aside, there’s a fabulous book by Barbara Ehrenreich called Getting Nickeled and Dimed in America and about, you can see it in health numbers, right? It’s not even unhealthy diets, the stress over the long term it takes on people to live hand to mouth, they pay more for things if you don’t have savings, you can’t put a deposit down on an apartment, right? Okay. Sorry to work in. It’s not really politics. It’s called economics in there. And I mean, I’ve lived it so it’s very personal to me.

But that you can get away with a lot like like, you don’t have to think about the long you’re not planning for long term anyway, so I get on the wrong side of reorg I’m like, screw you guys. I’m out of here. And then I was left angry. Yeah, I had to escape and I had to figure something out doesn’t mean it didn’t take me time to kind of you know, get my head straight cuz this was my home. It was like I was cast out of Eden. Okay, I mean, I walked out but it was like, but you’re supposed to like, run after me and fight for me. You know, it’s very again, very self centered. Kind of narcissistic and insecure at the same time.

So I had to grow up. And that’s a story of my life when I was, you know, 14, I’d be like, well, I can explain to you like, you know, why three dimensional fluid flow blah, blah works, but I couldn’t make toast, I’m like, I have to plug the thing in, like, that’s make any sense, I have to push a button first to start toasting. So I would say very uneven levels of common sense and weird theoretical knowledge. And that was also true in human relations.

I mean, I went into engineering or things in science to get away from human beings. You know, human beings are hard. they hurt your feelings, right? They call it they tell you, you’re weird. You don’t belong you. They’re messy. They’re inconsistent. And yet, and science is beautiful. You got these equations, and you’ve got these grids, why Excel is the tool of the gods, right? You put everything in this beauty, right angles, and it’s just fantastic.

CW: I have often said that the reason I got into programming was because it was so black and white. It was either faster, or it wasn’t it worked, or it didn’t, there was a bug, fix the bug.

LB: And it turns out the world is not binary, it’s quantum. And that’s where a whole lot of like programmers are now like having these existential crises. But yeah, and so I the whole, I was in denial of the human element.

Like that thing I said about time, you know, freedom. Like that wasn’t in my head, right? So I needed to live and then I was gone for like eight years. And in those eight years, yeah, I did adventure travel, I thought about being a weightlifter, I, I did literally read The Decline and Fall of the Roman Empire beginning to end I read, you know, Russian novelist, I’m like, I think I want to learn, earn, you know, or like all of these things you think about doing on your bucket list. And but then the travel was probably an adventure travel in particular was really the big thing. Because you know, what, you can’t control everything and adventure travel. If everything is controlled, it’s Disneyland, it’s not adventure travel, and you’re uncomfortable, sometimes. You know what, there’s nothing, I doesn’t matter if you’re staying in lodges. If you’re above 12,000 feet altitude, you’re just not comfortable, okay?

And, and I found I can’t like, but you might see something incredible. You’re not gonna see a Yeti or Sasquatch down at sea level, it’s just not going to happen. But who knows what could happen up in the Himalayas, right. And also be in these places I’d read about like, history came alive. And then you see the human condition. And things just makes so much more sense. Like you could read about something and think “that’s so stupid. That’s not logical.” But when you’re there in the geography, with the history, you totally get it.

And so I just sort of couldn’t separate the travel and all these history and all these things that were just theoretical that I sort of wanted to do, from the experience. And I so I grew up. And then it was at a startup for three years, I had no clue what I was doing. And thank you so much to Rich Stokely and Joe Matthews, who even like hired me that thing we folded and then Microsoft called me the next day, it was 2009. And I was like, I was such a different person.

But I got to kind of do things the second time, a little bit, in a different way. But I went, I knew from the beginning, when I started, like, I have a philosophy. And I have a value of what I’m going to bring. And honestly, I went back thinking I was Mary Poppins. I’m like, you guys, this is like a human right? This is a human rights intervention, these poor people, many of whom I’d work with on Windows 95 are being subjected to this terrible thing called Windows Mobile, just going through, it’s like 82,000th reset. And I’m like, they just deserve better. And there’s no way it’s going to be successful. And by the way, I think the problem — contrarian — as expressed is just totally wrong.

So and I knew that I had left once, and the world didn’t end, although it felt like it would. And that push came to shove, if I had to walk, I could. Now that said, it can’t be the anytime you don’t get something your way. It’s like I’m taking my choice going home. But weirdly, that freedom path freed me to be more in, I could be all in. Because I could I could fight and push for something that was if I thought it was right. And it was important. And if I got yelled at or I didn’t go my way, like okay, I can walk out of here still with my head, like the world won’t fall over. I think the first time I was still trying to follow the rules, maybe I was just trying to figure out what they were please people too much. or completely go out of my way to not please them because I hated the idea of that I’m supposed to please people as you know, an employee.

CW: I love the idea that what you’ve done is understand more about yourself, which makes you better at understanding how to be a leader. I mean, I think that’s, that’s really crucial. Right? I think it’s one of the first things that that I think there’s a number of people who think that leadership is all about power. And really, in fact, it’s the inverse, right? It’s very much in many ways about granting… power.

LB: Aren’t the most powerful, real powers be able to create more power for other people, isn’t it and you have power when you’re very comfortable with other people who have power you’re a petty dictator? Or not.

Yeah. I think there’s something to that. But before we even being a leader, I mean, even just to think to be a partner, right, whether as a friend or a spouse, or a colleague, like, if you don’t know what things like piss you off, what things are, which is separate pet peeves are separate from moral objections, right what your principles are. And you can’t, if you don’t know what your own are, and why you’re on, you’re doomed to be unhappy, and you’re doomed to be a crappy partner. And if you can’t figure those things out for yourself, and also understand the difference between, you know, style and substance, how can you respect somebody else’s viewpoints on the same thing. Right, because you’re not secure, you don’t even know what your what your variables are, you don’t know what your formula are.

And I don’t think you can be a leader if you can’t be a partner. Because I think part of leading at least the best leaders I have ever worked with, or worked for, know when the Best Leading leadership is following sometimes it’s all about being in the front. When to give other people, let them have a star have their starring moment. And when you’re a leader of leaders, what person what amazing person wants to work for somebody who takes all the credit, and then just shifts off all the blame? Like, you know, they, it’s not just about Oh, you own your area and owning your area means if anything goes wrong, you’re fired? That’s not it, right is that, hey, you’re the star of this area, you’re the star of this episode. And I’m comfortable, like, not just comfortable, but I’m going to actively work to get you you know, you’re starting credits.

CW: Do you feel like having technical chops was crucial to your ability to be a leader?

LB: Ah, this might get into is like tech management tech leadership different than general leadership?

CW: I was gonna get there…

LB: Yeah, well, I think it’s pretty mean. Yes, well, I do think you have to have, you have to have domain knowledge about some things, it’s just that there’s multiple domains. Let me backup.

Um, you’re a highly paid person could just picture someone who got hired and hired into a company and they’re new, they don’t know anybody … better be an expert, and contribute in something right away. I think it’s also very hard to settle conflict and disputes. The easy ones are, you know, the black and whites, right? The value is all in the gray. And I think it is hard to have good judgment. And it is hard to have people respect you. If it is just theory.

That doesn’t mean you have to have a PhD in computer science. I have also personally found that having been in the trenches and being being the first person to jump in the trenches. And I will take the things on that are grungy, A) because it helps me understand what’s going on the team, 2) because I’m an engineer and at my hands on it, 3) you earn a lot of goodwill. And 4) I am unblocking my team so that the domain expert, the person who is the world’s expert, in convolutions, right, can do her thing. And can put the maximum energy into this hard space and not have to worry about you know, the piling up diet cokes. Right, is that the only thing that you know, I’m overpaid, if that’s what I’m doing, and just just grocery shopping for the team. It’s also very approachable.

I think it also sets sets of tone of nothing is beneath any of us, we’re here to be successful. It’s not about status or title or what have you. But I just I think it would you would be miserable. How would you know you would not have this intuition? People even if you did, people would second guess you are like, Oh, he’s just the suit to have to find ways to have credibility. And it is okay to say, “Hey, I’m the GM of this group. And the reason I am I signed on to I mean, I’m the only person who could do this job I signed on was, the tech is obviously strong. But we’re having a problem with our product, like we cannot seem to explain to customers or potential customers like why this would be good for them. I am strong in that area”, like asserting your value.

And I think that’s a … but but if you are managing tech people, it is a bunch there’s a bunch of classic tech phenomenon. First of all, anyone who’s not a techie, is somehow inferior. Every tech person thinks she’s a leader. Every engineer, right? is a leader of her own DLL, you know, class, component, right? It’s like cat herding, not engineers are cats, not dogs. And so and the, “I said so”, just does does doesn’t work. Or I’m your manager. So please, you must do it didn’t work for me when I was an employee. And I think people that go into management or want to be managers, and when you ask them why they’re like, well, because then people have to do what I say you just like laugh your head off.

So I do I think you have to have otherwise why unless you can articulate that the value you’re bringing is complimentary, that the thing you’re doing more than anything is you’re providing a shield, but you have to articulate why your overhead because you’ve just added another layer right of hops justifies the dollars and potentially the latency that it adds.


CW: Part of what Laura learned in her years away from the tech industry was that the people side of problems are at least, if not more, fascinating than the bits and bytes. She even began to think about leadership in terms of the love in the team.

LB: Yeah, well, you know what engineering, the team is engineering. So I think that the single biggest spark, and this is probably only six, seven years old was that my job now or as a leader is my I’m still an engineer. But my engineering is engineering the civilization. And the civilization is the thing that engineers the product, and it has to endure, because I might get busy. There could be a reorg. Right, but it’s still engineering, the problems are all the same. You’ve got latencies, and flows and parallelism and, and errors, parity errors, they look exactly exactly the same as a distributed, you know, end to end service.

And then, if you believe as I do to make something great, takes a tremendous amount of energy and willpower, and it’s not linear. Right? If it takes 1000 X to make something good, it takes 10,000 X to make a great. Right. And then like, I mean, it’s relativity, right. It’s energy that that is you need a tremendous amount of energy to do those things. You can’t afford waste. And stress. I mean, this is neurobiology, right. Long term stress is an enemy of creativity, like it shuts down longer term thought process and risk taking. What about this? Are you sure I mean, people just in panic, right. And you see it in teams, and it just depresses people’s souls, it drains their self worth.

I mean, I just finished reading God, the book by Susan Fowler “Whistleblower”. And I mean, it just makes me so angry. And this isn’t a gender statement, just what Petit? Absolutely horrifically bad poor management. Right, in every possible way, technical human. And you could say, well, Uber succeeded… Did Uber succeed?, they’re still not profitable. Right? What could Uber have been, if they’d actually invested in human beings? Right and scalable systems? Anyway, that’s just a rant for another time.

So Love, love is that force. And it might seem like a weak force, like gravity, but that is the thing that keeps a group of people and I mean, love in a pure sense. And I don’t just mean acceptance and tolerance, because how dare I even think I have the right to tolerate you, Chris. Like, that’s pretty narcissistic, right? I mean, appreciation, and in exchange, you appreciate me. And it doesn’t mean I mean, there are bad families and bad love. And that analogy can hurt some folks. But that when we are in this place together, all other affinities go by the wayside. We might have opposite political views, we might have come from other sides of the planet. But we have this incredible thing in common.

Yeah, I think that that cohesion being unified, not unanimous, being unified. And also, I mean, I’ve been in groups where people were afraid to speak up. And you know what, those are not healthy products. Because by the time someone does speak up, or you catch a problem, it is really late. Right, and it’s so much better to mean prevention, and then or very early, you know, early detection and and solution when it’s really low cost.


CW: Laura gave a keynote speech at the University of Illinois a couple of years ago, and much of what she talked about was how essential diversity and inclusion are two great teams. I asked her to explain that in more detail.

LB: Oh, man, well, I am a radical on this topic. Because I think you know, it’s a love hate topic. You’re like one of the dudes and you’re talking about like, like, I don’t know, Watson cab processing improvements. And then someone reminds you your other? Or they ask, “Hey, Laura, I’m interviewing this woman for my team. And we can’t get any woman would you like…” and then and you want to help but then there’s this moment where there’s this invisible line and all of a sudden you’re on one side of it and the other. But then it doesn’t get better if we don’t talk about it.

Like I used to feel this way about talking about breast cancer. I’m like, Oh my god, I kept saying this word. Guess what people died of breast cancer for stupid reasons. And now it’s just normal. So we have to talk about it. Okay. We can’t talk about it. There’s just no way if we can’t measure it, like it just can’t get better. So we all have to get out of our comfort zone a little bit that said, it takes … it’s an extra energy drain. Right and in even in the best well intended circumstances, like someone who’s actually asking for my advice, and help.

So I just think about this completely differently. To me that it’s not actually unusual that the acronym of DIE spells die, diversity, inclusion, and equity. So here are the things that drive me crazy. First of all, putting that to the side, one of a bad, one of the set of behaviors in a bad team team dynamics is when people act like it’s zero sum. Right? If that guy got promoted, then I means I’m not that I don’t get promoted, that person got rewards, I don’t get rewards. And that guy’s a moron, and I’m not so like, they don’t value me that that idea that somehow, it’s zero. And it’s being taken away every time it’s distributed. When the reality of a team, a good team, is it’s better than the sum of its parts. That’s why we’re together. Right? Yes, you give up some things, you give up some things in society, right. But you get a greater whole. And there’s probably nothing more profound you can do as a leader than really beat down on that one.

Like, I used to say, look, let’s demystify how this whole thing works. In that we’re going to be public about who’s promoted. Because rumor is really bad. It’s one thing for people to be angry, it’s another thing for people to be angry and do stupid things on the basis of false info because you can’t even fight it. Okay. And that is a stated goal of mine that ever been in this team gets promoted, you have to do the work, but I am actually failing, if you don’t get means I have failed you. And by the way, like the budget is set up for that it’s my job to spend the budget. And I think kind of that relaxation, just whatever the makeup of the team. So I bring that up. Because I think that sort of zero sum behavior is the feeling that all of us get at a much worse and multiple dimensional level, when we often talk about diversity and inclusion, like somehow, it’s a tax we all pay. It’s charity. So we can kind of feel kind of good about ourselves, oh, we gave that guy job. Whoo, right. And it, and it’s this thing you should do, like you should get up at 5:30 in the morning and do one arm push ups that you really want to stay, you know, everything about it. The way we talk about it is emotionally loaded wrong, and makes people hate the topic. This makes me hate the topic.

And you can’t win, because you go to some like big, I don’t know, presentation of Microsoft, like let’s say it’s the the quarterly group meeting, and some dude gets up and say, I’m gonna talk to you about diversity and inclusion. And I’ll tell you what, I think instantly — this is me — I think this guy must have been like, had a problem in his team, or he drew the short, short straw. So that’s why this this white guy’s talking about, you know, diverse and inclusion, or if it’s a woman or a black person or a Latin or Latino, right, or an Asian. Oh, well, of course, they’re giving the diversity talk. And they can’t know and they must be incompetent somehow. And you’re like, Well, I think they’re pretty competent on the subject matter. Like you can’t win and that all staves from this, putting people in a bad place or the way we talk about it.

To me, it’s exactly the opposite. First of all, I like hard projects. I love bargains. Right? Like where you get something that’s amazing. And you got it at a discount besides, I like things where people wrote it off. And then you show them how wrong they were just makes me happy in so many ways. And I did it thriftily besides, and you know what, I’d have never worked on anything where it was a silver platter with an unlimited budget. I don’t think there’s a team at Microsoft that has an unlimited budget. I think it’s pretty funny when you hear people go, “Oh, well, yeah, that person got hired because of diversity.” And you go “Really? Like, are you telling me that your team has all this money and open positions, like and to just throw away” and nobody has that? You’re like, Oh, no, I can’t even get funding for my servers. I’m like, do you really think that a business is wasting its money on? Like spending money on that, like, that doesn’t happen? Right? And people like oh, yeah, I guess that’s right. When you talk about it in more of a scientific way than a guilt way, in an engineering way. Okay.

But because I’ve never gotten that, guess what, I have to be creative on hiring. I’m like I my chances of landing a top Silicon Valley bro engineer, relative to Elon Musk are vanishingly small. I can’t compete that way. I’m not going to run Elon Musk. I have outsmart him. So I have to go a different route. And one way it could be like cookies, but even that’s a lot of work. So I have to go fish in different ponds and moreover, guess what ponds with people that have more grit you know what those top entitled Harvards — which I know cuz I was one — Harvard. They’re like, I don’t want to have Amy Hood’s job. I’ve been a Microsoft for two years, right? Like the entitlement that comes with it. And then if there’s a tough time, they’re like, screw you guys. I’m getting called by recruiters every hour.

People with grit. People who are like, thrilled to have the job. It’s not that they’re, they’re trapped. But they try harder. They’re more in, they feel more valued. They put more of themselves in the group, so grit, and it doesn’t matter. Now, it just so happens that if you are an engineer who’s a woman or of color, or transgender, or an immigrant, or from the Midwest, or poor, didn’t go to an Ivy League school, you probably have more grit, things you had to figure more stuff out doesn’t mean you’re smarter. But it means you got more street smarts probably. Now there are lots of other things. aren’t so obvious, right? Like, oh, you had terrible parents even just because you, your parents were wealthy doesn’t mean you had it easy. It’s just that these things are more obvious, right? And a little bit easier to measure and see.

So that I think about and then I think about innovation, and so grit… First of all, ability to hire, and the ROI on that. Grit, which you really need on hard problems, because they’re just not going to get solved tomorrow, innovation, looking at these things differently. Willing, you don’t have to, you don’t have to try to think different if you are different. Like remember that Apple slow, think different, you have to try to think different if you are different already, like your camera’s already in a different place. And innovation doesn’t happen in the mainstream by definition. Right? It happens on the edges. So I think about that.

And then I think about scale and scope. If you want to change the world or world changing problems, you take these takes people of the world to do that. The energy that it takes to do those things, that energy, it’s getting wasted on not belonging, or people who are just ruling themselves out or patting themselves on the back or their their reason for being there as their with their friends only like those that’s energy that’s not going towards making the thing excellent.

So that’s just how I think about, I think I think about it as it’s about grit and belonging, and innovation, and scope, scale, and then succeeding at hard problems, which are the ones most worth doing. It’s just there like, you know, there’s no little like, I don’t know, solution for those things.

And also, if you think about last thing is change happens so much, especially in tech, there’s people change, environmental change, financial change, reorg. You know, every quarter, there’s a reorg at a big company, because of the way that finances work. It’s very hard to be resilient, if you don’t have connection, if you don’t feel like you belong and your network is limited you are electrons at the edge of the atom. When there’s a disturbance, those electrons just shake free. Right? So you really want a team that’s unified, that has cohesiveness when the hard things hit.

And you have to measure it and report on it. So I think I know people are leery about this, because oh yeah, what about quotas? I’m like, somehow we trust the sales team at Microsoft to have very hard targets have their entire compensation tied to this thing, and we report on it on a weekly basis. And we but we believe that ethics will will catch violations. And somehow we don’t think that having targets OKRs or anything else that’s people related is okay. Like that’s just ridiculous to me. If you don’t measure it, you don’t report on it, you’re not accountable. Right, you don’t have integrity, then you’re not serious. If you don’t make decisions in favor of something at the expense of short term dollars. You’re not really serious about it. And that’s fine, but just don’t fool yourself.


CW: One of the first things you note about Laura is that she’s a little off beat. Her email address includes the phrase “cat PJs”, and she frequently talks about baking cookies for the team. She seems to revel in being a little quirky. I asked her if this helped her build teams as a leader.

LB: Yes, absolutely. It helped. It breaks, it brings the defenses down. It’s like a virus that can slip into a cell past the immune system because people are relaxed. You can kind of help you can land concepts when people are relaxed, much more than you can land new things when people are defensive. Right?

But that it didn’t just relax me it relax the team. Because in that first round when I was made, I think I was so uptight it like I stressed everybody else out around me. And they wanted, like, I wasn’t nasty, I wouldn’t like scream at you until you were an idiot if you screwed up. But that like it was just tons. And that you know what if you’re a leader can just laugh at something like Oh, go, of course, we decided to upgrade SQL Server on our build systems the day before we have to, you know, ship an update to the EU, you know, you can laugh about it and be like, it’s just a bug. Right? And they can also be laugh at yourself. Be like, well, who knew that internet meme isn’t legitimate? Like when I put this presentation together? It lets it gives everyone else permission. And that people realize if you don’t take yourself too seriously, they can bring stuff up, but they would be afraid to say to somebody else, no, I mean, it should be respectful and timing matters, right?

And that that was a huge win for the team in many ways, both for the product and for themselves. And that a lot of other a lot of people who felt like outsiders or they were the misfit in their team, consider well this is Yeah, hey, look, there’s a Island whole Island of Misfit Toys. where I fit.

It was great for recruiting absolutely great. And people know what they’re getting in advance. There’s nothing worse than a lot of energy recruits a buddy and fooling them. And then they get there. They’re like, well, this isn’t what I thought was gonna be like you’re just not only wasted time you’ve created lifelong, you know, enemies, right? So people knew what they were gonna get. They knew what they’re getting when they when they would come. And they felt welcome from the beginning.

CW: Laura spent time in each of the last three decades at Microsoft, I wondered if her experience as a woman in tech had changed in the time she was there.

LB: Yes. And I’ve got to be really honest, that I am not the hugest fan of the, personally of the Satya Nadella era. And that’s not a statement about Satya. But I understand that a lot more people are happy, happier with it, because it feels a lot of feels superficially nice. And I can tell you that an enemy of career in particular is and that doesn’t mean you have to be mean. Like it’s not a you can be nice, or you have to be like, critically hard.

But But telling people they’re doing fine. And then when they get their annual review, or they don’t get a promotion, and then it’s out of the blue isn’t doing anybody any good. And I think that there’s a lot of superficial niceness and well intended. But that is an enemy of solving problems. And that it also causes a lot of conflict to go underground. Like you can’t say, you know what, like, I just don’t like you. It’s very hard, right? Or like your, your approach to programming, you know, the windows shell is just like so opposite everything that I like I like but we have to work together. So let’s work it out.

It doesn’t bother me like wasting my time bothers me more than like, a meeting where there’s a lot of shouting going on. If it’s genuine. I would rather know that like, oh, the reason we’ve just like gone nowhere for six months is because the head of our division freaking doesn’t believe in consumer products. Great. Than a superficially nice meeting or everybody? Yeah, okay, you need both truthfully.

I’m probably particularly looking for things. I think someone’s trading me with a kid glove, because I’m a girl. And I’m like, I can take it. I might cry, but I can take it right. So please don’t treat me like a child.

I think the thing that is frustrating about Microsoft today, for me, is the intent, at the level of the SLT seems to be very good. Okay, I believe it’s genuine. And there’s lots of PR, and there’s lots of programs and so on. And yet the reality is not there.

There is not a woman at the company who is has a chance. I mean, actually, Peggy Johnson was probably the only one who could be a successor to Satya truthfully, she’s more qualified. I mean, on paper than okay. And if you go one level down, there isn’t anyone in the engineering group. So Microsoft, an engineering company, right? It’s a platform engineering company. For the head of Office, Windows, the head of devices, the head of Azure and it’s not anybody’s fault, okay, it’s not evil intent, all of the ones that are for research that have been are gone. And that continues, and then that just sort of kicks it down.

And then thirdly, I would say, like, the people making the decisions are sort of, I mean, I would put myself, like, let’s be honest, the execs at Microsoft, including when I was there were a bunch of like, middle aged suburban like white people. Right? It doesn’t mean we’re, we’re evil, we’re bad. But like, if it’s just and we’re like hang out with each other, like that just can’t transform a company in the long term. Right? The same time, as you know, like massive blood transfusions, hurt patients like what’s the right level of insider outsider, an outsider taking over from Steve Ballmer. It’s just hard to believe how that could have ever worked. Right? Not even if that person whoever that person was, because everybody else, you know, would have kind of circled the wagons.


CW: We switched gears and talked about what she’s been doing since she left Microsoft last August. She’s been investing both her money and her leadership in a stunning array of startups. She had previously told me she only got involved in projects that interested her. I asked her how she got involved in so many things so quickly.

LB: I think as a small person, I am very, very good at seeming to take up a lot of space, like I call this woman spreading, you know, and on LinkedIn and Twitter, like, I am an amateur. I’ve been doing this for all of like a year and a half. And I’m a delighted total amateur. There’s not a lot I can do. If one of the people I’m connected to said, Laura, I’ve got this really complicated ratchet with a cliff and like, do I and I’m like, damned if I know, but I think Brad Feld has probably read you know, that’s about like, but what I can just put it on LinkedIn. And secondly, there’s a leading by example.

So backing up, like I was intimidated by this, and I don’t know why because I’ve always thought about I’m always investing, right? I’m investing my time, my brain, my heart. My knowledge, right like computing power versus expertise in people and things all the time. Charity is an investment. Right. And it’s an excellent defense investment, but you can’t win Super Bowls. Just defense, right? But I was intimidated by this. I don’t know where to get started. And then Okay, maybe these are lines of angels. And then I don’t look like most of those people. And I overthought it.

And the truth is, the best way to learn anything is just to like, do it. And then you know, you make sure your safety nets and what your budget is. And then well, what do you want to get out of it? Who so I wish I had just so I really just started year and a half ago with two people who I’ve known, I wouldn’t call them mentees. But that I had like met, either through like University talking at universities, who were not in a place where they could just, like, throw over their job and found a company but were very, like, they’re entrepreneurs. And I’m like, Well, can I like invest in your companies, like, I’m already invested in you, it was just a natural extension. And they were like, Okay, I guess I better incorporate them.

And I’m like, this is awesome. And then I’m gonna learn a lot. So it’s not just the I love being a fairy godmother, like, Can I be the spark, and then get every so you know, there’s a little bit of like, I was like this with music. I’m like, I’m the first person to like a band, you just kind of, and then everybody else sort of became a fan of, you know, Nirvana “well I was in Nirvana fan back…” you know that you feel good about yourself, right? But it’s also that, I don’t know, it’s that getting over the cattle that whatever that catalytic threshold is for combustion.

And then having just believing in people, because sometimes that’s all people need to hear is that there’s someone who believes in them and is there who will make sure they don’t fail. Or, or, if the business doesn’t work, that’s not failure. Right? And that I’ve been clear up front that like, my return is already sufficient. Like the day we’ve signed the papers and everything else is upside.

And that as I’ve been doing it, you know, realizing this has been incredibly valuable for me deciding to take a leap and found a company too which I was scared of. I’m like, well, these folks can do it. And I’ve learned a lot and I have an army of people I can ask questions of, I can even be like, Oh my god, Jessica Eggert of Leg Up makes like the absolute best business plans I’ve ever like, Jessica come, I could have borrow like eight of your slides, right? Or Ming Yang of Orchard.it, I’d be like, you’ve just won multiple competitions in Florida. I’m like, Can I look at your submissions. So that’s been wonderful.

I have a huge network. It turns out just by being in being in this industry for so long, and maybe being memorable, I feel like I’m like, like the Queen Victoria crossed with Kevin Bacon attack that starts since I could probably find a one hop route just about anybody. And so I’ve just met a lot of people with dreams and plans, and ideas. So it’s not as many investments as it might sound like, and I’m like, mostly hands off, but I’m there, hey, if you need a hug, I’m here.

I probably go for breadth over depth, like tipping point moments. Because you know, if you were a stock, if you were in the insurance business, or stockbroker, like small problems, or gambling, small probabilities make all the difference, right? they accumulate over time. So I like to, I would rather be able to nudge just one inch left 1000 people, I think, like, that makes me really satisfied. Once in a while, like a huge move for one person. Sure. But those are those are rare. And it’s totally achievable. I can’t go solve global warming, climate change. There’s a lot of big things I don’t know how to solve, but in my own local community, plus, I love Seattle. This is my home. Okay, and like, I’m gonna fight for it.

So people I know, right? And I’m already invested in in some other way. Right? Things I understand, like, plasma fusion is like super cool. And like, I don’t really understand it, although I know somebody who’s like she really is rocket scientist to work at SpaceX, Joy. She’s like, pretty awesome. She’s a […] systems now, like total badass. But anyway, things I understand, and things I want, like, I might understand it, but frankly, if I don’t care, I don’t care about another programming language. Like, good luck for you. I wish you well, and I’ll try to you know, be very fast about like, Yeah, no. So it’s fun.

And the thing is, if people figure out pretty quick, like, we can see that I invest, I’m hoping other people realize that they can do it, too. Okay. And it’s kind of fun. I mean, it’s not gonna get you a restaurant reservation when you know, Spinasse is full up, you’re not going to get a lot. “Did you know, I’m a renowned angel investor, former distinguished…”, like, it’s not going to happen, right? But it feels feels good. You’ve got to feel like a patron of the arts. Right? It’s offense. So it balances very well with charity. Right? They go together in ideas, and so like, it could be a small thing, but like I yeah, it was just turned out to be at overthought. It just tried to be a natural extension of things I was already doing.

So highly recommend people should do it more. It shouldn’t be so scary. Yeah. And I’m happy anybody who hears this and is scared and wants to get started: happy to talk to you.


CW: Laura is a force of nature, a bright star filled with boundless energy and enthusiasm. It was pure joy to be afforded this time with her. I want to thank her for investing her time with me, and for the generous use of her vast network. After this chat, she connected me with several great leaders who you’ll be hearing from soon.


Leading Smart is from me, Chris Williams. You can find out more about the show and discover other resources for leaders at my website: CLWill.com.

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That’s it for this episode. The next episode is another studio episode providing more of my insights on leadership. I hope you’ll listen. Until then please remember that each of the several dozen decisions you make today are part of Leading Smart.