Season 1, Ep. 6: An Interview with Heather Redman

Daniel discusses leadership with Heather Redman, Co-Founder and Managing Partner at Flying Fish. A former tax lawyer with an interest in technology, Heather saw an opportunity to start a venture firm focused on investment in artificial intelligence and machine learning based organizations. Learn from Heather’s journey, the lessons she gleaned that helped shape who she is today and take smart risks in your own life and leadership.

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(We use an audio transcription service so please disregard any errors below.)

Daniel Harkavy (00:00):

Well, Heather, it is absolutely great to be with you. I have so enjoyed our last few conversations and I look forward to, to learning from you and hearing what it is that you have to share, not only with myself, but all of those that are joining us today. So thanks for being with me.

Heather Redman (00:21):

Oh, thank you, Daniel. Super excited to do this.

Daniel Harkavy (00:25):

As am. I I’m really looking forward to your thoughts for the varied group of listeners with us today. I’m sure we have those that are leading large organizations they’re serving in the C-suite. Maybe they’re serving to help leaders as board members, and then we’ve got folks that are up and comers and they’re earlier on in their careers. And they’re wanting to learn about leadership, especially in today’s times. I think you are going to bring a really unique perspective as a result of your focus and your experience. So let’s get into it. My first question for you has to do with an absolute core belief of mine and ours at Building Champions. We say that better humans always make for better leaders. And I’m always interested in learning about you, the person. So who are you as this human? Maybe give us three to five things that will really help to understand who you are on more of the personal side.

Heather Redman (01:22):

Oh yes. Great. This is always my favorite part because it’s sort of free psychoanalysis, right? There you go. Who you are and the idea that people would want to listen is even more exciting. Yeah. So I, I like to start with just a little bit about my childhood. I had a super unsettled childhood. I was born in the sixties and my parents were you know, anti-war you know, anti-racism, pro-feminist activists. And I grew up in communes and was very poor, you know, as, as is sort of the, the tradition of, of that kind of lifestyle. So, you know, we had food stamps. We had, you know, I remember picking up the free cheese and butter from whatever the, I guess maybe it was the version of WIC at the time. And I didn’t really go to school until I was 10.

Heather Redman (02:12):

So I had a very, you know, eclectic and unusual upbringing and spent a lot of time with adults and lots of different adults. So that’s kind of the foundation. And when I was 10 and first started going to school, I went to a very rural part of Oregon. And so it was kind of out of the hippie milieu of Southern California where I’ve been to that point and into pretty conservative, rural Oregon and a very traditional public school environment. And so I had to go through that transition as well. And that was great too, because as a foundation for my future life and what I do now, even though it was trying at the time, because I started out at the bottom of my class, I was in remedial everything not having gone to school and also was completely a UFO in terms of how the other kids, you know, saw and even the teachers you know, as just a different kind of animal to deal with. So I had to figure out how to navigate that social environment and that academic environment, which I think is, you know, a great skill for kind of navigating in life, which is what we all have to do continually.

Daniel Harkavy (03:22):

So I’m going to just hit pause on that because when, when we first met, you had mentioned that you grew up with hippie parents and I assumed maybe we were somewhat close in age. So, you know, the sixties, born in the sixties were in that same decade, but I had no idea of the extent of the hippiness. So growing up in a commune and I love just how you said, you know, your experience having to go into the public schools and Oregon was great. I’m sitting there thinking, oh my gosh, it had to be so difficult. What a gift you have now having the ability to look back at it and see the goodness in it. But that had to be so hard, Heather.

Heather Redman (04:02):

Yeah, I think, you know, I think childhood is always, it’s challenged in a variety of ways. And you sometimes I think the robustness of the adult has a lot to do with some of the trials that you endure in childhood. And I guess, you know, all of us now try to avoid being helicopter parents so that we allow our kids to have some of those trials, but certainly some of those transitions of having to fit into a different environment were stressful at the time, but also just great learning grounds. And I wouldn’t have traded all of the crazy experiences I had as a kid for a more quote unquote, normal childhood, just because I got to do some cool things. And I did, you know, spend time doing not, you wouldn’t say enriching things. Cause a lot of it was like watching Gilligan’s Island. But I did some other things when I wasn’t going to school. Right. And, and I also learned that it’s not the end of the world. If you don’t go to elementary school, you know, you can, you can recover from that, which is a good lesson to know is as we look at the over-credentialing of society.

Daniel Harkavy (05:06):

Yeah, absolutely. We could probably do a whole podcast episode on this topic alone. My wife and I have homeschooled all of our kids. Plus we’ve had nine others live here over the years and yeah, we, we could have some fun conversations on that, but I, I think that those listening would say, Hey, that’s neat, but leadership. So, so big point number one about you is a very unique childhood that has definitely played a significant role in forming who you are today.

Heather Redman (05:35):

Yeah. And then I think big point number two is that if I look at the arc of my career, I don’t really feel like I took on the real challenges until midlife people would look at my career and they would say, oh my gosh, no, you had all these successes and you were achieving this and that. But I felt like I was taking in many, the medium path or even to some extent, the path of least resistance, the comfortable path. I turned down many opportunities to take on greater challenges earlier in my career and you know, lots of opportunities to be CEO of organizations and companies along the way. And I just, you know, I just didn’t want to make my life that hard or to challenge myself that much. And what I’m grateful for is that in midlife, I did get that impulse to do the hard stuff again or for maybe for the first time.

Heather Redman (06:38):

And so that’s another thing that, you know, that I think is interesting for other people is to think about, you know, wow, what feels right to me now, and to not stop thinking about whether you want to present yourself with a big challenge as you progress and to continue to ask, well, yeah, I’m doing well, but what, what’s my highest and best use. And that’s, you know, why I do what I do today is I feel like I am now using myself to my highest and best capability. And it’s really only at this point in my life that I feel that way.

Daniel Harkavy (07:14):

So a question I’m going to, I’m going to let you get through these, you know, big points with regards to who you are on the personal side, but as you look back and you see that there was this transition in how you approached challenge and how you approached opportunity, any insight as to maybe what the driver was behind the earlier years, why you would say no.

Heather Redman (07:36):

I think when I was making those decisions, I think I was thinking more about myself and less about my community. And I think what allowed me to give myself permission to try things that might be too difficult for me and where I might fail was when I decided that my highest and best use could be of benefit to others in a more holistic and concrete way. And really, you know, sort of my desire to serve the Pacific Northwest community, specifically the technology community, which I think is the economic driver for sort of everybody’s economic wellbeing here in one way or another. And then also, you know, my passion around women continuing to really sort of give back to society what we’ve received and to stretch the envelope of what we are seen as capable of doing. So sometimes it’s hard to be really ambitious if you’re just doing it for yourself and you feel sort of self-aggrandizing to take on these big challenges.

Heather Redman (08:43):

It’s like, why me? But if you see a gap there and you think if I fill this gap, it will help these other things that are not about me. I think it’s easier to do it provides with that motivation and can ameliorate some of the natural fear that you would have that you have if you were just doing it for yourself. And I think earlier in my career, it was just like, well, what do I need? And I was like, I don’t need that stress of trying to do something where I might fall on my face. And that was just a completely different set of motivations.

Daniel Harkavy (09:14):

So this podcast versus other Questioning Leadership podcasts, we’re diving into some deep topics and some concepts around leadership that need to be unpacked sooner versus later. So I apologize, Heather, I’m definitely going to let you get through the personal, and then I’m gonna talk to you about your professional career and your journey. But what you just said is so important for listeners to understand. And I have said for years that every great vision is always birthed out of a passion or a burden. And when you see that, that need, and it starts to become a burden or you see that opportunity and it becomes just this passion project. Well then all of a sudden that in itself will move you out of that self-comfort mode into the selfless mode, because you know, there’s real work to be done. There’s a need to be served. There’s an opportunity that must be seized and captured. And for people like you, what you learn to do, maybe as you said, at midlife, you started ask the question, why not me? And if not me, then who else? Right.

Heather Redman (10:28):

So you’re right on Daniel. And I love the way you, you stated that because it’s, I think it’s essential. And I think it may happen for a lot of people later, just because particularly if you’ve had a really challenging beginning in life, like, like I have, it takes a while before you recognize I don’t need to be worrying about myself anymore. It’s time for me to worry about others. And I feel very lucky that I got to that stage, you know, a lot of good things had to happen personally and professionally for me to get to that place where I had the emotional maturity to start really thinking about others more than myself. And not that I’m not still a selfish person, I certainly am and have lots of ego needs and all of that. But I did definitely break through my own barriers by having that outlook.

Daniel Harkavy (11:22):

Well, you’re in good company. We all do. So I think that was a really great point. So your point number two, a big one with regards to the real challenges that midlife, and maybe just a couple of the things that will help us to understand who you are outside of work.

Heather Redman (11:32):

I really only have one other, and that is the thing that a lot of people don’t recognize about me right up front, but I think it’s useful because I do think it helps others is that I am actually an extremely introverted person and I’ve become a trained extrovert and so very intentional extrovert. And that again is something that I had to come to over time and worked on for probably a decade before I sort of got to where I wanted to be. And so if you are that sort of person, it requires even a little bit of extra work to sort of keep yourself in the game and to not sort of decide that you’re going to be internally focused. And I think COVID is going to be a challenge for a lot of the introverts. I’m seeing this in CEOs, for example, who now want to go remote first or hybrid leaning heavily to the remote because we introverts lost some of our extrovert training over COVID. And I firmly believe that the path to happiness is extrovertedness and also the path to doing as much as you can for your fellow humans is extrovertedness. And so I’m, I’m hoping to join with the other community of, of introverts as we, you know, as we get back up to speed on our extrovertedness.

Daniel Harkavy (12:58):

Heather, huge, huge, I have never heard before trained extrovert, but I think it’s incredibly appropriate. Yeah. Fascinating and fascinating to, to hear your thoughts with regards to the impact of a global shutdown on the CEOs that are really comfortable now being home, you know wearing board shorts and dress shirts. I’m not saying that’s what I’m wearing right now, but anyways, yeah, there’s a challenge. We need each other. We have to be in community. We have to be in community. It’s where good things happen. It’s where ideas are sparked and it’s where we see the opportunities to serve and to create. So that’s a huge point. Huge point. Tell us a little bit about you and your leadership journey and what it is that you’re doing professionally, maybe some of the highs and the lows, and, and just take a few minutes to share that with our listeners.

Heather Redman (13:53):

Yeah, so I’ll try to keep this condensed, had a few different careers along the way, but given my upbringing, it won’t be a surprise to you that I didn’t really know what business was when I graduated from college and didn’t have any business people in my family, didn’t have a lot of people that had even gone to college in my family and so wandered into law school because I liked school and was good at it. And it seemed like a secure sort of job to get and really loved law school. Thought I might actually become a tax law professor, I loved it so much. And so started practicing law out of graduating from law school and quickly found that the business side of law, the developing of the business, the thinking about, you know, the ecosystem, how you, you had influence in it, how you were able to command the best clients.

Heather Redman (14:45):

That was much more interesting to me than the actual practice of law though I still do enjoy a good contract and law still fascinates me, but it was clear that I was much more of an entrepreneur than a than a lawyer just, you know, looking around at my peers in the law firm. I’m like, there’s a blue marble here and I think it’s me. So quickly left the law firm and joined one of my clients. And over the next couple of cycles ended up leaving law completely after, you know, being sort of a GC of a public company and doing a lot of M and A, left and became the head of product for a young, you know, very glamorous early, you know, media tech company. And you rode craze that ultimately became the crash with a lot of joy and fun and spent a lot of time in Hollywood talking about technology and really enjoying that, that little blip of mania around tech and tech stocks.

Heather Redman:

And after bubble burst, I went really following the context that my husband had. I went into energy for about a decade and did a lot of sort of cutting edge, climate oriented energy projects. So lots of wind and solar, carbon sequestration, a lot of new tech that was trying to, you know, get some of those renewable resources to be cheaper, really on the business and finance side. So big project finance, a lot of creative tax structuring back to my, my love of tax law. And only when I saw Seattle starting to almost exponentially grow in terms of its technology base did I go back into tech. And then it was really with the idea of becoming an investor, which of course is what I do now. So I spent some time just ramping up all of my connections in town, kind of up and down the coast, relentlessly networking, going back to the trained extrovert piece and building just a huge base of relationships across the business community.

Heather Redman (16:49):

Leading to some interesting leadership roles and things like the chamber and the Washington technology industry association, and a couple of other industry boards here in the Pacific Northwest, and then ultimately decided with a couple of other very geeky partners to start a venture firm that concentrates on investing in artificial intelligence and machine learning based companies. And I always like to just give a couple of examples so people don’t go like, you know, eyes glaze over, but you know, we look at things that use computer vision. We look at robotics companies we look at companies that figure out what humans are saying or writing using computers that’s called natural language processing, like what your Alexa does. And we invest in very young companies, often started by people who lead in Amazon or Microsoft and often started by very young people who maybe haven’t done it before. So, you know, near and dear to your heart, Daniel, lots of leadership opportunities along the way.

Daniel Harkavy (17:51):

Sure. Well, you’ve had a fascinating career and it’s just interesting to see how you go from a commune to law, to tax law, to business law, M and A’s energy and today back to technology and especially with your focus on AI and ML. And, and I think you’ve got a lot to share with our listeners in there. They’re going to be a few directions I want to take our conversation in just as a result of this broad, diverse career you’ve had, as well as the unique seat you sit in serving these diverse leaders. And I would love for you to tell us as a founder of co-founder of Flying Fish, where you’re looking to invest in companies that are going to make a meaningful difference. It all comes down to not just the technology, but the leader and the leadership. So tell us a little bit about what you and your partners are looking for in leaders and leadership teams. What causes you to say yes, we need to invest. We need to partner with them and then maybe what causes you to say no.

Heather Redman (18:55):

Yeah, yeah, no great questions. And of course, a continually evolving, and it’s a very interesting study, both in the psychology of choosing people and also the psychology of a group of in our case, four people on our investment committee trying to make decisions, but you put your finger on it at the stage that we invest, we are not spreadsheet driven. There is typically not a revenue base, not a large customer base. There’s no sort of conventional valuation metrics to run. And so we look first and foremost at the team because we expect their business to change a few times before they land on something that you know, is truly scalable and, and viable for the long run. And so we need that team to be the right team, not only to drive the business that they just pitched to us, but also to be able to pivot and drive a different business and to take the hits that sometimes come with those pivots and then also to handle success, because you can also have a founder who is so used to doing more with less, that you might end up with someone who’s not able to pour on the, you know, the fuel when it’s time to grow or not able to delegate enough when it’s time to grow or just think small.

Heather Redman (20:28):

We sometimes have founders who, you know, they are so shocked that they’re on success, that the first acquisition that comes along, they want to take it as opposed to saying, Nope, this isn’t a, a billion-dollar company. This is a trillion-dollar company. So I’m not taking your offer. So it is the evaluation of the team. And then the other component that’s quite challenging. And this happens surprisingly frequently is what we call founder divorce. We vastly prefer teams that are multi-person. So a team of two or three as co-founders is more compelling to us than a solo founder, mainly because it’s just such a hard thing to found a company and to do it alone just increases the psychological burden, I think almost too much. So we really prefer those multi-person founder teams, but we often see founder divorce and it’s almost always a bit acrimonious or at least emotional.

Heather Redman (21:27):

And then there’s the issue of filling in whatever gap that founder filled. And so you, you’ve got then a, you know, a chemistry problem that was difficult enough when you made the investment. And now you’ve got to create a new chemical compound. That’s at least as good as the one that you’ve invested in that consists of a new group of people, right? So that’s probably the hardest part of our job when we’re evaluating the company, you know, after we look at that team and when we look at that team, we’re looking for a lot of leadership elements, but also some just raw ability around technology because the early people have to not only be great leaders, but also great doers and very hands-on. And so it’s that rare combination of someone who can build something in their garage, but then also lead, you know, a much bigger team of people building something in an office.

Heather Redman (22:22):

And those are very hard to find that skill set in one person. So sometimes you just have to develop it. And then the other thing we’re looking for is a big market. We don’t invest in businesses that if they are wildly successful will have a market that is sub a billion dollars. We in fact, are looking for, you know, multi-billion-dollar markets. And typically that’s not that hard to see these days particularly given AI and ML, because what we’re seeing with AI and ML is that companies that are built on that backbone are just going to be so much more efficient than companies that are not, that you can pick almost any industry. And look at an incumbent who is built on a traditional software rules-based model, put them next to a hypothetical AI based company. And you just see that the ability of that incumbent to compete against that hypothetical AI based company is just, just not there. So if you believe the team has it in them to build that competitor, you know, you’re going to see a very large market,

Daniel Harkavy (23:34):

So a ton there we’re definitely gonna springboard and continue the conversation on a few of the points, but something struck me as I was listening to you. We’ve done a lot of work at Building Champions in the pharma where you’ve got groups of individuals that are trying to create new drugs, new cures, and listening to some of the things you’re looking for, as well as the challenges you find in single founder or in organizations where teams may not have the ability to pivot or the stamina to deal with the failures along the way. I think there’s probably some similarities, which is fascinating. Hadn’t given that much thought. I would love for us to keep the conversation moving in the area of leadership, because you did a great job unpacking what it is that you look for in leaders and leadership teams, their ability to handle it, their ability to delegate their ability to reinvent and to pivot, et cetera. Let’s talk leadership, leadership today. We’re recording this in July of 2021. We know that the work world is much different today than it was a year and a half ago. So when you think about leadership today and what you’re looking for, talk to us a bit about what you think leaders need to be doing today and how they’re leading in comparison to say even a few years back.

Heather Redman (24:56):

Yeah. I don’t pretend to have the answers here. And I think it’s very quickly evolving, but I would say that the themes that have been coming up for us, both in managing the portfolio, talking to founders, looking at the companies that we know that are scaling rapidly now, and then also, you know, I sit on some outside boards of some more traditional industry companies. The issues that are coming up are the need for the leader first and foremost, to have confidence in themselves that they can do this job. I, I said to one founder recently and he said, oh my gosh, you made such a huge impact on me when you said this, because he tends to puff himself up a little bit and to be overselling a little bit to any audience, the employee, the investors, the customers. And I said to him, I said, you need to let your freak flag fly. You need to just be, you, you do not need to be posturing. And that authenticity, particularly when you’re early stage and you don’t have it all figured out and you will have bumps in the road, that ability to be transparent and to be authentic, I think is just paramount. And so start, you know, put on your own life mask first. So I guess your own oxygen mask first.

Daniel Harkavy (26:31):

So I’m going to stop you there real quick, because that in itself is a big point. You know, that first point for leaders today, being confident in themselves, something that I would want, especially younger leaders to hear right now is that there’s no one leader who has it all figured out. And the best leaders are those that understand that it’s not their job to have it all figured out. They’re confident in who they are and the job they do and confident in their ability to surround themselves with the brightest and best people. And then when they have that confidence, knowing I’m the one that is supposed to, to cast vision, I’m the one that sees where we’re going. I’m the one that for some reason has found myself in this center of serving an executive team who will then impact an entire organization, the confidence in knowing that you have the ability to see destination, to question those that you’ve surrounded yourself with and you’re confident in their ability. You’re confident in the relationships that you have outside of the team, the outsiders, and you’re getting the right inputs from them. And the confidence that with all of them, there may be some bumps and bruises along the way, but we can get it done. And that’s, that’s the confidence that we really need to have, not the confidence in I’m the right gal. I’m the right guy. I know it all. I’ll have it, every answer to every question, I’ll have a solution for every problem that superhero leader, which is usually birthed out of some form of insecurity or some form of fear, the best leaders have dealt with that. And, and that’s a big deal. And truthfully Heather, as a CEO myself, I wasn’t, it took me all the way to the age of 46, at 46 is when I finally got comfortable with, I just don’t need to know it all. I just need to be really good at attracting brilliant people and then casting a vision that I really am excited about and then allowing them to fly. Right? So, yeah.

Heather Redman (28:35):

I love that and I could not agree more and I haven’t even slightly more radical view that I would love to test out on you. And this could probably be a whole other podcast as well, but I stole this from Spencer Rascoff because I think he really articulated it well, but, but he, he basically said the job of a CEO is extremely boring because mine is, is basically to, you know, get the money in the door so that we can hire those fabulous people, hire those fabulous people, get in the middle if those fabulous people are fighting. And then most of my job after that is whatever they collectively decide we should be doing, you know, whatever their collective vision is I get to go say that over and over and over again to every conceivable audience. And I don’t actually get to set the vision or tweak it and get bright ideas when I’m talking to people because my job is to just consistently communicate that message over and over and over again.

Heather Redman (29:35):

And then the next time the team gives me a tweak to it. Then I go do the tweaked one. But you know, really, I, I, I’m kind of like this vessel that communicates on behalf of the team in a way. And I, I, haven’t seen a lot of people be that radical. I’ve seen more of the view that you expressed of the CEO will have the vision and then help everybody else actually accomplish it. But I like that next sort of iteration of, well, what if the CEO isn’t even responsible for the vision, because maybe that’s the hard part. You know, maybe the, the team also has to do that piece and I’m not sure which is the right model, but I think it’s, it’s interesting to, to think about them both.

Daniel Harkavy (30:20):

Well, I think that it’s definitely, it’s a hybrid, it’s a combination. So I’ve been coaching vision for 25 years and I’ve definitely changed in my perspective on what makes for a meaningful and effective vision. And then whose job is it and how do we come together around it? And what have I’ve always said is that the CEO, if it doesn’t resonate deep in the mind, and in the heart of the CEO, they won’t be willing to take the sacrifices, endure the pain that is required in their role to actually be that one who’s taking that risk. So you have to bring a certain percentage of that vision to the team. You bring the bones, the structure, the base framework, and then the team comes and adds color. They add the meat, they add the structure and it becomes not just mine, but ours, that can evolve as you change with leadership teams, right?

Daniel Harkavy (31:14):

As new people come in and out and you learn along the way, then your vision can evolve as well. Because for many of us who’ve been in business for a long period of time. My organization, 25 years, you accomplish certain parts of your vision. And then if you don’t rekindle and re-imagine, well, then you can build a fence around it and try to protect it because it serves you well. So we always need to be looking for that vision. And I say, it needs to be both clear enough to plan from and compelling enough to cause you to take risk. If you have those clear and compelling factors, you now have the means to begin to build strategic bets, to move you from where you are, to where you’re going. But I lecture on this stuff all the time and my listeners are like, Hey, Harkavy enough on the seven perspectives. Get back to Heather. So Heather, Heather, Heather, keep going on a leadership today versus times past.

Heather Redman (32:07):

Yeah. Yeah. So second point I would make, and this is, I think is just really hard because of how humans are, is that in assembling that super talented team, you’ve got to try to balance two things. And one of these everyone will be like, yeah, yeah, yeah. But the other one I think is maybe new or at least a thing that doesn’t get articulated as, as as much. So thing one is that we have to somehow begin to recognize talent in all forms and really recognize that talent and sort of hold it close to us. So we all know that we have this tendency to hire people that are similar to us in lots of respects. And, you know, I find myself even now gravitating toward people who are like me and like to take a bunch of risk. And when I find someone who doesn’t, I’m like, what, you know, that’s weird and I want to run the other way.

Heather Redman (33:06):

And that’s just exactly the wrong reaction. It’s really getting into the place where you can see people, clearly, everyone has value, and this is not, you know, just around all of, you know, the isms that we’re all concerned with now. And rightly so you know, we need to be able to see people of other races and people of other backgrounds and certainly genders and sexual orientation and, and everything else as equal to us and as valuable as us, whoever we are, but it’s hard because humans have this tribal tendency to be comfortable with whatever they identify with as they’re short of identifiers, you know, whether that’s Ivy league schools or you have to be over six feet tall or people that love sports or, you know, whatever it is. We just have this tendency to flock together. And so truly successful leaders going forward will have this, I think innate joy in people’s difference and a fascination with what makes people different and run toward difference as opposed to run away from it. And so I try to cultivate that on myself as a inherent introvert. It’s not as easy for me as say for my husband who always makes friends with the person sitting next to him on the airplane just cannot resist a human. I mean, he’ll see a person across the street and he will think, oh, maybe they need help. You know, I shouldn’t yell to them and ask them, you know, and I’m like, what are you doing? You know, they’re just, it’s just an inherent difference. But that embracing of, of difference in that, looking for talent in every place and hiring as many different people and then creating a culture, you know, that, that idea of now I’ve got a referee between these different people.

Heather Redman (35:00):

So not only do you have to recognize and take joy and all these differences, but you’ve got to create a culture that allows everybody else to do that too, or the whole thing falls apart. So that’s a very hard job and one that can’t have enough sort of resources thrown at it. And then the other thing that I think is, is more unsaid, but boy, we got to grapple with this as leaders and as a society is that I just asked you to fall in love with all these different people and embrace all of that diverse talent. And then I think we need to get used to the fact that the team that we have today is not the team that we need in a year and not the team that we need in five years. And that we’re going to have much more need for either radical re-skilling, re-learning in our own teams.

Heather Redman (35:50):

And I’m including that in the board of directors and in the C-suite, we’re not talking about just the people on the front line or more and more turnover and change in our teams because technology is now moving so quickly. And there are so many human capabilities that are capable of being replaced now by AI and ML technologies. And we’re still at the beginning of that, you know, we’re at like, you know, day three of the 365 year, right? In terms of what AI and ML can do. We are going to have lots of jobs that are not needed anymore. And then we’re also going to have whole new sets of skills that are needed as a result of the new technologies. And so loving your people is going to require you to also find ways that you can help them to the next thing, which hopefully is in your company. But, you know, reality says that will not always be the case. And, and we have to grapple with that. And I think that’s very painful as humans, but also the path to success and the, the multi-stakeholder approach that leaders need to take to, you know, what success for the company means. You know, you’ve obviously got your shareholders and your employees and society and, and balancing those things is going to be difficult, but you will go out of business if you don’t weight yourself toward the continued viability of the business.

Daniel Harkavy (37:22):

So big. You said, you know, you said something there that caused my skin to even just like, Ooh, that’s difficult. I am so much about creating high performing teams that care like healthy families, right? And there’s something in that, the empathy and the human connection and the real care for those that you serve and lead on the inside of the business so that they better love and serve those outside. And so that together we make a more meaningful difference. It does engage heart. And when you said, you know, the team you have today, won’t be the team you will have or need in one year. I’m thinking in one year. And I don’t think you’re talking about complete restructuring and reorgs of entire exec teams every year. But I do think you’re talking about always looking for the opportunity to upgrade and to make sure you have the thinking and the diversity and the experience in all seats, which could be you know, just a lot more frequent change, a lot more frequent change than, than maybe we’re used to even five years ago. Is that what I’m hearing?

Heather Redman (38:35):

Absolutely. Absolutely. And I, and I think one of the little hacks that maybe CEOs could think about in trying to help themselves future-proof themselves against this reality that we’re facing is looking at their board because their, their boss is the board, right? And so if you’re thinking about how do I make sure that I’m being held accountable to do this really hard thing when I’m in love with every last one of my employees and we are a family and you know, who is going to hold me accountable, who’s going to push me that, building that into your board, which means your board also is not the board that you need in a year or in five years. Right? So start at the very top and think about that. And you know, it’s, doesn’t necessarily mean that you are, as you said, you know, I think just to reinforce what you said, Daniel, this does not mean that you are turning over your C-suite once a year, but it means that you better be creating opportunities for that C-suite to be continually learning and you better be bringing in, you know, the right people as advisors, you better be letting your C-suite serve on boards that will advance them in the knowledge base that they need to get to the next level.

Heather Redman (40:01):

You’ve got to build in as much as you can to give yourself a prayer of keeping your people, but having them always be best of breed and not feeling like, alright, you know, Billy’s been here forever and we just can’t let him go because of continuity and loyalty of the team and all of this. But, you know, if we put Billy up against all the external candidates, Billy is still our guy, you know, and I think that’s, that’s a hard discipline, but when, when you’ve got to embrace and right now, you know, boards are built by and large, too much for stasis. And we’ve got to see, you know, more turnover in boards, but also more thoughtful matrices around what do you need on your board? And I would say right now, boards need to weight themselves toward cutting edge tech, cutting edge business model knowledge, and stopped focusing, you know, sort of solely on cyber security when they think about what they need in a quote unquote digital director.

Daniel Harkavy (41:02):

Hmm. So many good thoughts. I had a guest on just a few weeks back. And when you join us later this year, Heather, you’ll, you’ll have an opportunity virtually to meet Frank Blake and Frank is the non-executive chair over at Delta airlines, former CEO of Home Depot, and also have as that same pedigree as do you being an attorney trained a lawyer in his early career. You’ll love him. We were in a conversation with one of our mutual friends, Phyllis Campbell. Who’s also been on Questioning Leadership. And we were about diversity inclusion equity. We were talking about all of that and a group of CEOs that were, we were together, the conversation was moving and Frank said, we cannot forget meritocracy. And he said, in all of this meritocracy still has got to prevail. And when I, when I listened to you, I think there’s just something for our, our listeners to really hear.

Daniel Harkavy (42:00):

And that is as leaders, we are stewards of a business. We are stewards of shareholders resources. We are stewards of a product or service that can make a positive, significant difference in the teams that we lead, as well as in those that we serve as our customers, regardless of what business you’re in. And that stewardship role has always got to drive us to this mission first, people always focus where the mission does come first. I have to make sure as the CEO, I’m surrounded with the best so that we can impact the most and so that we can be the best we can be. And I hear something in you, Heather, that just because of where you sit in this world, where all day you’re evaluating organizations that are focusing on artificial intelligence and machine learning, and, and we’re seeing what’s happening. I’ve been to factories in Mexico where robots are building chassis for trucks, and you’d look in these huge multi football stadium, sized factories. And you just see robots moving all around with a few people, you know, sitting high above the robots and overseeing and controlling. And it’s just fascinating, you know, 10 years earlier, there was thousands of people in there. And, and just this whole statement and belief that you bring to us around if we don’t embrace this, then businesses go away and we have a stewardship role. We can’t allow that to happen as leaders of our organizations.

Heather Redman (43:36):

Yep. No, I could not agree more. And we also have to speak up as, you know, as leaders of the society of, Hey, you know, we need to figure out a solution for this more volatile and continually shifting job market. And we need to figure out, you know, what is the safety net for people? How do we get people into new jobs? What are the pathways there? So we’re not absolved of that, but in terms of what we’re focusing on at the company we, we definitely need to focus on the business’s survival and it’s a non-trivial thing for every company right now. I don’t care how big and fabulous you are and how much you’ve been returning to shareholders and how happy your employees and your customers are. There are, you know, threats around every corner and rapidly changing environments around every corner. I mean, we all are dealing with climate change right now. I’m sure Frank has a lot to say about what’s happening with fuels and the airline industry, you know, it’s existential, right? So yeah, I, I, I’m a big believer in sort of survival. And growth, I think is part of survival is being the first imperatives and also the responsibility of business leaders and people with a lot of capital to deploy, to also think about society and take care of society and, and support policies that will do that.

Daniel Harkavy (45:06):

I love your balance in saying that it’s, it’s not only making sure that we’re surrounding ourselves with the best and getting comfortable with not only loving but upgrading teams as time goes by. But that second statement, which is the focus on retooling and the focus on developing and making sure that your teammates have every opportunity they can to grow and to evolve into who they’ll need to be with the skills they will need to have in order to continue to add value and to provide for themselves and their families. So a lot of good stuff, Heather, I want to talk to you about you as a leader, and I’ve just got a few questions and then we should probably bring this to close because we’re rolling and I know you’ve got a hard stop in just a little while here. So tell us a little bit about maybe daily disciplines. I, I say self-leadership always precedes team leadership, team leadership, always precedes organizational impact, and you know, self-leadership, daily disciplines that you have that enable you to be the best you can be at work and in life that are maybe non-negotiable what might a few of those be if you’ve got some of those?

Heather Redman (46:16):

Yeah, this is a, this is probably the hardest question and I, and I love it because it’s going to go cause me to reflect a little bit. I am the ultimately flexible person. So my husband always says, you seem to have this sort of infinite capacity and take on one more thing. And I do tend to do that. I don’t have anything about my life that’s non-negotiable and I probably should. I’m not great with boundaries. In fact, I talked to an old boss of mine the other day, like literally like 30-year ago, boss. And he’s now a VC as well in Europe, running a firm there and we were just catching up on deals and he said, you, I will never forget what you said to me. You said cause, cause he was talking about how he had said to me, oh, I like to have this, you know, really firm line between my life and my work.

Heather Redman (47:10):

And I said, oh no, no, no, no, no, no. It’s about integrating the two. You know, it’s not about the creating balance between the two it’s about, you know, having a whole life where everything is all the same. And, and he said that just like completely shocked me and horrified me. And I’m still like dealing with it now 30 years later. And that is kind of how I live. But I guess what that means in terms of what’s non-negotiable for me is that I don’t really think of my job as having any boundaries. So for me, I want to continually be exposed to new people and new things. I am a change junkie, a new junkie. So, you know, every new, crazy product that comes on the market, I probably have subscribed to it or bought it. I insist on meeting new people all the time.

Heather Redman (48:05):

So I, I have cold called people randomly that I saw something about them on an interesting blog and I want to know them and I will, you know, I will travel to see them. I will invite them to dinner even though I’ve never met them. So if I don’t meet, you know, at least two or three new people a week, I would start to go a little bit nuts and would feel like I’m not being adequately fed and ditto with things that are not really in my investment thesis, but that I want to try out and know about. So, you know, new musicians, new political candidates, new restaurant tours, new novelists, you know, anything that is sort of current and interesting. And I feel like will stimulate some part of my brain that maybe the AI, ML space is not and anything beautiful. You know, I have am big into beauty. So anything that I can look at or feel or taste it’s, it’s beautiful and wonderful and its own way. I want exposure to that. But that’s about the only non-negotiable thing I would say in, in my at least in my current existence, but I’m going to go see if I can find a couple of other ones.

Daniel Harkavy (49:17):

Well, you just may not be all that self-aware because I’m going to hit you here. You grew up as a hippie child and this no boundary, limitless free flowing. That’s just who you are. And it’s beautiful, really beautiful, but you do have one non-negotiable discipline and that is you are a voracious learner. And that might also be tied into those younger years because you know, maybe 10 through 20, it was a wonderful opportunity to learn the way you did. And, and you just see the beauty of feeding the mind with not just what’s in your lane, but everything. So what I hear from you is a very common thing that I hear with many leaders and you just have this deep conviction around lifelong learning, and you said it two to three liters a week, two to three people a week. I need to be meeting two to three a week.

Daniel Harkavy (50:09):

Oh, okay. I got ya. Yup. Yup. You’re listening. You’re learning, you’re viewing, you’re always putting yourself out there. And for anyone who gets to spend time with you, that gives you this energy where you’re pouring into us and we want to be around you. So we at Building Champions, we say one of our convictions is we strive to be lifelong learners because you can only give away what you possess. And just thank you for what you’re giving to me and to us today, as a result of that, non-negotiable for you, you will never stop growing or learning Heather. It’s beautiful.

Heather Redman (50:42):

Thank you, Daniel. That’s, that’s a very you know, the, the not having boundaries you know, it could be viewed as a problem. You just turn it into a positive and I love that.

Daniel Harkavy (50:53):

That’s great. That’s great. All right. Well, I wrote a book about, you know, the opposite, which I’ll send to you anyways. Tell me maybe let’s make this a, the last two questions. The first of the last two will be, how has your career impacted your personal life and what have you learned along the way? And then the second one is, has there been any one person that really saw you and they, they transferred hope and belief into you? They were a leader, they were an influencer and they just said, oh, Heather, you have this go. So those little final two, what do you got?

Heather Redman (51:23):

Great. Great. Okay. So for a first question, yeah, it’s interesting. You know, we think a lot about what toll does, you know, being a very driven person have on your family. And I would say perhaps, you know, I’ve neglected my parents a little bit more than, than would be ideal. Although I, when I think of, I do this thought exercise sometimes of if I’m an only child, so this is a total hypothetical for me, but if I had a twin brother, what would his feeling about XYZ be? Or how would the world perceive him if he were doing the same thing that I’m doing, or, you know, whatever it is, any situation. And I think that the amount of care and attention I give my parents is, would probably be on the very high side if I were my twin brother, but women do, there’s always a bigger expectation.

Heather Redman (52:15):

So sometimes I have some fear that, that maybe my career has taken some toll on how much time I can spend with them. But on a positive side, I would say that my career particularly this, you know, this last 10 years of me really challenging myself and taking on a lot has been super positive for my daughter who grew up watching me do this. And in fact, in some ways was one of the reasons why I did do it, was her observations about women in society and about kind of what made me happy. But I think it’s had just a tremendously beneficial impact on her. And I, I would certainly urge women when they’re feeling like, ah, my family versus my career to think about the positive impacts that, that really showing, trying hard at something that you might not succeed at and, and explaining, you know, the, the times that you fail and the times that you succeed in how this or that worked out, you know, some of your fears along the way to your children can really be beneficial to them and empower them in ways that you may not see initially.

Heather Redman (53:22):

So I’d say, you know, net, net, that’s great. And certainly, my husband, who also is very involved in his work were super compatible with our ability to, you know, to kind of enjoy each other, but also spend a lot of time doing other things. Then the last question, one of I think the problems with me being kind of an inherent introvert is that I’ve learned how to do the extroverted thing in one dimension, but I’m not particularly good at seeking mentors. And so I haven’t had a lot of true mentors along the way. And that the job is still available if there’s anybody that wants to sign for it out there. But what I would say is that my stepdad who died last year was just so in my corner, he kind of came into my life, not as an actual stepdad, but as a, as a person when I was five and was there, you know, every step of the way.

Heather Redman (54:20):

And unfortunately, the last 10 years he was suffering from early onset Alzheimer’s. So didn’t get to be, you know, the person that he was before during those 10 years. But my daughter expressed it really, really well. She said he was never anything, but 100% supportive of both me and her, and that is just so rare. And he had high standards and he was a super achiever himself, but he thought we both walked on a water and was just, just, you know, immensely proud and excited about everything that I did and everything that she did and I’m just sad he’s not there to watch her and her next chapters. But having that particularly in a stepdad, I think was super formative for me. And there’s no way I would be who I am or where I am without him.

Daniel Harkavy (55:20):

Hmm. Well, Heather, just a fantastic, fantastic conversation. And I’m really grateful for you. Thank you for joining me. Thank you for adding such value and insights to all of those that are joining us on this podcast.

Heather Redman (55:38):

Thank you, Daniel. That was just absolutely terrific. And I feel like I learned a lot along the way too. So I’m going to go work on those non-negotiables and, and read your book.

Daniel Harkavy (55:48):

I’ll send you a few, but Hey, if anyone wants to get ahold of you, follow you, I know you’re on LinkedIn. How do people track you down?

Heather Redman (55:57):

Twitter is probably the best way just @heatherredman and feel free to DM me. Of course.

Daniel Harkavy (56:03):

Great. All right, Heather, thank you so very much. Listeners, hope you enjoyed this. Stay tuned. There’s more coming.

Heather Redman:

Thanks, Daniel. Thank you.

In This Episode

Heather Redman
Co-Founder & Managing Partner