#11: Robin Matlock, VMware

Welcome to From Startup to Grown up, the podcast.

My name is Alyssa Cohn.

I'm an executive coach, an angel investor.

And the author of From Startup to Grown Up.

Each week I talk to founders, creators, advisors, investors, and builders of all kinds about their insights and experiences in going from Startup to grownup.

This is episode number 11, and I'm so excited today to have Robin Matlock on the show. Every time I happen to mention Robin's name to anyone, the answer always comes back to me. Oh, Robin is so great.

Which she totally is.

Now, Robin's not a founder, but she's been around founders quite a bit, and she's very reflective of her own growth in her own career journey. She was most recently the CMO at VMware, and she's also an independent board director with incredible startups turning into grownups, including Cohesity and People AI. In fact, I met Robin through the amazing Andre Axelrod from People AI. This is a rich, rich discussion where Robin talks about her own career growth and about the importance of not putting limits on yourself. She talks specifically about how you need to adapt your style as you get more senior, and then again when you serve as a board director. Robin also shares a recipe for how to bring culture to life, why you need to get better at failing, and about how playing the harp prepared her for a very successful business career. Please enjoy my conversation with Robyn Matlock.

Robyn, I am thrilled to welcome you to the show.

Oh, thank you. I'm happy to be here, Alyssa.

Thank you so much. Now, when we spoke, we had a little pre discussion, and when we spoke, you told me, because I told you about the theme of this podcast, and you said, well, nobody can survive in Silicon Valley without growing rapidly and repeatedly. So I wanted to start there. What did you mean by that? And can you share a story about. About a leader who did not grow and what lessons that maybe you learned from that?

Sure. I. I think the spirit of what I was thinking is the fact that Silicon Valley is the heart of innovation. And what makes the tech industry in particular so successful is this constant cycle of innovation. Well, that means that if you're not innovating, somebody else is innovating around you and ultimately is going to get an upper hand. And I think that's true. I mean, we all know there's the tombstones of companies that didn't innovate and change fast enough. And I think the tricky part of it is when you feel success, you have customers, you have momentum, you need to keep those customers happy, and that consumes A lot of your cycles. And yet if you're not constantly pushing and transforming and changing and innovating, you're kind of missing the next wave. And I think that is the spirit of the Silicon Valley and the success of tech. But it's very difficult to do when you are the operator.

Oh, that is so true. And, you know, I love the way you just frame that because you're saying really that companies have to innovate or get out innovated. But also it's true as you're a leader, you have to be constantly building yourself and pushing yourself as a leader and getting better as a leader, or you will get outlets. So it's also the same as individuals.

I think it's very true, whether it's the company as a whole, whether it's you as a functional leader, you as a CEO. At the end of the day, if you're not constantly evolving and improving and growing and pushing the boundaries, there's somebody else who is.

Yeah.

You know, at the end of the day, we need the best talent to be doing the best work to get the best results. So it's, it's just a constant.

Yeah, I totally accept that. I agree with that. And Robin, I'm just wondering, is there an exemplar in your mind's eye of someone who's fantastic at that, like a role model for you for that, and then maybe also a leader who's. You don't just. You don't have to name names, but a leader who's maybe not so great at that in your mind's eye.

Yeah. So I guess you know my history with VMware. I saw Pat Gelsinger put that in to action. And I first of all admire and respect Pat. What Pat did was fearless transformation and just never comfortable. Never let the organization get comfortable, never let the engineering teams think they'd cross the finish line. He just kept raising the bar and pushing and challenging. And I, I really watched him set some audacious goals, which I thought sometimes were ludicrous. They were so far above and beyond. And yet, you know, when you have these big crazy goals and you support people to get there, it's amazing what things can be accomplished. So I think he embodied to me a fabulous example of this. I definitely won't name names, but I worked for some of the bigger security companies decades ago.

Really.

This goes back 10, 15, 20 years. And I saw, you know, in many situations, them get really comfortable with maybe a successful product line, a family of products that was killing it, and just ride that wave too long, too long, too far, not thinking about the next generation fast enough. And I think it's, it's part of that challenge is sometimes your existing install base, your customers kind of are draining you of all your resources and if you don't think about the next generation, you're going to get caught basically not innovating. So I won't name names, but I think many of the big security companies kind of got stuck in a negative spiral there.

I. That makes complete sense. And I guess I would ask if you think about one or two leaders in your mind' or basically someone who is, to your point, using all the resources to service customers and to deal with their existing customer base and operations and they're not taking the time to step out of that and innovate. What would you say they should be doing again, personally, as a personal transformation? How should they personally think about that so that they can lead the organization to be more in that innovation loop?

I definitely think you have to really be self aware of where are your resources going and if you're doing really honest assessments of how much of your energy is consumed, your personal energy, your engineering talent, your customer success talent, whatever those kind of investments are. And I think you have to be pretty critical of looking at are you carving out enough space for your future and how many of those investments can you make? And you probably need some rigor in that process. When you're really small and you're in a startup, you're very focused, right? You have this myopic focus on one kind of prize as you grow. Now you have to have three or four bets that are for next year, in the year beyond. You know, one bet isn't good enough. You have to diversify a bit as you get really big. You have to have 20 bets, 50 bets, 100 bets. So these things always scale. But I think you really have to think very strategically about how much are you really investing in that future. And there's no perfect formula, right? Every business, every market, every technology space is going to be different. But I think the key is, are you aware of, of how much you're investing or are you just kind of going through the moves and using historical data or kind of last year's? Is the, you know, the moderation and evolving from there as opposed to being very strategic about it?

Totally. You know, CEOs I work with, they'll constantly show me their calendar kind of with pride, like, look at all my meetings. And I think what you're saying is you have to cut those Meetings out, you have to carve out white space for yourself to step back and reflect and not think about what should we do today or tomorrow, but next year and the next year's out and it's hard to do. That doesn't just happen. You've got to proactively carve out that time.

And I don't think it's just for your calendar. I think it's how are you creating that space for your teams? Right, because you know, you might be a thought leader as a CEO and a founder, but you've got to be surrounding yourself by others. And are you burdening them with so much day to day operational stuff? They too are struggling to do that. Are you creating forums where that brainstorming can happen? I mean, maybe that's what something you need to implement, which is no meeting Friday or you know, off sites every other month because it's just simply a brainstorming session. But I, I definitely, definitely think it's a leader. You have to figure out your style, but you've got to create space for that.

I love it. That's so great. Now in our discussion we also talked about the importance of influence. And I think people misunderstand that or they even discount that for CEOs. They're like, oh, the CEO is the boss, you know, they have the ultimate power. But that's really not true. What would you say is important for founders who are growing into CEOs to know about the role of influence as part of the job description of a CEO?

You know, it's interesting, there's two sides of that that I feel really strongly about. First of all, it's not at all about being in power. Like I never even use that language in operational roles. It's about empowering em. Right? Not in, but em beautiful. And I think as growing CEOs, your job is to empower that organization, that talent to do their best work, to lead, to be thought leaders. And you simply cannot do that for everybody. So if you're not good at bringing everybody along and empowering them to do their best work, I think you're really going to be limited. You know, on the other side, when you think about what that CEO needs to do, you do need to think very broadly and you do need to kind of help people envision the possibilities. So I do think that the CEO uniquely carries that vision, the realm of possibilities and kind of making sure people don't put limits on themselves. But at the end of the day, I don't think it's about being in Power. I think it's about empowering.

I think that it's such a beautiful distinction. And it actually, it just brings me back to Pat Gelsinger, who, you. Who you mentioned earlier. Would you say that's how he was able to get people to do big, audacious things and to kind of keep them focused on bigger goals or how. What was his empowering or influential leadership style?

Well, for sure, Pat empowered his team. Now, he expected outcomes and results. Right. But rather than worrying about always the journey on how you're going to get there, he very much focused on the outcomes, and he let you kind of control your destiny. These are the outcomes I'm going to deliver. Great. Let's. I buy into those outcomes now. Let's check in and go, are you making, you know, progress against these outcomes or not? So I think he was very. He might debate the outcomes if he didn't align to the outcomes. But he was, you know, very clear once those were agreed upon. But he held you accountable. So I think that the spirit of accountability is also an important dimension because if you're empowered, you also then have to be responsible for delivering a set of outcomes and held accountable to that and take, you know, your ownership of that, good or bad. And without that, it's a little bit fluffy. Frank?

Yep. Yep. Now, Robin, let's take you way back. You got a degree in music and you've talked about, by the way, I should just say that long ago I heard that the MFA is the new mba. So I love your thoughts about that. But I know that you've talked about.

Learning through your experience in music, important.

Things that actually translate to business, like competition and practice and performance. And I. I don't think that'd be intuitive to people. I'd love to hear how your experience as a harpist played out in your business experience.

Yeah, it's probably a stretch, but I always feel like it was a fairly good platform to develop. And here's why. In music, it's ultimately about the performance. Well, to end up on stage and perform, there's a ton of practice and preparation that goes into that. Before game time, before performance time, all that practice accumulates until it's almost like you're moving on autopilot. Like, you have to get so good at something that you no longer have to think about it too intensely. The second thing that you have to do is you have to be cool under pressure. So the more you prepare, when all that pressure hits, when the spotlight's on you, you're on stage. The stage is quiet. You know, you can be focused and you can deliver what you have prepared yourself to deliver under that intense scrutiny. And I do consider getting in front of a board, getting on stage at a conference, delivering a presentation to my employee base. All those experiences is kind of the focal point is on you. And you need to be at your best as a CEO. That's not when you want to be stuttering and fumbling and kind of losing your focus, you got to be at your best. So music really did that. And then the last thing I would say that music did is everybody plays a part when you're in an ensemble. And as a harpist, frankly, when it was my turn, it was like game on. Everybody kind of got real quiet and it was my time to shine and I either delivered or I didn't. And if each player didn't deliver on their part, the whole ensemble suffered. And so the quality suffered, the output suffered, suffered. And I, I think that is very similar to a. A company. Everybody's got to do their part, everybody's got to pull their weight, you got to work together. But ultimately, if. If there's a weak link somewhere, everything kind of is not at its best.

Yeah, that is a lovely metaphor, and I've never thought about it that way. Could you tell us a story? I'm not sure if you could think of one, but can you tell us a story about where you kind of really saw that all the preparation you had done was paying off right here and right now, and we're able to kind of tune out maybe a difficult mom. That training that you had undergone as a musician.

Ah, you mean in business, Applying that concept to how I. Business?

Yeah.

To be honest, I feel like every time I was on stage, anytime I had a big public speaking responsibility, it's the same kind of performance driven thing. I had to prepare, I had to practice, I had to know my timing. I know where I need to be on stage. I had to not get overwhelmed. I had to, you know, presenting to VM World. You know, there's 20,000 people in the audience. You know, it's huge. And you just can't let your nerves get the best of you. So I definitely feel like in those particular public speaking, I felt like there was a direct correlation.

You know, I spoke to Sunil Gupta, the author of Backable, and one thing that he talked about was exactly what you're saying is that, oh, some people are just born to improvise and they just get on stage and they're so naturally articulate and they're backable. Well, not really. They do all this practice that he calls them exhibition games. So low stakes practice experiences, so that when they get to the big game, like you called it, the real game, they're ready to go and they're, their mouth is around the words and they have kind of that muscle memory of what that was like to do all that practice.

Oh, I agree. I absolutely agree. And sometimes less is harder than more. When you can kind of ramble and articulate and explain yourself, then every ah and every stutter doesn't really matter. But when it's really short and tight, that's when your game has to be the best.

Yep, absolutely. So Andre Axelrod, he introduced us and he wanted me to ask you about your VMware transition from VP to CMO. So let me ask you about that immediately. Like, let's talk about you. First of all about your journey into marketing and then how you got from the vice president to the CMO of VMware.

Right. So in broadly my, my career, I started out more in sales, moved into business development, eventually got into product management, product marketing. And that was kind of my foray into marketing. So it was kind of like halfway through my career or so. Well, the VP to CMO story is actually a really, it's a really important story, frankly. And I'm public about this. It's not the most complimentary to me, just so you know. But it is, it's the real deal. The bottom line is I was second in command in marketing as a VP at marketing for four years and the CMO was going to be leaving, so they were going to hire a cmo. And my boss, the exiting cmo, asked me, do you want to throw your name in the hat for this job? I said no, because I loved VMware. And I just thought, you know what, if they wanted me to have the job, they would have just given it to me. And they weren't just coming to give it to me, so. So I figured they'd already decided I wasn't really ready for the job and I didn't want to spend all my cycles proving to them I was ready and then taking all their cycles to prove I wasn't ready and then they'd hire my new boss. And it just felt awkward.

Yeah.

So I said, no, I'll pass. No, I don't want to do that. And I had actually lunch with one of the gals in hr, a really powerful. She's an author now of Leadership and empowerment, and she heard that story, asked me the same Question. And bottom line is, when she heard my answer, she just said, robin, you're going about this all wrong, and you're crazy. Why would you not throw your name in the hat and at least let these senior executives get to know you a little bit and get to know your background? And you're right, you probably won't get the job, and you probably would have gotten it if they had that in mind for you. So the bottom line is, I thought that was kind of logical and I had been foolish, so I changed my mind and I threw my name in the hat and I went through the interviewing process and I gave it my best. And, you know, I kind of knew what they were looking for, and I knew I didn't have all that they were looking for. I knew I had some of the things, but not all the things. So anyway, I went after it pretty aggressively, and I thought it went well. And they called me back later, you know, a couple weeks, and said, hey, good news. We did get to know you a little different. We didn't know about all this stuff in your background. It was great to get to know you, and you made the short list, but you're three of three. And I thought that was victory. I kind of like, great. You know, I got through it. It wasn't awkward. Everybody felt pretty good about it, and I just went back to do my job. Well, the first candidate wanted to live somewhere else, and they didn't want that person out of state. The second person they went to negotiate with, and something got wonky in the negotiations. They didn't like the tone of it, so they dropped the process on the second person. And in the meantime, time is ticking on. They've now cleaned out their pipeline. I'm still sitting there, number three, but I'm still there just doing my job at VMware. And they eventually decided that they would stop the search and they would give it to me as an interim capacity, and it was mine to lose. And they gave me a couple months, and then they made it full time. A couple months, you know, official a couple months later. And I held the position for seven years and was the longest reigning CMO the company's ever had. But the lesson there is actually probably truly self empowerment. I almost didn't put my name in the hat for one of the best career moves of my life. And that was only me who held me back. Nobody else was holding me back. So I like to tell that story frankly, just because I think it's important. We all put glass ceilings over ourselves, men and women. And I think it's important that we try to acknowledge when we're doing that to ourselves, because there's enough barriers out there as it is. You don't want to be one of the biggest ones to yourself.

Totally. That's such a powerful story. And I think it's so important for people to see that and also to see that we can make a lot of small mistakes along the way and still emerge victorious. As in, you made a small mistake. As in, I'm not going to go for it. Well, turned out to be a small mistake because it was reversible. Right. But then you were saying, no, no, no, thanks, I'm good, I'm not going to take that job. And yet then you were lucky enough.

To have people in your life who.

Helped you rethink that. And so I think there's a lot of power in the kind of micro moments there because but for that HR person you happen to be having lunch with, you still wouldn't imagine the trajectory of your career and how different that would have been.

No, it's so true. And I think it also connects to another concept, which is, are you seeking input from other sources in your life? Because sometimes your own head and your own thinking, your logic sounds great in your brain. That self talk is working really well for you, but maybe it sounds not quite as rational when you get some outside in perspective.

Yeah, totally. How much of that do you think was ego also? Like, on the one hand, I understand that you don't want it to be awkward when your boss comes in and knows that you wanted the job kind of thing, but part of it is also. You can't tell me. No, I'm telling you no. Was any. Was anything like that going on with you, do you think?

No. You know, it's interesting. I've never really thought of it that way, and maybe it is, but I. I felt truly, at the end of the day, I loved the company. And I felt like by making that move, I was kind of forcing my hand. And I. I felt like by doing that, I was putting a stake in the ground that if I didn't get the job, I would have to be disappointed. I would have to. If I wasn't disappointed. What. What kind of. What does that mean? Right. And I just didn't want to challenge my position there. I was, I was happy to be there. And I decided I had kind of in my mind said, hey, number two is better than feeling like it's time to leave. So is that ego? Maybe it's also Part of that brand of being like, if you are a mover, if you are aggressive, if you are a growth person, you don't want to get labeled, that you can't grow anymore. Right. That you had a ceiling put over your head. So maybe there is a bit of ego there that says maybe that's not the right way to get branded internally. And I was a little afraid of getting branded.

Yeah. Yes, exactly. And we're all a little afraid. And so then it's helpful to have someone kind of push us out of our comfort zone and then for you to also do the work to kind of change your mind. So you moved into that CMO role. As you said, you were there for seven years, the longest reigning CMO there in, in their history. And also you're very successful. You really, you know, were part of the team that grew the business. I'm so interested in knowing, like, you were what we call peer to leader. Right. So you had a bunch of peers or you had you. You sort of stepped up inside of an organization who saw you at the vice president level and then they had to see you in the C suite as the. As the CMO level. And so I'm just curious, what advice do you have for other people who make that transition from, let's say, leader to executive?

Yeah, I think it's really an important transition, and I think you have to change your mindset and you got to get on the other side of that chasm because the worst thing you can do is cross that chasm. But act like you did and behave and lead like you did on the other side of the river. Like. Yes, yes, that's. That's a problem. Right. Because you are expected to lead at a very different altitude. So I think a couple of things. I think one thing we talked about at the very beginning, be very conscious about how you're spending your time. Be conscious of what you are going to let go, because you simply can't hold on to all the things you did at the level below and still operate at the level you need to. So I think you've got to really think about what are the strategic, critical priorities that warrant my time and energy and what are the things that I need to basically rely on my team. I think you definitely have to make sure you're surrounding yourself by really talented people so you can get sucked into the details if you. You haven't done a good job of building the team around you. And then I also think you have to think about your relationships in an organization and are you elevating those relationships because now you need to operate with a different peer group and you have to change that. You have to build those relationships and you have to change them because they maybe were a little bit subordinate before.

I'm sure they were below. Yeah, I'm sure they were below. Right, right.

And I think you have to be very conscious about those relationships.

How do you approach those differently? So on Friday you're the vice president of marketing, on Monday you're the cmo. How do you sort of step back and specifically what are the specific tactics you thought about in approaching kind of re? It's almost like re contracting your relationship with these other people who are now your peers.

Right. Well, first of all, I think you have to prepare for those discussions, put some thought into it. Even though you know them, but you knew them at a different altitude, you got to go in with a different agenda. So every job would be different how you look at that. But in my case, I went in probably with a point of view on a few key topics that I thought needed new, fresh attention. Things that I wanted to explore are, do you agree these are important? What's your feedback? I definitely extracted a lot of information. So I did a lot of listening and I thought it was good to go in and go. I want some open ended questions. I have some perceptions. I want to get your reaction, I want to get your thoughts, some things that you think need help. So trying to elevate the conversation from that first meeting and setting a new agenda. And I think then as you are engaging with that person, you're operating on a new agenda, new set of priorities, new set of, you know, initiatives, what have you. And now it kind of puts you in a different lane and then all the dialogue can kind of follow from there. But I think you got to be very conscious about doing that. And if you just kind of rely on the dimension of the relationship you had in the past, you're just going to talk about the things you used to talk about in the past. Well, you're no longer operating as a peer to them now, right?

Absolutely. You have to promote yourself. I think you get promoted by the organization, but you have to remember to promote yourself. And that's really what you're talking about.

That's right. And I think promoting yourself might be simply talking about ideas and a vision and getting feedback on that vision.

Right.

Talking about priorities and opportunities, but now brainstorming as peers about how can we work together to transform, to change, to have impact.

Yeah, yeah, that's fantastic. Now I'm going to shift gears and I'm going to talk about your service on boards of directors. I guess I'm curious when you started, what year, do you remember what year it was that you took your first director role? And where, where was it? What company?

Yeah, it was Iron Mountain and it was July of 2019.

July 20. Oh, wow. So it's pretty recent. And now you serve on how many boards?

I serve on four commercial boards and one nonprofit.

So if you think about when you started out as a board director, what are some things that you learned and that you sort of know now about what it takes to be an effective board director.

Where you shift that the whole level of influence shifts, you're no longer doing. And in the public, I do think they're very different private and public companies. So my first board was a public company. Your job is governance. Your job is watching out for shareholders. So you are just, you're not running the company, you're not fixing broken things in the company. You're simply providing inspection to make sure the company is operating and doing the things it should be doing to deliver shareholder value and grow and prosper. So you're kind of really gently probing for looking for soft spots. You're asking in ways that are not. You don't want your leaders to get on the defense, you don't want your leaders to shut down, but you want them to stay open with you. So you've got to ask things in a way that's non threatening, but yet is not afraid of kind of going to the underbelly. Do we have some weaknesses, some vulnerabilities and exposures? And your job is to test all that and make sure that not everything's solid and everything's being run according to the commitments that you're making to the market. So I think those are skills. They're very soft skills. They're important. How you phrase things, how you ask, what you ask, when you ask it to me is a really important part of board work.

Yeah, that totally makes sense. And I guess I'm curious, what is the difference between serving on a public board as compared to serving on, you say a private company board? But I would also add kind of a very like people AI, like a scale, a very fast scaling startup.

What.

How would you see your role differently in that way?

I, I see them quite a bit different. So the public to me is mostly about governance. I do mentor, you know, I do help their CMOs and I, you know, pride, pride, consultation, kind of that advisory stuff. But for the Most part, it's a lot more about governance, whereas in the private boards that I'm sitting on, it's all about helping them grow and they want your expertise and they kind of need it almost. You're more involved. You know, I'm, I'm meeting with their sales and marketing and business development and CEO twice a month. You're, you're opening doors for them, you're a sounding board for them, you're helping them think through new business models. So it's much more, you're not doing the work, but you're definitely much more engaged operationally in how the business is growing and what decisions they're making. On the public side. You're just checking in and making sure that they're kind of doing the big picture things that they need to do to be successful.

Yeah. So it's sort of more hands on in a, in a, more in a private company and also again, in the sort of the fast scaling environment it sounds like.

Exactly. And hands on is different than doing it like running it. But it's more hands on than public board work. For sure.

That makes sense. Robin, how would you say you personally have grown? If you think about your board Service starting in July 2019 till now, what are some things that you can look back on for yourself to talk about your sort of personal growth as a leader?

Well, I think first of all, when you're in that boardroom, you, you are seeing the business from just a different vantage point. And even though I was on the executive team and I, you know, participated in board meetings, at the end of the day I ran a function and I was part of a high growth. And you're responsible for that thing, right? This big, huge thing, but it's still a thing. And I think sitting on the board, you have to really look across everything from product to employees, people to sales to customers to shareholders to. So you have a much broader perspective, maybe more shallow because you're not really an expert. You don't get to go deep on all the data in the company. You're not really going deep on all the what's been tried and failed. You have this thinner slice, but it's broader. But it does give you a better sense of how do all the piece parts need to come together in what balance to make the engine run at its fastest pace. And I think in a board, board level, you're starting to see much more about do we have the right balance between sales and engineering or between support and engineering? Do we have the right product roadmap? For the future, are we growing the customer base at the right pace and you're kind of seeing how all those piece parts really must be operating to get the scale. And the more of those you see, then the more you have a good kind of best practice to compare against. And you've seen kind of this set of plays before and you're quicker at finding little gaps or areas of weakness or opportunity.

Yeah. I would wonder, when you first started on the board, after being so long in an operating role, was that a little jarring for you, like. Oh, it's hard. It's hard to know what's really going on around here.

Well, for sure, in the public company. And I also joined a reit which has its own, its own set of language and financials and all kinds of unique accounting considerations. So that was a whole foreign language to me.

Yeah.

So I. But like anything, you know, most of the folks that have made it to the C suite are pretty smart cookies. And I think as long as you kind of take a growth mindset and know not to present yourself as an expert when you're not, be curious, get. Be intuitive. I do think that the softer skills really help. When you're intuitive about when to ask a question, when not. Save that for offline. Make sure you do your homework. I, I think it's just kind of using good judgment and you, if you're open to learning, you will, and you'll learn fast.

Yeah. How has your vantage point now as a director on a. On boards, how is it just changed sort of what you think of when you think about effective CEOs? Has it, has it changed your, your sort of mindset or your point of view on what it takes to be an effective CEO?

It's probably accentuated what I already thought, but it's kind of, it's, it's almost been like a catalyst to those viewpoints. I think, if anything, I've come to respect the how CEOs do what they do, not just the what. And if I were to look at good versus great, I think the how is often the secret sauce. That's the difference from one to the next. In Silicon Valley, there's a lot of brilliant technologists, and I do think you do have to be a technologist to thrive in a tech company. But I also think if you can do the how really, really well, you inspire people, you're a good communicator, you listen to all the voices in the room, and you're good at getting people to contribute so you can pick out those best ideas and you can galvanize your teams. I think you have an opportunity to differentiate yourself. And so maybe I've really come to appreciate those that do that.

Well, yeah. How much the how is important it sounds like and how much it's important to be able to kind of operate those, operate those different parts. I mean I when as I coach CEOs because we're constantly looking at the difference or the distinction between when you bring in a whole bunch of voices and when you're driving for consensus and when you just need to decide with conviction. I guess I would ask you how do you think about when you need to. When you should bring in collaborative voices as compared to when you should just decide?

Yeah, well, I think at the end of the day there always needs to be a decision. So at some point a decision has to to be the end game. I not to do the name dropping thing but I have to say I thought Michael Dell did this and modeled this exceptionally well. So I had an opportunity to several to work with Michael when I was at VMware and what I saw from Michael is first of all an incredibly influential person. So he was very careful about his opinions and I it was fun to watch him. He would be the last person in the room to speak because he knew if he asserted an opinion everybody would just shift stage right to whatever Michael said. So he came up with kind of a. And I don't know this is exactly why he did it, but what I saw him do is he basically would challenge his teams to come present three options. So they're going to make decision A. He would essentially say come to me with safe choice, stretch choice and out of the box crazy wild ass choice. And then other than clarifying and getting a little bit of detail, he pretty much let them present. These are our options, pros, cons, you know, risk rewards, what have you and let the room react and digest that and and get to the bottom of pros and cons before he weighed in. And I thought he was exceptionally effective at that. But before we left that meeting a decision had been made, I guarantee you. And if it required him to do it, it there was no problem who was going to make a decision. But it allowed a conversation and it allowed ideas to come to the table. And I think he worked hard to not overly influence before he had really gotten a chance to hear the best thinking from his leaders.

Yeah, that sounds like a very deft way to handle. I bet it took him a lot of discipline and learning over the years. He's Been a CEO for a long time.

A founder, I'm sure, I'm sure that was, you know, trained into him through his own experiences. Yes.

Right, Right. So, you know, I'm thinking also about sort of the culture that would lead to that kind of environment. And I'm sure that you, in all your leadership roles, in all your. Your advisory roles and your board roles, you've thought a lot about culture, and I'm curious to hear your thoughts about how important you think culture is as a company goes from startup to grownup.

Yeah, I think, first of all, culture is super important in all dimensions of your kind of business life cycle. And I think you have to be really careful that what you want the culture to be and what the culture is are the same, because you can put it on a piece of paper what your culture is. But if the norms that actually govern the business and the norms that showcase how you make decisions and the way you hand out rewards and the behaviors that you acknowledge don't jive with your culture on paper, then I guarantee you what you really have are the norms, and that's the culture. The thing on paper is just nothing more than, you know, theoretical. So I think it's really important to be thoughtful about it. And I think. But more important, whatever you decide and you put down those attributes that, one, you need to know if that's how. How the employee base perceives your culture. So do you kind of have permission to say those are the cultural attributes that you desire? And two, when you audit behaviors of the company, how you make decisions, rewards, when there's friction, conflict, how do you deviate from the cultural things that you've defined? Those are the real tests to see if you're living your culture. But I think probably your behaviors and what you do in the reality is the most important thing.

I totally agree with that. And I think that it's very interesting where, like, the distinction between what you say it is versus what's actually happening. Have you ever seen a leader, a CEO, or any other leader effectively sort of really make a choice and specifically, you know, tell people, hey, that's not our culture, or make decisions, difficult decisions based on our culture around here?

Oh, yes. I. I actually feel I'm going to give VMware a lot of kudos in that regard. And it goes back several years. But in the beginning of my career at VMware, we were kind of more the culture on paper, which whatever we said the attributes were, that wasn't necessarily what the real culture was. But we went through a Body of work. Work to really define the culture.

What did you do? Could you mind sharing the tactics of what you guys did?

Yeah. And, you know, I was kind of a peripherally player on the whole thing, but basically was a whole bunch of internal focus groups and letting the people of the company define the culture and put the words behind what were the norms and ask ourselves, how do you prioritize these things? You can't have 27 different attributes to your culture. So what are the most important? That that was through a series of focus groups and focus groups and focus groups and culminating down until they got to kind of something that really resonated and they. They called it epic, too. Was. Yeah, it was.

I like it when we name things. Yeah. The little.

Well, it actually does. There is value as a marketer. It is. You have to have a little. But what happened then is then years of bringing that to life. Awards based on those values, not outcomes, not how much money did you sell for sales or, you know, what deadline you hit from a product, but rather, did you demonstrate the corporate values and celebrating the people who did that the best.

And what were they? What were the epic values?

Execution.

I remember. Okay, good.

This is like a year and a half ago. Execution, passion, integrity, customers and community.

Ding, ding, ding. See, it's so I tell you what I used to really minimize that it spelled a word or that it rhymed. Actually, it's really meaningful. Right.

I can see it's really helpful. It was. And then. But what is more important is once you've done that, you have to. You have to live it. As soon as you are inconsistent with those values, as soon as you reward and celebrate someone's success that does not act within your values, you know, nobody will believe. Your internal employees will just go, see, that's just all. It's just all fluff. As soon as. When a tough decision comes down to the line and you don't honor your values in making that decision and you take the easy way out, it makes more money or it's quicker or whatever, but you take a shortcut that goes against your values, employees absolutely. Then won't believe you in those values. And now it's just going to be the wild, wild west.

Right.

With.

With the epic culture at VMware, do you remember an example specifically of when someone, you know, that shift that got made of someone who, you know, was. Went against that culture and was in some ways, you know, disincentivized. I'm not saying punished, but in some way there was an experience that. That was unacceptable and that what are the ways that people shifted to start celebrating that culture and those cultures, cultural attributes?

Well, I don't want to call anybody out in particular, but I would definitely say long term you wouldn't make it at VMware if you did not fit within the cultural values. You just won't make it. Yeah, you might make it for two years, you might kind of scoot under the radar for a while, but you ultimately won't make it. The way they really put those values to practice is celebrating those values. Whether it was, you know, celebrating community service, whether it was highlighting execution in its finest, whether it was employee awards, whether it was departmental awards, whether it was, you know, storytelling at all hands. They did lots and lots of things to bring those values to life. And. But yeah, I felt pretty confident that if you didn't, if you know once in a while someone's going to go off the rails, but if you consistently did not lead in accordance to the values, you wouldn't make it.

So it sort of began to sort of just pick up in the fabric and people just had to embody those things or they just ultimately weren't going to be a fit for VMware.

That's right. That's exactly right. And that is not what culture is, because culture isn't really a, it's not a survey where I go ask you how you perform against these values. It's kind of how you act, see, do behave. Yeah. And you're kind of expected to fit within the culture. And if you don't, then it's probably not going to last.

Right, Totally. You know, Robin, I've heard you talk about the, the you personally making things up, sometimes taking risks, risking failure. And how you said it's important for companies to be able to keep the door open and allow people to fail. Otherwise there's going to be no experimentation and no innovation. How do you think a culture, or can you think of cultures that have been able to tolerate a certain amount of failure in order to get the risk taking and experimentation that is so necessary for innovation?

Yeah, I do think that those that are great at innovation probably are great at failure. If you're really good at the first, you're probably good at the latter.

That's a great way to put it.

It is. Because look, we all know how this works. Your first chime, you don't succeed, you never do. So you have to have three, four, five things in the fire at the same time. And I, I just think those that have, have innovation in their DNA Accept that failure is part of the journey. So how do you deal with it? I mean, one is you check regularly. Like there's check ins, like what are the small milestones that we should be seeing? You know, so you're not just waiting for this perfect success a year and a half into something. You're doing milestone checks along the way. So you're getting real time feedback. When you're getting real time feedback, you're adapting. So maybe you're throwing out your original thesis and you're adapting and modifying it. You know, I think also when you have a culture of innovation that accepts failure, you have very clear metrics that you're measuring against. And instead of it feeling like you didn't perform, you're able to say, I think this isn't performing because the market's not there, or we're ahead of the market, or we don't have some of the block and tackle that would be required to make the success. It's not a personal thing that I failed. It's I'm learning about what it would take to succeed. And I think that's really important because one, you might want to try again somewhere down the road. Two, you might need to go do some other innovation first because that feeds and breeds something else. So I just think anytime you're able to get insight and data and feedback, usually you're able to adapt. And that's part of the culture around innovation.

Yes. And then it's also part of the way we sort of say the thing failed, you didn't fail, the thing failed. And also it didn't fail, we just iterated it a couple of times and now it's different. And now it's either succeeding or it's, you know, sort of moving in some direction.

Yeah, and I think it's a really powerful thing to say. This is not worth our time. We have, we've, we've tested for these things, we've innovated, we've tried. These four things are, we're questioning the thesis and we frankly think our time should be better spent elsewhere. And hey, we probably got some new insights that we want to go chase because that work led to something new that we discovered.

Yeah, absolutely. You know, I think that really that that requires a culture that does, you know, tolerate failure and also, you know, has a whole bunch of things around it, around learning and innovation. And I think it also requires in some way confidence. And I know that a lot of founders and frankly a lot of successful people deal with imposter syndrome, intense self doubt, have you ever experienced imposter syndrome?

Well, I definitely have dealt with self doubt and lack of confidence. And that's kind of part of pushing yourself. Right. That kind of comes with the territory. The question is, how do you handle your vulnerability? Yeah, my personal style is, and I have a couple of different styles. Like it's not just a one style that I've got. Right. There's some times where I'm fake it till you make it. And I'm like, you know what? Nobody needs to know that I have no experience in this and I'm smart and I can ask the right questions and I'm a business person and I can fake this. And sometimes as a leader, I don't need for everybody to know how shallow my experience is. My job is to help others be successful and set the tone and pass. So that's one model. Another model says, hey, I just tell people this is new territory for me. I'm very transparent about it. I'm authentic about it. I surround myself by people who are experts in these things. And I don't try to be an expert in a thing I'm not an expert in. It kind of depends on what I'm trying to accomplish and it depends on what my role is in the journey of accomplishing. And I've used both those techniques. I have, I have done the fake it till you make it in some examples and on the other, I've been extremely open about. This is really, I'm out of my territory. Let me rely on the people around me who bring those skills to the table.

I think that's so important to be able to have people around you who can support you in those cases. And also sometimes to sort of step out there and say, well, I'm going to put one foot in front of the other. Is there ever any kind of internal chatter like the internal chatter might be? Who are you to think that you can do this or they're going to find you out? And if so, how do you handle your internal critics?

Yeah, I do think confidence, confidence is really an important attribute for leaders. Not arrogance, but confidence. And I think you have to believe in yourself. And even when you make mistakes, even when you don't know and have all the answers, I think you got to be kind to yourself. Like I personally, not that I don't have self doubt, but at least I try not to beat myself up. I try not to degrade myself. You know, if anything, I'm kind of wanting to give myself pep talks and also to play to my strengths because in any situation, you may not have all the answers, but you bring some strengths to the table. I always tried to remind myself, this is kind of interesting because I was in a tech world dominated by men, very technically based. I'm not an engineer by training. And frankly, sometimes in the tech worlds, the engineers have a little bit of an attitude that being technical means you're smart. And only, only technical people are smart. And I had to often start by reminding myself, I am smart, I'm a smart cookie. And then sometimes I would have to let them know, hey, friends, tech engineers don't have a monopoly on smart. We're all smart. We're just bringing different skills to this table. And sometimes I had to kind of push back a bit and assert myself, but it did come from a belief in my own heart and damn it, I am smart. And get, when you have that belief in your own heart, then you're able to kind of balance how you show up and bring that and not get bullied, not get pushed around, but also not over. You don't need to be arrogant either. And I think you got to start with a core set of beliefs, right?

Core set of beliefs in yourself. And also even to your point before that, you'll be able to iterate your way into the answer. And then if you make a mistake, it's not fatal. And so all those things have to play in your mind to be able to have you tell yourself and then tell other people, hey, I'm, you know, we're gonna, we're gonna work on this together. And, and to your point, I am smart.

I, I definitely think there's that growth mindset. If I, I love Carol Dweck's book about growth mindset. And to me that was always a really important part of my development journey, which is everything is a growth opportunity. And even the smartest of the smart, the most brilliant of the brilliant, still can learn. And when you kind of embrace that we're all on this learning journey, I think it can be really helpful on how you approach conversation, how you approach decisions, how you approach things you don't know about and you know, bring an authenticity to that that is non threatening and yet not self deprecating either.

Yeah, yeah, I love that. I love the growth mindset. I'm just curious, Robin, just a few more questions here. What do you wish you had known earlier on your journey?

Oh, gosh, I learned so much along the way. There was a point fairly early in my leadership where I got a wake up call and how I led and I Kind of probably could have used that, you know, a few years before. And the feedback was, hey, you lead up well, you lead down well. But across the table, a little bit tough. You know, I think I had a little bit of a I got a win attitude. And so that was really important feedback to think about. How relationship with my peer group were really important. I think I often was so focused on the work that I didn't invest enough time in my network and not networking to network just to get to know people and have a big LinkedIn following, but really to learn from lots of different skill sets and people outside of your sphere. So I wish I had spent more time doing that because I think it would have made me a better operator. And I, I love now kind of being retired, having that opportunity to do that, but I think it would have actually helped me be a better operator kind of back in the day. Those are a couple things and I guess, you know, I, that that story about the CMO journey obviously came pretty. That was two thirds to my career. But that would have been something good to know earlier. What ceilings am I putting on myself just because of how I'm looking at my choices and opportunities? And I probably would talk to myself a little bit about, hey, be willing to be a little more uncomfortable, a little sooner, a little faster.

Yep. Oh, that's so great. Good advice for everybody. And, and what specific advice do you have for founders as they embark on their journey to grow into leaders?

Yeah, I think obviously a successful startup is going to go through so many phases and founders are going to have to transform very quickly, many, many, many times if they're going to be with their companies through this journey. And frankly, it's hard. So if that doesn't work out, I don't think they should, you know, beat themselves up. At some point they might want to segue out of the leadership role and go to a CTO role in the company or head over sales or something else. And that's okay, that happens. But while they're at the CEO helm and plan to lead this through every phase of growth, I think, one, the growth mindset thing is vital. They'll never make it without constantly be thriving on learning and putting themselves in new situations. Two, they've got to surround themselves by excellence and not be afraid of people who are, are better disciplined in an area than they are, no more than they do. And rather than butt heads against that, embrace that and try to recruit the best you possibly can. I think sometimes we recruit underneath our skill sets and what we need to do is recruit above our skill sets. I think that outside in making sure they're carving out time to getting lots of inputs because the more they can see from other vantage points, the faster they'll be able to adapt their business. And we can get so inwardly focused. I think that's a critical success factor. And then recognize that every business, no matter what your business is, is a business of people. And so how are you treating your people? How are you listening to your people? How are you empowering your people? How are you inspiring your people? Do people want to work for you? Do they want to come to your organization? Are they just doing it because you're promising an ipo? Or are they doing it because it's is now in their DNA and it's in their heart? Ultimately, money will hold them for a while, but when you really get people passionate about what you're doing, you can, you can accomplish anything. So those would be a few thoughts.

Amazing thoughts. Robin. It's such a joy speaking to you and I know people are really going to benefit from this discussion and I just really appreciate the way you think about leadership and growth mindset and all the things you shared. So thank you so much for spending the time.

You bet. Anytime. Alyssa. Take care.

Take care. Thanks for listening to From Startup to Grown Up. If you like what you heard, give it a review on Apple podcast so other people can find it. And if you know of a founder or someone else who is meant to be on this podcast, drop me a line through my website, alyssacon.com.