Krista Anderson-Copperman (Asana): Today’s Team vs. Tomorrow’s Team

Blake Bartlett: Coming up on today's episode of Build.

Krista Anderson-Copperman: A lot of companies, these hydro startups, go from selling feature function to value, and this is also an area where CEOs can really look and ask themselves the question, " Can my current leader take me to the next place?"

Blake Bartlett: Krista Anderson- Copperman is a board member at top companies like Asana. Before that, she spent six years as chief customer officer at Okta, and 14 years before that, at Salesforce, in a variety of go- to- market leadership roles. In other words, she's seen both hypergrowth done right and operational excellence at scale. And guess what? Success in these high- stakes environments is much more about the who than the what. Sure, the what is important, your product and your strategy to win your market, but the what doesn't really work if you don't have the right who on your team. Most leaders are bad at assessing their teams through this lens. The most common pitfall is focusing on what somebody has historically done, versus their ability to do what's required at the next stage of growth. Yes, this leader did build your go- to market engine and got you to 25 or 50 million of ARR, but are they the right leader to take you to a hundred, 200, 500 million of ARR? That's an exceedingly rare phenomenon, but most leaders realize this way too late. Then there's also the trap of personal loyalty, of having been in the trenches with this person for years and remembering everything you've gone through together. The list goes on of cognitive biases we all fall into when trying to assess people and teams through this more objective lens. Krista has a unique knack for meeting the key leaders on a team and quickly knowing whether they're going to make it or not in the next phase of the company's growth, and that's exactly why she's in demand as an adviser and a board member for top companies, like Asana. In this episode of Build, Krista unpacks the mental models and pattern recognition she uses to assess whether a company's current team is the right team for the future. There's a lot of gold in this episode for leaders of all stripes, so let's dive right in with Krista Anderson- Copperman. So you recently told me that founders need to always be asking themselves the question, " Do I have the team for the future?" So what does that mean and why is that such an important question for founders to be constantly asking themselves?

Krista Anderson-Copperman: Yeah. If I think back to my early career and my days, and particularly at Salesforce, Salesforce is a company that is really cognizant of moving through leadership and moving people into different roles to challenge them professionally, but also just to provide a different level of insight into the business that it may or may not have had before. And at Salesforce, we always joked, " Okay, I've had six bosses in six years," and that was funny. And it is a little inconvenient, right? And I am not recommending that anybody has six different bosses in six years. But what I really learned through that was that, we were phenomenal in my time there, and I'm guessing they still are. But in my time there of really assessing the leadership team in a high growth company and really understanding, does this team have what it takes, or do these individuals have what it takes to make it to the next level? And most high- growth companies always, while they may not have a formal three- year plan, they certainly have an idea of what their revenue's going to look like in three years, or what they want it to look like in three years. Operationally, how to get there, whatnot, knows. But when I say, do I have the right team for the future? Thinking about that team in three years, and even five years, because three years, particularly from an executive perspective, is not a long time to have somebody at your company. And in many cases, they're just getting started with their real value after three years. So taking a look at that three to five- year horizon and saying, " Do I believe this person can really take me there?" And a lot of tech companies think about this at these 50- million milestones, 100- million milestones, 250 million in revenue. And a lot of companies are at that 50. And if you think about the profile that it takes and you think about sales or really, I think this is pertinent in any function, but sales is an easy example. If you think about the profile of a sales leader that can get a company from zero to 10 million or zero to 50 million, and then you think about the profile of someone to get you to 250, they're often... Sometimes they can make the leap, but it's often two very different people. Because from zero to 10 or zero to 50, you're scrappy, you're in it, you're selling. You're doing the work and leading a small team. Whereas at 250, you're leading a team and you're really figuring out what are the scalable, repeatable things so that we can do this more efficient, faster, bigger deals, faster closes? That kind of thing. And that doesn't always come naturally. That particular skill set that I just talked about, is often you've done it before.

Blake Bartlett: Yeah. What's coming through to me on that is, one of my favorite startup sayings is, first time founders focus on the what, almost exclusively, or at least first. And then second- time founders, or experienced founders, people who know what they're doing, they'll focus onto who first before the what, or at least the who and the what as equal importance. You're getting at some of the common traps that people fall into when they're either thinking about that question or not thinking about that question. What other common traps do people fall into? I imagine a loyalty thing comes in there, but what else do you see that causes people to be blind to this in the first place?

Krista Anderson-Copperman: So I transitioned to board and advisory work two and a half years ago. And I'll say this as the disclaimer, it is so much easier to see the forest through the trees when you're not involved in the day- to- day work of building a business. It just is. And the thing that I have noticed over the last two and a half years is, when I'm talking to these companies and thinking about, do I want to help them? Do I want to help them? Do I want to join their board, whatever, it's really clear to me the who. Do you have the right team? And the companies that are going to be successful, it is the who. So I want to underscore the importance of where you started with your question. I mean, the what, yeah, you have to have product inaudible fit, there has to be real pain, all those things yes, are clearly critically important. But once you get that, the who has outsize importance, because you have to make sure that you have the right team that can get you to that 250. And the biggest, and I wouldn't even say they're mistakes, because I think they're human. I get it. It's not like, " Oh, you are making a mistake." They're very human things to do. If you think about it, you started this company, you selected this group of people that were incredibly capable to do the, usually it's the what are we doing in that first stage, and then it's really hard work. It's hard, hard work. You are in it, how many ever hours a day and you guys are together, and you usually have crappy office space, or maybe now with COVID, you're all working remote, so it's a little better, but it's a bonding experience. You were incredibly bonded, incredibly close with those people, and you built this thing and it's pretty cool. And now, you're getting traction, you're seeing this result and you're celebrating together and it's starting to become... It's still hard work, but the scale from hard work, just a grind to fun is starting to shift a little bit. Because wow, this is fun. We're having some success. And if you apply that to any relationship that you have in your life outside of work, " Yeah, I want to party with that person. I want to enjoy. I want to have a good time." And so you, I mean, you said it, loyalty is one way to put it, but it is this incredible, really unique bond. And it's exceptionally hard for anyone to look at that bond and say, " This is still really functional. This is working. We work well together, everything's going fine." But you are not the person who can get me to 250. And human nature, what human nature will do is, and this is good. And as again, this is good, we want those people to get to 250 million. We believe that they can make it, because they did it with us. That's just hard, that's hard. That's getting out of a really good relationship, or I can't think is the right comparison, but it seems almost, in many ways, in the context of relationships, it just doesn't seem like it makes sense, but in this it does. Because if you think about that really good spot that your relationship is in, but then somebody in that, Todd stops performing in the same way. And so when you think about that scale of work to fun, that starts going back the other way, because that person isn't delivering what you need them to. And so then that once phenomenal relationship starts to erode and that thing that you built and that thing that you did together is a little bit, I guess, stained, for lack of a better term. It's not the same because you let it go too far. I think that's a really personal way to appeal to founders, to think about this. You want to end on a high note. We did this awesome thing. It's never going to be easy to let somebody go or to move on, but that's the biggest thing that I see is this bond and this loyalty in this relationship, that's the biggest obstacle people have.

Blake Bartlett: Yeah. There is a key distinction between person and role, and a lot of times that's the same thing in everybody's mind. But just disaggregating those two and breaking those two apart and say, " I could love this person more than anything in the world, and I could love them and all of the things they've brought to our team and all the things they've done, but let me talk about this role and the role that we're going to need for the next phase of growth, whatever it is, is that person the right fit for that role?" You can be a little bit more objective and dispassionate about it. You can still be human, you could still be kind in the way that you deliver that feedback, but having this juxtaposition of person versus role is an unlock to me and super helpful. One thing, I guess, getting into some of the specifics here on what founders experience and what founders, the day to day looks like, a lot of times, or almost all the time, founders have one quarter strength or one quarter superpower, and that comes from their background. And so, for folks that are listening right now that are in that position, I'm that product engineering founder or I'm that go- to- market founder, I have a blind spot on the other side. How do you address that in this context of evaluating, do you have the team for the future?

Krista Anderson-Copperman: Yeah. I mean, I see it all the time. And in the best CEOs, what I see them doing is being really honest and saying, " I don't know anything about go- to- market or I don't know anything about product engineering. I can interview somebody and see if there'll be a good fit for the team and if they understand our space," that kind of thing, but the easiest way, and you don't see a lot of CEOs doing it, which is really interesting to me. I don't know why. I don't know if there's this idea of these people have to have a formal relationship with me or they have to be on my board. But surround yourself with people who have the opposite skill. So if you're the founder, who's got the engineering product stuff nailed, when you think about your board, obviously you're going to have your investors, but you're going to have your independents, you're going to have some advisors that are surrounding you. Think about those people. Who do I want to bring in who can really work with me on a one- on- one basis. Maybe you're not ready for an independent on your board or you don't have space right now, but who do I need to work with me to help me understand what great looks like, at 250 million, in a sales leader? What great looks like at 500 million, a billion? And do they have the network? Are they willing to bring me into their network? Not only from a recruiting perspective, but from a coaching perspective. Can I get these people, in addition to this individual, but will they share their people with me? And there's so many people out there who will do that. I mean, people love talking about their experiences and what's worked and what's not. And obviously, you have to make sure that you're choosing well and that you're choosing the right people from really successful companies. And it takes some work networking to get there, but anybody who's venture- backed, most venture companies have these relationships, and so you just have to ask.

Blake Bartlett: First off, lean on others, just so you can outsource and lean on their brain. And then, per your point of what does good look like, what does that future role look like? What should I be solving for that are not currently thinking about today? And really leaning on those outside experts for the who, not just the what, is huge.

Krista Anderson-Copperman: Yep. Yeah. Hundred percent. And I think in that scenario, if you're having somebody come in and get involved in your team, it's sometimes just easier to have them in an advisory aspect that's really easy to do. And it's not usually a cash scenario, if you're worried about those types of things. Getting those people involved and just saying, " Hey, I just want you to meet with my go- to- market leader or leaders, and I want you just to have the conversation." And the conversation that I usually have is super casual. I don't ask them to prepare anything for the call, because I don't want to freak them out, I don't want them to feel like they're being graded. I will say just the standard and really generic, " What are you super excited about and what are your challenges?" And I usually have some context from others around what are the growth rates look like? And certainly some leading questions if there are concerns. And many times there are concerns with the CEOs or the boundaries of these companies, but those concerns will come up in my conversations when I ask questions like, " Okay, well, what metrics are most important to you?" And I hear new revenue. That's not a real sales leader if you're only concerned about new revenue, right? Or, when I ask a question of, " What does your quarterly revenue look like? What's the mix of install base expansion versus new revenue?" And it's really skewed in one way or the other for a really early- stage company, to me, I'm like, " Okay, tell me a little bit more about that." And if it's a non- issue, I'm like, okay, so we have a business leader who is, when they are at a hundred million or 250 million, they're not going to be able to think about those two books of business, because they will be similar sized in how you manage them, how you prioritize them, that kind of thing. So that's one example of a question, just really simple questions. But if you're a CEO and you have no idea about what... You might know to ask that question, but you're not always really going to know what the good answer is, because it's very nuanced and there's a lot of data and information and vocabulary that you may or may not be familiar with.

Blake Bartlett: So, when you're in those contexts and you're interviewing a team and you're getting answers like that to questions that you might ask, what are you ultimately looking for in terms of characteristics? And this is obviously through the lens of this person's going to make it, this person's not going to make it, based on my pattern recognition. What are those characteristics that tell you if it's one versus the other?

Krista Anderson-Copperman: Yeah, I mean that one is really clear to me. The individuals who come to the call suspicious, close- minded with... I mean, they don't say, " What do you want?" But they're like, " What do you want to hear? What can we talk about," type of thing, versus the individuals who come to the call and they're excited to talk to someone who has this experience of where they want to go and what they want to be. They have some questions. It's not that they're formally showing up with these questions, but they do have some questions like, " Oh, my gosh, tell me about this," or" Tell me about that," or, " I'm having this challenge." And it's just really a fun conversation and a open dialogue. And there's no sense of holding back. I mean, transparency is key, inaudible to any of these types of conversations or relationships, and people who show up that way and they show up curious with passion, those are the ones who always, I mean, you're going to do better in life, you're going to do better in your career. You're going to do better in anything if you show up that way, versus closed off and, " No, you can't really help me," or, " No, This is not my thing. I got it under control. We're good. This is what we're doing." Nobody has it under control in a company that's growing revenue at 90% year over year. That's impossible. You just don't. There's lots of things that you're not going to have the bandwidth to deal with.

Blake Bartlett: Yeah. So what I'm really hearing through that is curiosity. And what it looks like in real life is, does the person come to the meeting with the advisor that's here to help and view it as being called into the principal's office?

Krista Anderson-Copperman: Right, yeah.

Blake Bartlett: And so, that's more of the, " What do you want from me? What are we here for? I was told I had to do this, so here I am. I'm doing it. What next?" That could be a response that you get and that doesn't show curiosity. The other side of the equation, what you were describing is somebody who's like, " Oh, my God, thank you. There is an amazing expert that was gifted to me that I can go and get help from. I got a list a mile long of questions to ask you, Krista. Please help me." One very much clearly shows curiosity and engagement, and I want to develop and I want to improve and I want to get to the next level, and one shows resistance and lack of curiosity.

Krista Anderson-Copperman: Yeah. And I think that there is a detail there that you might have somebody who shows up with that passion and curiosity, but it's not, they might not be a fit for the role. I will go back to the CEO and say, " Hey, this person really showed up in an amazing way. I think that they can make it or I'm not quite sure, but I'm not convinced they can't. And so here's how I would think about surrounding that person with support." Because, I mean, the CEOs are almost always, it's pretty rare that I'm put into a situation of like, " Hey, I don't think this is the right person. Will you go check?" It's more of like, " Hey, go talk to my team, tell me what you think." And so, they come to it from a positive place and a positive point of view. And so if I can go back and say, " Hey, this person is showed up great, had great questions, but I'm not quite sure they're going to get there. So here's what I would do to make sure that you can continue to lean on this person, who has been with you for so long and who has done all this with you." That's also a great outcome.

Blake Bartlett: Just a quick break in today's conversation to make sure that you're getting all the latest in PLG content from OpenView. First things first, if you haven't subscribed to Build in your favorite podcast app, make sure you do that now. We drop four episodes per month and subscribing is the best way to stay in the loop. And while you're at it, drop us a rating and review for the show so that others can find it as well. And secondly, did you know that I'm a YouTuber? I put out weekly videos on the latest and greatest in PLG with my show called the PLG 1, 2, 3. Every video is two minutes or less and features VC perspectives, from yours truly, on the latest in VC, SaaS and, of course, product- led growth. So find me on YouTube by searching Blake Bartlett, and make sure to subscribe to my channel so that you don't miss a single video. Okay, now let's dive back into today's conversation. Yeah, and in addition to curiosity, another thing that strikes me here is, how willing is somebody to change and how do they view change? And people talk about that a lot, " Are you comfortable with change or not?" But it's a different thing to ask the very basic high- level question and get a yes or no answer, and be able to actually assess somebody on that. And so what do you think about, is that an important part to you when you're doing some of these sessions, is evaluating somebody's appetite towards and posture towards change, or is that less important than curiosity?

Krista Anderson-Copperman: Yes, 100%. But on the change thing, in particular, again, curiosity and openness to change go hand in hand, and you can usually tell if somebody shows up not curious. And then something in the conversation becomes pretty clear that they do not want to change whatever it is they're doing in any way, shape or form. Which should be a flag for CEOs, like, " Wow, I'm in a high- growth company, and I have somebody who wants to keep doing something the same way." That doesn't work. Just fundamentally, that is going to clash. You know? But when I was in an operator role, one of the questions I always asked in my interview was, in my interviews with people, was, " Are you open to change?" And everybody's, " Oh, yeah, yeah. I'm good with change, blah, blah, blah."

Blake Bartlett: Love change.

Krista Anderson-Copperman: Right. " I love change. It's great." You know? And then I would say, " Well, I have yet to interview somebody who says that they don't love change or that they might not love it, but they can manage through it." And I would always say, " Before you really, truly think about taking this role, you need to have a long talk with yourself in the mirror and be really honest about how open you are to change. Because high- growth companies are different companies every year. The company that you join one year is going to be, in many ways, a completely different company a year later. And being able to institute change and be a change agent, but also just to roll with change, both inside and outside your purview, whatever the scope of your role is, is so incredibly important. And I think what I do see sometimes is you... And I could even say that I was probably a little bit of this when I first joined Okta, where you have somebody who's... I came into Okta as a CCO and I'd done the role, I'd done it all. I'd been at Salesforce for 14 years, I had this incredible experience. And you see some people who come in and it's really easy to just institute your playbook. And there were a couple of times where Todd, my boss and the CEO of Okta was like, " Are you just doing your playbook or are you actually..." And I was like, " Oh, yeah, you're right. I'm not actually looking at what, I'm just doing my thing." And so it's also, the onus is on us, as leaders, to really think, " Okay, this is complete." Every time you go into a new role, this is different than my last one. It's a different company, different culture, different product, different customers, different everything, and your playbook will be different. You can take things from it, but don't do that.

Blake Bartlett: Because I agree that this is a really hard thing to actually get the truth on, because everybody will say what you said, which is, " Yeah, love change, it's great." So how do you, whether it's in an interview context, if you're bringing somebody new in, because that certainly applies here as well, or if you're assessing your team for, " Do I have the team for the future?" How do you get to the root of that? How do you actually find truth there versus just people giving the right answer in an interview?

Krista Anderson-Copperman: Yeah. I will ask... As I say, " Listen you just got to be honest with yourself." And I actually think that works, because it underscores the gravity of what you're talking about. You need to be honest with yourself, are you really good with change and are you good at it? And can you manage it and can you create it? Because if you can't, you will not be successful here. And just being really direct and upfront with people about that. Because some people will say, "you know what? Maybe I'm not. I didn't really think about it, but maybe I'm not." It doesn't happen very often, by nature of what they're interviewing for and they're interviewing for a startup, but the other things, the other questions that I will ask around this is, " Tell me about a fundamental shift at your last company. Whether it was a product pivot, it was...," and these are go- to- market questions, "... but a product pivot, if it was a fundamental change in how you positioned your products. How did you lead your team through that?" And I'll give you some context behind that. A lot of companies, these hyper startups, go from selling feature function to value. And this is also an area where CEOs can really look and ask themselves the question, " Can my current leader take me to the next place?" Feature function is, " Oh, we have this, this, this. And yeah, our competitor has, that, that, that. And here's the use case it solves for you." Selling the value is a very different conversation, right? Here's what this is going to bring to your business from an efficiency perspective, from security perspective. And it's a different person that you're talking to. And particularly, for go- to- market leader, going from zero to 50 is often that feature function sell and sometimes even zero to 100, but then there's a shift where, and particularly if you're going upmarket into larger enterprises, where you have to start selling this differently. And so, " Tell me about that process at company X, Y, Z, and what did you guys do? And did you lead it and how did it go? And what were the obstacles?" And you'll get a sense of, I mean, that's a very specific example of have they done this? But the way that they talk about it, you will get a sense of, if it was a pleasant experience or not. And if it was not, that's an indicator of, oh, okay, so maybe this person won't be able to work through this type of change that we'll have. Because you'll have those changes many times.

Blake Bartlett: Yeah. Yeah, I like that a lot. And another one that jumped into my mind as you're describing that is, assuming that they're coming from another startup or another high- growth company, it's like, " Hey, so it looks like you're at company X for a handful of years. You joined and it was a hundred employees. You're leaving now and it's 500 employees, that's a lot of growth. What was most challenging about that experience?" And just open ended. And if you start to hear things, like, " Well, I wanted to have a plan that was the same plan the whole time through, and then it was just constantly changing things. And the dog was chasing the tail," and all these things. Obviously, there could be some validity there if there's bad management there. But if what you were saying, it's how they answer the question. It's the energy you're seeing and your frustration that they're pointing to, that will tell you what you need to know about, are they comfortable with change or not? So yeah, going to those real- life case studies and not just asking the explicit question, " Do you like change or not?" But, " Tell me about this experience, tell me about this journey. Where was it most painful? Why was it most painful? How frequent was it painful?" That can really get you to the truth.

Krista Anderson-Copperman: Yeah. And I mean the other big sign is, " Because it got too big." And there are some companies... I mean I was at Salesforce from 20 million to three billion. And we went from a couple hundred employees to 14, 000 employees. For me, that was too big. That's different than someone saying, " Oh, 500 employees or 250 employees was too big." Because if you're a 50- person shop, you're going to be at 250, if you're a high- growth organization and you're having success, you're going to be 250 or 500 pretty quickly, and it'll happen in three or four years, most likely. So that, " It got too big," or the politics of it. Because there's often in organizations, like old guard, new guard, when it's time to look at the leadership teams and shift and like, " Oh, these new people came in, blah, blah, blah, blah." That's also a sign of... I mean maybe the new people really were terrible. Chances are not all of them were, but that is also a sign of, " How are you going to do when this happens to us?"

Blake Bartlett: Okay, so wrapping it up here. A lot of folks listening right now are those founders and leaders at younger companies, companies that might be in that couple million of ARR, up to maybe 20 million of ARR or something like that. And they primarily have been focusing on getting their team in place for the first time ever and might not have asked themselves the question of, " Okay, great, I have them in seat, but are they the right team for the future?" And so, if somebody's looking to practice this and embrace this in real life today, but they've never done it before, what's a good starting point?

Krista Anderson-Copperman: I'll say buckle up, because you will be doing this for as long as you're a CEO of this company. And just when you finish, you will start again, which I think... One of the companies I work with is a first- time CEO and co- founder team. And I started with them and they already knew that they needed to make some changes in their leadership team, and they made one and they made two and he's like, "Okay, I'm done." And I said, " No, you're not. Something's going to happen in the next month and you're going to see, 'Ugh, now I got to do this.'" Because it takes a long time to find the right leaders. I mean, you're talking about the top leaders in your organization, your directs, and those are not quick hires. Those are anywhere from three months, at the very best scenario, to a year. And in some cases, a year and a half to really find the right individual. So if you take that across exec team of six and just do the math, just when you think you're done, there's going to be the one that you started with, who you might have to go back and look at again, or the next level down. So, I think that is the first thing. Just make peace with it. This is part of your job. The same CEO said to me the other day, he's like, " I'm basically a glorified HR leader. It's all I do is people. I don't get to do the product." And I laughed and I said, " There is some truth to that." Yeah, there are ways for you to extract yourself from much of this. And as you grow, you will. But really the key piece of it is the people piece, and it comes down to, like you said, the who.

Blake Bartlett: Yeah. And basically, what you're saying there is that as founders, as CEOs, people need to be comfortable with change themselves, because you're leading the organization that will never stop changing. And so, your advice of buckle up, because you're never going to stop doing this is exactly right. And so everybody listening right now, buckle up, take notes on this episode. But yeah, lean into it. I've heard many people say there's a direct correlation... Success in life, in general, I think, but especially success as a leader in a growing organization, like a startup, there is a direct correlation between how successful you are and how willing you are to have uncomfortable conversations and do uncomfortable things. And so, this is front and center in that. And so, buckle up, lean into it, because it ain't stopping.

Krista Anderson-Copperman: Yeah, and specifically, lean into your instinct. Your instinct is usually right. And if there's something, if you don't know where to start or you don't want to, listen to your gut. There's something there, almost always. And it... Yeah, we'll leave it at that.

Blake Bartlett: Perfect place to leave it. Well, Krista, thank you so much for joining us on the Build podcast. This has been fantastic, and I'm sure incredibly helpful to everyone listening right now. Thank you.

Krista Anderson-Copperman: Yeah, thank you for having me. It was fun.