#69, Rahul Vohra, Co-Founder and CEO of Superhuman — How to craft core values, tactics for implem...

Welcome back. This is From Startup to Grownup, and I'm your host, Alisa Cohn. And today I'm thrilled to welcome Raul Avora back to the podcast on his second appearance. Raul is the co-founder and CEO of Superhuman, the email app which allows you to crunch through your inbox super fast. I loved this discussion so much. This episode is all about values and culture. Raul first explains why values are so important to have at your company, even when you're just starting out. And he goes step by step through the superhuman process for how they identified their values. You can literally cut and paste his process and do this yourself. Raul and I also talk specifically about how they assess for values of their hiring process, and then especially how they use values in their execution of the company and the evolution of the product. And we talked about what happened when the company evolved enough to hire a president and what that meant for Raul to be more divorced from the day-to-day of his company. This is a really practical and realistic conversation on a topic that many can see as fluffy, and Rahul is so articulate that you're gonna enjoy it and get a lot out of it. So please enjoy my fantastic conversation with Rahul Vohra, co-founder and CEO of Superhuman.

Rahul, welcome to the show. I'm so excited to have you. Before we get into sort of topics of value and culture, values and culture and whatnot, what's new with Superhuman? I, as a proud user and delighted ambassador of Superhuman, Superhuman. I've noticed a number of changes myself, but what— just give us sort of updates on Superhuman.

Gosh, well, I think we last spoke at the end of 2021, so it's been some time since then. We launched our full-screen calendar week view. That's one less reason to switch out of Superhuman. We launched Superhuman for Outlook, making it available to the 350 million people who use Office 365. We launched Get Me to Zero, so you can imagine an inbox that only contains the things that you need to do. Uh, but what if your inbox overflowing? What if it contains thousands or even millions of emails? Well, with Get Me to Zero, we can get you to within a stone's throw of inbox zero. Maybe my favorite is we launched AutoCorrect, which fixes errors as you go. You've probably seen this— extra characters, missed characters, transposed characters, punctuation, capitalization, to name just a few. And it actually does better than the autocorrect in Gmail and in Outlook. And then most recently, we launched Superhuman AI, which can now write entire messages effortlessly, even in your own voice and tone. It can translate languages, summarize long emails, research almost anything, and it can do that, all of that, I should say, in an instant.

Wow.

So that's all the stuff that we've launched publicly since then.

Since then. Okay. So I knew, I have been experiencing autocorrect. It's working really well. I have not had the courage to work in Box Zero yet, but I'm still getting my courage up and I had no idea about the AI feature. So I'm very excited about trying that. That sounds amazing. Now, Something that we've explored before that I really wanted to get into today is kind of this topic of value. So you are a second-time founder and, you know, you were an entrepreneur, or just, I want to say, like, obviously a first-time founder, but also just earlier in your life. How do you think about the importance of values and maybe culture now than you did kind of in your earlier days as an entrepreneur? How has that changed?

Well, for my last company, Reportive, we didn't really think too hard about our values, but at Superhuman, values are actually always something that we've taken incredibly seriously. So almost the opposite points of view. And I think that most companies take a few iterations to get their values right. They often write down vague concepts that are table stakes and which don't really differentiate them from any other company. So to avoid that, we went through a fantastic process from the book The Advantage by Patrick Lencini. And as you know, in the book, He introduces the idea of core values, and even better, he gives you an efficient process for identifying them. So core values are those which you can credibly claim to uphold more intensely than 99% of all other companies, and they're so important that you would continue to uphold them even if that would be detrimental to the company. So he has this 5-step process to get to the values, and for us it ended up in 3 core values, namely create delight, Be intentional and remarkable quality.

I want to dive into all that. And of course, I'm a big fan of that book, which is really amazing in so many ways. But even before that, when you were at Reportive and you said, or when you founded Reportive and you said, we didn't really focus on values, I guess I'm curious, why was that so important to you to start with at Superhuman? Did you have an experience that shed light on that? Was there something either good or bad that made you realize, oh my God, we really need to focus on values from day one?

There was no particular catastrophic experience from Reportive that led me to wanting to do values at the start of Superhuman. More a recognition that it was going to be a bigger company. Reportive was, including myself, 5 people, whereas Superhuman today is north of 100 people, and we intend to continue growing. We want to create a generational organization that'll be here for hundreds of years to come, hopefully. And in order to have that work, you really do you need to define your values and what it is you're all about. When you're 5 people in one room, you actually probably don't need to. I mean, you should, it's helpful to have things written down. You can point towards why you take decisions. And if you ever do scale, you'll know what got you there. But for when you are getting past the size of a single team, past, let's say, 7 people, I would say it becomes critical.

I see. I think that's great. And it, it's very, I think it's very important that you have this, you know, consistency that scales even when you can't talk to everybody one-on-one. So if we go back to your process, can kind of double-click on it, like even give us a little bit of a slice of life, like if someone were a fly on the wall watching your process, who was in the room? What kinds of discussions? Was there something that surprised you or was even maybe controversial or uncomfortable about that process? Give us a little bit of color.

Yeah, I mean, all of the above. Okay, so who's in the room? Well, you want your leadership team in the room. And for a typical startup, this will be the founder, the CEO, and their direct team.

Yeah. Who is it for you? Who is it for you?

Yes. So it was, it was that set of people. So 4 or 5 of us, and this was done many years ago, but it was basically my direct report. Through this 5-step process, step 1 is identifying past or present team members who embody what's best about the company. And once you have those names, dig deeper. What makes them so admired? And those qualities are the starting points for your list of potential core values. And At the time, the kind of things we came up with were things like, and this is going to be a long-ish list, but for us, there were things like think deeply, loyalty, fun or fun to be around, eye for detail, caring about delight, willing to do any task, seeing why it's valuable for the company, fearlessness or a belief that anything is possible, precision of thinking and communication, initiative, ownership, caring about others, optimism or positivity. And so on. So you can see that's already a long list and you need some way of narrowing that down. And then this is where maybe it gets a little bit awkward. You then have to step 2, identify past team members who weren't a good fit. And again, once you have some of those names, ask the tough questions. What exactly was it that made those folks difficult to work with? What are the problematic traits? And then list their opposites. And then you can add those to your potential list of core values. So for us, some of the problematic traits were things like pessimism, recklessness, entitlement, giving up when things get hard, not doing what's asked, uncomfortable being uncomfortable, not being collaborative. But then you invert those, and so you can turn those into things like optimism, thoughtfulness, humility, persistence, resourcefulness, the mindset to do what's asked, a growth mindset, collaborativeness. And then you can merge those two lists, the list from step one and then the inverted list of positive traits that you just came up with in step 2. Then step 3, you discuss whether the team that you have today— this can be a little bit awkward as well, but worth doing— actually embodies those values. So this is honest self-reflection. So you go through each value and you ask whether everyone on the leadership team shares and embodies that value. Now, if the leadership team does embody that value, it's a potential core value. This is really important. You, you need core values that your leadership team actually does embody, not ones that they wish they embodied or ones that they think they do, but ones that they actually do embody. If the leadership team does not embody a core value, then it's a potential aspirational value. And so we were able to start to distill these down. And then ultimately we get to wordsmithing. Step 4 is isolating the core values. Does it come naturally to us? Has it existed in our company right from the start? Can we credibly say we do it better than 99% of all other companies? And if you can say yes to all three, then you found a core value. Value. And then step 5 is actually where most companies jump to in the beginning, which is never a good thing, which is wordsmithing the core values. You know, we all glaze over when we hear values like teamwork, integrity, creativity. Integrity. Right, exactly. Who really, uh, can you credibly say that you have greater integrity than 99% of all other companies? I mean, the answer is probably not. So most of us can't even imagine what that would mean. But this is when you get to the wordsmithing. And that's how we got to create delight, be intentional, and remarkable quality.

I love that. I love that so much. So you mentioned this sort of, like, uncomfortable awkwardness about, like, hmm, those people who left, how come they were hard to work with? But then also even more, I think, uncomfortable is the people in this very room, this leadership team, you know, which are the values that we embody? And I'm just curious, You know, did you find— and I know this happened a little while ago, but I'm just curious— like, did you find that maybe not everybody had the full self-awareness that you would have wanted? Like, they're like, "Absolutely, I'm very, you know, I don't know, collaborative," or something. And you, your assessment was, "Mm, not so much. There's room to improve on that." Like, was there any sort of uncomfortable conversations that had to happen on the topic of self-awareness and how people related to themselves and these values?

I don't remember that aspect of the conversation being uncomfortable because of a lack of self-awareness. We had a list that I think was along the lines of clarity, precision, striving for excellence, growth or self-improvement, efficiency, empathy, impact, taking risks, experimentation, perseverance, create delight, and fearlessness. And it was a group of 4 or 5 of us. We'd worked together years at that point. So we knew each other really well. We were doing this out of the office. We were doing this in a breakfast setting. So it was very calm before the day had an opportunity to take over. And we were just reflecting on what each of us thought we embodied and what we didn't. And I remember some people saying, I don't think we as a leadership team do all exhibit Persistence, or I don't think we as a leadership team do all exhibit some other thing. And persistence is an interesting one. It's one that I feel like I exhibit. I feel that I have a lot of persistence. I'm very gritty. And I remember somebody else on the team calling us out. And there is a way to do this that doesn't make it personal. They didn't say, I think the person X does not exhibit value Y. What they said though was, I think that we as a leadership team don't all exhibit this value. And we talked about it and we were like, okay, Maybe you're right. And the challenge, and this is where Leoncini's book is so helpful, that they put forward was, Rahul, do you really think we're more persistent than 99% of all other companies? I said, well, maybe when you put it like that, we're not. Okay, fine. And I dropped it.

Yeah, I see what you're saying. I think that's really helpful to put it like that. So then you had this beautiful list and you got it down to, I think, very elegantly worded that you got to that wordsmithing part, elegantly worded Traits and values, and then you're like, ta-da! You come out of the room. And what changes in the company when you do that? Or if nothing changes, what is the impact of having really gone to the— this is a pretty ornate process you went through. What changes as a result of that process?

Yeah, let me think about that for a second. I think hopefully not that much because this is how you've been acting anyway. But I think what you have to start to do is agree on how you're going to reinforce the values over time, how you communicate them, how you spread them when new members join the team. So we did a few things along that dimension and actually starts before we even make a hire. The very first thing we did is describe these core values with a little bit of exposition on our jobs page, and they are still there to this day. The second thing we did is when you join, it's one of the first things that we actually cover in our Welcome to Superhuman Notion page. Each value is covered in detail and we have dozens of examples on how we've upheld those in the past. And then the third thing that we did was we made it part of our vernacular when we were taking decisions that Maybe they don't seem obvious, or even when they did, we tied it back to the relevant value. We actually still to this, to this day, we have a Slack emoji for things like create delight or remarkable quality so that when other people on the team exhibit these behaviors or we see decisions being made like this, folks can use these reactions to sort of tag those messages and say, I recognize this behavior as creating delight, or I see that this decision is in service of remarkable quality.

I love it. So good. You know what's so powerful about that is that, that is the whole point is it's embedded. It's embedded in your Slack emojis. It's embedded in your process. You talk about it. So it's not, you know, the whole notion of it's on the walls, but not in the halls. So you're taking it and making it real life so that people actually live and breathe it, which is kind of the name of the game when it comes to values. How do you introduce interview for values? How do you make sure that the candidate understands them on the way in and also is going to be the kind of person that cares about, for example, creating delight or the different areas? Like, what questions do you ask?

So I think, first of all, you say, this is what we look for. This is what we're hiring for. Everyone at the company has these values and cares deeply about them. Here are some examples of ways that we we have created delight or that we have pushed for remarkable quality. And then you simply ask for times in the user's history where they've been able to do the same, or a time in the candidate's history, I should say, where they've been able to do the same. Now, not everyone will have had the opportunity to do so. It's a fairly unique company culture that we have that we actually do put on a pedestal the idea of creating delight or that we do prioritize remarkable quality. And actually, that's a lot of the reason why folks want to come and work Superhuman because they were looking for precisely that and their existing company is not giving it to them. So if people aren't able to articulate how they've done that at work, we let them articulate how they've done that outside of work, maybe in their personal life or in a side hustle, or perhaps they're able to show us how they've done it in a hobby or in a passion. And if they're not able to do it there, or if they haven't been able to show it there, then the very least that we look for is a very explicit enthusiasm that that is the thing that they're looking for, that that is why they're they want to join. But I should say that at that point, when all you have to go on is the candidate's enthusiasm, it's going to be a bit of a risky hire because there's no— it's only words at that point. You haven't been able to point to previous actions or behaviors that show they really do embody those values.

Right. Totally. Have you used your values to make difficult decisions either about people or strategic direction or anything, any other kinds of choice and decisions you've made at the company?

Absolutely. An example would be our white glove, one-to-one concierge onboarding. And in that case, all three values are at play: create delight, be intentional, and remarkable quality. I should say that we've actually evolved be intentional. We now call it embrace the extraordinary, but that's a slightly separate story. So we can come back to that.

Yeah.

And I've seen a lot of companies, especially in our space, which I would broadly describe as productivity, essentially launch badly. In fact, I no longer believe in the traditional launch. Let's say you've built a new email client or a new task manager or a new calendar app. Now, the surface area for these products is absolutely massive. It's bigger than almost any domain you can think of. And what that means is you also get a massive surface area for bugs, as well as massive variability in how users want to use the product. Now, most companies would just launch their app, and because demand for these things tends to be so high, they quickly get tens of thousands of users. But guess what? Those users will find thousands of bugs and your company would quickly get overwhelmed. You would not be able to fix the issues fast enough. And so then those users become disappointed, they'll churn out of the product and they'll tell everybody about their experience. That isn't delightful, it's unintentional, and it's the opposite of remarkable quality. In fact, it's the remarkable lack of quality. So we took the very unintuitive and controversial decision. No other company at the time was doing this to onboard customers at a fixed and measured pace every single week. And that way we had the bandwidth to fix any issues that they found. And through addressing those issues, we were able to focus on making them exceptionally happy. And you know what exceptionally happy users do about your product? Well, they remark upon it. And so that's a good example of how we used all three values to end up with a very unusual and widely misunderstood decision.

I love that. I love the way you say that. I remember my own onboarding process into Superhuman, and I was actually very surprised, like, Really? We're going to work? Well, I was a little annoyed. Like, are we really going to work on this one-on-one? Like, I don't exactly have time for this. And yet it kind of unlocked a whole bunch of secrets. I was like, oh, okay, I can sort of see how this— use it— how this will work. But also, I'm the kind of person that when I get a new piece of technology in any way, shape, or form, I tend to just put it— I'm like, oh, I don't know if I can do it— and put it off. So it forces you to kind of double-click on the thing, like to open the thing. And I think that's also very helpful. Are you still doing doing that white glove onboarding?

Yeah, well, so, so here's the interesting thing is that is something that has changed over time. Now, I would say we've never had to do a big pivot. We've never had to sort of drastically change direction. But a few years ago, we were 85% concierge and 15% self-service. And today, those numbers are reversed. We are 15% concierge and 85% self-service. In fact, we have a new mantra for this, which is an application of the Create Delight value, which is simply to meet users where they are. Some people still really want and crave that one-to-one onboarding experience. I know it's what I would want. I'm too busy to think about how to do this stuff, and I just want someone to tell me how to do my email. For that kind of person, perfect. But some people are on the other extreme. They don't really want to talk to anybody, and we've now built out a really polished self-service experience for that kind of person. And interestingly, some people are in the middle. They're happy to turn up to a training,, but they don't want to share their screen or apply the techniques to their own email during the session. They want to do it afterwards. And for them, we've built a group training experience. So by asking the question, what's the best way we can apply the value of Create Delight to each type of user, we've now ended up with a very different shape of go-to-market motion than we had even just a few years ago.

I see. That's very interesting, right? And also it gave you time. I think that your first experience in onboarding gave you time for people to take up the product and to your point, to sort of suss out any bugs, and then it gave you time to build out the training tools that are more customized to different demographics or different audiences.

Yep. That's right.

I love that. Now you were talking about evolution of which evolution of which value of be intentional. Was that the right one?

Yes.

Tell us about that. How did you, how did that evolve and why was that important to evolve?

Those original 3 values served us very well, at least I think for 5 years, but just recently we tweaked them. We retired "be intentional." We originally used it to describe how we think things through from first principles. And as a result, we've often come to unintuitive results or decisions. For example, deciding to charge $30 per month in a market where the competing products are free, or deciding to onboard users with that white glove concierge one-to-one experience that we just talked about. But we saw that "be intentional" was being misused internally. It was actually being used to slow decisions down. For example, people might say, We shouldn't rush through this, or we shouldn't do that. What we should instead do is think this through from first principles and perhaps come to a different conclusion. And of course, that doesn't work well at a startup. You need to move really fast. So we've replaced the value with embrace the extraordinary. And what we've tried to do is in the definition, hold onto the idea that we're not afraid to do things differently. So the way that embrace the extraordinary reads is we form bold visions that push the limits. We defy the status quo. And we inspire results. We are not afraid to do things differently when needed, even if it may be misunderstood in the short term. And we have relentlessly high goals, goals that others may find unreasonably high. And so with that, we've evolved that value. It's now embraced the extraordinary. It still has the do things different aspect to it, but it no longer has the, perhaps the, the slowness or the bias against action that be intentional, if misused, could have.

I love that. And I love the way you sort of had the insight on, huh, on the one hand, this is good. On the other hand, it's slowing us down. But I think the same question I asked you before about the values, you guys, who decided this? Was it just you and your leadership team? And then let's say you decided on a Friday. What happened on Monday about this value? When did you first hear about it? When did you first hear about it?

It was first brought up over the course of the last year or so. We were trying to diagnose certain things that weren't working as well as we would've liked inside the organization. And the reflection that was brought to me was that, hey, this value is being misused. And I would say, well, that's really weird. Here is how we intended the value to be used. What are you seeing? We'd talk about it, we'd reflect. And then a few months later, we decided to make the change. Now, that decision happened at the senior leadership team level, which currently is just 3 people. So it's me, the president of Superhuman, and our head of people and our foundation teams. We talked about the issue with the value. The recommendation was made to me that we retire the old value, that we come up with something new. And I said, that's fine, you two can make this decision if that's what you think the right thing to do is. All I would ask is that we preserve the key aspect of the previous value that I think made it special. And that key aspect was this, uh, almost this gleeful joy of, of doing things differently when it makes sense, because as a startup, kind of by definition, you have to, you have to do things differently, otherwise you're not going to succeed. And so they ran with that. They then involved the various managers and the other leaders at the company.. And that was a process I wasn't taking part in. And it was actually the first time we've evolved our values with a process that I wasn't taking direct part in. I provided my input at the very beginning. I looked at the output afterwards and I was like, yep, I fully agree with where we've got to. And that's how we came to embrace the extraordinary.

Well, that is amazing. I'm going to go back to, in a second, I'm going to go back to asking you how that felt to kind of be divorced from that process. That's kind of amazing that you were able to let go, right? That speaks really well of your team and of you. But before we get there, I guess I still want to know, it's like you've got, you know, 100+ people in the company and they're all living the dream of being intentional, right? And you're now asking them to embrace, you said the Embrace the Extraordinary, right? And so how did they get the message? And surely in the first week or two, decisions that you were concerned about were still slow. Can you kind of map that process of how, first of all, you had the— not the eureka moment, but you were able to say to everybody, "Ta-da! Here's what we have. It's new," and then do the hard work of change management inside the company?

I think this is best solved, like so many other similar decisions, with cascading communication. First of all, the The set of people who really needed to know was actually the set of people who came up with this, the leadership team and the managers who collectively took part in an exercise to first of all observe, look, we have an issue here with this existing value. Let's align on that. You can't skip that step. That's super important. And then secondly, let's design something better. And because the design process was collaborative, there really wasn't any selling of the value to the people who most needed to internalize it. They were the folks who came up with it. So we then cascaded communication. Those people then go and tell their teams and explain why the things that they've learned, the reflections that they've had over the course of coming up with this new value. So it was a very simple exercise in cascading communication and in involving the people who most needed to make change with first aligning on the issue and secondly coming up with a solution.

I love it. So good. Cascading communication. So simple. So often overlooked. So useful. So useful. But now I come back to you being able to give input into the process, walk away, and then come back and get the outcome that, you know, it was actually a pretty good outcome that you approved of, that you felt, okay, this makes sense. I guess I'm just curious, was that uncomfortable for you? Were you concerned? Like, this is, you know, you're the founder, this is your baby. You're also, you know, the CEO, the leader. It has to go well. This is an important topic and something near and dear to your heart. Did it feel uncomfortable for you to let go?

It actually didn't. I think over the last year or two, I've become a lot more comfortable with letting go of the things I'm less good at, or perhaps I'm good at, but they don't bring me that much joy, and really leaning into the areas where I am excellent or they do bring me a lot of joy. For example, leaning into product design and certain parts of marketing. And that was also the same change that led to hiring a president. So our president started, I think, in the middle of February. This is our first true C-level executive. And honestly, it's changed my life significantly for the better.

Oh, yeah. Tell us about that.

Well, before I was very focused on, I mean, just sort of the operational execution of the company. And so that is everything that, you know, that goes into that. So hiring and firing the leadership team, setting their goals, holding them accountable, marrying that to the strategy of the organization, evolving the strategy when it needs to be evolved, cascading the communication of that. And somehow at the same time, doing all the things that got us here, building a world-class product, making something people want, helping them realize that they want it, doing world-class marketing, world-class design, and so on and so on. Now, when push comes to shove, when you have to choose between those two things, especially at scale, it has to more and more be the former and less be the latter. And of course, that's really dangerous. What can then happen is your product quality starts to drop, or the velocity at which you ship starts to drop, or the quality of your design or the efficacy of your marketing message starts to decrease because the thing that got you here, which is this cohesive understanding and alignment between all three of those things starts to fade away. And what you instead start doing is just spending all of your time running the company and probably not particularly well because, you know, I'm a, I'm a founder. I'm not a professional manager. I didn't grow up learning how to do that, and I've probably acquired all kinds of bad habits or at least idiosyncrasies along the way. And so it was a realization that that's what was happening and it wasn't best for me. It also wasn't best for Superhuman. And so with that realization, we went ahead and hired a president. The president has a very wide scope of control. They run engineering, product, and design as well as marketing and sales. So go-to-market. And alongside them we have this head of people and foundation. So that is talent, that is HR, as well as finance, legal, security, and compliance. And so I've gone from 8+ direct reports, I think it was actually more than 8, down to just 2. And then in terms of how I spend my time, it's gone from mostly being in meetings and dealing with personnel issues and all of the stuff I just described. To mostly unscheduled. And what I actually spend that time on is what I used to spend time on, which is product design and marketing. And as a result of sharing this load of running the organization with someone who's much better at running organizations, that has freed me up to focus on these things. We're now shipping much more than we ever used to ship. Our customers are way happier. We're having record weeks. In fact, last week was a record week in terms of the business output of the company. And I think it all ties back to this, just this observation that we should be living in our zones of genius and doing what we do best.

I love it. It's so true. But I think it's very difficult for founders, especially founder CEO, to kind of have that realization. I think there's a lot of founder CEOs who think I'm supposed to be able to do that all myself. And it's kind of a sign of weakness to I want to bring on a president. And then I would add, again, it's like, on the one hand, I want to bring in a president. On the other hand, I can never find the right person because I just can't let go. But there's something going on. What do you think about that? Was it hard for you to come to that realization? Or have you seen that with other founders? I think—

so you made two points there. The first concern is it takes a while to realize that the weakness is present. And the second concern is it takes a long time to find the right person. So for the first concern, it takes a while to to realize the weakness is present? I think we kind of always know. I think very few founders are out there saying, I am a world-class manager and an excellent operator.

That's true.

I think if you just like point blank ask them, are you a world-class manager, an excellent operator? They'll probably be like, no, I don't think so. Like, why do I have any credible claim to be so? And then you can ask the question, well, do you think your company needs one? And maybe the answer is No, in which case that's fine, and that's a belief they'll have to sit with for a while. But hopefully at some point the answer is yes. There are some other issues that I think happen, issues like, do we deserve one, or is it the right time? We hired a president early. Most people wait until they're much later stage than Superhuman to hire a president or a COO. And so that was actually the thing I had to get over. It wasn't the— it wasn't the question of, am I good at this? I'd known for a while I wasn't. It was, can we actually credibly in market go and hire someone excellent? And for the longest time, especially during the zero interest rate years, I thought the answer was no. And so the market does have to align. Part of what made me believe it was possible was in November of last year, I could see the entire startup market just crumbling, right? The growth growth funding had basically come to a halt. And as a result, I saw the executive talent market starting to turn over at a rate that I honestly had never seen. And so people who simply wouldn't return our call a year prior were now inbounding to us, which I thought was crazy. Okay, something is happening here in the executive talent market. Maybe we can really punch above our weight. Maybe we can hire someone who is phenomenal to come in and help us build this company. And so we went out to markets and that turned out to be true. Like we were able to speak to candidates that even a year ago we wouldn't have had a chance of talking to. And so that also then addresses the second concern, which is, is it going to take a really long time to hire the person? In our case, it didn't. We were actually able to hire the person relatively quickly, all things considered, especially compared to how long it would— it was taking to hire executives during 2019, 2020, and 2021. One. Yeah, it's still not easy. You still need to find someone with whom you have amazing chemistry, someone who is a missionary, not a mercenary, and someone who agrees with your proposed split on time. And we ended up hiring this amazing person, Paul. In our very first conversation, we broached the topic of, let's say we were working together, what am I going to stop doing and what am I going to keep on doing? And of the things that I'm going to keep on doing, how is that time split? In fact, he's so precise on this that he asked me in that first conversation, can you break down, let's say I join after 90 days, can you break down how you are going to be spending your time in percentage-wise? Which I thought was a great conversation. Let's just jump straight to it. What is going to change here and how are you going to spend your time? So I gave him my wave the magic wand scenario and he was like, oh, that's really interesting. That's not what I thought you were going to say. And it's not something I've ever tried, but it could be really interesting.

Well, what did you say that he was surprised to hear?

Well, I said that, and this part wasn't a surprise because this is just obvious as the CEO, that I'll always do whatever the company needs me to do. In some ways, the role is do whatever it takes to scale and grow. Okay, so that part's obvious. And then the next part was also obvious, which is once you're ramped, there are a few things I won't be doing anywhere near as much of. And that is, uh, number 1, managing people. Number 2, one-on-ones. Number 3, running executive team meetings. And then number 4, building and developing the leadership team. That is very much the role of the president. And then here was the surprising part, which is for the time I have, here is how it will break down. And I said that 40% would be coaching our individual contributors on the craft of product design and marketing. It's things like upholding our product principles, coaching on how we write copy, on what our voice and tone is, on what makes a narrative, a marketing narrative truly superhuman. Then 30% of my time would be on medium-term to long-term product strategy and vision. And so this is things like staying close to the market, to customers, to problems and technology changes. And in fact, a really great example of that is Superhuman AI. It's amazing. People love it. We would not have been able to do it without Paul in place because Paul in place freed me up to go, "Oh my gosh, there is a sea change happening here in technology. Nobody at Superhuman understands this stuff, including myself, but that's fine. I'm just going to throw myself into this with 30% of my time and become," I wouldn't say experts, I'm far from it in AI, but become knowledgeable enough to be dangerous and to lead the organization in shipping an incredible feature." 20% of my time is externally facing press, media, things like Web Summit where you and I get to hang out every now and then, which is always fun. Investor relations, partnerships with other organizations, thought leadership, doing things like writing articles such as the product-market fit article, which is the gift that keeps on giving. And then the last 10 to 15% of time is with Paul and with the other senior leaders. And then the very last little bit of time was internally facing meetings. So things like our all-hands and rituals like Friday Wins.

Oh my God, I love it. It's so well thought out. It's very impressive and well thought out. And I appreciate your tangible example of like, you know, AI became a thing. And because I wasn't doing the budget meeting, right, I was able to like launch myself into it. And we, Superhuman, were able to launch a product. That's amazing. I want to come back to culture and values in a second. But before I do, I really have to ask you about Paul coming on board and what that was like. This is a truism. And when I had Scott Belsky on my podcast, I asked him about how you deal with the fact that there's always the risk of organ rejection when a new, especially a senior person, comes on. And he really talked about about having to hold the line and let everyone be uncomfortable as this change took on. How did you feel? Was there any moment of discomfort that you really had to say, everybody, well, he's in charge, not me anymore, and he's just what he's doing, or anything like that when he first came on board?

No, not along those lines. There were definitely moments of discomfort. But it wasn't because of that. So one of the things we'd explicitly asked Paul to do was to make the organization move faster, take decisions faster, build faster, ship faster. And that made the organization uncomfortable. That process of, well, maybe some people had sort of settled back into a little bit of a lower gear and we were like, nope, that's not okay anymore. This is the change. This is the new leader of execution and operation, and they're asking you to move twice as it's going to hurt for a while. But guess what? You are perfectly capable of doing this. And Paul, to his amazing credit, did such a good job in his first 30 days of meeting basically everybody and developing those personal relationships, establishing trust, and then leaning into driving the organization as hard as it can go. And he and I would have constant conversations about that. I'd say, Paul, can you drive it harder? And sometimes he'd say yes, and sometimes he'd say no, I think people are at their limit of uncomfortableness. And he has a really pretty good finger on that pulse. Like, how, just how uncomfortable can you make people? And the answer is people should be uncomfortable because if they're not, you're just kind of chugging along in a steady state. So whoever is, whoever has Paul's role, whether it's the CEO as it often is, but it's also often the COO or the president, needs to be pushing so that people are operating at the right level of uncomfortableness. You know, your goals shouldn't be easy. You shouldn't be sort of achieving everything. Equally, you shouldn't be achieving nothing, but everyone should be uncomfortably striving to achieve really ambitious goals.

Yeah, totally agree. It's like you want to have people bend but not break and sort of finding that right balance for sure. Did anybody, especially with some of the older employees, come to you as like an end— like, I don't want to say end run, but like come to you to say, you know, Paul's a little pushy. Or anything that they came to you about where you really had to say, you know, actually, he's the one who's in charge now, and I'm supporting— in fact, I'm asking him to go even faster. I'm asking him to make you more uncomfortable. So don't come to me.

That did not happen. And we preempted it would happen, that it might happen, or that in the worst case, it happens in some kind of public forum, like an all-hands, where someone says, well, mom said this, but dad said that. Okay, you guys, duke it out. And we agreed that if that ever happened, that we would not disagree in front of the company, that we'd sort of take it offline. But amazingly, it has not happened.

That's impressive. Yeah, that's really great. And probably, as you said, a testament to Paul and maybe his skill in sort of having his finger on the pulse. That's amazing. So if I sort of come back to— we've had this long conversation about values, and we really haven't actually explicitly talked about culture. And I think my— I have a little bit of a pet peeve around culture, which is when I ask anybody about culture, they immediately go into, "We like each other, we hang out all the time, we're friends outside of work," or whatever. By the way, there's nothing wrong with that. It actually— I think rapport and good feeling, good relationship, and liking each other is actually a great, really important tool in getting work done. But it's not really culture. It's not the totality of what culture is. How do you think about sort of the word culture, and, and how would you describe the culture of Superhuman in light of the things we've talked about with— about relative to values?

I would say that if values are how we act and take decisions, then culture is the environment that we create to reinforce those values. So for example, how do we reinforce the value of create delight? One of the most powerful cultural ways to do that is this ritual that we have called Friday Wins. Every Friday we get the whole company together to celebrate the wins from the week, which by itself is not unusual. I think a lot of that is startup best practice. You have to celebrate the wins as you go. However, at the end of every Friday Wins, I or one of our team will celebrate the word-of-mouth viral moments from that week. So we literally read out loud, reenact every tweet about Superhuman, every LinkedIn post, every TikTok video, and that sends a clear signal that actually word of mouth virality is the most important thing to the extent that we will end our wins celebration by going through all of the word of mouth virality. And how do you get word of mouth virality? Like what is the fundamental root cause of it? Well, it's remarkable quality. It's delighting users. It's making something so striking, so compelling that people can't help but talk about it. And what I love about that example is is it can be traced back to every part of the company. Obviously, product design, engineering, those folks get called out all the time, but just as consistently, our customer-facing teams like support, sales, and success, they get called out by our users in social media. And we even every now and then get call-outs for folks like our recruiting team. We've had candidates that we've said no to publicly say how amazing we were when we did that and how we were the only company that gave real substantive feedback whilst still saying no, they had a delightful experience. They had a remarkable quality moment. They went to social media, they, you know, put this out in the world. And so we celebrate it at the end of the week. So this is a good example where if you want to have a company where the most important thing is creating delight, remarkable quality, embracing the extraordinary, you actually have to create a culture that celebrates it.

I love that. That is so impressive, especially to your point about sort of candidates feeling like they were so treated that even it didn't work out, they're able to be ambassadors for you. That's quite beautiful and very unique, very distinctive, I have to say. Now, how do you think that culture— I love when you talked about sort of creating the conditions for these to happen, for these values to sort of be brought forth and to come to light. How do you think that culture expands or develops as new people join the company? Do you have examples of things that you can think of?

It definitely changes. You will, for example, get subcultures within certain groups or departments, and in many ways that isn't a bad thing. For example, you would probably expect your sales team to have a somewhat different culture to your engineering team, to pick just one example. But in some ways it can also be risky. You need to ensure that even if there are pockets of certain types of behavior, everybody knows and upholds the core values. You also need to ensure that as you onboard new hiring managers, they continue to uphold the pay-to-play hiring values, which we haven't really talked about. But in addition to our 3 core values, we also have 4 hiring values against which everyone is screened. And we actually had a time in our past when our hiring values were not explicit. They hadn't been written down, and that did cause a drift in the kind of person that we hired. It took a while to diagnose what had happened, but when we did, we realized it was because we hadn't written those values down and we weren't screening against them properly. Properly.

Oh, okay. So then how did— so then you decided we needed just to codify those with more specificity?

Exactly. Uh, so those 4 values ended up being grit, growth mindset, ownership, and proactive positivity, which we then screen for in addition to the 3 core values. And those 7 together have played a key role in getting Superhuman to where it is today.

I love it. That's so powerful. You know, just a few more questions. How would you say you've personally grown as a leader in the past year or so?

I think the biggest change, as I mentioned, has been hiring a president. In some ways, this is self-compassion. It's giving myself the ability to focus on the things that not only I'm good at, but that which also give me joy. But also it's It's just developing the trust that other people can and will do a great job. And sometimes that's hard, especially if you've had a checkered set of results with executive hiring. And, and we definitely have. I don't think our odds are any worse than most startups, uh, but you know the numbers for most startups. It turns out that 30 to 40% of executive hires simply don't make it and they're fired very early. Into their tenure at a company, which is a shockingly high number. And it takes an emotional toll. And if you're going into that for the first time, you may not be ready for that because actually what you've probably had to do in the early days of the company is put up with quite a lot of stuff, put up with, you know, personality issues, collaboration issues, performance issues. You just have to get from A to B, from B to C, but eventually you have to switch how you run the company. And it's, it's almost actually an immediate gear flip where you go from, okay, we have put up with these behaviors in the past because we just needed a team. We needed a team when there was nothing to believe in to, okay, we now have all the money that we could or that we needed to raise. We have a brand, we have a product that people love, we have scaling go-to-market. Really what it comes down to now is operational execution. So all the things that we used to put up with, that we used to tolerate, we're not tolerating that anymore. And I think that's a hard transition for founders to go through, especially when their lived experience is the former.

Yeah, it's, I think that's such an important element to realize that you kind of earned the right at some point to then hire people and then have certain, like, higher expectations for them. And I think that's part of the journey of every startup founder. What advice, Rahul, would you give to other startup founders?

Oh gosh, let's see. I would say that many startups have been through a tough year or two over the last two years, but despite that, it really is one of the best times I can remember to build a startup. Let's say you're starting to build something around now. Once your product becomes more mature, the economy will be improving. We've seen at Superhuman already that companies are starting to buy more. From our point point of view, it looks like we're well past the slower months of Q4 last year was fairly slow. Q1 this year was really slow, but things are heating up again. And like I said, in fact, last week was a record week for us.

Amazing. Start now, startup founders. This is the moment. This is your moment. And last question, what do you wish you had known earlier on your journey?

Well, I was told this lesson often and early, and it, it's really what we just talked about, but somehow I refused to take it on board, which is when things aren't working out with a leader, stop, have the hard conversation, and then move on. And don't do what I've done in the past, which is let things drag on for quarter after quarter. Now, I would often do that partially out of misguided compassion and partially out of a belief they could do better. But it turns out that once you're, once you're past the point where you don't need to tolerate that kind of behavior, then moving quickly is not only the best move for the business, it is also the most caring and compassionate thing to do. It's a tough lesson to learn, especially when you want so hard for everybody around you to succeed.

Totally. So such a hard one, knowledge, so important to everybody. Everybody has to listen to that and tattoo it on their, on their wrist right now. Thank you. Oh, Oh my God, this is such a rich conversation. I so enjoyed talking to you and I just appreciate your taking the time. It was such a delight and I know people are gonna get a lot out of this.

Well, thank you again for having me. Glad to be back.

Thanks for listening to From Startup to Grownup. If you like what you heard, give it a review on Apple Podcasts 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, alisacohn.com.

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