The Exchanges

Q of that and how you apply it and what you've learned in your role. But before we get there, I've been thinking a lot lately about automatic rules for success at a personal level. What are the rules that we can make for ourselves that put us on the path for success? For each person, these are different. And I'm curious to hear what your automatic rules for success are.

A Yeah, um, I'd have to say the first one that applies to work in personal is delegation, and that may seem pretty simple, but as a person who is taught, I'm here to provide for others, to serve others, the fact of having someone else do something for you was a really difficult concept, but in working with people that I've worked with and in my own personal life, I've realized that you should only be doing the things that you can do. And yes, this might cost a little bit of money, but I've realized that And I've seen in other people, whether it's people that I've worked with or the people that I've worked for, that if you can free up your mind space, free up your time to be doing the things that only you can do, you'll be a lot more successful in the things you're trying to do versus me trying to, you know, figure out why my, my roof is leaking or, you know, it's a very simple and obvious, um, answer, but answer, but there are a lot of parallels in life. Um, another thing is constant learning.

AI assessment note: “the first one that applies to work in personal is delegation”

Q That's really interesting because we all tell ourselves these stories about ourselves, and then we see the world through those stories. And then, you know, unintentionally, we probably insulate ourselves to people who might poke holes in those stories. Are there patterns that you've seen that we can prevent that or catch ourselves when we're starting to walk down that path?

A Yeah, I think maintaining relationships that you've had for a long time, you know, it's, it's difficult, especially when your life changes. You know, a lot of people could think, oh, well, that person's too, they're too good for me now, or they have important friends now. But, you know, those are the people that you want to hold on to, those people that have known where you came from, known who you are, who are going to treat you disrespectfully and, you know, in a Friendly kind of way. And ask those people to call you out, invite them to come. Will you come hear me speak at this thing? You know, and like, what did you think about that? Tell me for real. Open up yourself to that kind of feedback. And it's, it just really goes back to the, that sense of being willing to learn and to grow, I think is just really key.

AI assessment note: “maintaining relationships that you've had for a long time... ask those people to call you out”

Q Are there things that you've learned about making better decisions from working at these companies, uh, Twitter specifically, you worked at Yahoo before, but Twitter specifically in Slack that you would like to share with other people?

A I, I come from a set of beliefs that, especially in the startup world, and this is actually proven in a lot of things, like, you've just gotta, you've gotta make the decisions. You've gotta, like, the market changes so quickly. Of course, have all the information that you have, and at Slack, we adopted a form of the Amazon memo. Thinking through something, having someone think through something in advance, write about it, Um, be able to spend time with a group reading against it, and the format that I always like to follow is, here's the situation, here are three different solutions, here are the pros, here are the cons, here is my recommendation, and then also communicating, like, I don't care which one you choose. In fact, we could brainstorm something else completely different, and the real key there in that thing is the person who's You know, or the group of people that are writing that memo or coming up with these propositions understand the full context. So they don't understand the full context of the situation. Then they're going to get into that group of executives and someone's just going to brush them off. Like, well, they don't, they don't really get what we're trying to do here. You know? So I think that's the huge key. I think you have to make sure that you have as much information as you can in a moment. And at some point you've got to, like we talked about earli…

AI assessment note: “at Slack, we adopted a form of the Amazon memo.”

Q Yeah, let's double click on that. Let's double click on releasing the ego. How do we learn to do that? What does that look like? How do we recognize what's holding us back?

A I think if you surround yourself with the right people, you will get that feedback, but you have to ask for it, and you have to want it, and people know the difference. People know when you're just asking to ask, and they know when you really want to know, and you have to ask repeatedly, especially if it's for the first time. But I believe one of the keys is, you know, staying grounded, and ways to stay grounded are, you know, seeking out the things that are greater than you. Putting yourself in uncomfortable situations. And you think, well, as a CEO, they're in charge. They're always uncomfortable situations. Actually, no, they're put into this other level, like the conferences they're going to, the dinners they're being invited to, the, you know, conversations that they're having with investors. It's, it's the hot seat in a lot of ways. So seeking out things greater than you could be, you know, you're in your peer group. Um, and also curiosity, you know, if you're curious about something, explore it. Especially, in a lot of ways, if it's unrelated to what you're doing, it'll free your mind up in so many ways. You'll find parallels and relieve your brain from the same problem that you've just been trying to nail on. When I think about my own personal journey, like, coming, you know, into the world is kind of how I describe it and having to, like, figure out how does one even o…

AI assessment note: “if you surround yourself with the right people, you will get that feedback”

Q Is there a point where you think people reach the ceiling of their capability? Like you said, hiring often comes from word of mouth, but are you hiring for the next growth phase? Are you hiring for the existing job? How do you think about that?

A Took the words out of my mouth. That's exactly it. I think you should hire for where you want to be, you know, and all you need to do in that case is work on your narrative and on your story, and how do you convince that guy who's in some ways too big for this job to come work for you? You know, you convince them to come on, they're going to want that to succeed, and they're gonna bring on people that are, you know, you You hire people that are of the same quality, you know, or hopefully even better than you are. They're going to, they have a lot of, a lot of at stake there, a lot of risk. So they want to bring on the best people that they know. And it's this trickle down effect of who you hire. But I wanted to mention that other thing that someone talked about recently, and that's called no transfiring. If someone's not fit for a role, a lot of times what they do is just put them in another role. You know, let's just, let's just move the mother to the Somebody else's problem. Exactly. Um, but I love that term, no transfiring.

AI assessment note: “I think you should hire for where you want to be”

Q Well, let's double click a little bit on delegating. What are the ways that we delegate more effectively? What have you learned about delegation? How do, how do we become more effective at delegating?

A It's, it's really a mental hurdle, honestly, for people. There is the perception of like, I don't want to make someone else do this. Well, a lot of times people need the opportunities or they need the growth experience. Um, a lot of times you think it could be expensive or, I think the real fear that a lot of us have that we don't want to admit is based in anxiety, and that's no one can do it as good as I can. And let's just go with that and say, perhaps no one can do it as good as you. It's unlikely. But if that's the case, is that, like I said before, are you doing all the things that you, that only you can do? And, and making sure that the things that only you think you can do are actually those things. You know, there, there are a lot of talented people out there and you have to give up and release That anxiety of, this may not be perfect, you know, this may not be the way that I would do it, but I've gotta let go.

AI assessment note: “It's, it's really a mental hurdle, honestly, for people.”

Q Is there a particular place in growth where companies tend to experience hiccups when you're scaling from 150 to thousands of people? Is it Because one 50 is sort of that threshold for a human network, and then what happens after that as you go through these? Are there patterns between growth from one 50 to over a thousand?

A Yes and no. It depends on the leadership and the company. Uh, at Slack, we would use this comparison of, um, you know, when you go from one stage to another, so let's say, you know, 50 to one 51 50 to 303 to five, we would refer to it as a, a snake eating a horse, I think, or a snake eating a goat, I believe, and you're taking this big thing on, and you just have to sit for a bit, and you gotta let that digest, because you've got Recruiters who have just been hired, and they need to go and recruit, but first they have to actually figure out what you are and what you're about, and giving yourself a break, a break just in terms of, let's sit for a moment, let everybody kind of get to know each other. At, um, at both Twitter and Slack, there were tools that were put into place, internal tools, where it was kind of like a game-like mechanism, where you could see a picture of two employees, and you have to, like, guess, you know, this name is the name of which employee. And, uh, there's little things like that, that obviously aren't sustainable in the long run, but can give faith from the people into the leadership that, you know, there's still an attempt to try to keep like what you had at the beginning. Um, I mean, I'm not being completely succinct here, but that that's because like every, every startup is a snowflake. All of the challenges are different depending on what the prod…

AI assessment note: “50 to one 51 50 to 303 to five, we would refer to it as”

Q Yeah, totally. Um, one of the reasons that growth is hard is because it's really hard to scale the CEO. Well, what is leadership to you, and what are the best leaders tend to have in common?

A So in this particular case, I'm talking about founders. So a lot of times, and what's so interesting about, you know, the work that I do and want to do in the future is these are people who have never run a large organization before. Thinking a lot about your distinction between necessity and sufficiency. That sufficiency, you don't know what the magic sauce is, but something happened. You launch something, it's taking off. Now what's next? You have to transition from creating a product to building a business. And I see that there's a lot of different characteristics of those individuals. There's like the dreamers, the world builders, like the Elon Musk, and then there's the problem solvers. And then there's entrepreneurs or opportunists who just love the game of business. And just a quick, uh, story in terms of problem solvers, I, I believe that's kind of what Stuart, the CEO of Slack is. We would travel together all across the world. We'd go through an airport security in a foreign country, and I would get up like, wow, that was so smooth. Like, they really got to figure it out here. And he'd come out shaking his head like, oh, that could have been so much better if, and he'd just rail off 20 things. And I'm like, oh, like, yeah, I guess you're right, but it was fine. You know, and there's just certain people that Think that way. And, you know, we would, he would speak at a c…

AI assessment note: “there's a lot of different characteristics of those individuals. There's like the dreamers”

Q Yeah. You've taken the proverbial sort of like rocket ship twice now, once at Twitter, joining as a small team in Slack, uh, and you scale both of them through the IPO. Can you walk us through that journey a little bit and the important things to look out for in terms of, um, successful companies? I'm thinking specifically kind of patterns of success, patterns of failure,

A Right. Well, I'm, I'm going to kind of answer you a little bit with some of your own, your own thinking here, and that's in your book that I was just reading, A Mental Models, the first one, you talk about necessity versus sufficiency. You can probably describe this better than I can, but it's like, what's necessary for success? You know, working hard, having financing, what's sufficient? You know, that's kind of the, like, I would say it more like je ne sais quoi of success, right? It's, it's not something you can define in advance. In fact, you can't go back and necessarily point to exactly what the right things were. Butterfly flaps its wings, and you have this product that takes off. Um, but there are some key things. Um, the people, of course, hiring the right people and firing the right people. Honestly, there's that, you know, montage, hire slow, fire fast. In startups, you're moving so quickly. That you don't have time. You've got customers knocking at your door. You need a head of sales. You need one now. So you've got to hire the right, hire the right people. And then when you see that there's not a fit, you don't have time. You don't have capacity. It's, it feels like sink or swim if you let that person go. And it feels like it's better to have, you know, someone who's maybe not completely what they should be, but all of the mistakes will set you back. You know, six …

AI assessment note: “there are some key things. Um, the people, of course, hiring the right people”

Q You mentioned hiring and firing as being very important and sort of firing quickly. Talk to me a little bit about that. What have you learned about hiring and firing and in cases where you've left people in their position too long when you know all along it should have been addressed earlier? What's happened?

A Yeah, I think a lot of times People that I've worked for and with, and the reason I work for and with them is they are kind people, you know, and I think especially as a first time CEO, which people I might be working with in the future and similar to folks I've worked for in the past is you care about people. You see this person, you see that they're trying, you see, you know, you know their family situation, you know that this is a huge opportunity for them, you know, both in their career and also, you know, in, in their industry. When you, when you see that they aren't the person you, you don't want to believe it, you know, like, oh, they can, they can get there. It's almost kind of like being a relationship you shouldn't be in anymore. Like, ah, you know, they'll, they'll figure it out, or I can help them, or we can just get them a coach. And a lot of times the, the, you know, small things can be solved, but overall you've got to develop that understanding that it's, it's best for them in the long run. And there's ways to treat people kindly and Of course. In terms of the hiring aspect, it's really interesting, you know, startups rely a lot on their investor base to introduce them to people. You know, Silicon Valley is, talk about a cult, you know, the cult of Silicon Valley in the community. It's all about who, you know, all the jobs I've gotten have been through someone t…

AI assessment note: “When you see that they aren't the person you don't want to believe it”

Q What are some of the biggest mistakes without getting into names, maybe, uh, that you've seen leaders make inside these organizations and what was that impact and how was that even recognized by the organization? Was it quick or slow?

A I mean, I'm not going to talk about specifics, really, but I have a lot of friends who are in this line of work in tech. Um, I know a lot of other chiefs of staffs of companies that, you know, you would know, and, you know, you get together and you talk about things, and it's pretty much a lot of the same things, and they're all kind of applicable to our daily lives. There's this, this sense of leadership that, you know, you're Have this higher perspective, right? Not that you're better than someone, but you are the only person that can sit in this seat who can have all of this information, and if you're spending your time in down in the weeds, you know, because you know you can make it better. There's this error in the UX, and I'm the only person that saw it, and if I'm not here to see every change that happens, then, you know, these things aren't going to be fixed, and you know what? Maybe that's true. Likely you should hire someone that's good and perhaps they won't catch everything, but it's almost like some people want to wait around for that one thing that's wrong so they can prove, ah, see, look, you need me here. On the other hand, there's this other role for you, you know, sitting on this kind of mountaintop, if you will, seeing what's coming in the different, in the, in the distance, uh, market awareness, competitors, potential acquisitions, setting a strategy, Consta…

AI assessment note: “if you're spending your time in down in the weeds”

Q You were the chief of staff most recently at Slack. What does that role consist of? And what is the hardest skill to transfer to somebody else that takes the mantle after you?

A Yeah, it's, it's a great role. It's, it's very interesting. I'm a musician, and I'm, play some instruments, and I'm a singer, and the way that I think about it is, you know, there's this person, it's the leader, and they're kind of, they're singing the melody, you know, and they're, they're marching forward, they're doing their thing, and then, you know, my favorite thing to do in singing is harmonies, and you're kind of, you don't stand out of something different, You know, you're so one voice if you're doing it well, and you're kind of just dancing in and out of the melody, and just, you know, you know, filling in, like, the bass, filling in, like, this, like, higher harmony part that's, like, following along. That's, you know, visually how I imagine it, and in reality, I, I read something the other week, and it said the most, the most thinkless decision you can make is the one that prevents something bad from happening. And that kind of epitomizes the chief of staff role, because you're out there not just solving problems, but finding problems. Ideally, you are keeping so much from coming up to, for the leader, you're taking things off of their plate, you know, and there's different types of chief of staffs. It depends on the person that you're working with in particular. Um, there's people who, you know, are very much about, like, The exec, I'm here to manage your goals. I'…

AI assessment note: “you're out there not just solving problems, but finding problems”