Superhuman CEO: AI Moved the Career Ladder (Most People Don't See It Yet) | Shishir Mehrotra

Shishir Mehrotra ran product for YouTube, founded Coda, and has sat on Spotify's board for over a decade. He now runs Superhuman, the company behind Grammarly, which 40 million people use every day. In this episode, he reverses the career advice he gave for twenty years — stop trying to be a great executor, start learning to manage. He explains why the best jobs never come through the recruiting funnel, walks through the framework he built at Google for how promotions actually work, and points to the moment mid-career where the rules quietly change and most people panic. He pushes back on the word "replaced," gives away the interview question he used for hundreds of hires until he talked about it publicly too much, and shares what Bill Campbell told him in 2000 that changed how he measures his own success. 📩 7 skills that get you promoted —https://siliconvalleygirl.beehiiv.com/p/7-skills-that-make-you-irreplaceable-adc6?utm_source=spotify&utm_medium=description&utm_campaign=futureproof-sub&utm_content=7-skills https://siliconvalleygirl.beehiiv.com/p/7-skills-that-make-you-irreplaceable-adc6?utm_source=spotify&utm_medium=description&utm_campaign=futureproof-sub&utm_content=7-skills 𝕏 : ⁠⁠⁠⁠https://x.com/siliconvalleymm⁠⁠⁠⁠ https://x.com/siliconvalleymm 🔗 Instagram: ⁠⁠⁠⁠⁠https://www.instagram.com/siliconvalleygirl/⁠⁠⁠⁠ https://www.instagram.com/siliconvalleygirl/ 💼 LinkedIn: ⁠⁠⁠⁠https://www.linkedin.com/in/marinamogilko⁠⁠⁠⁠ https://www.linkedin.com/in/marinamogilko 📌 My Companies & Products: ⁠⁠⁠⁠https://Marinamogilko.co https://Marinamogilko.co

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:02Speaker 00

  The action's on the court and as the official beer sponsor of the NBA, Michelob Ultra is getting fans closer to the game with a chance to win courtside seats, merch and more. Visit michelobultra.com/courtside to enter. Michelob Ultra Courtside, 26 to 27. No purchase necessary. Open to US residents 21+ Begins on October 1st, 2026 and ends on June 30th, 2027. Multiple entry periods. See official rules at michelobultra.com/courtside for free entry, entry deadlines, prizes and details.

• 0:30Speaker 01

  This episode is brought to you by Subaru. You know that place your mind always wanders to? The lake, the mountains, the homes of the people you love most? The completely redesigned 2026 Subaru Outback is built to help you get there. With legendary capabilities, standard symmetrical all wheel drive and the confidence to go further. The 2026 Subaru Outback. Love never looked so good. Visit subaru.com/outback to learn more.

• 0:56Speaker 02

  You learn to be a manager. I spent years giving people the opposite advice.

• 0:59Marina Mogilko?

  What would you say to people whose job is already automated? This is Shashir. He spent 20 years deciding who gets promoted. He ran product for YouTube. He sits on the board of Spotify and now he runs the company behind Grammarly. Forty million people use it every day.

• 1:15Speaker 02

  You think about a world with AI everywhere, what happens? It actually pushes that entire ladder up. The original skill didn't go away, it just shifted.

• 1:23Marina Mogilko?

  The job you're doing today and the job you get promoted for aren't the same anymore.

• 1:27Speaker 02

  Since it's become my number one indicator of someone I want to work with, someone I want to hire is how good are you at?

• 1:33Marina Mogilko?

  You represent someone who's been in multiple careers. So you worked at YouTube, you worked at Spotify, you started your own company. Now you're the CEO of Superhuman, which also incorporates Grammarly and helps humans become superhumans. So if you had to start your career from scratch today, what would you do in the next 12 months to stand out on the market?

• 2:00Speaker 02

  I'll give a couple pieces of advice. I think one thing that people often don't think about is how to stay out of the recruiting folder. What I mean by that is the most interesting jobs, in fact, all my transitions for the most part, have happened through an interaction where we weren't talking about recruiting. We weren't, we weren't going through a job conversation. And so I think a lot of people focus their energy on how do I interview well? And how do I get through the screening and so on? But actually, the most interesting candidates I've ever hired or places I've, I've jumped in usually happened through some interaction that didn't start with a, I'd like a job or would you, would you take this job? So for that, I think it's be interesting in the world. Start projects that people might see, write things that people might see.

• 2:43Speaker 02

  Not only is it easy to produce those things, the outlets for being able to spread them are so wide. I think that's really important. I mean, the way I ended up at, I've been on the board of Spotify for over a decade now. And the, you know, it started with a paper I wrote. You know, Daniel was interested in it and we started talking about it and then it led to, hey, would you, would you do more at the company?

• 3:03Marina Mogilko?

  On social media?

• 3:04Speaker 02

  Actually, it wasn't even shared. In this case, it was passed around through different people. It's called formats of bundling. It's how, how to think about bundles. Somebody sent them the idea and said, you should talk to Shishir about it and we ended up chatting about it. So I think the main advice I give people that in a world full of candidates trying to find spots, you have to find your way to stand out. And the best thing to do is actually avoid recruiting. That's not the funnel you want to be in. You want to, everybody has a, you know, in your email, you got your, you know, we use Superhuman. So they, we have our splits and you know, I have my one for recruiting. It's a lot of people looking for jobs and you know, those all go right to my recruiting team. Then there's other ones that are interesting people I want to have a conversation with.

• 3:41Marina Mogilko?

  Huh.

• 3:42Speaker 02

  And that's, that's the pile you want to be in.

• 3:44Marina Mogilko?

  I like how you visually presented it to me right now. Because once you're applying for a job, you're ending up in a folder that's full of other candidates.

• 3:52Speaker 02

  I mean, I have, I have an auto split for it. Superhuman allows you to write AI based prompts for auto organizing your emails. And so the, I have one that explicitly takes everybody looking for a job and puts them in a, in a corner. And I go through them and I read them, but you know, all I'm doing is directing where, where they, where they might go. I'm not really thinking, is this an interesting person that I want to come spend time with and, and learn something? And then unexpectedly, it might lead to, lead to an interesting opportunity. The second thing I'd say is, I think it's fairly generic advice that everybody should learn every AI tool that, that you possibly can. I think the more interesting advice is you learn to be a manager. This is tricky because I spent years giving people the opposite advice. Learn to be a proficient executor.

• 4:33Speaker 02

  The, the, the best managers we hire are ones that can do the job themselves and kind of work their way, work their way into management. And I think the world is reversing a little bit. And the, the skill of the, how do you write code or how do you, you know, how do you write the specific blog post and so on? It's very important still, but as we use AI tools, we're put in a position of feeling like, feeling like managers. And I think that's a, that's a, it's a different skill.

• 4:57Marina Mogilko?

  How do you learn it when, in my opinion, becoming a manager? And I've learned this through practice, right? I started by myself. I did, I did a lot of manual things by myself. I learned what's good, what's bad, and then I hired. So this is how I transitioned into becoming a manager. What would you say to people whose job is already, like manual job is already automated? How do you even learn what's good or bad?

• 5:22Speaker 02

  To be honest, that's what we're hiring, right? So we're hiring judgment. I think it's really important that every skill that you learn takes practice. And you have to put yourself in a position to, to practice. I also think every skill you learn is best learned in low stake scenarios. So one of the things I, I have a framework for something we call IAGAN questions, which is the art of asking the right question, just very related to, to what being a manager feels like. I also, I wrote a post about it and a huge section of the post was how do you learn to do this? And one of the things that I think people miss in learning is they try to apply it in the highest stakes situation they can. If you think about other things you learn in life, you learn an instrument, you learn to play a sport.

• 6:05Speaker 02

  Imagine if the only way to learn was to do it, you could only learn the sport and you could only play in, in, you know, broadcast games. Or you're trying to learn an instrument and every single practice was actually a recital. And everybody was watching and the stakes were super high. It wouldn't make any sense. You gotta, you know, you gotta come down to your basement and play your guitar. You gotta get out on the driveway and, and shoot some hoops. Like that, that's how you, that's how you learn. And so I think what I advise people is if you're trying to learn the skill, if you're trying to be good at how to do AI centered design, for example, do it in a side project. Do it in something that's very low stakes. Do it with a friend. Do it in a thing that you can repeat over and over again and get very quick feedback loops on. Because then you'll get good at it before it's in that high stake situation.

• 6:47Speaker 02

  And I think it's not easy to do because you have to force yourself to, you know, the equivalent of get out on the driveway and shoot hoops is different in every job, but it's become easier now than ever before. As you're learning your skills, find your way to practice, find your partners to practice with and do it, do it in a lower stake situation.

• 7:02Marina Mogilko?

  So basically work on a project by yourself and then when you're applying for a job, you have something that you can show.

• 7:08Speaker 02

  It might not be by yourself, but don't do it, you don't have to do it in the main work scenario. It's particularly true of skills that are creative, that are judgment, that are, you know, how do you, how do you learn that form of judgment? Well, it's hard. When you're, when you're in the job, you're in the recital. Every, every meeting has lots of, lots of people in it and you're the one that's trying to learn. And so for you to be vulnerable and say, well, I thought that was pretty good is, you know, you're going to get judged. And so you want to find lower stakes places to do it.

• 7:33Marina Mogilko?

  So when this happens, when somebody who comes to your company has already some management skills, has some experience starting a side project, what happens to career ladder? When you came in, no experience, did manual things, then you got promoted, do you think it's getting erased?

• 7:50Speaker 02

  No, actually I think, so let me tell you about my view on career ladders. I have a framework I use for this. It's called P S H E, problem, solution, how, execution. So you start off as, in this case, I'll say product manager and I'll, I'll describe the others in a minute. You start at the bottom, we hand you a problem, we hand you a solution, we hand you the how. We tell you, you should go talk to this team, you should write this document, so on. And all you have to do is execute. You just have to do that, do that task. At some point, we hand you a problem, we hand you a solution, you figure out the how. So you figure out how to organize the team, you figure out how to do the milestones, you figure out the cadence. At some point, we hand you a problem and you come back with creative solutions. You know, and ideally solutions that nobody thought of, solutions that are really solve the problem beyond what people expected. And at the very top of this, we hand you a space and you tell us the problems.

• 8:34Speaker 02

  I know you told me to go work on activation, but actually our biggest problem is brand. Or I know you told me to go work on sales, but our biggest problem is marketing. That ladder, P S H E, is a very different axis than, than, than scope. And one of the, the leaders is the woman who's running infrastructure for Google. She went and very mathematically took her whole team and put them on both axes. What came back was really interesting. It came back as an S curve.

• 8:57Marina Mogilko?

  Hmm.

• 8:58Speaker 02

  So she said, as early in people's careers, they mostly moved on the scope axis. You're mostly working at that E level, you know, where you're the execution level. And we're just giving you bigger and bigger projects. Later in your career, that happens again. You're at that, that P level and we're handing you spaces and you're working on bigger and bigger projects. But in the middle, it reverses and then, and so it looks like an S. And she put a big circle around it and she called it the trough of disillusionment. She said, this is the moment where everybody freaks out. Employees look and say, I thought you told me the game was scope and now it's not scope anymore. And managers and promotion committees look and they say, well, these two people, actually the same scope, but what matters now is how they do the job.

• 9:39Speaker 02

  You can use the exact same technique for engineers, for designers, actually for salespeople, marketers, so on. It changes your value system and says, what are we actually valuing with our more senior employees? What is the ladder guide about? It's about identifying the right problem, about finding the best solutions, about figuring out how to take that and deliver it and then how to execute. You think about a world with AI, with AI everywhere, what happens? It actually pushes that entire ladder up.

• 10:06Speaker 00

  The action's on the court and as the official beer sponsor of the NBA, Michelob Ultra is getting fans closer to the game with a chance to win courtside seats, merch and more. Visit michelobultra.com/courtside to enter. Michelob Ultra Courtside 26 to 27. No purchase necessary. Open to US residents 21+ begins on October 1st, 2026 and ends on June 30th, 2027. Multiple entry periods. See official rules at michelobultra.com/courtside for free entry, entry deadlines, prizes and details.

• 10:34Speaker 01

  This episode is brought to you by Subaru. You know that place your mind always wanders to? The lake, the mountains, the homes of the people you love most? The completely redesigned 2026 Subaru Outback is built to help you get there. With legendary capabilities, standard symmetrical all wheel drive and the confidence to go further. The 2026 Subaru Outback. Love never looked so good. Visit Subaru.com/Outback to learn more.

• 10:59Marina Mogilko?

  Yeah, it seems like the problem and solution can now partially be handled by AI. But at least that's what I'm seeing in my company.

• 11:07Speaker 02

  Actually, I would say executing, if you can define a problem, and if you're good enough to find the right frame for the solution, then sometimes, and if you can figure out how you're going to get to market, AI can help you execute it. Sometimes AI can help you one level up and say, all right, I understand you can build this. Can you help me understand how to get everybody on board? Can you help me understand how to test the market, so on? Sometimes it can invent solutions, but your ability to judge that is in your head. And it can very rarely do something without a good prompt. And so the ability to identify the problem you should be going and working on is almost entirely in the human's head. I mean, AI can help at every level. So it's just like having a great thought partner.

• 11:49Speaker 02

  But the idea of, you know, does a ladder guide go away? If anything, what we've done is we've just given everybody this great set of executors.

• 11:57Marina Mogilko?

  So basically the execution part, then, how much of it is getting replaced by AI?

• 12:00Speaker 02

  I don't like the word replaced, because I feel like replaced signals a zero sum game. It's interesting that this particular technology has drawn that word in a way that most past technologies have not. Maybe I'll give you an example. When power drills came out, there was a lot of questions about, does this change the need for a construction worker, for handyman, for so on? And of course, that's not at all what happened, because what happened, we decided we're going to build skyscrapers. Did it replace jobs is one, is a very interesting way to think about it. The net number of people who worked in construction skyrocketed. I think change is hard. I do think we're going through change faster than most people are used to. And I think it's easy to paint a boogeyman narrative around any new technology.

• 12:43Speaker 02

  Amazon came as the end of bookstores and we've watched these stories before. And I don't mean to say that there's not going to be change, but I think the word replace in particular, I don't like that word. Because I feel like it starts with a zero sum frame.

• 12:57Marina Mogilko?

  So what's happening at that execution level then?

• 13:00Speaker 02

  I think you're getting a much broader workforce. What do you do with that workforce when all of a sudden you can deploy them? You go and build skyscrapers. Go build bigger and bigger things.

• 13:11Marina Mogilko?

  Tell me about the progression from execution to problem in terms of a career. This is something that's already happening, right? The careers have diminished for people from, I think it's 18 to 25 beginners in their career. And sometimes, you know, I am hiring someone who is just starting and they're a social media manager and all they can do is can come up with stories, but I don't want them to just be able to draft a story. I want the strategy, because I already have Claude, right? And it can do so many things. What would you say to those people then?

• 13:43Speaker 02

  I think you have to adapt. I mean, I think every industry change is, leads to a change in roles. And if I go back to the construction analogy, being the person who can, you know, run a screwdriver really fast stopped being important once power drills came out. Now there's a different set of skills and so you have to retrain. And I do agree with you, it's happening so quickly that sometimes, sometimes people haven't adjusted. I think marketing, the example you gave, is a really interesting one. This change in marketing is large, but if you go back in time 20 years, this is, you know, marketing has dramatically changed. And in the last, you know, if you go to 50 years, you think about marketing in the Mad Men days. You know, marketing at the time was you would hire an agency. They would work with a very small number of companies.

• 14:27Speaker 02

  They would build one ad, would last an entire year with one jingle, one perfectly crafted thing. And then digital marketing started coming out. And I watched this happen while we were at Google, we'd watch these firms change over how they operated and said, hey, you're not building one ad, you're building millions. And now the type of people they hire completely changed. And it's people that were systems thinkers, people that had a different approach to marketing. But honestly, like the original skill didn't go away, it just shifted. And you said, actually taste in coming up with that great message and that great jingle was actually elevated. But now you have to do it in a way that scales across a million ads instead of across one.

• 15:05Marina Mogilko?

  You don't have to be like this genius who comes up with just one good thing a year. You have to be able to produce like multiple times a day.

• 15:13Speaker 02

  Actually, I think you need to, like, if I go back to your example of, I don't need someone that comes up with stories because I have Claude. Actually, I don't think that's true. You need somebody who comes up with great stories.

• 15:23Marina Mogilko?

  Great stories. It gives great ideas, not just editing.

• 15:26Speaker 02

  That's right. They give the great ideas and Claude can go amplify them.

• 15:29Marina Mogilko?

  Yeah.

• 15:29Speaker 02

  And Claude can create hundreds of variations of them. But if you can't come up with that great idea, then you're not, you're never going to be able to create the next ones. And then you, now that you have hundreds, now you have to be able to judge. And so that ability to come up with great stories makes you also need to be a great reviewer of great stories.

• 15:43Marina Mogilko?

  How do you learn that?

• 15:44Speaker 02

  This is back to where we started. I think you have to practice. I don't think it's an easy thing to learn, but it's a thing that, you know, how do you learn judgment is you practice over and over again. Maybe it's worth, I mentioned earlier, this technique I call eigenquestions. So eigenquestion, it's a made up word. It comes from a mathematical term, eigenvalues and eigenvectors from linear algebra. So an eigenvector is the most discriminating vector in a multi-dimensional space. The math doesn't really matter. An eigenquestion is the most discriminating question in a set of questions. Or another way to say that, it's the question when one answered, it will answer the most other questions. The question that was number six on the list is actually the one that answers all the other ones. So this idea became called eigenquestions, or another way to say this is,

• 16:27Speaker 02

  the hard part is not about finding the right answer, it's about asking the right question.

• 16:32Marina Mogilko?

  Yeah.

• 16:33Speaker 02

  And so you go back to P S H E, that's what, you know, P versus S versus H versus E. P is the question, S is the answer, H is the delivery mechanism and E is the actual execution. The, so it's a very connected idea. This technique, eigenquestions, became a technique that we trained for, that we recruited for. Since it's become my number one indicator of someone I want to work with, someone I want to hire, is how good are you at eigenquestions? And so we spend a lot of energy on how do you learn this? And I'm coming back to your, I come back to your question.

• 17:01Marina Mogilko?

  Fascinating.

• 17:02Speaker 02

  And it turns out that it's a very learnable skill. But the easiest way to learn eigenquestions is to do it in safe environments. So I'll give you an example. One of my favorite interview questions, I can't use this question anymore because I've talked about it publicly too much, so I can, I can give it away. But I've probably done hundreds of interviews with this question. So I said, okay, a group of scientists have invented a teleportation device. How do you bring it to market? I've asked this question to engineers, to salespeople, to marketers, doesn't really matter. Usually what happens is people then start asking me questions. Teleportation, what do you mean? I'll answer a little bit, but mostly I'll say, why don't you get all your questions out? And so they'll start asking questions and they'll say, how big is it? And it does destroy the person or not? Is it two sided? Is it, you know, is it fast? Is it slow? Is it expensive? Is it safe? People ask all sorts of questions. Is it black? Is it green?

• 17:47Speaker 02

  Is it, they'll ask all sorts of different questions. And I'll just say, okay, keep asking your questions, we'll make a list. And then I say, okay, hold on a second, these scientists, they are really annoyed with all your questions. You only get to ask two questions. Which two questions do you, do you ask? And it's really interesting to watch people go back to that list and say, okay, I only get to ask two questions. Which one? There's lots of good answers, there's no, there's no right answer. But one, one answer that stood out to me was this person ended up drawing a two axis chart and said, one question I would ask is, how safe is it? And he said, I think it can, like, all I really care is, is it safe enough for humans or not? That's a really important axis.

• 18:22Marina Mogilko?

  Question, right?

• 18:22Speaker 02

  That's one.

• 18:23Marina Mogilko?

  If it's not safe, then.

• 18:24Speaker 02

  If it's not, well, actually, it's interesting. If it's not safe enough for humans, does it have a market? And I think that's actually a good question and I'll get to that in a second. And then the second axis was, is it more expensive capex or opex? So capex, you know, is it more expensive to buy the teleportation units? Or is it more expensive to use the unit? So if you just think about that as a two by two, you get these interesting quadrants. So you say, well, if it's safe for humans and it's more expensive opex and capex, meaning that's pretty cheap to buy, but expensive to use, then you want to put them everywhere. You want to put them where you put telephones and fax machines. And in every house, in every corner, you never know when you're going to need one, but we're going to put a teleportation device there. Okay, let's take another corner. So it's safe enough for humans, but it's more expensive capex and opex.

• 19:08Speaker 02

  Well, then you want to put them where you put airports. Like, we're pretty good at finding, and then your go to market motion is probably pretty close to how airports get funded.

• 19:16Marina Mogilko?

  That's a brilliant answer.

• 19:17Speaker 02

  You got to work through the government. What about the other axis? What if it's not safe enough for humans? All right, so what are the cases where it's not safe enough for humans? Like, what would you, what would you do with it? And I mean, I've had them, I often will prompt people into that category if they, if they pick this axis. And, you know, say, oh, actually, maybe what we should do is use it for hauling away trash. I don't really care if it disappears. I don't care if it gets all mangled up, it's going to get disappeared anyway. Or maybe it's actually things that are really high stakes. So like, one, one of my favorite answers was, we're going to use it to ship organs to Africa. You know, people need, need transplants. How do you get organs there? It's actually really hard to get them there. You know, this is, this is maybe a way to get there. So this idea of like, how do you come up with eigenquestions is really hard.

• 19:59Speaker 02

  That particular prompt, the teleportation device, what would you do with it? You can ask a five-year-old that question. You should try it with yours. And you'll get, you'll get good answers. I mean, and interestingly, sometimes you'll actually get better answers than you get from adults. Because they'll like, they'll even say it in a funny way. It's like teleportation. Do you blow up? But they'll quickly get

• 20:20Marina Mogilko?

  That's a great question, because this is the safety issue, blow up. So they're asking their question.

• 20:25Speaker 02

  Yeah, that's right. That's the question, right? So they may not frame it in the like, in the businessy terms, but they get to the heart of the idea very quickly. This idea of teleportation, as an example, I have a list of a hundred of these, and you can come up with them. If you want to get good at asking the right questions, find domains that maybe it's low stakes. Do it as a game. Do it with friends. I think it's important to practice in very low stakes environments.

• 20:47Marina Mogilko?

  I think you highlighted a very important mind problem that we're all having. We're focused on a problem we want to solve immediately, and we're not thinking about big picture.

• 20:56Speaker 02

  Yeah.

• 20:56Marina Mogilko?

  And where you're talking about reminds me how we were discussing with my husband, having eleven nanny nurses, like just hiring help by hours, like all my arguments, but oh my God, we need help in the morning. But his bigger picture is like completely different. Shishir has been hiring for the same thing for 20 years. He ran product for YouTube, founded Coda, and now runs Superhuman, the company behind Grammarly. Forty million people use it every day. Because Shishir is hiring a lot, I thought that pulling out the seven skills he's actually hiring for is an interesting exercise. What do these skills look like and how to practice them without putting anything at work at risk? It is in this week's Future Proof Newsletter. It's free. Link is in the description.

• 21:40Marina Mogilko?

  Okay, we're working on taste. Can you actually show me some AI workflows that you're using since you're running an AI company? And what my audience is really interested in is not another morning briefing agent, because we've heard of them. We know how to set them up.

• 21:55Speaker 02

  I get lots of morning briefings. Now I need a morning briefing of the morning briefings.

• 21:58Marina Mogilko?

  Right? Because there are so many. But is there something that a lot of people who are watching can set up in their job to make themselves stand out in their company, or if they're a solopreneur in their business?

• 22:11Speaker 02

  I'm happy to share. I think I'll take the excuse to talk my own book. And so I'll talk about a product we're building. I'll just give a little context before I give you the demo. So I run a company called Superhuman. We build an AI native productivity suite made of multiple different products. We make a really popular mail product, a really popular document product. But the product that we're probably best known for is a product called Grammarly. Grammarly is a very popular product, over forty million daily active users. You know, does hundreds of millions of dollars in revenue. The interesting thing about Grammarly is that the core technology of Grammarly is actually not about grammar. So the core of Grammarly is about bringing AI to work right where you work. So two fun stats about Grammarly.

• 22:50Speaker 02

  One, Grammarly does over a hundred billion LLM queries a week, works out to per user per day, over three thousand per user per day. So if you use Grammarly, we are likely your number one generator of LLM queries. It's mind blowing to people to think about it. And it's easy to understand why, because it works at the speed of typing. As you type, we're constantly trying to figure out what are the different suggestions that we can, we can give you right in this moment. So we have to do it very quickly, and we do it at that huge scale. Second interesting stat is Grammarly works in a million unique surfaces a day. It works in every web app, desktop app, and mobile app that you can think of, where we can observe what you're doing, we can annotate it in a way that's unobtrusive to you in the application,

• 23:30Speaker 02

  and we can make changes on your behalf. We sometimes describe this technology, we call it the AI superhighway. It's we bring AI right to where you work. The interesting part of that analogy is today, we are up till three weeks ago, we only ran one car on that highway. And that's the one that happened to be, happened to have your high school grammar teacher in it. And it's an incredibly valuable car. Tens of millions of people find it immensely valuable every single day. But it's a vast underutilization of that infrastructure. So we decided to split the product into two. And so we took Grammarly and turned it into what we call an agent. And we took the bottom half, the AI superhighway, and we built a new product around it called Superhuman Go.

• 24:11Speaker 02

  It's a very simple idea. It allows you to build AI agents that can do everything that the rest of the agents can do, including sending you morning briefings. But the unique thing it can do is it can work right where you work. It's like Grammarly, but with your own knowledge, your own connectors, your own tools, so on, and with your own prompts. If you download Grammarly, you'll get a big G in your extension bar, or you can do the same thing with the desktop app. And you can just go and say, use Superhuman Go, and it'll flip it over to Go mode. And at that point, what used to be a G turns into the Superhuman logo, which we call Hero. And you get a set of agents, and you can go add your own agents.

• 24:48Marina Mogilko?

  And is all yours, or?

• 24:50Speaker 02

  These are, I have a demo account here, but I use a very similar set for myself. So, but you end up with very personal data. So this is, but it's very close to what I do. So I'll show you some examples. So one of my, one of my personal favorite agents is this one. So this is called a knowledge checker. And so what this is doing, so this is the agent builder. So you can build an agent that does anything. And I think a lot of agent builders are quite similar these days. You give it a set of tools it has access to. You can connect any different tool to it. We have a wide set of connectors that'll, that synchronize data, or you can connect any MCP. You have some instructions on what you want it to do. But the most important part is the triggers.

• 25:30Speaker 02

  So these triggers are, you can trigger on anything. You can trigger on a schedule. So that's like you were saying, the morning briefing every, every day. There's a set of events you can trigger on every time I get a Slack message, or so on. But the most important trigger for us is what we call the while writing trigger, that says, while I'm writing, I want you to go and make these types of suggestions. You can pick a color and so on.

• 25:56Marina Mogilko?

  Do I understand this correctly, or are you saying, when I have this agent on, like if I'm replying to someone with a summary of another email, like I'm planning a party, and somebody sent me information about their home, and I'm replying to guests, I can just ask Superhuman to pull that information, like fact check what I'm saying, like?

• 26:15Speaker 02

  Exactly.

• 26:16Marina Mogilko?

  Oh.

• 26:17Speaker 02

  Exactly. So I'll give you an example.

• 26:18Marina Mogilko?

  You don't have to have multiple windows and like go back and forth?

• 26:20Speaker 02

  So it's not only just not multiple windows. So I think if you think about some of these use cases, I'll show you, I'll show you a couple of different cases. This is a professional use case. I'm writing a launch announcement. I'm a marketer. So these are, these underlines look like Grammarly. And some of them are, this one is literally from Grammarly, but some of them are coming from other agents. So this, this one, for example, is coming from, I have a launch project manager agent that tells me that this is not actually pending legal review. I still need to go deal with the design, design review. Or this one might come, and this is my legal guardrail agent that says, you're not supposed to say it that way. Here's a more correct way to say it.

• 26:56Marina Mogilko?

  So it checks everything you wrote?

• 26:58Speaker 02

  It checks everything. So you could use it, maybe you use it in Gmail, or maybe you use it in a document. Here's an example where maybe you want to use it in an email.

• 27:07Marina Mogilko?

  If I write, so my revenue for this quarter is this, and if it's connected to whatever is connected?

• 27:12Speaker 02

  It'll go fact check it.

• 27:13Marina Mogilko?

  And I don't have to trigger it. It just fact checks.

• 27:16Speaker 02

  It just fact checks it. Fact checking is one of my favorite agents.

• 27:18Marina Mogilko?

  Where does the knowledge come from? So it's fully resolved, meaning it's a project somewhere?

• 27:23Speaker 02

  Each of the agents has different, has different data sources. And so, you know, for example, that agent I just gave is the source finder agent is this one I have here. And I can go see, this one has access to, in this case, I gave it access to my mail, my calendar, and my docs. But you can give it access to anything. And so that'll come through and give you suggestions based off of what's happening with, you know, each of these tickets, or you can, you'll check a revenue number, or so on. And I think in that way, you can design an agent that feels like, I mean, one way to think about it is if Grammarly felt like it's magical to have your grammar teacher follow you everywhere. It's like sitting on your shoulder. Who else do you want sitting on your shoulder?

• 28:08Speaker 02

  And one of the things, that's, that's the main part of the demo, but the, one of the ways I think about this is if you think about the world of AI, I think there's sort of three metaphors for how people think about AI. So one is, the most common one is chat. And that's like this. It's like I, I have this, this, this agent that feels like a human, and it's magical. And so it obviously captured everybody's imagination. There's lots of products that have a chat metaphor. Another metaphor is what we call do. So that's a metaphor of I have a task list. I want you to take things off my task list. It's also a really powerful metaphor, and many tools that are, that are focused on that. Our, our view is that there's a third metaphor we call assist. So you can think about assist, chat, do. Assist is, I need an agent that comes where I'm working before I ask anything,

• 28:48Speaker 02

  and helps me in a way that I didn't expect. So for example, this, you know, would I go check a fact on, on a particular email? You might remember to do that. And if you're, like you're saying, you're writing an email to somebody about the, the party, and you put in the wrong address, or you put in the wrong time, or you put in the wrong name, you know, would you remember to take that and put it into one of your chatbots that's connected to the right data and actually get back that reply? Probably not. And that's the reason why we get out, you know, our users give thousands of queries per day. If you're a really good ChatGPT or Claude user, maybe you would generate 10 queries a day. That would be a lot of interaction. But we get thousands. And the reason is because we're there working with you right where you work, without you having to ask. So I think it's a very interesting way to rethink AI.

• 29:34Marina Mogilko?

  So what are the top three life-changing agents? The fact checker?

• 29:38Speaker 02

  The fact checker is a, is a, is a really interesting one, for all the reasons you already, you already got to.

• 29:42Marina Mogilko?

  No, I'm already, because this is what I'm doing. Like I have two phones, because I'm checking one email and replying to another.

• 29:48Speaker 02

  That one's amazing. I have another one I use personally called the placeholder filler. And I have a, these are very personal, by the way, because if you think about, like, you want an assistant that knows you. So mine is, I have a writing pattern, which is when I'm, when I'm writing, I'll often leave empty things that I'm, I'll come back to. And I just put them in brackets. And so I'll say, you know, I'll be outlining something. I'll say, I should start with a quote, your customer quote. About this and then I'll keep writing and I'll I just put it in brackets and it'll go and find it. And it'll go and try to fill in my placeholders with whatever the best suggestions it can. And I I give the agent access to all my information and so I can go and and fill those things in. So that's a really productive one for me.

• 30:29Marina Mogilko?

  Can it do online search as well?

• 30:31Speaker 02

  Yeah, anything. Yeah. So anything you wanted to connect it to. I mean, you have to decide what you want to give it access to. You can have these agents be they can be collaborative. So you can you can share them with other people. You can put them in collaborative spaces. You can you can put them in Slack or wherever else you like as well. So like another common use case we see from customers is customers will use it. For example, for compliance checks. So for for some companies, that's a we're working right now with a a major magazine publisher. Actually, they have they have a dozen or so magazines. And they have sixteen review departments. So if you're a reporter and you're writing a story, you go to the fact checker, you go to the brand people, you go to the the

• 31:13Speaker 02

  the citation checker and the source checker and they gave all these different folks to do. I'm not even sure I know all the departments they go to. They took all of them and turned it into an assistant that they just deployed and it works everywhere. And so rather than remembering to go to every department, now your story slowed down. It's just happening while you're going and you also get it much earlier. So instead of waiting till the end when, oh, I thought my story was done. And, you know, I I wrote the whole story based off of this fact that turned out to be wrong.

• 31:40Marina Mogilko?

  Yeah.

• 31:40Speaker 02

  Like you want to know that much earlier in your process.

• 31:43Marina Mogilko?

  Yeah, I really like that the the proactivity and also being where you are in the moment.

• 31:47Speaker 02

  Yes.

• 31:47Marina Mogilko?

  Anything else? Number three?

• 31:50Speaker 02

  Oh, boy. Um, let's see. Number three. I mean, I think there's a set of use cases. For me, the calendar one is really interesting. So I have it connected to my calendar and it'll do the like the example you gave of you're suggesting a time check that that's accurate. The more interesting ones is it'll come and see if I'm trying to schedule something. And I'll underline it with my availability and with an option to go and book the meeting. And so I'll come in and, you know, say, we should meet tomorrow and I'll come underline it. And say, actually, I've checked both your calendars and tomorrow 2 P M. Works.

• 32:20Marina Mogilko?

  What would it highlight if because this is what happens to me all the time. I have two different email threads where I'm discussing the same date.

• 32:26Speaker 02

  Yeah.

• 32:27Marina Mogilko?

  Would it tell you like, hey, you're actually

• 32:30Speaker 02

  You just have to build that in your prompt. Just imagine you can take Grammarly and give it your own instructions. And, you know, anything that you want it to do, you you can do.

• 32:37Marina Mogilko?

  Yeah. So the main difference I see because my audience experience and like using this little Claude extension or like comment browser is that you don't have to trigger anything.

• 32:48Speaker 02

  Yeah.

• 32:48Marina Mogilko?

  It's just there.

• 32:49Speaker 02

  Those are still in this frame of assist chat, dude. Those are still chat, right? Those are still. I need to remember to open it and think about.

• 32:57Marina Mogilko?

  Yeah.

• 32:57Speaker 02

  Okay, can you check that that time? I didn't promise to anyone else. If you remember it, if you remember that, you know, that's great. But how many times are you going to remember that?

• 33:04Marina Mogilko?

  You're gonna forget, yeah.

• 33:05Speaker 02

  And the key about what what made Grammarly so interesting is it works everywhere. Every web app, desktop app, it'll work in iMessage, it'll work in Apple Notes, it'll work in, you know, it'll work in, you know, Google Docs and Word and, you know, all the all the different tools that you might might be in. And so this idea of, you know, this really feels ever present. And now you can design that that assistant to do, you know, the set of them to do whatever whatever you like.

• 33:31Marina Mogilko?

  I think it's great. I think this is really the mode that you have because people people want their assistants. Want them there without asking.

• 33:40Speaker 02

  Without asking.

• 33:41Marina Mogilko?

  Yeah.

• 33:41Speaker 02

  Otherwise, it's A I becomes a chore.

• 33:43Marina Mogilko?

  Yeah.

• 33:43Speaker 02

  Because I have to remember to go use it.

• 33:45Marina Mogilko?

  To use A I.

• 33:45Speaker 02

  Yes.

• 33:46Marina Mogilko?

  By the way, if you want to know what actually gets you promoted now, subscribe to this channel. I sit down with the people making those decisions, founders and CEOs who write the promotion criteria. And I ask them what they are really looking for. Okay, I wanted to wrap up this conversation with the most valuable advice you got from Bill Campbell. You worked with one of the most iconic coaches in Silicon Valley, who unfortunately already passed. But he mentored some of the top CEOs. And whenever I have a problem, I ask my chat G P T to become a coach like him. What would you tell people who are watching, who are in this transition era? Maybe they're scared, maybe they're excited because they see all the opportunities, something that he told you.

• 34:30Speaker 02

  I worked with Bill. I started working with Bill in two thousand. So this was at the time he had left Intuit, he was hanging out at Kleiner Perkins. I got to know Bill at a period where he was in his coach mode, but it was before all the big shots. And so I, you know, I got lucky and that period is he's helping out. All I had started a company that was funded by Kleiner Perkins and he would hang out and and help out whatever he saw as the most interesting companies. Immensely helpful person. I mean, he was. I don't know. I can't overstate how how much impact he had on me and on the team. You know, almost I was a twenty one year old first time C E O, learning how to do everything. He told me he taught me how to run my first staff meeting. He taught me first time I had to fire someone, he walked me through this is how your talk track is going to work,

• 35:15Speaker 02

  how to deal with my investors, how to hire people, like there's so many different pieces. The most memorable conversation with Bill was I'd been working with him for about a year. And I came to him and I I said, hey, Bill, I just realized that we haven't done an advisor agreement with you. And, you know, I felt really bad because, you know, we had other advisors at the company and, you know, we had given them some cases, some compensation, some equity or or so on. And you've been, you know, immensely valuable and I don't want to. I don't want to take advantage of that. So I'm happy to put something in place. And he said, Shishir, don't worry, I don't need it. I was offended. To be honest, it was it was the, you know, what's wrong with my equity?

• 35:57Speaker 02

  And and he said, no, no, I didn't mean it that way. He says, you know, I've been lucky through my life. At this point, everything I get goes right to charity. So if you want to give it to me, it's fine, but you could also just give it to charity and that that that's okay, too. But honestly, you should hold on to it and use it to grow the company because it's not not the not the way you should use it right now. And I said, well, that's really interesting, Bill. It feels like I'm surrounded by people that all want a little piece of the company. And you're like the only one that's putting you adding so much value and that somehow that's not that's not what you're what's motivating you. So what motivates you? And he gave me this really interesting answer. And he said, well, I just look at all the people that that have worked for me or that I've mentored.

• 36:40Speaker 02

  And I just make a list of how many of them are Fortune five hundred CEOs. And that's my bar. This was back in two thousand. So there's, you know, since then, it's, you know, Larry Page and Steve Jobs and Jeff Bezos and so on. But in two thousand, he already had a list of twenty people.

• 36:53Marina Mogilko?

  Wow.

• 36:54Speaker 02

  And they and he's just working through this list. And you could just see this sense of finding success in other people's success.

• 37:01Marina Mogilko?

  Yeah.

• 37:01Speaker 02

  It was such a different way of thinking about about the world and it completely changed my worldview of, you know, zero sum games. What are you? I'm sure everybody's had that experience of somebody somebody you love is working for you and decides to go on to do something else. And Bill taught me if you're going to be a good partner, a good manager, a good leader, you need to root for your people's success. You need to judge your success that way. It's actually it. That's how that's how it carries on. And I it was interesting. When Bill passed, they held his funeral at Sacred Heart. You know, up the road here. And every single person who came up to the stage

• 37:41Speaker 02

  had almost the identical story. He had infinite time for me and he only cared about me being successful. And as far as I could tell, you know, that that's that's all that mattered to him. And every person looked around and said, how do you have time for you? And how did it? And how did he, you know, it could just seem like he was in your corner rooting for you in a way that was that was very different. And so, you know, very much changed my way of thinking about interacting with people.

• 38:03Marina Mogilko?

  This is such a great metric to optimize for.

• 38:07Speaker 02

  Yeah.

• 38:07Marina Mogilko?

  Because we're always looking at numbers. This could be a number, a number of people.

• 38:11Speaker 02

  Oh, he was very numeric about it. He was not a, you know, he was a sales guy. I mean, he had he had a he had a metric. Is it? And he had he had the list. He knew them by heart.

• 38:20Marina Mogilko?

  Yeah.

• 38:20Speaker 02

  Yeah.

• 38:21Marina Mogilko?

  That's amazing.

• 38:22Speaker 02

  Yeah.

• 38:22Marina Mogilko?

  I think everyone who's watching this, try if you don't have this metric yet, think about it.

• 38:27Speaker 02

  Yeah.

• 38:28Marina Mogilko?

  Like, how do you measure people who become successful thanks to your work?

• 38:32Speaker 02

  Yeah.

• 38:33Marina Mogilko?

  That's awesome. Thank you so much.

• 38:34Speaker 02

  Thank you.

• 38:35Marina Mogilko?

  If Shishir made you rethink what are you being promoted for? Watch my conversation with Ryan Ruslansky. He was the C E O of LinkedIn at the time of the interview. And Ryan will tell you exactly which jobs are appearing and what companies are looking for right now in the age of A I.

• 38:50Speaker 04

  Where some see heroes and others see egos. Bloomberg sees the era of billionaire athletes. While others follow the noise,

• 39:01Speaker 04

  we follow the money. Learn more at Bloomberg dot com.

• 39:06Speaker 05

  Does anyone know where the bass is? Hey, Bose here. When your next track starts, listen for the decisions that the artist makes. The vocal pushed right up front. The bass that waits half a beat. That sample from a seventies underground gem. Every choice deliberate. With Bose, you'll hear it all. Your music deserves Bose.