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

0:00When you need to build up your team to handle the growing chaos at work, use Indeed Sponsored Jobs. It gives your job post the boost it needs to be seen and helps reach people with the right skills, certifications and more. Spend less time searching and more time actually interviewing candidates who check all your boxes. Listeners of this show will get a$75 sponsored job credit at Indeed.com slash podcast. That's Indeed.com slash podcast. Terms and conditions apply. Need a hiring hero? This is a job for Indeed Sponsored Jobs. This episode is brought to you by Google Chrome. You think you know a browser, but Gemini and Chrome, that's new.

0:36It can help you with practically anything on the web, like restoring a vintage motorcycle from a 50-page restoration block, or finally break down that long article you've had open for weeks. Gemini and Chrome is here for it. Ready to make anything online make sense? There's no place like Chrome. Check responses set up required compatibility and availability varies 18+. You learn to be a manager. I spent years giving people the opposite advice. 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.

1:10And now he runs the company behind Grammarly. 40 million people use it every day. 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. The job you're doing today and the job you get promoted for aren't the same anymore. 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 all? 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.

1:51So 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? 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 of my transitions for the most part, have happened through an interaction where we weren't talking about recruiting. 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.

2:26But actually, the most interesting candidates I've ever hired or places I've jumped in usually happen through some interaction that didn't start with a I'd like a job or 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. 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.

3:00And then it led to, hey, would you would you do more of the social media? 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 to think about bundles. Somebody sent him the idea and said, you should talk to share 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.

3:30So 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. But then there's other ones that are interesting people I want to have a conversation with. Huh. And that's that's the pile you want to be in. 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. 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 corner and I go through them and I read them.

4:05But, 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 learn something? And then unexpectedly, it might 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 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. The best managers we hire are ones that can do the job themselves and kind of work their way into management.

4:40And I think the world is reversing a little bit. And the skill of the how do you write code or how do you write the specific blog post and so on is very important still. But as we use AI tools, we're put in a position of feeling like managers. And I think that's a different skill. 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 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?

5:19How do you even learn what's good or bad? 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 practice. I also think every skill you learn is best learned in low stakes scenarios. So one of the things I have a framework for something we call eigenquestions, which is the art of asking the right question, which is very related 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?

5:52And 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. Imagine if the only way to learn was to do it. You could only learn the sport and you could only play in 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 got to, you know, you got to come down to your basement and play your guitar.

6:21You got to get out on the driveway 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 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 stakes situation. And I think it's not easy to do because you have to force yourself to, you know, the equivalent to get out on the driveway and shoot hoops is different in every job, but it's become easier now than ever before.

6:56As you're learning your skills, find your way to practice, find your partners to practice with and do it, do it in a lower stakes situation. So basically work on a project by yourself. And then when you're applying for a job, you have something that you can show. 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 in the job, you're in the recital. Every meeting has lots of, lots of people in it.

7:23And 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. 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? No, actually, I think. So let me tell you about my view on career ladders. I have a framework I use for this.

7:56It's called PSHE, Problem, Solution, How, Execution. So you start off as, in this case, I'll say product manager, and 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 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.

8:31And at the very top of this, we hand you a space and you tell us the problems. 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, PSHE, is a very different axis than scope. And one of 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. So what she said is early in people's careers, they mostly moved on the scope axis.

9:02You're mostly working at that E level, you know, the execution level. And we're just giving you bigger and bigger projects. Later in your career, that happens again. You're at 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 so it looks like an S. and she drew 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.

9:39So you can use the exact same technique for engineers, for designers, actually for salespeople, marketers, so on. It changes your value system. It 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 everywhere, what happens? It actually pushes that entire ladder up. When you need to build up your team to handle the growing chaos at work, use Indeed Sponsored Jobs. It gives your job post the boost it needs to be seen and helps reach people with the right skills, certifications, and more.

10:15Spend less time searching and more time actually interviewing candidates who check all your boxes. Listeners of this show will get a$75 sponsored job credit at Indeed.com slash podcast. That's Indeed.com slash podcast. Terms and conditions apply. Need a hiring hero? This is a job for Indeed sponsored jobs. This episode is brought to you by Google Chrome. You think you know a browser, but Gemini and Chrome, that's new. It can help you with practically anything on the web. like restoring a vintage motorcycle from a 50-page restoration block or finally break down that long article you've had open for weeks.

10:49Gemini and Chrome is here for it. Ready to make anything online make sense? There's no place like Chrome. Check responses set up required compatibility and availability varies 18+. 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. 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.

11:27Can you help me understand how to get everybody on board? Can you help me understand how to test the market? 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. But the idea of, you know, does the latter guy go away? If anything, what we've done is we've just given everybody this great set of executors. So basically the execution part, then, how much of it is getting replaced by AI?

12:01I 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 a 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 a very interesting way to think about it. The net number of people who worked in construction skyrocketed.

12:33I 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. 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. So what's happening at that execution level then? 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?

13:06You go and build skyscrapers, go build bigger and bigger things. 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?

13:44I think you have to adapt. I mean, I think every industry change is, um, leads to a change in roles. I mean, if I go back to the construction analogy, being the person who can run a screwdriver really fast, stop 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 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, marketing has dramatically changed. And in the last, if you go to 50 years, think about marketing in the Mad Men days.

14:20Marketing at the time, was you would hire an agency. They would work with a very small number of companies. They would build one ad. It 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 operate 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.

14:55It just shifted. And you said actually taste and 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. 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. 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. Great stories.

15:24It gives great ideas, not just editing. That's right. They give the great ideas and Claude can go amplify them. Yeah. And Claude can create hundreds of variations of them. But if you can't come up with that great idea, then you're never going to be able to create the next ones. And then 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. How do you learn that? 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.

15:53Maybe 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 multidimensional 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.

16:26Or another way to say this is the hard part is not about finding the right answer. It's about asking the right question. And so you go back to PSHE. That's what 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'm coming back to your questions fascinating 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.

17:10So 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 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 answer a little bit, but mostly I'll say, why don't you get all your questions out?

17:35And 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? Is it, you know, 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 ask? And it's really interesting to watch people go back to that list and say, okay, I only get to ask two questions.

18:06Which one? There's lots of good answers. There's no right answer. But 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 they said, I think all I really care is, is it safe enough for humans or not? That's a really important answer. That's the eigen question, right? That's one. If it's not safe, then. 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?

18:36So CapEx, is it more expensive to buy the teleportation units or is it more expensive to use the units? 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 tax 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.

19:08Well, 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. 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 do with it? And I mean, I often will prompt people into that category if they pick this axis and 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.

19:41It's going to get disappeared anyway. Or maybe it's actually things that are really high stakes. So like one of my favorite answers was we're going to use it to ship organs to Africa. People need transplants. How do you get organs there? It's actually really hard to get them there. This is maybe a way to get there. So this idea of like, how do you come up with an eigenquestion is really hard. 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. Yeah. And you'll get good answers. I mean, and interestingly, sometimes you'll actually get better answers than you get from adults.

20:14Because they'll like, they'll maybe even say it in a funny way. It's like, teleportation, do you blow up? But they'll quickly get. But that's a great question because this is the safety issue, blow up. So they're asking their questions. Yeah, that's right. That's the question, right? So they may not frame it in the business-y terms, but they get to the heart of the idea very quickly. This idea of teleportation, as an example, I have a list of 100 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.

20:44Do it with friends. I think it's important to practice in very low stakes environments. 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 yeah and the bit where you're talking about reminds me how we were discussing with my husband having 11 nanny versus like just hiring help by hours and like all my arguments but oh my god we need help in morning but his bigger picture is like completely different shashir 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.

21:2040 million people use it every day. Because Cheshire 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. Okay, we're working on taste. Can you actually show me some AI workflows that you're using since you're running an AI a 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.

21:55I get lots of morning briefings. Now I need a morning briefing of the morning briefings. Exactly, 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? Yeah, 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.