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Superhuman CEO: How to Position Yourself Now Before the Next AI Phase (2026–2027)

Silicon Valley Girl · 38m · transcribed Sep 2026
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# 0:00

Navigating Career Transitions in an AI-Driven World

How can individuals stand out in a job market increasingly influenced by AI?

To stand out in the job market today, individuals should focus on building relationships and engaging in conversations that are not strictly about job recruitment. The most interesting job transitions often occur through informal interactions rather than traditional job interviews.

  • AI is shifting the skills required for jobs, pushing the career ladder up.
  • Focus on networking and relationship-building rather than just job applications.
  • Interesting career opportunities often arise from casual conversations.
# 7:44

Understanding Career Progression and the 'Trough of Disillusionment'

What is the significance of the 'trough of disillusionment' in career development?

The 'trough of disillusionment' represents a phase in career development where employees realize that the criteria for advancement have shifted from scope to execution and problem-solving skills. This shift can lead to confusion and anxiety among employees.

  • Career progression involves navigating different axes of scope and execution.
  • The 'trough of disillusionment' is a critical phase where employees reassess their skills.
  • Understanding the evolving value system in organizations is essential for career growth.
# 15:29

The Importance of Asking the Right Questions

How can one improve their judgment and decision-making skills?

Improving judgment involves practice and the ability to ask the right questions. The concept of 'IEN questions' highlights the importance of identifying the most discriminating questions that can lead to deeper insights and answers.

  • Practice is key to developing good judgment.
  • Asking the right questions is often more important than finding the right answers.
  • IEN questions can help in discerning critical information in decision-making.
# 23:14

Leveraging AI for Enhanced Productivity

How is Grammarly evolving to better serve users with AI?

Grammarly is evolving by splitting its product into two: maintaining its core grammar checking capabilities while introducing 'Superhuman Go,' which allows users to create AI agents tailored to their specific needs and workflows.

  • Grammarly is expanding its functionality beyond grammar checking.
  • The introduction of AI agents aims to enhance user productivity and personalization.
  • AI can be integrated seamlessly into existing workflows for better efficiency.
# 30:59

Integrating AI into Daily Workflows

What are the practical applications of AI in content creation and scheduling?

AI can streamline content creation by integrating various review processes into a single assistant, allowing for real-time feedback and corrections. Additionally, AI can assist in scheduling by analyzing calendars and suggesting optimal meeting times.

  • AI can enhance the efficiency of content creation by providing immediate feedback.
  • Integrating AI into scheduling can simplify the process and reduce conflicts.
  • Proactive AI tools can improve workflow by being present during the creative process.

Transcript

0:00 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 and 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.

0:31 >> 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. >> 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 Superhum, 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?

1:04 >> 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 happen 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. Not only is it easy to produce those things, the outlets for being able to spread them are are 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 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 >> social media?

2:08 >> Actually, it wasn't even shared in this case. It was passed around through different people. It was called formats of bundling. It's how how to think about bundles. Somebody sent up the idea and said you should talk to Shashir 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 we have our splits and you know I have my one for recruiting and 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.

2:45 >> 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 autosplit 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 in a in a corner.

3:07 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. you're 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.

3:35 Learn to be a proficient executor. the the the you know 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 is 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. 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 >> 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 a framework for something we call iing questions which is the art of asking the right question very related to to what being a manager feels like. I also I 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 stake situation they can. And 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 a sport and you could only play in in you know broadcast games or you were trying to learn an instrument and every single practice was actually a recital and everybody was watching and the stakes were super high.

5:22 It wouldn't make any sense. You got to you know you got to come down to your basement and play your guitar. you got to 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 AIcentric 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 stakes situation. 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.

6:06 >> So basically, work on a project by yourself and then when you're applying for a job, you have something that >> 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. 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 a framework I use for this is called PSH 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 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. 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, PS, is a very different axis 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. M >> so what she said is early in people's careers they mostly moved on the scope axis you'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 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 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 have the same scope, but what matters now is how they do the job." You can use the exact same technique for engineers, for designers, actually 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 with AI everywhere. What happens? It actually pushes that entire ladder up.

9:08 >> 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 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?" and so on. Sometimes it can invent solutions, but your your ability to judge that is 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 in in the 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, do 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?

10:08 >> I don't like the word replaced. >> because I 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 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 one is a very interesting way to think about it. The net number of people who worked in construction skyrocketed.

10:41 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 a boogeyman narrative around any new technology. Amazon came as the end of bookstores and that you know we we've 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 I feel like it starts with a a zero sum frame.

11:06 >> 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 when all of a sudden you can deploy them? You you go and build skyscrapers go build bigger and bigger things. Quick pause here because what Shishir just said is such an important shift. AI is turning young professionals into managers much earlier. Not just managers of people, but managers of workflows, tools, and agents. And the real advantage is not just using AI, but knowing how to build systems around it.

11:38 And that's why I want to mention today's sponsor, MongoDB. If you're building an AI product right now or even experimenting with agents, you run into one problem very quickly. Where does the agent keep memory? Where does it get context? How does it retrieve the right information without you rebuilding the whole stack? MongoDB is built to be the data layer for AI applications and agents. What I like is that it already fits into the tools builders use every day. Cloud, cloud code, chatgpt, codec, grock build, devon, cursor. So you can connect your data to AI without jumping into separate system. And that matters because a real agent needs current context, reliable retrieval, memory, and state. It needs to understand what's happening in your app right now, not answer from a stale copy of your data from 3 days ago. With MongoDB Atlas, you can keep your operational data, embeddings, retrieval, and context in one platform. So you can build rack apps and AI agents without adding a bunch of extra infrastructure or locking yourself into a completely new stack. And if you want to learn it hands-on, MongoDB also has the Atlas learning hub with free courses and skilled badges, including vector search fundamentals. You can spin up a free cluster and start testing today. If you want to be the person who doesn't just use AI, but actually knows how to build with it. This is a good place to start. The link is in the description. Big thanks to MongoDB for sponsoring this video. And now, let's get back to our conversation with Share.

13:09 Tell me about the progression from execution to problem in terms of a career. This is something that's already happening right the 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 cuz I already have claw right and it can do so many things.

13:40 >> What would you say to those people then? >> I think you have to adapt. I mean I think every industry change is leads to a change in roles. 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 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.

14:08 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 madman days you know marketing at the time was you you would hire an agency. They would work with a very small number of companies. 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 to to marketing. But honestly, like the original skill didn't go away. It 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 multiples.

15:12 >> Actually, I think you need to like if I go back to your 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. It gives great ideas, not just editing. >> That's right. They give the great ideas and Claude can go amplify them. >> Yeah. >> And then 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.

15:41 >> 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. maybe it's worth I mentioned earlier this this this technique I call IEN questions. So I en question, it's a madeup word. It comes from a mathematical term igen values and igen vectors from linear algebra. so an igen vector is the most discriminating vector in a multi-dimensional space. The math doesn't really matter. An igen question is the most discriminating question in a set of questions or another way to say that it's it's the question when where when 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 questions or 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 PS >> that's what you know P versus S versus H versus E P is the question S is the answer H is the the delivery mechanism and E is the actual execution the so it's a very connected idea this technique I en questions 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 questions? And so we spend a lot of energy on how do you learn this? And I'm coming back to your coming back to your question.

16:59 Fascinating. >> The and it turns out that it's a very learnable skill, but the easiest way to learn questions 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 I've talked about it publicly too much, so I can I can give it away. but I 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 engineers to sales people to marketers doesn't really matter usually what happens is people then start asking 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 is it they'll ask all sorts questions and I'll just say, "Okay, keep asking your questions.

17:50 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 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 >> question, right? That's one.

18:21 >> If it's not safe, then >> 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 a second axis was is it more expensive capex or opex? So capex was, you know, is it more expensive to buy the teleportation units or is it more expensive to use the the the units? So if you just think about that as a 2x 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.

19:04 So it's safe enough for humans, but it's more expensive capex and opex. 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 get get funded. You got to work an answer. >> You got to work through the government. What about the other axis? What if it's not safe enough for humans, 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 I mean I've had them I often will prompt people into that 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.

19:37 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 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 an iing question is really hard. That particular prompt, the teleportation device, what would you do with it? You can ask a 5-year-old that question. You should try with yours.

20:05 >> Yeah. 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 may even say in a funny way teleportation. Do you blow up and but they'll quickly get >> but that's a great qu cuz this is the safety issue blow up. So they're they're asking their question. >> Yeah, that's right. That's the question, right? So they 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 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.

20:45 >> 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 and the I what you're talking about reminds me how we were discussing with my husband having a living nanny versus like just hiring help by hours and like all my arguments but oh my god we need help in the morning but his bigger picture is like completely different. Shashir has been hiring for the same thing for 20 years.

21:13 He ran product for YouTube founded KOD and now runs superhuman the company behind Grammarly. 40 million people use it every day. Because Jeser 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 company? And what my audience is really interested in is not another morning briefing agent because we've we've heard of them. We know how to set them up.

21:53 >> I get lots of morning briefings. Now I need a morning briefing of the morning briefings. >> Exactly. Right. There's 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 solarreneur in their business? >> 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 just give a little context before give you the demo. So I run a company called Superhum. We build an AI native productivity suite made of multiple different products. We make a really popular mail product, really popular document product. But the the product that we're probably best known for is a product called Grammarly.

22:28 Grammarly is a very popular product over 40 million daily active users. You 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 the core of Grammarly is about bringing AI to work right where you work. So two fun stats about Grammarly. One, Grammarly does over a 100red billion LLM queries a week. Works out to per user per day, over 3,000 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. It's 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 and so we have to do it very quickly and we do it at at 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 and the application and we make we can make changes on your behalf. We sometimes describe this technology we call it the AI superighway. It's we bring AI right to where you work. The interesting part of that analogy is today we or up till 3 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 under utilization 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 superighway and we built a new product around it called Superhuman Go. And it's a very simple idea. It allows you to build AI agents that can do everything that the rest of the AI 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 Superhum Go, and it'll flip it over to to go mode. And at that point, what used to be a G turns into the superhuman logo. We call it hero.

24:42 And you get a set of of agents, and you can go add your own agents. And >> are these all yours or they're >> these are these are I I have a demo account here, but I I use a very similar set for for myself. So u but I it it's 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 and I think a lot of agent builders are quite similar these days. you give it a set of tools that it has access to. You can connect any different tool to it. we have a 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. 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.

25:38 you there's a set of events you can trigger on every time I get a Slack 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 pick a color and and so on. >> 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 send 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 >> exactly. Oh, >> exactly. So, I'll show you an example.

26:17 >> Multiple windows might go back. >> So, it's not only just not multiple windows. So, I think if you think about some of the use cases here, I'll show you I'll show you a couple 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 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.

26:55 >> So it checks everything you wrote. >> It checks everything. So you could use it maybe you use it in Gmail or maybe you use it in in in a document. Here's an example where maybe you want to use it in an email. If I write so my revenue for this quarter is this and if it's connected to whatever is connected >> it'll go fact check it >> and I don't have to trigger it just fact check >> it just fact checks it one facteing is one of my favorite agents >> where does the knowledge come from so it's fully resolved meaning it's a project somewhere >> each of the agents has different has different data sources >> and so you know for example that agent I just gave is the sourcefinder agent is this one I have here and I can go the 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 it'll check a revenue number or or 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?

28:06 >> And one of the things that's that's the 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 it's magical. And so obviously captured everybody's imagination. There's lots of products that have a chat metaphor.

28:28 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 dos assist is I need an agent that comes where I'm working before I ask anything >> 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 on a particular email? You might remember to do that. And if you know, 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 chat bots that's connected to the right data and actually get back that reply?

29:10 Probably not. And that's the reason why we get thou, you know, our users give thousands of queries per day. If you were a really good chat GPT or cloud user, maybe you would generate 10 queries a day. That would be a lot of 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.

29:32 >> So what are the top three life-changing agents? The fact checker. >> The fact checker is a is a is a really interesting one for all the reasons you already got to. >> 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. >> 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 cuz 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 and I'll say we should I should start with a a quote, you know, 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 it can go and and fill those things in. so that's a really productive one for me.

30:28 >> Can it do online search as well? >> Yeah, anything. Yeah. So anything you want it 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 so for for some companies that's a we're working right now with a a major magazine publisher.

30:58 Actually they have they have a dozen or so magazines and they have 16 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 the citation checker and the source checker, and they 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.

31:28 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 wrote the whole story based off of this fact that turned out to be wrong. >> Yeah. >> Like you want to know that much earlier in your process. >> Yeah. I really like that the the proactivity and also being where you are in the moment. Yes. Anything else? Number three. >> Oh boy. 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 it'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 it'll come underline it and say actually I've checked both your calendars and tomorrow at 2 p.m. works.

32:18 >> What would it highlight if because this is what happens to me all the time. I have two different emails, right? Where I'm discussing the same date. Yeah. >> Would it tell you like hey you actually propo you would just 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 wanted to do you you can do. >> Yeah. So the main difference I see cuz my audience experienced in like using this little cloud extension or like comment browser >> is that you don't have to trigger anything.

32:46 >> Yeah. >> It's just there. >> 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 >> hey can you check that that time I didn't promise to anyone else and if you remember it if you remember that you know that's great but how many times you're going to remember that >> you're going to forget yeah >> 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 a of you know really feels everpresent and now you can design that that assistant to do you know the set of them to do whatever whatever you like.

33:29 >> I think it's great. I think this is really the mode that you have cuz people people want their assistants want them there without asking for >> without asking. Yeah. >> Otherwise AI becomes a chore. It's like I have to remember to go use it >> to use AI. Yes. >> 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. We 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 child 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 opportunity? Something that he told you.

34:29 >> I worked with Bill. I started working with Bill in 2000. So, this was at the time he had left into it. 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 that period was 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 21-year-old C first- time CEO 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, 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 I felt really bad because you know we had other advisers at the company and you know we had given them in some cases some compensation some equity or 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 she sure 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 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 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 put you're adding so much value and that that somehow that's not that's not what you're what's motivating you.

36:28 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 and I just make a list of how many of them are Fortune 500 CEOs and that's my bar." This was back in 2000. So there's, you know, since then it's, you know, Larry Page and Steve Jobs and Jeff Bezos and so on, but in 2000 he already had a list of 20 people.

36:52 >> Wow. >> And they and he's working through this list and you could just see this sense of finding success in other people's success. >> Yeah. >> It was such a different way of thinking about about the world and it completely changed my world view of, you know, zero sum games. What do you And 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 that's how that's how it carries on. And I it was interesting when Bill passed, they held his funeral at at Sacred Heart you know, up the road here. And every single person who came up to the stage 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 how 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. This is such a great metric to optimize for because we're always looking at numbers. This could be a number a number of people.

38:10 >> Oh, he was very numeric about it. He was not a you know, he was a sales guy. I mean, he he had he had a he had a metric is and he had he had the list. He knew them by heart. >> Yeah, >> that's amazing. I think everyone who's watching this, try if you don't have this metric yet, think about it like how do you measure people who become successful thanks to your work? Yeah, >> that's awesome. Thank you so much.

38:33 >> If Shishir made you rethink, what are you being promoted for? Watch my conversation with Ryan Roslansky. He was the CEO of LinkedIn at the time of the interview.

Summary

Shashir Mehrotra discusses the evolving landscape of work in an AI-driven world, emphasizing that traditional career ladders are shifting. He shares insights on how to stand out in the job market, the importance of developing managerial skills, and the necessity of practicing in low-stakes environments to enhance judgment and creativity.

- AI is transforming job roles, pushing skill requirements higher rather than eliminating them.
- To stand out, focus on building relationships outside of formal recruiting channels and engage in projects that showcase your skills.
- Learning to be a manager is becoming crucial as AI tools automate execution, shifting the emphasis to strategic thinking and problem-solving.
- Practicing skills in low-stakes environments is essential for developing judgment and creativity, akin to practicing sports or music.
- The career ladder is evolving; early career roles focus on execution, while later roles require creative problem-solving and leadership.
- AI can enhance productivity by acting as an assistant that proactively supports tasks without needing explicit prompts.
- The ability to ask the right questions is a critical skill for success, and this can be developed through practice and experimentation.
- A successful manager should prioritize the success of their team members, measuring their impact by the achievements of those they mentor.

Questions Answered

How can individuals stand out in a job market increasingly influenced by AI?

To stand out in the job market today, individuals should focus on building relationships and engaging in conversations that are not strictly about job recruitment. The most interesting job transitions often occur through informal interactions rather than traditional job interviews.

What is the significance of the 'trough of disillusionment' in career development?

The 'trough of disillusionment' represents a phase in career development where employees realize that the criteria for advancement have shifted from scope to execution and problem-solving skills. This shift can lead to confusion and anxiety among employees.

How can one improve their judgment and decision-making skills?

Improving judgment involves practice and the ability to ask the right questions. The concept of 'IEN questions' highlights the importance of identifying the most discriminating questions that can lead to deeper insights and answers.

How is Grammarly evolving to better serve users with AI?

Grammarly is evolving by splitting its product into two: maintaining its core grammar checking capabilities while introducing 'Superhuman Go,' which allows users to create AI agents tailored to their specific needs and workflows.

What are the practical applications of AI in content creation and scheduling?

AI can streamline content creation by integrating various review processes into a single assistant, allowing for real-time feedback and corrections. Additionally, AI can assist in scheduling by analyzing calendars and suggesting optimal meeting times.

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