Is AI Coming for Your Boss? + How To Become a Better Storyteller

Scott Galloway weighs in on whether AI will decimate middle management, how companies are hemorrhaging money on enterprise AI without seeing returns, and the habits and techniques that separate great storytellers from everyone else. Want to be featured in a future episode? Send a voice recording to [email protected], or drop your question in the r/ScottGalloway subreddit. Learn more about your ad choices. Visit podcastchoices.com/adchoices

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

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• 1:36Scott Galloway?

  Welcome to Office Hours of Prop G. This is the part of the show where we answer your questions about business, big tech, entrepreneurship, and whatever else is on your mind. If you'd like to submit a question for next time, you can send a voice recording to officehoursofpropgmedia.com. Again, that's officehoursofpropgmedia.com or post your question on the Scott Galloway subreddit and we just might feature it in our next episode. Our first question comes from a Reddit user MXAGNC asks, hi Scott, love your brain and dulcet tones. We all know junior and middle management roles are being decimated by AI, but what might be next? Experience by independent contractors, senior leadership, or even CEOs. There seems to be different cases for each and would love your thoughts. Yeah, it seems to be a big topic lately that AI can replace all management layers.

• 2:19Scott Galloway?

  Gartner projects one in five companies will eliminate more than half their middle managers by end of this year.

• 2:26Scott Galloway?

  By the way, Gartner doesn't what the fuck they're talking about. I just don't.

• 2:30Scott Galloway?

  I don't, I don't buy that. Anyways, Coinbase caught 14% of targeting pure managers. Microsoft laid off 6,800 citing AI and flatter org goals. Here's what Jack Dorsey had to say about his company Block and layoffs. Open quote, "For the first time, a system can maintain a continuously updated model of an entire business in ways that previously required humans relaying information through layers of management." So this is my take. AI is just not going to replace management and mentoring. What's really happening here is that a group of CEOs who over hired want to juice their valuations and engage in AI washing. Management is an ability to soften the chaos created by leaders. They're the ones that actually remember why this actual fucking company works.

• 3:14Scott Galloway?

  And as you grow, you need people that these people can roll up to in terms of mentorship, job descriptions, solving problems. And what happens is eventually, over time, people get hired, sometimes out of their competence into management roles, and you end up with fatty deposits everywhere. And it's a natural, healthy part of the cycle to go through and cull the ranks, not only of managers, but of some doers, if you don't, if you need less done in that field or they're not that productive.

• 3:40Scott Galloway?

  The notion that your AI is going to bring everybody in and they're not going to need to have contact with anybody else, and the AI will manage them, tell them what to do, and at the end of the year, give them their performance review and a bonus. Even if that was possible, which I don't think it is, it's a nihilistic fucked up vision of the world. And that is, okay, even if you could figure out a way for one person to own everything and create so much shareholder value that you could, I guess theoretically, give people enough cheap calories and entertainment, bread and circuses, so they could just watch Netflix all day and be fairly happy, which they wouldn't because work gives people purpose. I don't think that's going to happen because. I work in a company that's growing, that's considered a new economy company.

• 4:20Scott Galloway?

  We use AI on almost everything, but the last mile involves people and it involves judgment. And the idea of me sitting down and outlining job objectives, providing feedback at the end of year review, bonus, solving conflict with AI, I just don't think anyone is going to go for it. And also, AI gets it wrong all the time. And purely AI-driven businesses, AI is essentially predicting the seventh word after looking at the first six and coming up with patterns such that it can answer any question or find any data and spit back a reasonable facsimile of a correct answer to any question. But it's regression to the mean. And that is, it gives you great data on a question, but if you're asking it to brainstorm,

• 5:05Scott Galloway?

  if you're asking it to solve a problem, if you're asking it to manage somebody who clearly has a substance abuse issue, it can give you facts and best practices, but everything's driven to the medium. The most successful companies will be companies that I believe that AI would say this will never work because they're thinking unconventionally. So I just don't buy, we always have these fever dreams of flattening the organization and reducing costs. My father was laid off in the eighties in this big kind of wave in the corporate America called reengineering, where people, basically after World War II, we had a monopoly on all manufacturing globally. And as a result, companies just kept growing and hiring more people for no real reason. And they woke up in the eighties when Japan was starting to come online and go fuck, we're

• 5:50Scott Galloway?

  fat and happy. And they essentially fired anyone that had the title VP in it, and they found they didn't miss them much. Anyways, yeah, it's healthy on a regular basis to go through the company and call and figure out where you can delayer, have fewer reporting layers. I get it. This again is individuals who, quite frankly, in my opinion, don't know a lot about management and think that technology Or the capital can replace people. And there will be, I think, job destruction, management destruction across certain industries. I don't think it's going to happen as fast as anyone thinks. And I, I hope and I believe that the opportunities AI will provide in terms of an increase in productivity,

• 6:33Scott Galloway?

  margin, profitability, shareholder value, and the wealth and capital to go start new businesses that leverage AI, that that hopefully will create as many jobs, if not more, than are destroyed. The key question is, is will the velocity of decline overwhelm our ability to repair and renew and create new jobs? That's the question. And unemployment actually isn't the issue in terms of social unrest. What causes social unrest usually is not someone who can't find a job, but someone who's working 16 fucking hours a day and still can't afford to buy, you know, meat. Those are the people that tend to get really, really angry. So I don't, I don't, I think this flattening of the organization is a bunch of people

• 7:15Scott Galloway?

  who overhired during the pandemic and also maybe overestimated the demand for their product or service, want to sound revolutionary, but I don't, you know, I'm a big fan of player coaches and every company I've had, everybody has to do something. I do podcasts in addition to managing. The woman who runs our company, Catherine Dillon, manages a lot, but she also edits things, is fantastic in terms of design. She gets very involved inside. She's, everyone does, if you will. I think that's a good, a good general psychiatrist within a company. But you absolutely have to have managers. You have to have people communicating who create institutional and corporate knowledge. So in sum, I think this is more nihilistic bullshit from a group of people who have no,

• 8:00Scott Galloway?

  or very little humanity, are very nihilistic and also, in my view, don't understand or aren't willing to admit that, you know, managers evolved for a reason. And a good manager motivates people, figures out where the overlap creates a whole that's greater than the sum of its parts. So will there be a calling yes? Will there be a lot of quote unquote, middle managers? A hundred percent. And they're the ones, quite frankly, that understand why we're all fucking here.

• 8:31Scott Galloway?

  Question number two comes from Aaron, who emailed us. Scott, I'm a strategy lead at a Fortune 10 retailer and my AWS agent usage on Claude is probably running a few hundred dollars in tokens a day. Multiply that across an engineering org and you've got seven or eight figures a year fast. Companies are simultaneously telling employers to use AI for everything and quietly watching the meter spin. How does this resolve? Do enterprise AI bills become a real P and L line that competes with headcount? Hmm, that's a good question. So, most individuals pay a flat monthly fee for AI tools, but when companies build AI under their own workflows, things like coding assistance, automated pipelines, internal agents, they pay per use with no ceiling.

• 9:14Scott Galloway?

  And the more engineers that use it, the bigger the bill automatically. In other words, modern enterprise AI is metered, similar to electricity or mobile data. The number of organizations that reported AI costs as a serious budget concern doubled in a single year from 31 to 63%. Now, the question is, will AI just get cheaper? Partly. The cost of a basic AI query has dropped roughly 50x in three years, but the more powerful the task, including complex reasoning and AI agents running autonomously, the more compute it burns and those prices haven't followed the same curve. Think of it as Moore's Law, where processing power doubled every 18 months and the cost got halved. But people continue to find more and more uses for bandwidth or for processing power.

• 9:58Scott Galloway?

  And the same thing's happening here, that these technologies are usually highly elastic and that is as the price of compute plummets, you'll see more uses for AI and it'll broaden the market and there'll still be more demands for compute and for inference. Is this becoming a real P and L line? Oh, 100%. 59% of companies are investing over $1 million annually in AI, but only 29% report significant ROI. So, right now, the investment is out of the return. And in practice, the usage costs are frequently not the dominant expense. Once you add integration, security and change management, the full cost of AI is much larger than what showed up on the bill. I appreciate the question.

• 10:43Scott Galloway?

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  Find out why Nutraful is the best-selling hair growth supplement brand at nutraful.com, spelled N-U-T-R-A-F-O-L dot com, promo code PROP G. That's nutraful.com promo code PROP G. Support for the show comes from Vanta. As AI adoption grows, so does your company's security risks and requirements. New frameworks, audits, and vendors keep piling on, but your team isn't getting any bigger. Most compliance tools promise automation, but you're really stuck doing all the work by hand, chasing screenshots, validating controls, and playing catch-up when audit season comes around again. Vanta works differently. Their Agentic Trust platform is built to scale with you, not slow you down.

• 12:12Scott Galloway?

  With over 1,400 automated tests across 400-plus integrations, Vanta collects evidence and monitors your controls year-round, cutting your audit prep by 82%. Plus, you can access the Vanta agent everywhere you work, whether your team is in Vanta every day or living in tools including Claude or Cursor. Want proof? Over 16,000 fast-growing companies like Ramp, Ryder, and Harvey save time and resources while scaling fast with Vanta. Learn more at vanta.com/profg and get $1,000 off. That's spelled V-A-N-T-A dot com slash PROP G for $1,000 off.

• 12:53Scott Galloway?

  Support for the show comes from Vanta. As AI adoption grows, so does your company's security risks and requirements. New frameworks, audits, and vendors keep piling on, but your team isn't getting any bigger. Most compliance tools promise automation, but you're really stuck doing all the work by hand, chasing screenshots, validating controls, and playing catch-up when audit season comes around again. Vanta works differently. The regentic trust platform is built to scale with you, not slow you down. With over 1,400 automated tests across 400-plus integrations, Vanta collects evidence and monitors your controls year-round, cutting your audit prep by 82%. Plus, you can access the Vanta agent everywhere you work, whether your team is in Vanta every day or living in tools including Claude or Cursor. Want proof?

• 13:38Scott Galloway?

  Over 16,000 fast-growing companies like Ramp, Ryder, and Harvey save time and resources while scaling fast with Vanta. Learn more at vanta.com/profg and get $1,000 off. That's spelled V-A-N-T-A dot com slash profg for $1,000 off.

• 14:02Scott Galloway?

  Welcome back. Question number three.

• 14:05Speaker 05

  Hey Scott, my name is Andre and I'm from Edmonton, Alberta, Canada. My question to you is related to a point that you've made in several podcasts, and it's the importance of being able to craft a strong narrative and being a good storyteller. I'm an avid listener of all of your podcasts. I've read several of your books, and you're definitely an amazing storyteller. And so, my question to you is, what tips do you maybe have for either content creators or business professionals, or even professors, to be able to craft a good narrative?

• 14:47Speaker 05

  I notice in a lot of your books and in a lot of your podcasts, you're really big on research and leading with numbers and facts. What other tips do you have for individuals who really want to strengthen this skill? Thanks for everything that you do.

• 15:02Scott Galloway?

  So I would refer you, at least first off, Prop G Markets Research Lead Mia Severio did a livestream on Substack on this very topic. She puts together my decks for our speaking gigs and she put together a deck on storytelling. And it's still, I think, to date, the most popular livestream we've done on Substack. And this is kind of top line, the Cliff Notes on what she said. You want to create drama. Drama is what makes people care and there's three ways to do it. You make it emotional, even on sexy topics can evoke anger, sadness or excitement if you've, if you find the human stakes. I talk a lot about my personal life and things that have moved me emotionally, whether it's my kids.

• 15:41Scott Galloway?

  You know, I talk a lot about my parents and I'm not afraid to sort of be quite vulnerable and talk about, you know, success and I mean, I try to be pretty raw up there. And I find that of all the things I've ever done, the most popular newsletter I've ever done was when I talked about putting down my dog and just the emotions I was feeling. I write about stocks and I'm a quote unquote, a business analyst or write books about economics. And the most popular piece of content I ever put out there was about my dog. Most recently, the clip I had go viral that got, I don't know, 400,000 or 500,000 likes and I think seven or eight million views was on Diary of a CEO.

• 16:26Scott Galloway?

  I was talking about how much I miss my mom. So emotion, right? Surprise, unexpected information triggers dopamine, which literally enhances memory formation. And then kind of wow factor data. Before adding any data point ask, would this make someone say, I didn't know that? If not, cut it. You also want to zoom out. Don't settle for the obvious first order take. Ask what the upstream causes and downstream effects are. Let's look at GLP-1, for example, instead of covering Novo Nordisk, Mia followed the supply chain to Catalent, then followed patient behavior all the way to a spike in plastic surgery. That's where, you know, that's where the fun starts is, okay, we know that GLP-1 drugs are big, but what else is going to be big?

• 17:10Scott Galloway?

  Try to provide context. Big numbers mean nothing in isolation. Data center water use sounds alarming until you learn one data center uses half as much water as the average golf course per year. So context is what makes data meaningful rather than fear mongering. And then aesthetics, visualizations, people process images faster than words. We look through every day, a deck and say, how do we, how do we show this versus say it? How do we replace it with visuals? The Nvidia versus Intel market cap example, you can say it in a sentence, but showing it lands harder. We do these McCandless graphs that show spatially market cap of, you know, Nvidia is greater than the market cap of Germany. And you show every single public company and then one square is bigger than the other. And then trying to find an authentic voice, I think it's a little harder.

• 17:55Scott Galloway?

  Understanding whose voice you're telling the story in determines what to cover, how to frame it and how to make it sound real rather than generic. So some other just tactical things. It sounds pretty basic. I think great storytellers are usually pretty big readers at a young age. I didn't read into Norton amount, but I did read quite a bit when I was younger. Also, if you want to be a great storyteller, I think you have to be a competent writer. I think the discipline of trying to write out grammatically correct prose, organize it, chunk it. You know, Jeff Bezos is famous for anyone who pitches an idea has to do it in a five or 10 page deal memo. I think that, and by the way, I got, I got a C in English my senior year in high school. I found writing very difficult.

• 18:39Scott Galloway?

  I now technically communicate or write for a living. But I think if you want to be a really great communicator, you have to be at least a competent writer. Then what I want you to do is I want you to pick a medium that you feel comfortable in. It might be LinkedIn, it might be a podcast, it might be videos, it might be presentations using PowerPoint. But I need you to find a medium or a platform that you think you could be in the top 1% of and try and get to the top 0.1%. And that is say, all right, I'm going to really be an outstanding orator, or I'm going to commit to writing amazing content on LinkedIn and I want to be the top 1% of LinkedIn content creators.

• 19:19Scott Galloway?

  But discipline is small acts of, well, what does success look like? Success is small acts of discipline every day that add up and compound similar to investments. And to be a great storyteller, I want you to read a lot. I want you to write a lot. And then I want you to find different mediums where you think you could be in the top 1% and start investing in those mediums and have sort of a ready, fire, aim. I'm going to do three LinkedIn posts a week. I'm going to try and amass 10,000 followers on Instagram by a certain, by a certain time. Right? Whatever the medium is, or my goal is to get, I want to start a sub stack and I'm going to put out at least one 1,500 word article on this topic every week.

• 20:03Scott Galloway?

  So find your medium, set deadlines, set goals and benchmarks and just start. I make my living communicating. A lot of it was because I got a ton of practice teaching twice a week for, or sometimes four times a week for 24 years. And also as a consultant, I was constantly presenting my ideas. But this is something you really want to get your kids into. You want to get yourself comfortable with. But if you're not a great presenter, everybody thinks a great communicator is someone who gives this moving eulogy. Well, you might be the person who's really good at handwritten notes. You might be the person who's really great at doing 30 second TikToks. Find your medium, find your weapon and your sport of choice, if you will, and commit to being in the top 1%.

• 20:47Scott Galloway?

  But again, I think it starts with simply reading and writing. That's all for this episode. If you'd like to submit a question, please email a voice recording to officehoursofpropgamedia.com. Again, that's officehoursofpropgamedia.com. Or if you prefer to ask on Reddit, just post your question on the Scott Galloway subreddit and we might feature it in an upcoming episode. This episode was produced by Jennifer Sanchez and Laura Janer. Kami Reek is our social producer. Brad Williams is our editor and Drew Burrows is our technical director. Thank you for listening to the Prop Shee Pod from Prop Shee Media.

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