AI, Improv, and Sales Walk into a Bar...

In this conversational panel, university professor and sales instructor Robert, moderator Gerhard, and industry veteran Tricia explore the intersection of artificial intelligence, improvisational techniques, and modern sales practice. Robert introduces a set of seven "happy hour" rules for AI adoption, emphasizing human oversight, proactive enablement, the gap between AI confidence and competence, the need for adaptable, script‑free interaction, the distinction between speed and quality, the mismatch of top‑shelf AI with bottom‑shelf management, and the importance of learning under disruption. He argues that true value emerges when artificial intelligence (AI) is combined with human intelligence (HI) to form collaborative intelligence (CI). The discussion touches on governance and ethical differences between Europe and the United States, citing Gartner data on AI strategy gaps and rollout failures. Robert shares concrete ways AI is reshaping sales education—automated role‑plays, rapid syllabus generation, and feedback loops—while acknowledging risks such as hallucinations and over‑reliance. The panel also examines generational shifts: Gen Z and future "AI natives" demand speed, purpose, and trust, yet may lack critical filters. Improv exercises are presented as a method to build adaptability and trust in salespeople. Finally, they envision a future where AI handles lead qualification and hand‑off to human reps, highlighting European pilots that integrate chatbots with full customer context before human intervention. Throughout, the tone is conversational, anecdotal, and enthusiastic, with occasional cautionary notes about ethical and practical pitfalls.
Chapters
Well, it's funny because, you know, AI, improv, and sales walk into a bar. You're gonna— they will all order 3 different drinks, but they're all, they're all solving for uncertainty. AI will order efficiency, improv will order adaptability, and sales will Well, Sales 3.0 is going to pick up the tab no matter what happens that night. All right. And so they're always the last person standing. So I had a little— I had some plane time recently this past month. I've got to Croatia. I got to go to a couple of conferences over in Europe, which were phenomenal. So I was sitting there on the plane saying, okay, we need a good title. And I, so I, I got the title and I'm like, we need some happy hour rules for the AI areas. So if you indulge me for a second, we have rule 1, never drink alone, which translates is that technology without any human oversight or adaptation is a risk. 2, rule 2 of happy hour is buy the next round before you're thirsty. Meaning that sales and sales enablement should anticipate the change, not just react to it. Rule 3.0 is the loudest person in the bar usually knows the least. So AI confidence is not AI competence. So confidence versus competence, because they can tell you stuff. And, you know, if you don't have a skill You know, if you don't have a skilled mind or at least exposure to what the topic is, you'll just take it. And because they're all very authoritative until you call them on it, like, oh yeah, my sorry, I'm bad, I just forgot. Yeah. Rule 4, there's no scripts, meaning the, the night is ending for script readers. The future belongs to those who can lace up. And what I teach lace is listen, adapt, collaborate, and engage. Listen to depth, collaborate, engage. If you're, if you're speaking from product points or whatever you're speaking on, that's not listening to depth and collaborating, it's, it's just not going to happen for you. Now, rule 5, we're going to leave the bar for a second to make sure we take care of our barista friends, is don't, don't confuse espresso with energy. AI can AI can make work faster, but it doesn't automatically make it work better. You know, a double espresso can make you faster. It doesn't make you any smarter, though. I will tell you, when I was at that conference in Italy, they had— I think every break they had a full barista bar, people, two guys just sitting there making these fancy drinks, fancy coffee. I'm not a coffee guy, so I don't know. But one of my friends came up in the afternoon, she says, I ordered a latte. I'm like, okay. She says, yeah, you don't order lattes in the afternoon here. I was like, oh, I didn't know that. That's, that's a verboten. Okay, number rule 6 of 7, drink top shelf. Companies, typically they're buying top shelf AI. But they're mixing it with, you know, bottom-shelf management strategy. And if you— I don't care what you're mixing, if you're mixing something really good, a bourbon, a whiskey, a rum, and you mix it with something that's garbage, it's just going to be garbage. So make sure— well, we'll talk a little bit about that. And the last rule is closing time. You don't learn to hold your liquor during last call. So you don't learn to adapt during disruption. So, you know, I've spent years teaching undergrads and also business folks, sales reps, you know, improv skills because you don't learn to be adaptive under uncertainty. It's— you learn it while there's not chaos. And if you're old enough to remember the Bulls, the Chicago Bulls in the '90s basketball, no one was going to beat them in 7 games, not because there weren't other skilled people in the NBA, but they worked so well together. That you need to work well with your AI and know when it's— we'll call it hallucinating, but when you know it's a little bit off track. And just like Sherylynne was talking, I mean, she frontloads it with a, you know, a 9-page diatribe of, hey, this is how I want you to act or think. And again, like you mentioned, Gerhard, you ask it the 3rd iteration or something, and all of a sudden it forgets. And I'm like, okay, all right. I like, I learn, you know, fool me once, but I'm like, okay, let me, let me work with you. So, um, the whole AI thing is to me is, um, and oh, we also, AI is also applied improv. So it's kind of wild. Um, and it's also artificial intelligence because I work at a university, you know, out in farm country. Um, so AI has a lot of things, but you, you, like the old saying goes, you, you, you build the, you build the bridge before you need to cross the river, and you have, and you make friends before you need them. Because nobody wants to see, nobody wants to see a sales rep coming around asking for something. Nobody wants to see a colleague who only talks to you when there's a problem, and nobody wants to see the leader of the company only communi— only communicate with you during a crisis. So, um, so if you can marry the artificial intelligence with the human intelligence, you know, to end up with collaborative intelligence, we have a fighting chance to make the customer happy.
I like your analogies. By the way, I'm, I'm, I'm going to challenge you now, uh, because you and I had a conversation, uh, in 2021. That was 5 years ago. And, and I ask you, how does sales effectiveness change through digital transformation? And 5 years ago, digital transformation was the hot topic. And today, AI is the hot topic. So what was your answer 5 years ago?
5 years ago, you're asking me for what my reply was? I live with a woman for the last 30 years who does, who thinks I don't know what I say 10 minutes ago. Do you remember?
Your reply was, I remember it well because I recorded it. Automate time-consuming tasks like a quote, a proposal, getting an e-signature, send video messages instead of emails, accelerate onboarding, turn training from an event into an ongoing flow. So are you still sticking with your answer?
Well, yeah, we got to update it again because 5 years ago we didn't have the tools that we have today. But even so, I'm going to say that, you know, everybody's talking about AI as the story, and I think the story is still the human, the human intelligence, the HI, because we're always going to get new tools and we have. But the advantage comes from you taking that tool. I mean, the old saying, I think it was Riley, Riley, I've forgotten her first name, but I think she coined it, which was a fool with a tool is still a fool. So you got to leverage, you've got to leverage that. And I think what it regards AI, and I'll grab a Gartner quote because I'm a professor and I love, I love actual research reports, and they said 27% of us don't have a comprehensive AI people strategy. We're kind of using the technology, but we're not marrying the human into it. And that's why I love the AI with the HI—human intelligence equals CI, which is collaborative intelligence—together. Because there was another note from that Gartner study that said 74% of of, of us had to roll back at least one AI customer-facing agent experience because of governance failures. So that just tells us we just can't turn the switch on and make it hum and make it go. I think this is, you know, I think everybody should know and they do know that there's some issues with this. But if you look at last month, what happened in this country, in the US commencement speakers, and not just one, several of them, they mentioned AI in their commencement address and they got booed. They booed them. I mean, the same students who a month earlier probably used their AI to help them with their homework now are actively booing because right now companies are a little bit apprehensive and not sure what it's going to do. So they're not hiring as easily or readily. And so, because they don't know what they're trying to predict the future, it's hard to predict. Um, and so that leaves the recent college grads a little bit unnerved or unemployed. Um, but that hasn't been the case for the students, and it hasn't— and I've been doing this job for many years. Even in '08, the downturn, all my sales students still got job offers. The students at where I'm at now at Indiana University, they don't feel the same AI angst, at least the sales folks are still hiring because they need people to interact with customers, help solve problems, etc. So if you looked, if you looked at, so you're asking about AI and what I, what I double down. If you look at the Industrial Revolution and, you know, steam and the ability to harness that and refrigeration and lighting and all kinds of stuff. That improved standard of living, longevity of life, etc. But, you know, it really didn't change the way human beings interacted with each other. Right. This one is— this one is changing. And because I get to teach Gen Zs now, they want— somehow they want a contact-free experience, but yet still go to the bars. It's— so it's— it's— it definitely has changed this leap that we— this industrial— whatever, I guess we're on 4 or 5, I can't remember from the book I read. No, it's changed the way we— we definitely interact with people.
So do you think that AI is accelerating and enhancing the transactional experiences that students want?
Yes and no. And, and I say that because, and I was the one who dropped something into the chat, every single one of our students, and there's hundreds of each semester that take the sales program, that takes the, the intro sales class, and we use AI for all of our role plays to get a lot more feedback. And they put up with it to start, and then they hate it because they want to have a one-on-one sales call with the other student, which we record as well. Again, it gets them a lot more feedback than I could do given the number of students that I have. But then I watch, spot check, and then I add some more flavor in. So yeah, they do like the speed, and we all do, the speed at which we can get answers and get a deal done. But at the same time, they want that human interaction as well. Probably less than the millennials and the Xers and the boomers, but Yeah, they're looking for that as well. It gives them purpose and meaning.
Has AI made you a better teacher?
Yeah, yeah, yeah, it has, it has. Um, I— because I just created a course on sales enablement for the grad, for the grad, for the MBAs, and without it, it would have taken me forever, me forever. And I you know, wrote my stuff, outlined this, outlined that. It says, all right, what do you think? And just this morning, it's an 11-week summer class. And after we just did session 6, and I'm like, uh-oh, I got a little bit less. Again, it's summer, but I get a little less attendance. I'm like, no, I got to change it. So I gave them my syllabus. This is, hey, I don't like— if you were going to change something, what would you change? And it picked out week 8. KPIs and metrics. I'm like, you are not taking out KPIs and metrics from an enablement course. I mean, like, that's the whole purpose of making sure that we're inspecting what we expect. We're not doing that. So I'm leaning toward this, this, this coming, this coming week. But either way, I says, okay, what do you want to do? I says, I want them to do something that disrupt their thinking because they've got, they're starting to get into a rhythm and they're, and they're not, they're going to slowly disengage mentally. And it came up with some ideas, nothing that was earth-shattering to me, but I'm like, okay, I got some options to work with. Let me tweak that. Let me go. Maybe they talk to— and I said, okay, you're giving me individuals. What about teams? Because it's a team-based class. They said, oh, well, then have the entire team. Someone talks to the CRO, someone talks to a sales rep, someone talks to— easier said than done to get all these people doing all that in a week when they all have jobs. But no, I think bottom line, It has made— if a tool in the right hands, it has made me stop, think, make decisions, and also, ah, that's possible. How would I evaluate that? It gives me some Rubik ideas. I'm like, well, that's crap. Or like, ooh, that, that's easy. They can do that. No, I think it has overall, it has benefited the, the student. Again, in the end, we have to change those who are the sales reps of those who are the, the, the professors. We just can't give them things because they, they tell me 'cause Gen Zs are very forthcoming, but they'll tell me, it's like, oh yeah, Dr. P, I had a final yesterday and I was at a coffee shop. I just AI'd all the answers. It's like, that professor needs to change the way they engage you because you're not, I mean, it's an easy way to get your, you know, I don't wanna say your diploma, but when you get out on the street, I'm gonna eat your lunch.
You know, when you, when you, you, you were recently in Italy at this conference. When you, uh, compare the thinking about AI and all the changes in the United States, how does that compare in the European market? Uh, what are their thoughts? Uh, how are they thinking about this differently? And how do they seize the opportunities related to AI in a different way?
They certainly are generally ahead of us when it comes to oversight and ethics, without a doubt.
And why is that? Why do you think that is?
Well, you would probably be more qualified. I think it's when you get a group of EU people together and from different cultures that it's like, hey, what are our rules of engagement going to be? Let's agree upon them.
Whereas— the German quest for order, you know.
But anytime I was doing, you know, work over there and anytime I went to websites, I had to, you know, agree or not agree to everything. On the cookies. And I'm like, oh, you don't get, you don't see that as much in the States.
So, yeah, what was, you had another point? You said they're ahead of us. So let's drill down. What are they doing better?
Maybe this exists here in the States. I just haven't, I haven't seen it or haven't been to the right conference. But in Italy, they, you know, we were talking amongst the Sales 3.0 professors across the world. But also, we, you know, they bring in corporate folks, and they were talking about truly using the— the prospect comes in, and they just knowingly talk to the chatbot. And they get very far along the way and they agree to have information collected. And so when they want to talk to a rep, then all that information, all that they consumed, everything they did, then goes to a sales rep, says, okay, this is where the person is. They've done— they don't even want to talk to anybody yet. So they— but it's all set up so they can do it in a format that right now a lot of us here are just doing our own research anyway and collecting all this information. But here it was all compartmentalized and given to you and says, okay, and you tell us when you're ready. I'm like, oh, and I forgot who said it was earlier today, but it's like, um, by 2030, which is not too far away, um, you know, my AI is going to be talking to, uh, to Gerhard's AI, and then eventually the lead will go to, um, Tricia, and, and she'll, you know, then she'll in charge of the relationship. And I'm like, I see that coming. And so the pushback I get from the students, I say, look, and this is years ago, I says, look, by the time you're done, you're going to be talking to the AI before you talk to the human. And I think the AIs are going to be talking to them before they hand it off to the human. There's no research from academia yet on that. It's like, okay, what point do you hand the relationship over to human beings? And, um, How do you build that trust when information has already been exchanged? And it's very similar. You mentioned the Germans, they, you know, before the negotiation, because I teach that too, they kind of, they not kind of, they exchange information with each other and say, so this is what we're going to do and this is what we can assume so we can run. I'm like, when I first learned that, I'm like, wow. And so that's kind of what the AI, the bots are doing. And then you and I come in to be the human in the loop and to make further decisions. So I think they're in some ways, the way they're using it, they, at least for that use case that I got exposed to, I'm like, wow, that's pretty cool. Tricia, what do you think? Uh-oh. I'm fascinated by how—
well, first of all, thank you very much. Very exciting. And having the passion to really support our young people and help them navigate in a really meaningful way, but also a human way— I just love to see you, Robert, so thank you for that. And then, and then I, I spent 18 years in the market research industry in Toronto, Ottawa, Washington, DC, and then I went back up to Toronto and built an insights practice inside of a $28 billion media company. And there was this constant reframe the whole entire time I worked on this project, which was the benchmark of health benefits for workers. And that whole entire 18-year period, people kept saying how, uh, you know, Gen Xers and the younger generation were so different in their work expectations. And the fact of the matter is, the data didn't say that. And so I'm, I'm so curious and I'm curious to, to know what your thoughts are in terms of how much smarter the next generation is and will be because of these tools to maybe get to what the results actually need to be. And, and that was the thing that I picked up in literally 18 years of research is they were no different. In terms of what they wanted. They wanted meaning, purpose. They wanted their, their voice to be heard. They wanted to be treated as respected humans, you know, some pretty basic things that hopefully we taught our children. Um, and, uh, and but the thing was they weren't prepared to go through the hazing that we all went through to get to the positions we held. They wanted to just skip straight through to get the thing done that needs to be done, and So I'm curious with that kind of headset and where you live in between these worlds, what that looks like to you and how you see that playing out over the next 5, 10, 20 years.
It's been a hell of a ride, trust me. When I started, I was the young, cool, hip professor, and now I'm the old guy who still acts like an adolescent, I'm told, at least by my daughter. Yeah, they, they're, they are different. Do they want some of the same, you know, How to Win Friends and Influence People basic human traits? Yes. Do they want it faster? Absolutely. Uh, do they have the same loyalty or willingness to wait? I would say no. Um, um, they're much more, uh, driven by less reading and more experiences, um, to the point where they— some of them are not going to be driven every year to make, to make Presidents Club. I've been there, done that. Now I'm looking for another experience. And I'm like, whoa, that's kind of, that's kind of crazy. But, you know, the one thing that, that I'm given is that every year I'm a year older and every year they stay the same, um, stay the same age. So I would say that I think some of your best people are the people who just graduated a couple years ago. Because they had to do everything the hard way, the way us three had to. But if they can learn how to add the AI tools, they're going to be gold. My fear is, is the kids I'm going to get in about 5 years, you know, you talk about digital natives, these are going to be the AI natives where unless they have a different filter, unless someone's taught them, their parents have helped filter that, they're going to think that the answers they get are correct. And that will be a challenge. For us, especially the old dogs, who'll be like, that doesn't pass the sniff test. Why would you think that that makes sense? Why? And then you copied and pasted and put it right into the email and sent it to the customer or the prospect. That's insane. So I think that's probably going to be an elevated danger. It's always a danger. My, I mean, my letters and emails to my prospects and customers probably could have had better spell check. Trust me, I'm guilty. But the, I think that's the probably the bigger fear of how this is going to change. And I changed. I changed. I don't, I used to have 3 books in the negotiation class. How to Win Friends, The Art of War, and Bargaining for Advantage, and Getting to Yes. I'm like, these students are not going to read that. So I've got to change. And the marketplace has changed. So they, I have different things that I can access in order to get them to learn. But then I have to hold their feet to the fire. It's like, are they blowing through it? Or doing 2 things, 3 things at once while they're watching some of the video content, or they actually letting it sink in. So your question is adept. The, the, the, the challenge is still mine in the, in the, again, I worked 100% commission when I started in sales. So sorry for the students who've had me in the past, but I ripped the COVID off. Let's go. If you're not helping the customer solve their problems, you're, and if the order didn't stick, you got a chargeback. So you better deliver value and be honest about it, or don't sell to them. And that's something that I learned early on, is like, you can't sell to everybody, you can't make everybody happy.
That's fascinating to me too, because, you know, it's the age-old challenge of getting that right salesperson in place, the Hail Mary types of scenarios and all of those kinds of things. So, um, how— what would you, what would you say is the key that you're really focused on for all of your young people going through to actually be able to deliver when they get into the workplace?
Well, I definitely like the Michael Eaton cat because it's all to me. I do a lot of improv in class. Let's feel it, let's laugh, let's make, you know, and you can, you can throw in the improv while you throw in the lessons. So when I was thinking of when I teach voice messages, which none of them have ever left, um, I like, okay, pair up. Okay, they get a pair. It's like, okay, you got 30 seconds, leave your best breakup voicemail. And they're like, what? Like, 30 seconds, it's going, let's go. And like, oh, sorry, it's not you, it's me. By the time you get to the second person, no, it's you, man. You're scary, you know. And then we do another one. And then I was like, okay. And then I hit them, was like, okay, you've got, you're calling your prospect from the semester's role play. You get their voicemail, go. They don't know what to say or do. And we do it the other side and they're all uncomfortable. I said, how many people are uncomfortable? Like, how many people are willing now to listen to the, and understand how to do the fine art of voicemails? And they're like, grab a seat, let's do it. Let's start. So you can throw that in, have a little fun with it. And there's always laughter because everybody has, you know, a face plant. Um, so for me, I think the repetition and opportunity to laugh and learn in a safer environment, because you know you're going to face plant— some of the worst people I, I, I, I, I train are seasoned sales reps because they don't want to look bad in front of anybody. And so it's hard for them to feel like, okay, now let's learn so we can make customers happy and make more money. Are you willing to do that? Um, the other thing is, at least What I recently hit on is that, you know, technology is going to accelerate information, but trust is going to— or humans are going to accelerate the trust. So that's their role in the system. And they better understand that they've got to be knowledgeable, but they have to be trustable. And if you give people the wrong information or information that's not vetted or they can't trust because you just copied and pasted, I'm going to go somewhere else with my money.
So powerful. That's our brand promise, you know, the most trusted network. And I get to hang out with people like Gerhard and you, Robert. So I'm all for what you just said. And thank you. This has been incredible. My pleasure.
Gerhard, good luck on Saturday.
What's happening on Saturday? That's the, that's the soccer match.
Oh, you're gonna, you're gonna watch it whether you want to or not.
I mean, the greatest thing you could do is if you happen to be in Europe during the World Cup, and I've happened to be there several times, and I happen to be in Japan when they hosted too, just the energy and the excitement. And so, I mean, I was in Croatia for 10 days and I got to see a live match, and so I had to watch last night's match. I don't know, I like the field of competition, which is exactly what most sales reps want. They want a chance to compete. They want to run, well, also fall on the ground faking a leg injury. But it's, you know, who said it? Was it today about keeping score? Yeah, yeah, it was the first speaker. He talked about We always kept score. But when my grandson walked off the field, he knew— oh, we don't keep score. He knew what the score was. Salespeople, you get these Gen Zs and everybody thinks they give me— they do give me the Gen Z stare. But when push comes to shove, the sales students, it's in their DNA or they wouldn't be in the class. They like to compete. They like to win. They will eventually learn how to better serve the customer, and that's their understand that that's, that's the variable, variable train that you got to— the end is all about the, the customer. Are you making them happy, satisfied, and will they repeat? Because loyalty is where you make your money.
So one more thing I'd like to say about Robert, he's not only elevating the profession of selling by passing on those skills and teaching young people to become professionals, or impersonate a professional, if you will. But Robert has one more quality which deserves to be mentioned, which is he brings joy to the process of training and educating people. And that is a real talent. Thank you.
No, it's an honor for you to say that, Gerhard. I appreciate it. It's a lot of fun. It's a I wasn't selling, although I'd probably be financially richer, but I love what I get to do and all the students and the trajectory that sales as a career can change a young person's life.
Um, it's a— yeah, and the word that comes to my mind is enthusiasm, and that ends with, uh, 4 letters, I-A-S-M, which stands for I am sold myself.
Well, there was— if I can't— one— there's one other quote that I like, and I don't remember who said it, but, uh, while age may wrinkle my face, a lack of enthusiasm will wrinkle your soul. I appreciate you having me on today.
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