Are You Smarter Than an AI Chatbot? A Workshop on Listening, Signals, and Strategic Judgment
Speakers
Bob London (Bob London, LLC)
Session Abstract
In this interactive workshop, customer discovery expert Bob London explores why effective customer conversations depend on uncovering the right signals—not just summarizing what was said. Attendees will analyze a real customer transcript to identify renewal risk, expansion opportunities, and value indicators before comparing their findings to AI-generated insights. The session also covers practical questioning frameworks, techniques for uncovering hidden customer signals, and how AI can enhance judgment, prioritization, and customer understanding beyond simple transcription and summarization.
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I'm a roamer, so those of you who think you're smart by sitting in the back are going to be in the front in a minute. Thanks so much for being here. I really appreciate it. And you're going to hear some...
How many of you have talked to customers actually talk, speak to customers? Okay. Does anyone not speak to customers? Okay.
Just a personal version of yours or you just don't like to... No, your job is more digital maybe or... It's supporting the CSM. Thank you.
Your customers might be considered CSMs, but thank you. I didn't mean to pick on you so quickly. I'm sorry. So if you talk to customers, I want you to think of it as talking with customers and not to customers, not at customers.
Because the point of today is to find out what happens when... And this is the journey I've been living for the last over 10 years. What happens when you take away all the trappings of vendor customer interactions? You take away slides.
You take away a tight agenda that always pivots back to your solution. You take away the fact that you're supposed to keep solving and selling. You take away the fact that you didn't give the customer a chance during the meeting just to talk about what was most important to them. That's the experiment I've been living for 10 years and 3,000 customer conversations.
That's right. I get paid to listen to my clients' customers and tell them what they're really thinking. But the good news is that methodology is now... It works.
It worked. It doesn't have to be me, Bob London, doing it. So what you're going to hear today, part of what you're going to hear today are questions that you can and should be asking your customers that are a little more challenging for you to ask. Because you're not used to it, but customers love these questions.
The questions reveal the truth. And then also, of course, you can't be a better listener unless the other person's talking. So once they start talking, how do you listen? Then we're going to do some stuff here where you're going to work together at your table based on what you heard.
And there's going to be a little gamification going on to compare how well you listen and summarize versus an AI chatbot. So this is me. I guess I have enough logos. I found enough logos on the Internet to make me look successful and important.
But these are the companies... No, seriously, I shouldn't say that. These are companies I've worked... Well, everyone has a logo slide.
If you don't, you shouldn't be up here. These are companies I've had the privilege of working with over the years to do both the customer insights... I call it a customer listening tour, but also to teach this method called radically authentic discovery. Rad, very 80s vibe to it somehow.
You know what I'm talking about. It's a weird... I used to be a marketing guy. I knew I had to spell something.
So I had Rad and I was like, "It's too much work to come up with something different." So Rad's okay. But some good companies, some companies that all have something in common, they're curious. They're curious about a better way to listen to customers and understand them. So here's the challenge that we're all facing.
Too many renewal risks, expansion opportunities, use cases, and all kinds of good, important stuff... Never show up in that beautiful, magical AI meeting summary. Mine is powered by Fathom. We have a...
Raise your hand. We have a Fathom representative in the room. It's fantastic. That's not an influencer paid post.
That's a real testimonial. The reason those expansion opportunities and use cases and opportunities don't show up in the AI summary is because the customer never let them out of their mouth because we didn't set the stage. So you're gonna... Yeah.
So we're gonna... The conversation can be better. It can be deeper. It can be richer.
It can be more strategic. It can be more anchored in the business context that the customer is facing. All of which is what they're experts in. They're not experts in your product or solution.
So when you try to drag them into a discussion about adoption and innovation and roadmap, they'll listen. But are they really leaning in? When you ask them questions about what's on their side of the wall, they'll listen and they will engage. Thank you for those of you who are nodding your heads, have either experienced this pain or recognized the opportunity.
Thank you. The good news is there is a very simple solution. Everyone is wrestling with the human AI fight between what skills are gonna go away. We have curiosity.
In real time, in the context of a customer conversation, we can be curious. When we hear something, we don't just go to the next question. We can double down, double click on their answer and say, "Wait a minute. You said tension.
Can you just tell me what that looks like? Tell me what the cost of that tension is in the business?" You can ask better questions and then, and only then, can AI become that amazing thought partner, listening partner, because it doesn't have biases, it doesn't get tired. It is pretty accurate. It's pretty amazing how accurate the meeting summaries are based on the transcripts that you get.
But that magic is 24 months old. The meeting summary itself is not the magic. The magic is what you feed the AI. And again, I'm gonna demonstrate that today.
So, here comes the part where you have to do some critical thinking and listening. Hopefully, you'll want to do it. I'm gonna play three clips from it. I'm gonna bring you from this theoretical down right into the room, the virtual Zoom fathom room, where I had a conversation with one of my client's customers.
You'll hear two voices. One of them is me. The other one is a VP of customer support for an online B2C jewelry brand. The product he uses is my client.
It's a SaaS help desk platform. So, I picked this because it's a pretty simple equation. It's got some consumer aspects to it. You'll hear me asking some questions.
You'll hear some answers. While that's happening, I want you to, you could do it on your phone or write it down, take notes individually. What is happening? What are you hearing?
What does it mean? What might you do if you were the vendor? Okay. Neatness doesn't count.
Doesn't matter what it looks like. I'm not gonna have you stand up and show us what you wrote. It's more about, did you understand the conversation? Did you listen?
And did you, are you connecting the dots? So, I'm gonna play the first three clips now with the help of my good friends in the back. We're gonna go to the video. Okay.
Let me go back. I'm saying, I'm amazed. Alright. Try it again.
Is there something that surprised you since you started working with me? I would say I'm amazed that people have, I feel like people from various departments all over the country, and for you, I contacted you, and I'm very hands-on and involved in creating a meeting. We're both transparent, and we have my last company, we partnered with, and we would have discussions with our customer success manager, and that was it. I never knew marketing or sales or managing or anything, but I have a relationship, I was with RCSM, but I routinely speak with me when their sales representative closed the deal for us, so that they took care of the launching a last company.
I think that's right. If I said to you, I need to take away all of our tools and resources that you use to do your job, which one would you beg me to have that first, and just say I can't live without it? Yeah, yeah. It would be for sure, if we all thought the backbone of what we do, and we were watching so many of them on it.
I get chills thinking about if we were all working out for Gmail and Gmail and I was just thinking so much of it was uncomfortable for us. The backbone of what we do, and of course we have additional vendors. We have all our outreach tomorrow on a lot of the metrics that you mentioned. On a COO one, however you react, one is you put it forward, you leave the message, the bottom is you probably get back to that, too.
You want to know a little bit more about what that competitive is all about. What do we have to do? Well, I'm very curious. That's going to be the way we are more fully reached out to be, and I appreciate it all flattered for very drastic work, but I would not be needing any possibility to switch it over at this time.
So I guess we're pretty close to the bottom here. I would have been more than flat. I would definitely shoot it down pretty quickly. By the way, he said he was courteous.
I'll give you one guess of where he's from. If you know, if I've already told you don't say it, where is he from? Minnesota. Where is it?
Texas? What? Yes. Minnesota was a close second because that's the second place where people talk like that.
If I got a call from a competitor, yeah, just to be nice, I would call them back. I'm like, man, it's pretty cool. Wish that would rub off some Americans I know. So show of hands, how many of you think that customer on the simplest terms is red?
Raise your hand high so I can see it. Red? Anybody think it's yellow? You've got to raise it higher than that.
Okay. Thank you. I started to be that guy. Why do you think yellow?
What did you hear? I just don't know what they're going to do with this. Yes. So you have to keep it underline.
They mentioned what they didn't like about other people, so there's got to be things that they might not like about your course. Hopefully you can hear that. Is there such thing as a green customer in your mind? I mean, yes and because there's always some position out there that could be leading you in some area.
So it's not always right, it's not always product, it's a suite of all things. And eventually, no matter what, I feel the best customer could be sweet. Okay. Are you a CSM?
I manage a team. Okay, perfect. So the question is, again, do you believe in green at all, or do you just challenge it all the time? I think I always have a bit of talent in the back of my head.
Okay, got it. Good, thank you. So I hope you can hear the answer. It's like there is a persona of leaders and CSMs who just think no matter what, no matter how positive it sounds, and I think we can all agree it sounded pretty positive, there's always some risk, and just because of other factors we may not be aware of and such.
Now, why did you say yellow? Because when you asked the question if a competitor reaches out, they would not ignore them. Okay, thank you. Yeah, I didn't think about the microphone if you guys need it.
Who said green? Raise your hand high again. Okay. Okay.
If you don't mind, sir, I just happened to look at you. Why did you say green? I mean, it didn't really seem like the intonation or sentiment seemed any other than green. And what you mentioned that a competitor or whatever they used in prior, they only met with the CSM and then they met with the AE once.
If you sound like the intonation and the sentiment wasn't anything other than green, but then the question was, what is the likelihood of an accident? Sorry, what's the likelihood of what? It's the likelihood that you were going to renew with us in the... Right.
Good. Good. Really good. These questions are maybe questions you haven't seen before.
They are part of the methodology, the questions I just showed. What's the biggest thing that surprised you? What would happen if... How would you react if a competitor reached out to you?
And they have something in common. They're part of the methodology I teach. They're very real. It's radically authentic discovery.
They're based on things that happen in the customer's real world all the time. You buy platform, product, there's surprises six months later. There's going to be. Sometimes, by the way, 50% of the time, in my experience, there are positive surprises.
So then you can gather information on what they think you do really well based on the expectations they had. So those are some of the questions. Now, we're going to go into round two. Whoops.
Jumpy. My fingers must be jumpy. Now we're going to go... You don't know when you're going to find the truth with this methodology.
So you have to keep asking different questions. Now you're going to hear a question that's sort of at the very beginning of the conversation. It's a tone-setting question. It's if I could sneak into your next board meeting or your ELT meeting, what would I hear them discussing as the biggest priority or challenge?
Excuse me. What would I hear as the biggest priority or challenge they'd be discussing for the next six to 12 months? Again, that's what they relate to more than questions specifically about their adoption of your platform, et cetera. There's nothing wrong with those questions, but this is how you disarm them.
So let's listen to these three and see what happens. I think it goes up to around a 30 or 50,000-foot level of our moments. So if I could sneak into a board meeting there or a senior leadership meeting, what do you think is the biggest priority or challenge that's being discussed for the length of the next six months or three years? I think the biggest challenge that would be discussed during the board meeting would be, you know, so I think you might be aware of who I'm here to help with these serious changes to their privacy laws, or what the data I believe it was, and that's how the massive impact on digital marketers, customer acquisition, the cost of customer acquisition is much higher, it's harder to track what customers are looking at than the privacy of the cookie standpoint.
And with that, it's been a big challenge for us, I think a lot of track and sewer grants, because it just makes it that much more difficult and expensive to acquire from customers. What is an amazing thing that you need to get better at in the next, you know, six to 12 months? I don't know what to do, but it's been discussed, and I think they've done a great job, they definitely went to their customers and continued to, you know, offer new products or features within the platform and they are likely to be easier for us. You know, one thing I think I'd like to do is to be around happy shows and to some of the competitors, including Ann, they offer, you know, means to basically tell their viewers to come to the reservation, and the competition is cheaper.
And I think that if I spoke with our internal finance team, and they said, hey, you know, when your contract is coming to an end, we really need to reduce some of our customer service, the way the expenses, and it's irresponsible to identify ways, you know, for us to reduce cost on that platform. And yeah, I think I would have to do some most, because yeah, there are significantly less expenses than, you know, if we did, of course, make the choice to continue our partnerships with, despite approaches from where I think they were cheaper, but, you know, I think that in the future, it's significantly happier to reduce our customer service, that I wouldn't have to do other consumer issues. You know, I wouldn't like to do very transparent in terms of our needs to reduce cost and hopefully make it work close, but I think that's much cheaper, and people in the customer service world are aware of that. So I think that's, you know, one of the strong things is that they are cheaper than some of our competitors, I think.
All right, I'm going to move on. So show of hands, how many think green? How many say red? Nice and high.
Okay, what did you hear that makes you think red, please? He's very aware of pricing and the effect in specific features that would impact the business revenue, and he hasn't been able to articulate the value that he's got from the solution yet. Okay, thank you. Did he say he was cutting costs now?
No, okay, just to be clear. Who said red? I asked that already, didn't I? Yeah, who said yellow?
Sorry. Yeah, the worm has turned, the mood has shifted in this call. Did anyone notice a point at which the whole, from all six clips, where in one of these clips it changed very quickly? Does anyone remember a pivot?
Thinking, thinking, yes, we see a half a hand raised. He went into a lot of detail and depth about things that he hadn't necessarily, I think my voice is carrying, sorry, that he hadn't necessarily gone into as depth about in the previous set of questions. Do you remember how he started that answer? If the competitor offers this.
Well, so the question that I'm thinking of is what do they need to get better at? What do you need them to get better at? And he started by saying, I don't know, they're really good, they listen to their customers, but, so it's unbelievable, and if I had been in the CSM, I might be marking it green and just thinking ahead and just, okay, don't need to worry about anything else. I mean, he said a lot of green stuff.
He said a lot of green stuff. But now we see it's gone primarily in this room from green to yellow. What I'd like you to do is huddle at your tables. You actually have to interact with each other a little bit.
And for the first few seconds, just anoint a note taker, somewhat a scribe who's going to, like, what, and answer these questions together. List what you heard, just the key insights, and the implications or actions you would take as a CSM. You don't have to know anything about SaaS help desks or B2C jewelry brands. I think you can, you know, connect the dots a little bit there.
So take six minutes, seven minutes, to do that, and then at the end, we're going to have, I'm going to give you a scoring model, and we'll see how that goes. And based on what you put down on your notes and what you have in your findings, anyone have any questions before I shut up for a while? Okay, seven minutes. Okay, we're less than one minute remaining.
Polish up your PowerPoint presentations. No, I'm just kidding. Okay, scared myself. Okay, pens and laptops and pencils down, please.
Wow, thanks for getting, settling down so quickly. Okay, so here's the next part of this. It's the, you as a human, let's say you asked the good questions, you listened, right? You did all the right things.
You put it into Fathom or Zoom or hopefully Fathom. And I had some guy leave early and he said, "I'm definitely checking out Fathom." I'm like, "Fathom, what about me? Why don't you?" So this is what I would call the typical meeting summary. In other words, if you're a CSM, you say, "This is what you're going to get." I'm going to call this, with all due respect, it's a below-the-line meeting summary.
It's accurate, it was timely. It captures a lot of things that are important. But look at the, I'll call it the emphasis. This is what came out of Chatchee PT.
I have an AI coach that I created based on my methodology. This is what comes out of it. This is what comes out of it, right? Look at all the positives.
Customer sees vendor as operational backbone, deeply values-responsive, et cetera, et cetera. It does mention some of the issues, but like it's kind of almost an afterthought, and therefore the summary is it's green. I said to it, "Do you think it's red, yellow, green?" The chatbot said, "Green," right? Based on the same transcript, though, that's why.
So the conversation was richer. We used red. You can take a shot of this. I'm not going to dwell on it, or you can reach out to me, and you'll get the slides from Gainsight, of course, and the recording.
But the principles of red, the aperture is starting at the business level, nice and big, really wide open. That's what they love talking about, and they're happy to share. Then ask some of these bolder, more disruptive questions. Make it a two-way conversation.
Silence until you fully understand, which happens to spell STFU or dollar sign FTSU. Connect the value dots. See, we did that. The next question is, "Are we settling for basic call summaries?" Are we settling for basic call summaries?
We cannot settle for that. I'm going to show you these prompts very quickly, and then I'm going to show you what happened when I used the last one. You're a salesperson for our competitor. Assess the likelihood of you winning this customer's business.
If you had the chance to pitch them, how would you forecast them? But the last one is the one, if you want to get an above-the-line summary analysis of that same exact call transcript, use that prompt. You're my CEO. Sorry, what's your first name?
Sam. I'm Sam. You're my company's CEO. What did you hear?
So let's see what happened when we did that. Look at how much more urgent and strategic it is. At the board level, customers grappling with rising acquisition costs. What could be a bigger issue for a company?
Well, that doesn't have anything to do with our little help support platform, does it? Oh, really? You don't think there's a ripple effect to that or a direct impact? Okay.
So that's one thing. Turn CX, I'm looking at the lower left, turn CX into a growth lever rather than a pure cost center, support revenue generation, and then I don't know if this was in the recording. There's a new leader above this VP, cheaper competitor. We must act with urgency because all of our customers are in the B2C online world.
They're selling stuff. They're all impacted by Apple's privacy changes. I don't want you to go back and rewrite what you've put, right? That's not the point.
The point is this is the gold standard of what you should be thinking about and listening for. So what I want you to do is look at your-- So let's do it this way. Take a minute and look at what you've written as a group, whoever was the note taker, and how did you score out of eight? How many of these points did you capture?
And I took these from the CEO summary. So raise your hand if you're the note taker real quick for your table. Okay. So just take a look, and you're going to have a number between one and eight.
I'm just going to give you a few seconds to do this. I hear whispering. Darn it. We almost had eight.
Okay. I'm going to call. Okay. I'm going to call.
All right. You didn't have to get eight, right? Okay. Stop.
Pause. If your table--if you're the note taker for a table that got eight out of eight, please raise your hand. It's hard. If you're a note taker at a table that got seven out of eight, please raise your hand.
If you're a note taker at a table that had six out of eight, please raise your hand. Okay. Raise your hand high. So we have one, two--am I missing any?
Okay. Please read us your summary. Actually, hold on one second. Yeah, wait until the microphone comes over.
Sorry. Please read us your summary, and don't add anything that I said. Sure, yeah. One of the first pieces of the summary was that the first three questions mentioned being polite and not having necessarily a fully honest conversation because they're just being polite.
Yep. We need to ask for further context and attempt to prevent the risk here. Competitors are always asking for attention, so--and know that price sensitivity is the lowest hanging fruit for them to approach their executives. Understanding it for conversation is just a check mark, or if we can move the needle today, are they the right person to make the decision?
So we got to talk through executive changes. Okay. And then we also need to understand product pain points and asking how others are solving it. Okay.
Good. So it sounds like--I'm not sure--that the rising customer acquisition costs-- I didn't hear that from yours. Okay. And the board--well, that is the board priority, essentially, but that that's connected to--they want the platform to be able to support revenue generation.
So, okay, very good. Hold that thought. Yes, sir. Do you mind reading your--we need a microphone.
Do you mind reading your summary, and don't embellish, please. The customer doesn't understand the value proposition. Do we need to review the value proposition and understand what they're getting out of the tool today? Product and engineering needs to showcase current capabilities and the roadmap, focusing on features on upsells that we offer today.
Change management on the privacy laws and the impact of customer acquisition around that. Benchmarking usage and experience of solutions versus the rest of the clients that we offer related to up sales. And then review client-specific and industry-specific pricing models. Very good.
Which one did you not get? You missed two. Which two do you think you missed? C and G.
Yeah, C, I think, was a--I'll call it an Easter egg. I guess it wasn't really there. G. Yeah.
So, the summary at the CEO level, again, if you're being really strategic and above the line, it should be very urgent and rich. What we're hearing is Apple's privacy changes is causing a ripple effect among a lot of our customers who are B2C online merchants selling stuff. It's driving up their customer acquisition costs. They're not panicking, but they're in motion trying to solve for that.
Meanwhile, we are sitting on a platform that currently is a cost center, doesn't generate revenue, and there's essentially a competitor-- and it sounds like a very active competitor--that's less expensive that it has that capability. So, it's red, basically. I think that the CEO summary might have said green when I used that prompt, but it's definitely red. I'm not going to tell you the end of the story because it's confidential, but you can guess where it went from there.
So, I'm going to say with respect, this--the two you missed weren't as important. So, I'm going to say we had two sixes. Those were the best scores. I have good news and I have some other news.
The good news is everyone at these tables is going to get a free version of my online course on Radically Authentic Discovery, which is--it's a $300 manufacturer suggested retail price of $300. Seriously, if you want it--if you want it, come up to me afterwards. I'm going to give you a business card and you can use that to redeem it. But the other news is I think we all have the opportunity, and I'm included in this too.
I mean, I have clients. I have to listen strategically. Is to basically up the level of our--again, I refer to it as opening the aperture-- is hold the conversation in the beginning above the line about their business. Hold it there.
When they say something like the board level thing, follow up on that. Well, what's the ripple effect of that? Is that affecting your job? And I think if I had asked those questions on this call, we would have gotten very quickly to the fact that, well, yeah, there is kind of an issue that you guys are costing us money, which is fine.
We know we're paying for you, but you're not able to generate revenue. And where is that feature? We would love to know if that's a potential feature on the roadmap. So as a CSM, if you hear that and you hear it times 10 customers as one CSM, or however many customers--I'm afraid to ask how many you have in your portfolios these days-- times 10 CSMs, you might have 80 out of 100 customers at risk for that same exact reason.
And again, I'm not going to tell you the ending of the story, but it wasn't pretty, partly for that reason, was you have to take that urgent view, that strategic above the line view. So with all that said--and that's what I'm referring to here-- with all that said, I have time for a few questions, if you have any. About how this went, but also how to have these conversations, questions, skepticism, anything, pushback? Okay, so it's not possible that I answered every single question already, so I'm hoping there is some brave soul.
Okay, well, I appreciate you showing up and being here and engaging so much. Oh, we have a question? You've got to raise it higher. Okay, I'm sorry.
We have a digital team, so we don't actually talk to customers. Do you have any suggestions or strategies to implement a similar tone and approach? Yes, through the magic of AI, which I have heavily leaned into and invested in, there are some platforms where there's an agent-based approach where it feels like-- bear with me--it feels to the customer like they're having a voice conversation with your agent as long as that agent is really well trained on how to do this. But the key is, with digital and any survey, is you have to let the customer go in a direction that they need to go in, don't create too many guardrails in the questionnaire or the digital motion that doesn't allow them.
Then through the magic of AI, it's much easier to synthesize a lot of open-ended data, a lot of unstructured data. So you can absolutely use an agent to do it. I don't have evidence today that customers are more likely to give feedback or answer questions through an AI-- let's call it "agent" versus a "survey," but I think there's some evidence that customers will be more open if they're talking to an AI agent versus a human. So we can all benefit from that.
It's a really good question. Did someone else have one? Okay. [inaudible] Yes.
[inaudible] Right. [inaudible] Right. I think what we learned in this conversation, it may not be his decision, right? He may come and go, just like any customer may come and go.
Are you asking partly about how to get beyond him into some executive champion, and is that what you're asking? Or are you asking how to factor in the risk of having this BFF factor, as you call it? Yeah. Yeah, I think that, first of all, he did reveal the truth, right?
I mean, he did this method-- I have to say again, the methodology is designed to speak on their terms. It's disarming. It's engaging. And it induces truth without any-- you don't have to give them truth drugs or truth serum.
And so I think what you find out is he can give you the truth. Then the question is, what do you guys do? And in this type of situation, I would say it's not the most urgent situation I've ever heard in terms of product market fit, but this guy, the VP of Supports Leadership, needs to get involved in the product issue. It's like, can we generate-- can we help them generate revenue from the support platform, number one?
And number two, can we correct misperceptions and build a relationship? But it's hard for an individual CSM to do that. They're not always-- they don't necessarily-- they haven't set up the relationship. The relationship's below the line, I'll say.
And I think we-- today's conversation bore that out a little bit. So is to engage at a different level using the mechanism that I teach, which is, hey, we have-- we're doing a customer listening tour, and we'd love to engage-- our CEO or chief product officer would like to have some just open-ended conversations about what's going on in your world. And that would be you and maybe your CFO because of all the things-- we know that-- this was five years ago, Apple changing their privacy rules. You set it up on their terms.
We just want to have a step-back conversation because we're committed to delivering-- the more we understand about your world and the board level, the more value we can deliver long-term. And that's what they want to hear. And that helps you engage people around him. Because, yeah, I think in the beginning, he didn't want to say certain things or-- it's also a big pain in the butt for him to have selected this platform and then have to undo it.
And he's just not going to do it unless someone tells him to do it. Great, great question. Give yourselves a round of applause-- oh, I'm sorry. Do we have time for one more?
Real, real quick. Real quick. Do you offer those types of services to companies where you can come in and teach CSMs? That's all I do.
I love to do it. Thank you. What's your name? I'm sorry.
I couldn't resist. How could I not resist? Amazing. Thank you for your attention today.
I really appreciate it. Hope you had fun. Thank you.