E21 | Uncovering the Secrets of Deep Listening: A Conversation with the Uh-MAYZING Bob London!

In this episode of the Trailblazing podcast, hosts Speaker B and Speaker C interview Bob London, the self‑styled "Chief Listening Officer" who teaches companies how to truly hear their customers. Bob recounts his career path—from a corporate marketing executive who was fired, to a marketing strategy consultant running "elevator rant" discovery calls, to a solo practitioner who has conducted over 2,700 customer conversations. He critiques the superficial, lip‑service use of terms like "customer‑centric" and argues that most teams talk at customers with slides rather than listening. Bob promotes "deckless" conversations, the use of authentic, truth‑seeking questions (notably the "competitor question"), and the cultivation of three core power skills: deep listening, authentic questioning, and genuine authenticity. He explains why people struggle to listen—self‑delusion, brain overload, and a cultural pressure to have all the answers. Bob shares memorable customer rants about false partnership claims and the value of competitor curiosity, showing how those insights can drive product and marketing decisions. The conversation closes with Bob’s favorite piece of advice: focus on the windshield (future) rather than the rear‑view mirror (past), emphasizing forward‑looking action and self‑empathy.
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Yay.
Oh my gosh. Oh my gosh. Oh my gosh. We are so, so lucky today to have our dear, dear friend and supremely interesting awesome dude, Bob London, who is, as we all know, or you do now, the chief listening officer of the world.
Of the world.
Of the world. We're just saying. Of the world. So welcome, welcome, Bob, to trailblazing for.
Thank you. Likewise. Although I show it in a different way. I am very excited, I'm very excited to be here. Now I love, love you guys. Amazed by the levels of enthusiasm that you have and that you transmit to others and so anyway, I feel fortunate that we got to meet and I'm really happy to be here.
Oh my gosh, Bob, me too.
We're like an ooze. We're like a salve for the soul.
To make people don't love ooze because that sounds like it needs medical attention now, some might argue medical attention.
So, Bob, this is going to be a fun conversation. I can tell you that right now. Tell us more about, for our listeners. Tell us more about who you are and what you do and more of your background because it's fascinating to us.
I know. Love it.
So I, I'm happy to do that. So I, I'll start briefly in the present. So I, I teach companies how to really listen to and understand what their customers challenges and priorities are and then if, if necessary, work backwards from that to help them, you know, develop whatever strategies are necessary to help them, these companies grow. But you know, it's, I guess I'll just say that the idea of being customer centric or customer obsessed or customer driven is all over the place. You know, it's out there. Everyone says it. But I'll just, I'll, I'll just say a lot of times it's lip service. So I'm trying to get people to be more intentional and invest in the idea of really listening to understand their customers. I come to this, I've been doing it for, I've been doing the teaching of this, the training for about four years. And before that I was, I was a marketing strategy consultant who was doing customer listening tours to help my clients and me understand what was really going on with customers. I called it the elevator rant. What are your customers bitching and moaning about when there's no vendors around? Like what's their truth? And then converting those into marketing strategies. And when I started doing the listening tours, I Guess it's been nine years or something, 2,700 customer discovery conversations ago. That's when my niche really paid off, and my differentiation was really much more significant in the market, and my clients were more successful because we were starting with this old idea of the voice of the customer. So. And then before that, I was in the corporate world getting fired, basically working my way up, hitting the ceiling, because I hated managing people and I hated going with the flow and stuff. And I'm not saying I hated it. Like, I was righteous. I just was not easy to get along with because I was in over my head. Or, you know, when you become a VP of marketing or chief Marketing Officer in a company and you've gotten there by knowing a little bit, then you become a pretender. And I just didn't like that. And so neither did my bosses. So I was fortunate to be fired. Fortunate to be fired because then I was able to explore what was really what. What I'm really good at or what I'm told I'm really good at. So I know that was a long explanation, but hopefully that's helpful.
Perfect. It's a perfect explanation. Like one of the things that you said that really resonates well, you know, because we've known you and, you know, kind of some of the work we do that we're pretty passionate about, those power skills. And of course, really meaningful, deep listening is one of them. And, you know, you're so right. Everyone thinks they do it well, and they don't do it well. Do you find that the customers that come to you are already in a bit of a crisis and worried about losing a customer, or they've had some really bad feedback through assessments, et cetera, or NPS scores or whatever? Or do you find that most of them are proactive or is there some kind of a nice balance between the two of them?
I think there's a balance. I would say that it's. I wouldn't say they're ever in a panic because we're talking about behavior change on their team. And. And in order to change the behavior, they need inspiration and guidance and skills and tools, all of which I provide. And that takes a little while. I would say. The main thing is companies that realize that they end up in dozens or hundreds of conversations a week with customers where they're talking at the customer, they're all armed with their PowerPoint and Google Slides, and they are ready to fill up the hour with talking and presenting and pitching. And the reality is that squeezes all the humanity and life and interaction out of the conversation, so they end up talking at customers and checking boxes and you know, we've talked about the whole QBR thing and what, what I'm trying to get them to. So they, they come to a realization that, that, that that's happening. And then they come across me or they read some of the crazy stuff that I post on, you know, mostly on LinkedIn. And I'm saying, hey, why don't you try going deckless? You know, like actually don't use slides because it's a crutch. Or train people to train your team to be able to have a more strategic conversation where they're asking better questions, which is 50% of the equation. And then once those questions land with the customer, then the customer opens up and then your job is to listen and clarify. And I'm fortunate, I guess, that enough companies get to the point where they realize they have a problem and an opportunity to change that dynamic and they reach out. I wouldn't say it's panic mode, and if it's a panic mode, then they probably have bigger problems than I can solve, to be honest.
Yeah.
Bob, I'm curious. Why do you think this is something that we, Gail and I talk about often and it is amazing to us. One, everyone thinks already that they're great listeners, that they know how to do it, that they don't need training, that there's no practical framework for people to do it. Why do you think it's so difficult for people to listen? What do you think is the real barrier? There's.
Well, so there are two things I think you said. One is that they don't have the self awareness that they're not good listeners or they think they are, they're a little bit delusional. And the other is what, what keeps them from becoming great listeners. And so I guess in, in, in order, those two things in order. The first is there is a stat I've read that 85% of people think they're above average listeners, which for anybody who's taken math, we know that that's impossible. And so people are generally a little bit delusional. And I, and I can empathize because I was a serial interrupter when I was an executive. It was terrible. One guy took me aside once and not even a boss, a fellow member of the C suite. And he said, you know, you interrupt all the time, right. And the worst part is I didn't even change after that. I didn't even flinch. So I probably interrupted them. And so I think there is this idea that we're all trained or we're all indoctrinated. With the idea that, hey, the better and more that you talk, the better you communicate, then you'll have a better chance of being successful. And where that's true is if you're talking and communicating based on something you've heard and listened and learned that's important to the other person, you are going to win the day. But if you don't start by taking a step back and saying, like, let me just get my bearings here. Back to that elevator rant concept. I got so tired of people in marketing and sales talking about, oh, you gotta have a good elevator pitch. Well, how could you ever have a good elevator pitch if you don't know the customer's elevator rant first? Like, what are they bitching and moaning about again on the elevator when we're not around? So I think there's a cultural thing like, you have to learn how to talk, you have to learn how to toast in Toastmaster. You know, I love Toastmasters, but I. That's the orientation and that. And I don't think social media has helped in this regard because it's all about. It's. No one gets on social media and just list, you know, they have videos of them listening to something. That's just not how it works. Everyone's communicating.
You should do that.
Then it's become right. Then it becomes the second part of. I guess the answer is, why is it hard to listen? Because we are full. So our brains are so full of things, and when we hear things, we immediately think of how it affects us, and we start to formulate a response and we start to judge a little bit, or we start. Or it's so boring that we start to take a knife in our kitchen. We start to clean the crumbs out from between the, you know, the burners and the stove. Whatever we want to do when, when we're bored and we're not listening. So we. We check out or we check in too hard where we. We can't wait till the other person stops so we can say the answer. I have the answer. And I think that's another problem is we all. We are trained to think that we always have to have the answer to everything. And I deal with a lot of teams, sales, customer success, account management, that they, they. They freely admit that they feel too obligated to have all the answers all the time. And the behavior that. That results in is. Is just doesn't foster. It doesn't give customers the feeling that they're being heard. It just feels like they're being Debated. You know, whenever I hear, hey, we get a lot of objections, we need to overcome objections. That's a. That's an important step. But I'd rather listen six months before and uncover the objection and then prevent it before it becomes a commercial issue. Like, that's my thing.
Yeah. Yeah, I love that. Yeah, very. And you know what's interesting about what you mentioned, especially when you. When I kind of think back to talking to teams about how to go deckless, I love that, by the way. And I love when you. And whenever you post, you know that I'm like, I like that I'm celebrating that because I just think we rely so heavily on technology and tools and other things to do the work of connecting with someone else. And you can't do that. Technology will never replace the genuine connection you can have with someone. And I've been in situations to your point about just the immense power of a good listener. I've been in situations, and I'm old enough now that I recognize what it is when. Where I'll meet someone. And it doesn't occur to me until much later what their superpower was and that it was listening and that I didn't know what that magnetic force was that drew me to them because they were giving me space and creating space and asking really great questions and just providing me an opportunity to share. And you walk away with this sense of, like, I really like that person. And you don't necessarily know anything about them. They know more about you than you do them. And that's kind of a superpower Bruce has. It's a superpower a few folks in our world have. It's. And I'm with you, Bob. Like, I'm on a lifelong journey to, you know, correct the interrupting, the inner. The great interrupter in me and the compare and one upper, which I tend to be, and. And really hunker down. So I love that you shared that. How do you appreciate that? Yeah, how do you. Because I feel like when I was growing up, we had speech and debate. We had, you know, Toastmasters is great, too. I feel like we've moved away from storytelling and. And also the sensitivity we need to have for the listener to be able to share that message. How do you work with a client who's so focused on their 42 page PowerPoint, you know, 42 slide PowerPoint document that they need to use as their crutch. How do you. What's maybe one of the first things you do to help them realize they don't need that?
Well, I'M just gonna start by saying as a, I'm a solopreneur, I'm a one person operation. So I don't need a pipeline of, you know, 50 leads a day to feed an army of salespeople and other, you know, chief little chief listening officers who are going to do the work. Therefore, I go out of my way to work with people who are. They know there's a problem and they know they need to change. So I don't have to convince someone at the beginning of an engagement why we're doing this. Rarely, I mean, when, when, if someone brings me in chief customer officer for their whole team of 20 or 100 or 1500, then I, yeah, it's my job to educate them on the importance of this stuff. But they're being. But, but I guess my point is I don't like to chase and convince people that of why this is important. So I don't really have a lot of experience trying to argue with somebody or convince them. I've had discussions like that. But they don't end up being clients. And I always say I'd rather, and I'm fortunate in this regard or maybe I'm old because I've got to the point where I can be choosy, but I'd rather spend more time even for free with people who get it than and pour kind of kerosene on the spark that they have than go out into the woods and rub sticks together until a spark comes up. Because that's just, it's too wishful. And I get to choose how. I just like you guys. We get to choose how we spend our time. We're very fortunate in that regard. So long answer is you have to. Short answer now is you have to tell them how customers experience all this. So I've done all these customer discovery conversations and I know that customers don't like to sit through presentations. There's a great stat from Forrester research that 88% of executives would rather have a conversation than sit through a presentation. Why? Because they don't like to be controlled and told what's important. They want to talk about what's important to them and what they need and how their business needs assistance. So it's a very important dynamic that you have to explain to people so that they don't think, well, if I don't walk in with 20 slides and a script, then I'm not prepared. Okay, but what do you, how do you know the 20 slides in the script align with what's important to them? Did you ask, did you clarify, did you have a step back conversation a month ago where you said, look, we think we're on the same track with you, but let me just ask you some bigger picture questions and step back for a second and make sure that what we're doing with you is exactly what you need us to do. And those step back conversations happen. When you see them happening, it's because you're with someone who's a good listener and they're strategic and everything else. Great salespeople know how to do this. Really successful enterprise salespeople, but not enough other people I think are. And I guess since we're both sort of oriented in the post sales like customer success and account management, you know, again, I feel bad sometimes because they feel like they're on stage and they have to have all the answers and it's a, that, that mindset is a big shift. Yeah.
I'm curious to know, Bob, you've mentioned the 2700 conversations that you've had, the elevator rants that you've experienced and listened to. What are some of the most unusual or interesting rants that you've heard that shocked you or surprised you?
That's a good one.
I don't think of it in terms of being shocked. I think of it as, I'm glad the customer said that because I've wondered about that. And one of them is customers will say stop to vendors, stop saying you're our partner because you're not acting like it. And when I read on your website that, oh, we partner with our customers, we're an extension of their business, it feels inauthentic and, or like bullshit. And it works against you because a partner means your interests are aligned with mine as the customer. What does that mean? It means that, not that you're going to do everything we need you to do when we, you know, that everything we demand. That's not what a partnership is. It's a back and forth where both parties understand that alignment and what the outcomes are. And there are some wonderful businesses that do partner with their customers and clients lines. But that's a, that rant is sort of like it's, it's not a commercial risk. Like it's not. But, but I think it's, there's sort of like scar tissue on customers from hearing this all the time. Like, oh, we want to be your partner. You know what you're sent, you're in sales. You're telling me you want to be our partner. How do you do that? How do you walk the walk so that I don't just leave feeling like you're just another salesperson telling me that, you know, you partner with customers. So that's a, that one resonated with me a lot. A lot. I'll give you one other example, which is, so I asked this question. I teach people to ask this question. So if you got a call from our competitor or an email tomorrow morning, how would you react? On a scale of 1 to 5, 1 is you probably ignore delete. 5 is you probably get back to them pretty quickly to learn what they're all about, what they offer, what it costs. The average answer is over 4. So people are leaning towards getting back to that competitor. And when I talk to teams about that on the vendor side, I say, like, what do you think the reasons might be in your business? Oh, well, they're unhappy. That's not what customers say. They're not saying four or five because they're unhappy in looking actively. They are craving context and insights of how other vendors and other companies are solving the exact problems that they have. And they always say, like, we're not looking, but hey, man, I'm just one person using this piece of software for this one use case. I have no idea if we're doing it right. So if I attend a competitor's webinar, it's not because I'm cheating on you, you know, it's because I need information. And the beauty of that is it gives you a chance to say, oh, is there something a competitor might thanks for being so candid because you want to reward their behavior and thank them for being candid because that's what you want. And thanks for being so candid. Is there something a competitor might say that would definitely get you to respond? And then they'll say, yeah, how do you expand globally? Or whatever. And then you have this insight that's called an insight. And that insight is something that you can use to provide more value or you can share it with the product team, or you can share it with the marketing team at your company to be more customer centric.
Yeah.
And by the way, that's typically what a partner would do is a partner is going to listen to that and then do something about it.
Right.
So great. Let's put together some use cases of five different ways that people are solving a similar challenge that, that you're currently having and let's determine which one might be right for you.
Right.
Like it's, it's, it's the simple stuff and yet we suck at it. That's that's what's astonishing to me. And I think part of that is, you know, some of it is. Is left over from, you know, this concept of you've got to be selling all the time. The only way that we're going to make money is if you're selling. So get out there and sell, sell, sell. You know, that model has changed a little bit over the last 20 or 30 years, where it's much more of a. Of a gentle hug, I would say. It's not that the hard sell still isn't out there. It's just it has changed over time. And then, and then looking at, from a leadership perspective of the command and control, which is still out there, it's still. That still is a model of leadership that isn't as effective as a more collaborative structure, in my opinion and Gail's opinion. I think I could speak for you on that.
You can.
I don't speak for her often, so I have to be.
Oh, oh.
Otherwise it gets ugly. So I just have.
I've seen you do that. And it's. I've seen you do that. It's not pretty.
Yeah, that's right.
I just. You can't see the.
I'm joking. So.
Okay, so I love that you shared that. And I, I think, you know, it's so interesting to me because in my mind, I'm thinking so many people are afraid to ask those questions because they're afraid of the answer, as opposed to, again, being genuinely concerned about what their client's experience is with them and. Or what they're missing and you might not be able to solve all of the things they're looking for. And isn't it great when you have a relationship with a client or where they will be that candid, where they do feel like you're hearing them, and when you do, then go back and, you know, pull together data or information or case studies or you studies, whatever, to kind of help them understand why something's possible or not possible now and what you might or might not be able to do for them. And I just love that. I love that honesty. And so I have another.
I love how you. Oh, yeah, no, go ahead.
No, go ahead.
I love, I love how you said it better than how I said it.
I don't know about that. I might be available to hire. So I'm thinking I know for you that, you know, genuine, deep and meaningful listening as well as really good clarity, clarifying questions, unique questions. Because I kind of, when I think about, you know, some of the work I've seen you do and some of the things that you send through your newsletter, the posts you make, the things that you can get if you sign up and follow Bob, I read those things. I'm like, oh, these are so good. They're just little golden nuggets that are so helpful in those relationships with, you know, we're in the business of improving power skills along the lines of empathy, emotional intelligence, certainly communication, all of those things. What is another thing that you see or have heard that clients are missing? Another kind of power skill that, that clients are missing in their relationships with their vendors and with their customers?
Yeah, well, I was going to say, what are they missing? They're missing the budget to pay to have us do these skills improvements. But in terms of power skills, what are they missing? I think that, so I would say listening, it's hard. So listening is kind of at the top of the pyramid to me. And then asking what I, I would call more authentic truth seeking questions like the one about the competitor. And I got a whole list which I can share. And then I think the authenticity which you just mentioned is, it's a little bit, it's a little bit abstract because authenticity is something you have to exhibit in many interactions. And, but, but I think the, I think the combination of those three things is just incredibly rare. I think that the problem is it's not a skill, necessarily a power skill, but it's this idea that we just talked about, which is you have to know everything before you get on the call. You have to have all the answers, and therefore that's inhibiting you from asking questions you don't know the answer to. But where does all the new information that we learn come from? It's stuff we didn't already know. So if you go into it assuming or being taught that, hey, here's, here's what you need to present to this customer in order to get them to sign a renewal for the next year, then the odds of you nailing it, I think if you haven't taken a step to understand authentically, curiously listening, what's most important to that customer, the odds are, you know, what, 50, 50 that you're gonna get them to renew. I think that this comes from, you know, in the, like in the tech startup world, especially this idea that there's a brilliant founder. And I don't mean brilliant in quotes, I mean there's a brilliant founder and they come up with a great idea and, and they've had success and now they need to hire people to go Sell it and support it and scale. And therefore, one way you scale is you give people the deck that you created as the founder and then you expect everyone to deliver these decks, you know, to customers. And I think it breaks down very quickly because you're not, they're not the founder and they need to, they need to, they need to act as students of the customer's business as much as they do teachers. And what I've learned is, you know, there's a reason that customers end up talking like 70, 75% of the conversation in my work. Because it turns out a customers love these questions because they are so bold and authentic and they signal that, oh, we're breaking through the wall here, we're breaking through this. This vendor really wants the truth. And I like that. And I'm going to tell them and I'm going to open up so it helps achieve that. And we're asking about things like the competitor question. A lot of times customers start by saying, yeah, I get one a week. It's funny that you asked, I got one today. You're asking about stuff that happens in their real world instead of fake questions like, you know, about us, about our product, you know, those are more leading questions. Even if they seem open ended, they're obviously geared towards getting them to say something nice about our product instead of just, nope, let's let me know what's going on in your head. Hypothetically, if you got a competitor. Oh, it's not, I think they did just call you. Oh, well, tell me what happened. You know, it's. And another question like that is this question about if, hey, if I could just big picture, if I could sneak into your company's board meeting or executive leadership meeting.
Yep.
What's the biggest challenge or priority I'd hear them discussing? So even if they're not in those meetings themselves, they hear what goes on, they get filtered information out and they will give an answer. But by asking that at the beginning of a conversation with a customer, you're signaling that you're not just diving into the details of how to get them to renew. You're signaling that you're interested in their big picture. And that is very, very, very disarming. And it fosters that authenticity that in both directions that we're talking about here. And I think, Bob, those are just some mini lessons.
It's still so unusual, right? So it's still, it's still different enough that customers haven't heard those questions before. Maybe they've been asked one or two, but they're not, they don't have the whole lexicon, the whole, you know, Bob London lexicon to kind of go through and, and, and ask them. So it's, it's such a useful tool and a useful skill to be able to kind of master as you're, as you're relating to your customer on a very, what we believe is a very different level. Right, that's, that's, that's the goal.
Yeah, I think, I think that's why we, I think that's why we get along and have hit it off is because I think we have a shared philosophy in this regard.
Yeah, 100%.
One last piece, one last question for you, Bob, as we wrap up our conversation. And you may have already shared it because I do recall you saying something, but what's the best piece of advice that you've ever been given in your career? Either it can be career or it could be personal. Either one the best piece of advice you've ever been given.
There's a reason the windshield is bigger than the rear view mirror. So the idea of letting go of things that have already happened and that are behind you and focusing on things that are happening today. And coming up now, I'm going to just tell you, I don't think I've ever said this before, like on the air with anybody. I've never published it. The guy who first told me that worked for me and I was the worst boss to him. And I know I was. Well, I mean, I have actual regrets about how I was in those days. I'm a recovering asshole. Most people don't know that. And I'm talking 20 years ago. And so he told me that I shamelessly have used it in raising and helping my wife and I raising our two sons. And they were at an age where at one point they did listen to us and doted on every word we said. And I started saying that and darn if it didn't seem to work a little bit. And you know, it's a simple thing, but I fell in love with it because it meant so much to me because I had trouble with the rearview mirror or the side view mirror. And the windshield is really where it's at. And I also started to notice that, yeah, the people I admire that are really successful, I don't hear them complaining about stuff that already happened. I hear them very action oriented about what to do next, what we can't control. Someone said recently to me, we can't someone who's going through a horrible situation, you know, you can't control what's happening around you. You can only control how you deal with it. And that's the most simple advice yet. I think the most valuable thing I've ever heard that. Those kind of ideas.
I really love that, Bob, and I needed to hear that today, too, for whatever. For a multitude of reasons which I won't share at this particular moment. I think it's so powerful to be reminded that, yeah, you. You can look back and you really need to be looking forward. It's important to know what's happened. Right. We learn from things that have happened in the past. And if that's where our focus is, we're going to crash because we need to be. We need to be here and in the present and looking forward. You gave me chills. Like, that is a really. It resonated with me, that visual and that idea. And I think that's a powerful kind of concept to keep in mind when you're thinking about just self empathy, forgiveness, you know, comparison, jealousy, any of that. Just action. Move forward.
Yeah.
Love it. Love it. Thank you so much, Bob London, for being with us today.
Thanks for the opportunity.
Yeah, you are a force to be reckoned with, and we will definitely highlight how to get in touch with you, how to take advantage of. Of the wonderful gifts that you have out there and the value you provide for folks, as well as how to bring you in and help teams listen better as the chief listening officer.
That's great. Thank you, Bob. We really appreciate it.
You're amazing.
My pleasure. One day I hope to have a podcast and I can't wait to have you guys on it.
We're there. 100%. We'll be number one. We're there.
Thank you for the opportunity.
You bet.
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