You'll Become a Better Sales Leader by Asking These Questions With Chief Listening Officer Bob London
16 Nov 2021 · 30 min
In this Sales Game Changers webcast, host Fred Diamond interviews Bob London, the self‑titled Chief Listening Officer. London explains how his background as a fractional CMO led him to conduct a "customer listening tour"—over 2,400 discovery calls that shaped his consulting practice. He introduces the "Radical Authentic Discovery" framework, which consists of three core actions: (1) ask disruptive, customer‑centered questions, (2) keep the conversation focused entirely on the prospect, and (3) deliberately mute yourself (or stay silent) to give the buyer space to talk. London cites Gong data showing top reps talk only 46 % of a call versus the industry average of 68 %, underscoring the value of listening. He walks through a structured list of 11‑15 questions organized into three buckets—business priorities, the prospect’s role, and the seller’s own positioning—designed to elicit long, insightful answers. He stresses authentic curiosity, a pre‑call mindset of quiet focus, and the need to avoid judging the customer. Authenticity, he argues, fuels likability and differentiates sellers. The session ends with a concrete action step: pick two of the questions and use them on two separate calls the following week, aiming for genuine silence and follow‑up probing. The conversation also includes live audience questions about talk‑time percentages, handling short answers, and maintaining authenticity without sounding scripted.
Chapters
All right, thank you so much. Welcome to the Creativity in Sales webcast. My name is Fred Diamond. Of course, I'm the co-founder of the Institute for Excellence in Sales and the host and the producer, Bob, of 4 Sales Game Changers learning sessions. We now call them virtual learning sessions. So we convert them, of course, to Sales Game Changers podcast. If you're listening to this as a Sales Game Changers podcast sometime in the future, Thank you so much for doing so. And if you're watching today live, thank you, Bob. We have people from all over the world watching today. And of course, we have a couple thousand people who download the podcast as well. So we're getting the word out here, and it's a, it's a really important topic. Again, every Tuesday is our Women in Sales virtual learning session. Every Wednesday, I, Fred Diamond, interview a sales VP, a sales leader from around the globe, about how they're working with their customers and how they're leading their teams. Every Thursday is our Optimal Sales Mindset. And every Friday, Creativity in Sales. We talk about sales tactics and strategies. And today we're talking about listening. Again, you can read the complete transcription to today's show, salesgamechangerspodcast.com, salesgamechangerspodcast.com/boblondon. So Bob is the Chief Listening Officer at And Bob, I'm so excited to have you here today. And by the way, again, if you have a question for Bob, submit it via the question panel. We will get to all your questions. So Bob, Chief Listening Officer, that's your brand, that's who you are. Congratulations to you. I believe it's brilliant. We've talked about this many, many times. You've helped so many companies develop effective and execute effective marketing strategies. So the background for this show is we've done over 450 Sales Game Changers podcasts. We've had over 1 million interactions with listeners who have either downloaded the show or read the transcripts. And a lot of times, Bob, when I would ask sales leaders, why are you so good? What made you such a great sales leader? They would give a bit, you know, they would always say, I'm a great listener. And for the first 100 or so shows, Bob, I would say, OK, great. You're a great listener. And then I started realizing, Bob, that all of these great sales leaders from companies like Salesforce, Amazon, Oracle, you know, IBM, Microsoft, they would all say that they were great listeners. So then I would go a little bit deeper. I would say, all right, give us a tip for the sales professionals who are watching or listening to the podcast. Give us something that you do that makes you a great listener. And, you know, they would come up with great ideas. I would ask better questions. I would focus. I would look them in the eye, whatever it might be. So you are the Chief Listening Officer. You are the expert. You've done over 200— sorry, over 2,400 customer discovery calls to understand how do people ask the right questions and how do people answer these questions. So we're going to take us through one of your processes, which is Radical Authentic Discovery. authentic discovery questions, and then some of your techniques. But first of all, career marketer, you know, when I first met you, you were an outsourced marketing VP, Chief Marketing Officer for hire, fractional, as they call it today. How did you pick up on this brilliant idea that it really is all about listening?
So first of all, I'm really excited to be here. We've known each other for a long time. And I'm, I'm glad we're doing this. Thanks for the opportunity. So, you know, I would work with clients, as you indicated, you know, several clients at a time where I was helping them come up with marketing strategy and then kind of run it. And I was very aware that I would meet with CEOs and founders and I'd say, well, tell me, you know, let me just ask you a few basic questions. Why do people buy from you? Or why don't they buy? And then, you know, in the world of software, software as a service, I'd say, so after 11 months, 12 months, how do they decide to stay? Why do they stay or why do they leave? And they've— and also, what problem do you guys solve for your customers? And I, as I would ask and they would answer, we would both look at each other and recognize that they didn't know. I had to point it out sometimes, sometimes. And if they did give an answer, it was a little bit of a guess on their part. So what I started doing was basically saying, look, before we start shooting the lock off of the marketing wallet, you know, and spending money, which we all know can be easily wasted, why don't I go out and I'll talk to some of your customers and former customers one-to-one. Just a phone call, actually. And let me just ask them some questions and see if we can find out what's going on with them in their business and how that translates into what they might need from you. And that was 7 years ago and 2,400-some conversations ago. So I found that it was the most effective thing I had ever done in marketing. I mean, in terms of the Time well spent. The insights that came out of it helped us shape much better, clearer positioning strategies, value prop, all that, which of course translates into better go-to-market messaging and other things, product roadmap, all that stuff. And so I decided to keep doing it with every, in fact, I don't really work with companies unless they commit to this sort of customer listening tour. And it's just been on a number of levels, my clients are more successful, therefore it makes me look better. I've been able to move up the value chain and I've been able to differentiate myself from the many people out there who talk about brand strategies and, you know, building websites or, you know, even fractional CMOs because I spend so much time in the field with my clients' customers and former customers. So that turns out I love it.
Nice. So let's get to it. As we like to know, I mean, every time you talk to a customer, it's a win. When you get to have that meeting, I mean, all sales, we talk about this all the time, is about getting to the next step. Next play, next step. And usually that's, we want to get to some type of meeting so that we can engage. So I want to go through your process here. So let's start with the radically authentic discovery. And you basically say there's 3 steps: asking disruptive questions, keep it about them, and then go on mute. And, you know, it's really interesting. And the intriguing part is the go on mute part, because we talk about this all the time. You know, sales professionals are so anxious to talk. You know, and they want to make sure they get their 50 bullet points across. And we spend so much time, Bob, on the Sales Game Changers podcast talking about silence, talking about asking the question and waiting for the answer. You know, we're talking about, you know, ask for the deal and then wait for the customer to reply and then shut up and leave. So talk us through that part first, and then we'll get to the discovery questions that you've spent a lot of time with.
Yeah, I mean, I think you kind of nailed it. And I mentioned this statistic to you the other day. There's a company called Gong. Gong, G-O-N-G, that helps companies analyze recorded sales conversations, B2B, and they found, they analyzed 1 million sales calls, and they found that the average sales rep talks 68% of the time, so that's more than two-thirds, which doesn't leave that much time for the customer to share what's important to them, time and space to just talk. And without leading them towards what's important, like, well, if we— if they say that's important, we can jump on that and close the deal. But the top sales reps only talk 46% of the time, which means they're able to listen more. So to your point, I think we over-choreograph and over-script a lot of interactions, not just in sales, but account management and customer success, which is an area where I've spent a lot of time in the last year. So Going on mute is either a figurative or, if you choose, a literal way to force yourself to let them talk about what's important to them. So if you ask, we'll talk about the questions. If you ask the right questions, sometimes I do put myself on mute when I'm on these discovery calls and I find that it helps. The worst case is I start talking while I'm on mute and then I realize, well, maybe I didn't have to talk. But it's really started as a figurative thing, you know, just mute yourself. But You know, now that everything's virtual, there's a mute button, free to use it. So it is not as important to jump in and interrupt. It really isn't. Or even to respond in a way that you think is gonna lead you to a quote unquote, to a sale.
So Bob, we have a question here. We have a question here that comes in from Rich. And Rich says, even 46% seems kind of high. What does Bob think about that?
Yeah.
So, you know, one thing we talk a lot about is that if the customer, it's a, people know this, I say if the customer is doing 95% of the talking, with the exception of maybe a demo, it's a successful sales call. Well, do you think 46% is still too high? And Rich, thank you for the question.
Rich, that is a great question. So I take the view that, because I don't, there's not a lot of granularity in this study, but I take the view that on average of all types of sales calls throughout the entire cycle, 46%, okay, yeah, I wish it was lower. But in, so I was a little surprised that it's that high for the top reps, but my, in my calls, I talk 10 or 15% of the time, so if I ask a question that takes 20 seconds, they'll go on for 2 or 3 minutes, which is good, because if they're talking about it, it must be important to them. So that's a really good question, Rich.
So let's talk, yeah, so and once again, if you have another question for Bob London, submit it via the question panel, we'll get to all your questions and Once again, you can read today's transcript: salesgamechangerspodcast.com/boblondon. So Bob, let's get to the questions because I love your list here. I have the— I love the way you, you broke it out about questions about their business, questions about them, and then questions about you. So, so take us through your Radically Authentic Discovery Question Process.
Right, thank you. So, welcome. I'll preface before I mention a couple questions that I think are, that I know are really helpful, actually really insight-producing. I'll just say that what Fred is referring to is an inverted pyramid that starts with questions about the customer's business and literally about, it might have nothing to do with what you're selling, but the reason that you ask those questions, like the first one on the list is, So let me— and I do this in a very conversational way, that's why I sound like this— is like, it's like Columbo, for those of you who might be old enough to remember. So just let me start off with, what do you think is the biggest priority or challenge that your board is wrestling with right now? Now, why is that important? First of all, it's disarming, to use a word that we discussed earlier, when you don't jump in and start asking leading questions that are obviously geared to lead them to the answers you want. That's number one. Number 2 is, yeah, the board is probably focused on 1 or 2 or 3 things, and guess what? That's where all the money's going. So that's not a new concept. It's kind of consultative selling in a way. But if you can understand the pain points at that level, the priorities and the problems and the way that the C-suite or the board thinks about it, you get a leg up on how to position what you're doing, right? And, and the reality is you might hear sometimes We're spending money on digital transformation and cybersecurity. Nothing else is getting budget and you're selling whiteboards. Well, guess what? Maybe you should move on to the next. You know, that's an extreme example. Maybe it's not a good prospect, but keep asking questions. So you start with those types of questions about their business and you let them talk because those questions are the ones where they really tend to go on and on. Then you get into— there's kind of a bridge between their company priorities and their their team's priorities. So here's what I mean by that. So the question is— so thanks, that's really helpful. Appreciate you being so candid.
So out of—
I'm going to guess that your job description is 1 or 2 pages long, single-spaced. It's kind of what you signed up for, you know, when you were hired. So, but usually there's one thing in that job description, one bullet point or one section that the company is absolutely counting on you to get done this year? What is that one thing? Now, what's interesting is the responses you get. The initial responses are, hmm, which is— I view that as a positive because they're thinking. They're going to give you a thoughtful answer, not a cliché. And sometimes they'll say, that's a good question. Since I take pride in my, my art, I say, well, thank you. And then the third reaction often is, no one's ever asked me that before. Now, if you want to talk about a competitive insight, you know, if they've never been asked the question before, that they probably haven't shared what they're about to share with anyone else. And it also has a brand halo, right? If you're curious enough and bold enough to ask a question like that, that's out of the box, you're rewarded with the insight, but it also casts a nice reflection on, wow, that person's really curious about me and my business. So, and every question that's on this list, there are anywhere between 11 and 15. Every one of them is really kind of crafted around a hook like the job description or the board of directors. So, so let me pause there. So, am I making any sense? You are.
We'll make this list available. We'll put it on the show notes again. You can find them at salesgamechangerspodcast.com/boblondon. We have a couple questions coming in here, Bob. First question comes in from Jane. And this is a very good question. What if the person only gives you short answers to open-ended questions? So thanks, Jane, for the question. So talk about that for a little bit about how you can get— we talk about this a lot too, about how you can get better at physically asking the questions so that you can get some information that's going to help you get to the next step.
Yeah, so there are 2 things here. You know, I guess one thing That— so I know that that happens, and I know that that can be stress-inducing because you're— you got to get something out of them. First of all, there's some people you can't— you just can't force it. You can't force them to open up. I have not experienced that in my world, partly because I'm independent, you know. So I— and I guess I have a way of asking the questions, and my curiosity comes through, whatever, and they start talking. If you get— if you get short answers, You don't really have to say anything at first. So the pause there could be effective because then they— it comes back to them and they're, they're, they're, they're just thinking, oh, I guess I should say more. But there is also a second level of question that said, well, first of all, the questions are geared not to give— these questions not to give one-word answers. So one of them is— another one is So let me ask you, whether you have a whiteboard or not, literally, what's one thing that absolutely has to be off your whiteboard in the next 90 days? So the short answer to that might be hire a new marketing director. Then, okay, that's a short answer. Why? What's— how's that gonna make your life different if you hire a new marketing director? What do you— what's the first person— what's the first thing you're gonna tell them to do? What's the— go back to the job description. What's the one thing in the job description that that marketing director has to get done in the next—
90 days.
In the first 90 days. So there's always somewhere you can take it. I love your question, Jane, and I do agree with Fred, it's a very good question. But I think that it's up to the pause and then the next level question, and you can always move on. But what I found is, again, if they think you're asking questions that are somewhat leading towards the pain points that you solve, Mm-hmm. they are less likely to engage if you start with these bigger-picture, open-ended questions about the stuff that they're experts in, which is their problems and priorities, they're much more likely to open up, and you won't get those one-word answers.
So, Bob, I have a follow-up question for you. And thanks again, Jane, for the question here. Once again, if you have a question for Bob London, the Chief Listening Officer, today, submit it via the question panel. You know, there's always the premise that you should know the answer to every question you ask. And as I'm looking at these questions, they're so brilliant. What absolutely has to be off your whiteboard in the next 90 days? What request or call do you most dread getting? What's one thing that surprised you since you signed the contract with us? Talk about expectations a little bit and how you can go— because I like what you said, the customer knows if you're asking questions that are leading towards what you want to say. And one thing we hear a lot about listening is that, well, people are really just listening to get to what they want to say. You know, it's like, Right. hopefully they're gonna answer the question, then I'm gonna have my Zing follow-up, or whatever it might be. Talk a little bit about, I don't know if it's mindset or approach or procedure, so that you're not that person. So you're not the person who is, you know, even the old joke, you know, her ad-lib lines were well rehearsed. You know, you want to be— as a matter of fact, yesterday, on yesterday's webcast, we had the great Dr. Todd DeWitt, and the topic was being authentic. You know, we talk about that a lot— authenticity, vulnerability. Give us some of your insights into how you don't come across as being scripted or fake, and even with these beautiful authentic discovery questions. Once again, do you mind if we make this available to people on our show notes, people can download?
No, if you'll allow me to send you the one that doesn't have a typo, yes, I don't mind. So, you know, I think that your mindset as a sales executive or salesperson or an account management person is so important here, and I think you really have to buy into the notion that, first of all, customers do not want to be sold to in that leading way. I believe that. I think that there was a time and a place where that probably worked really well. I think it's working less well because customers are so much more educated, prospects are so much more educated before they even contact a salesperson. But I also think that, so, but A lot of it is contextual. If you tell them that the purpose of the call or the purpose of these next several questions is really just to really deeply understand their world, then you've set the expectation for them and yourself that you're not there to— you're not going to sell them anything in that moment or solve a problem. You're just there to learn. I mean, it's the most basic principle in the world is listening to learn and understand versus listening to respond. So it's, you know, I always say the vendor is usually the one who puts up the vendor-customer wall. You know, we don't realize it, that we're the ones putting up the wall and we can bring it down and we can choreograph in a way. If we lead in an honest, authentic way where we're curious, they will follow. And I've seen it work too many times to believe anything else.
All right. So once again, part of your process, you have these radically authentic discovery techniques. So I want to talk a little bit about them. And some of these are brilliant. Once again, we're talking to Bob London, the Chief Listening Officer. So you talk here about keep it all about them. So I agree with that so much. We talk about that all the time on the Sales Game Changers podcast and Institute for Excellence in Sales events, that it is all about the customer, and that you need to make that— talk a little bit about how you can ensure that you come in with that frame of mind.
Well, there are a few things. There's this little graphic that looks like a Jeopardy board that Fred is referring to that you guys will see afterwards. But keep it all— these, they're all, they all kind of work together. There's 12 tips, techniques. Keep it all about them is a reminder that it's basically back to this, you know, talk time versus listen time, that the more they will open up more and be more valuable in their comments. If you ask about them, it's like almost like, you know how that feeling when it's your birthday and everything's about you, you, you, and it feels really good and people want to know about you and how your day was. That's how you should make the customer feel. And without getting into, oh, I'm glad it's your birthday. Well, by the way, my tire is flat. Can you come fix it for me? You know, that's just, it's a feeling that you want to establish where they start to become more transparent. And that can only happen if you're asking questions about them and not pivoting towards selling or leading them down. You're lighting the runway to your solution. The other sort of technique that goes hand in hand with that is this idea of— you mentioned authenticity, I'll repeat it— being authentically curious. I'm maybe, I guess, blessed with a little bit of authentic curiosity because when I— the reason I started enjoying these customer interviews so much was because I like hearing other people talk about their business and I have nothing to sell them, right? I'm just there to learn. And I think the authentic curiosity is something that you can learn by— and I'll go to another one of these techniques— by starting your conversation with a quiet mind 30 seconds before, 1 minute before. Just say like, breathe a couple deep breaths and Put a smile on and just say, I'm only interested in this person. I really want to know what goes on in their world and what's going on with their company. Once that happens, you're much more likely to get insights that you can then later in the conversation or in a subsequent conversation leverage to your advantage during a sale, you know, a sale, a more traditional sales process.
So that's very powerful. And actually, Daniela makes a comment here. authentic communications, conversations to see if we can help each other. And that's actually a great angle there. You know, usually you think when you're going on a sales call, you know, it's about me trying to get you to do something. And Daniela, thank you for that point— me trying to do something, which is get you to become either a customer or a bigger customer. But, you know, because of what we've been through over the last couple of years— obviously months, but years— you know, the customer can give us some value. And the customer, again, a lot of your questions here about, you know, what would it, what would make you a customer for life? You know, what a brilliant question. That's a great point. You know, we've done some interviews. We did an interview last Tuesday with a woman named Jennifer Cady, who is a VP of Sales at IBM. She's been at IBM for 22 years.
Wow!
And ladies and gentlemen, if you're like a salesperson at one company for 22 years, you're going to have relationships with customers. We talk about this a lot, Bob. Salespeople might jump places, but customers usually don't.
Right.
You know, especially in the IT, finance, or operations side. You know, they want the stability. They want to be there for their career, whether it's government or commercial. So, you know, they want to be your partner. You know, they want to feel that they're adding value, something to you. One of the other things you bring up here is don't judge. Talk about that a little bit, because that's an interesting angle to think about.
Yeah, so I think that companies, and it's a lot of it's from the top down, companies sometimes tend to blame the customer for things. And a classic example would be you're talking to, let's just say, an existing customer, and they say, yeah, we're having an issue because we don't, you know, the reason we bought this software was so we could do X, and we don't even know how to do it, and it's been 6 months. And then you go, well, geez, we— some of the reactions that you hear are you're thinking to yourself, well, we gave them— we literally pointed them to the training video on this date. Here's the email. And I always get very— I kind of get very aggressive about telling my clients, like, you can't— first of all, don't blame anything on the customer. There's always something you could have done differently or better. Assuming that the customer has good intentions and isn't just a complete, you know, just a train wreck that they're trying to be difficult kind of thing. Because customers get a zillion emails, they get a zillion links to training videos. Why don't you call them and set up 15 minutes to go through that video with them and make sure that they see it? If it's that important to them and it's that important to you and you wanna avoid getting those kind of comments, That's what you have to do. So that's just a tiny example, but I mean, there's— that's the type of judging that we do, even if we don't say it back to them, but it might come through in our tone. And in all of that, the judging, even 10 seconds or 5 seconds of mental judging while you're on a call takes away from your ability to learn from them and listen.
Absolutely. Yeah, it's a two-way street. And we have one more comment here from Andres, and Andres says, people like to buy from people they Like, and authenticity is the foundation of that liking. So thank you, Andres, for that comment. You know, Bob, as you're asking these questions, let's talk about that for a second or two. We don't really get too deep into likability, but sometimes it comes up on the Sales Game Changers podcast and our virtual learning sessions. Talk a little bit about how you should be— and of course, most of us are virtual right now. And I would say, it's still going to be like that for the foreseeable future. But people are going to go back to live at some point. But even virtually, it doesn't really matter. Talk a little bit about, you know, wanting to be liked, you know, and wanting to develop as compared to, you know, some of these questions. Yeah, they look kind of, they could be challenging. But the way you've created the question is very affirmative. And Andres, thank you for the comment.
That's a really interesting point. I mean, I think there is a component of likability. And I'm not a scientist in terms of social scientist or behavioral, but I think that's true. People buy from people they like, assuming all of the things are pointing in the right direction, like they have a decent product and other things. I mean, I guess what I can say is that the authenticity and the curiosity that you show fosters likability because part of it's your manner, part of it is the way you respond to what they say, but it goes back to that birthday thing. Make them You want to make them feel like you're really interested in them, and that makes them kind of feel special. And by the way, other vendors don't do that. I don't care if they're competitors or not. You're setting yourself apart, which is the authenticity and the curiosity is a key to likability. You're not, you're not trying to force them to do anything they don't want to do in this conversation.
And they're not going to. One of the points that I always love to bring up is, do you know Gary Milwit with J.G. Wentworth? Did you ever come across him? So he was a He was a guest. He's been an award winner at the Institute for Excellence in Sales. He once said that whoever you talk to, make them feel that they're very important. So that kind of goes back to what you're talking about here. So once again, we talked today with Bob London, the Chief Listening Officer. I want to thank Bob. Bob, I want to just acknowledge you for, you know, you've, you and I have talked about marketing for a long time. We've had many, many conversations.
Right.
And, and I think I even brought you on to a project or two, you know, way back in the day. And You know, I really love, like I mentioned at the beginning of the show, how you've become the Chief Listening Officer. And that's been the cornerstone of your consulting and the value that you've brought to hundreds, if not thousands, of companies along the way. So kudos to you. Congratulations to you for all the help you've brought to companies to help them understand how they can understand the value that customers need and how they can bring that to them. You've given us so many great ideas. Give us one final action step, something specific that our listeners or people watching today's webcast should do right now to take their sales career to the next level.
Yeah. So first of all, thanks again for having me. I, I, you're a very good interviewer, better than almost anybody I've ever been interviewed by. So, you know, I, I think that the way this breaks down is that when you see this cheat sheet that's going to be posted. Take 1, 2— take 2 of the questions. And today's Friday. Next week on Monday or Tuesday, ask 2 of those questions on 2 different calls, 2 by 2. And you will see that if you ask them authentically and you just kind of mute yourself and let them talk, that you will gain insight that will be useful to you. I mean, it's— and then, and then from there Once you see that, then there's other questions on this list that you can ask, but don't ask the question that feels super comfortable to you. Ask one that you don't know the answer to. That's the whole— we, we, you said it before. I thought it was really, really eloquent that we spend so much time looking for the answers we want. And we forget the value of the questions we don't know the answer to. So 2 by 2, ask 2 of these questions. You pick the 2 next week on 2 different calls. And I promise you, you will be better for it.
Once again, you can find this, this document that Bob's referring to at the salesgamechangerspodcast.com/boblondon. salesgamechangerspodcast.com/boblondon. Of course, we transcribe every show that we do. Bob London, thank you so much. To everybody who's watched today's webinar, thank you so much. Today's virtual learning session, I need to train myself to say that. Or if you listen to this podcast sometime in the future, thank you as well.
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