EPISODE 434: Chief Listening Officer Bob London Says You’ll Become a Better Sales Leader by Asking These Questions

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[EDITOR’S NOTE: This is a replay of the Creativity in Sales virtual learning session sponsored by the Institute for Excellence in Sales on September 10, 2021. It featured an interview with the Chief Listening Officer Bob London.]

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BOB’S TIP: “Here are three radically authentic discovery questions to ask. (1) What do you think is the biggest priority or challenge your board is discussing? (2) Who is your customer and what’s the biggest challenge they need you to solve? (3) Out of your entire job description, what’s the one thing your company is counting on you to get done?”


Fred Diamond: Bob, I’m so excited to have you here today. 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. The background for this show is we’ve done over 450 Sales Game Changers podcasts, we’ve had over a million interactions with listeners who’ve either downloaded the show or read the transcripts. A lot of times, when I would ask sales leaders, “Why are you so good? What made you such a great sales leader?” they would always say, “I’m a great listener.”

For the first hundred or so shows I would say, “Okay, you’re a great listener.” Then I started realizing that all of these great sales leaders from companies like Salesforce, Amazon, Oracle, IBM, Microsoft, they would all say that they were great listeners. Then I’d 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.” They would come up with great ideas, I would ask better questions, I would focus, I’d look them in the eye, whatever it might be.

You are the Chief Listening Officer, you are the expert. You’ve done over 2,400 customer discovery calls to understand how people ask the right questions and how people answer these questions. You’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. 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?

Bob London: First of all, I’m really excited to be here. We’ve known each other for a long time and I’m glad we’re doing this, thanks for the opportunity. I would work with clients, several clients at a time where I was helping them come up with marketing strategy and then run it. I was very aware that I would meet with CEOs and founders and I would say, “Let me just ask you a few basic questions. Why do people buy from you? Why don’t they buy?” In the world of software-as-a-service I’d say, “After 12 months, how do they decide to stay? Why do they stay or why do they leave? Also, what problem do you guys solve for your customers?”

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. If they did give an answer, it was a little bit of a guess on their part. What I started doing was basically saying, look, before we start shooting the lock off of the marketing wallet 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 hone call, actually, and let me just ask them some questions, 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.

That was seven years ago, and 2,400 some conversations ago. I found that it was the most effective thing I had ever done in marketing. In terms of the time well spent, the insights that came out of it helped us shape much better clear positioning strategies, value prop, all that, which of course translates into better go to market messaging, product roadmap, all that stuff. I decided to keep doing it. In fact, I don’t really work with companies unless they commit to this customer listening tour. 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 building websites or even fractional CMOs, because I spend so much time in the field with my clients’ customers and former customers.

Fred Diamond: Every time you talk to a customer, it’s a win when you get to have that meeting. All sales, and we talk about this all the time, is about getting to the next play, next step. Usually, we want to get to some type of meeting so that we can engage. I want to go through your process here, let’s start with the radically authentic discovery. You basically say there’s three steps, asking disruptive questions, keep it about them and then go on mute. It’s really interesting and the intriguing part is the go on mute part, because we talk about this all the time. Sales professionals are so anxious to talk and they want to make sure they get their 50 bullet points across.

We spend so much time on the Sales Game Changers podcast talking about silence, talking about asking the question and then waiting for the answer. We’re talking about ask for the deal and then wait for the customer to reply, and then shut up and leave. Talk us through that part first, and then we’ll get to the discovery questions that you spend a lot of time with.

Bob London: I think you nailed it and I mentioned this statistic to you the other day. There’s a company called Gong that helps companies analyze recorded sales conversations, B2B. They analyzed one million sales calls and they found that the average sales rep talks 65% of the time. That more than two-thirds, which doesn’t leave that much time for the customer to share what’s important to them, time space to just talk, without leading them towards what’s important. 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. 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. 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 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, maybe I didn’t have to talk, but it really started as a figurative thing. Just mute yourself. Now that everything’s virtual, there’s a mute button, you’re free to use it. It’s not as important to jump in and interrupt, it really isn’t, or even to respond in a way that you think is going to lead you to a “sale.”

Fred Diamond: We have a question from Rich, “Even 46% seems kind of high. What does Bob think about that?” One thing we talk a lot about is if the customer’s doing 95% of the talking, with the exception of maybe a demo, it’s a successful sales call. Do you think 46% is still too high?

Bob London: Rich, that is a great question. 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, I wish it was lower. I was a little surprised that it’s that high for the top reps, but in my calls I talk 10%, 15% of the time. If I ask a question, it takes 20 seconds, they’ll go on for two or three minutes which is good, because if they’re talking about it, it must be important to them. That’s a really good question, Rich.

Fred Diamond: Bob, let’s get to the questions because I love your list here. I love the way you broke it out, questions about their business, questions about them and then questions about you. Take us through your radically authentic discovery question process.

Bob London: I’ll preface before I mention a couple questions that I know are really helpful, 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, 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, and I do this in a very conversational way. That’s why I sound like this, it’s like Columbo, for those of you who might be old enough to remember.

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 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 two is yeah, the board is probably focused on one or two or three things, and guess what? That’s where all the money’s going, so that’s not a new concept. It’s consultative selling, in a way. But if you can understand the pain points at that level, the priorities and the problems in a way that the C-suite or the board thinks about it, you get a leg-up on how to position what you’re doing.

The reality is you might hear sometimes, “We’re spending money on digital transformation and cyber security, nothing else is getting budget” and you’re selling white boards. Well, guess what? Maybe you should move onto the next… That’s an extreme example. Maybe it’s not a good prospect, but keep asking questions. 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 a bridge between their company priorities and their team’s priorities. Here’s what I mean by that.

The question is, “Thanks, that’s really helpful, appreciate you being so candid. I’m going to guess that your job description is one or two pages long, single space, it’s what you signed up for when you were hired. 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?” What’s interesting is the responses you get. The initial responses are, “Hm…” which I view 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 art, I say, “Well, thank you.”

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 that if they’ve never been asked the question before that they probably haven’t shared what they’re about to share with anyone else. It also has a brand halo. 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.” Every question that’s on this list, there are anywhere between 11 and 15, every one of them is crafted around a hook like the job description or the board of directors. Let me pause there.

Fred Diamond: We’ll make this list available, we’ll put it in the show notes. We have a couple questions coming in here. First question comes in from Jane, “What if the person only gives you short answers to open-ended questions?” Talk about that for a little bit. We talked about this a lot too, about how you can get better at physically asking the question so that you can get some information that’s going to help you get to the next step.

Bob London: There are two things here. I know that happens and I know that can be stress-inducing, because you’ve got to get something out of them. First of all, there are some people you just can’t force to open up. I have not experienced that in my world, partly because I’m independent and I have a way of asking questions and my curiosity comes through and they start talking. If you get short answers, you don’t really have to say anything at first. The pause there could be effective, because then it comes back to them and they’re just thinking, “I guess I should say more.”

But there is also a second level of questions. First of all, these questions are geared not to give one-word answers. Another one is, whether you have a white board or not literally, “What’s one thing that absolutely has to be off your white board in the next 90 days?” The short answer to that might be hire a new marketing director. Then, “Okay, that’s a short answer. Why? How’s that going to make your life different if you hire a new marketing director? What’s the first thing you’re going to tell them to do?” 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 first 90 days? 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, they’re 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.

Fred Diamond: Bob, I have a follow-up question for you. 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 white board 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, because I like what you said. The customer knows if you’re asking questions that are leading towards what you want to say.

One thing we hear a lot about listening is that people are really just listening to get to what they want to say. Hopefully, they’re going to answer the question, then I’m going to 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. Even with the old joke, her ad lib lines were well rehearsed. On yesterday’s webcast we had the great Dr. Todd Dewett and the topic was being authentic. 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, even with these beautiful authentic discovery questions.

Bob London: I think your mindset as a sales executive, salesperson or account management person is so important here. 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.

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 just to really deeply understand their world, then you’ve set the expectation for them and yourself that you’re not there to sell them anything in that moment or solve a problem, you’re just there to learn. The most basic principle in the world is listening to learn and understand versus listening to respond. I always say the vendor is usually the one who puts up the vendor-customer wall. We don’t realize it that we’re the ones putting up the wall and we can bring it down, we can choreograph in a way. If we lead in an honest, authentic way where we’re curious, they will follow. I’ve seen it work too many times to believe in anything else.

Fred Diamond: Part of your process, you have these radically authentic discovery techniques. I want to talk a little bit about them and some of these are brilliant. You talk here about, “Keep it all about them.” I agree with that so much, we talk about that all the time on the Sales Game Changers podcast and the Institute for Excellence in Sales events that it is all about the customer. Talk a little bit about how you can ensure that you come in with that frame of mind.

Bob London: There’s this little graphic that looks like a Jeopardy board that Fred is referring to that you guys will see afterwards, but they all work together. There’s 12 techniques. Keep it all about them is a reminder that it’s basically back to this talk time versus listen time that they will open up more and be more valuable in their comments if you ask about them. It’s almost like that feeling when it’s your birthday and everything’s about 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 without getting into, “I’m glad it’s your birthday. By the way, my tire is flat, can you come fix it for me?”

It’s a feeling 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 technique that goes hand in hand with that, you mentioned authenticity, I’ll repeat it. Being authentically curious. I’m maybe blessed with a little bit of authentic curiosity because 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, I’m just there to learn.

I think the authentic curiosity is something that you can learn by – and I’ll go to another one of these techniques – starting your conversation with a quiet mind. Thirty seconds before, one minute before, just take a couple deep breaths, put a smile on and 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, a more traditional sales process.

Fred Diamond: Daniela makes a comment here, “Authentic communications, conversations to see if we can help each other.” That’s actually a great angle there. Usually, you think that when you’re going on a sales call it’s about me trying to get you to do something, which is get you to become a customer. But because of what we’ve been through over the last years, the customer can give us some value. A lot of your questions here about what would make you a customer for life? What a brilliant question, that’s a great point. We did an interview last Tuesday with a woman named Jennifer Kady who’s a VP of Sales at IBM, she’s been at IBM for 22 years and ladies and gentlemen, if you’re 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, especially in the IT, finance or operations side. They want the stability, they want to be there for their career whether it’s government or commercial. They want to be your partner, 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.

Bob London: I think that companies – and a lot of it’s from the top-down – tend to blame the customer for things. A classic example would be you’re talking to an existing customer and they say, “We’re having an issue because the reason we bought this software was so that we could do X, and we don’t even know how to do it and it’s been six months.” Some of the reactions that you hear are you thinking to yourself, “But we literally pointed them to the training video on this date, here’s the email.”

I always get very aggressive about telling my clients, 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 train wreck, that they’re trying to be difficult. 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 want to avoid getting those kinds of comments, that’s what you have to do.

That’s just a tiny example, but 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. All of that, the judging, even 10 or 5 seconds of mental judging while you’re on a call takes away from your ability to learn from them.

Fred Diamond: We have one more comment here from Andre, “People like to buy from people they like and authenticity is the foundation of that liking.” Bob, as you’re asking these questions, talk about that for a second or two. We don’t really get too deep into likeability, but sometimes it comes up on the Sales Game Changers podcast and our virtual learning sessions. Of course, most of us are virtual right now and obviously 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 wanting to be liked. Some of these questions could be challenging, but the way you created the question is very affirmative.

Bob London: It’s a really interesting point. I think there is a component of likeability, and I’m not a social scientist or behavioral, but I think that’s true, people buy from people they like, assuming all other things are pointing in the right direction like they have a decent product and other things. I guess what I can say is the authenticity and the curiosity that you show fosters likeability because part of it is your manner, part of it is the way you respond to what they say, but it goes back to that birthday thing. You want to make them feel like you’re really interested in them and that makes them feel special. By the way, other vendors don’t do that. I don’t care if they’re competitors or not, you’re setting yourself apart. The authenticity and the curiosity is a key to likeability. You’re not trying to force them to do anything they don’t want to do in this conversation.

Fred Diamond: And they’re not going to. One of the points that I always love to bring up is – do you know Gary Milwit with JG Wentworth? 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. That goes back to what you’re talking about here. Bob, I want to acknowledge you. You and I have talked about marketing for a long time, we’ve had many, many conversations and I think I even brought you onto a project or two way back in the day.

I really love 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. 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.

Bob London: First of all, thanks again for having me. You’re a very good interviewer, better than almost anybody I’ve ever been interviewed by. I think that the way this breaks down is when you see this cheat sheet that’s going to be posted, take two of the questions and next week on Monday or Tuesday, ask two of those questions on two different calls. Two-by-two. You will see that if you ask them authentically and you just mute yourself and let them talk, you will gain insight that will be useful to you. Then from there, once you see that, there’s other questions on this list that you can ask. But don’t ask a question that feels super comfortable to you, ask one that you don’t know the answer to. You said it before, I thought it was 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 answers to. Two-by-two, ask two of these questions, you pick the two, next week on two different calls. I promise you, you will be better for it.

Fred Diamond: Bob London, thank you so much. To everybody who’s watched today’s virtual learning session, thank you so much. If you listen to this podcast some time in the future, thank you as well.

Transcribed by Mariana Badillo

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