How to teach CSM and Sales Reps to ask disruptive questions and just $TFU -- with Bob London
12 Dec 2023 · 17 min
In this episode of the Closing Time podcast, host Val Riley interviews customer discovery expert Bob London about how go‑to‑market teams can improve their conversations with customers and prospects. London explains the concept of a Customer Listening Tour – a systematic program of market‑side interviews designed to uncover real customer problems, inform brand positioning, and surface churn or win‑loss insights. He introduces the STFU framework (Silence Till You Fully Understand), urging reps to stay quiet after asking a hard question to let the customer speak, and even stylizes the “S” as a dollar sign to link listening to growth. The conversation then shifts to what makes a question “disruptive”: it must avoid cliché, be rooted in the customer’s current reality, contain a hook, and add personality. London shares several concrete disruptive questions – probing board‑room priorities, how customers would react to a competitor call (using a 1‑5 scale), and asking what has surprised them since signing the contract – and illustrates how these questions surface deep insights, help prevent churn, and can even uncover latent issues before a customer leaves. He also advocates going “deckless,” focusing on authentic dialogue rather than slide decks. Throughout, London provides anecdotes of teams applying these techniques, the impact on discovery ratios (customers speaking 70‑85% of the time), and practical advice for early‑stage reps to build credibility by listening. The episode ends with a call‑to‑action to visit Bob’s website for more resources.
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The art of asking the right questions. Can it be taught? We're talking all about asking disruptive questions and waiting patiently for the answers in this episode of Closing Time. Thanks for tuning in to Closing Time, the show for go-to-market leaders. I'm Val Riley, Head of Content and Digital Marketing at Insightly CRM. Today I'm joined by Bob London. He is a customer discovery and listening expert. Thanks for joining us, Bob.
Oh, it's my pleasure. Thank you for having me.
Bob, you and I connected after a conversation I had with Udi Liedergaard from Gong. And in that episode, he was sharing some great data on talk-listen ratios on sales calls. But we're gonna shift some of those lessons today to customer calls.
Absolutely. Absolutely.
So in your prior role as a fractional CMO, you mentioned that you had implemented what you called a customer listening tour. Can you talk us through that?
Yes, I'd be happy to. So the customer listening tour on the face of it is what it sounds like. It's a project where someone goes, someone from a company goes out into the market. Ooh, scary. Actually talking to customers with only the only agenda really is really to understand what the customer's perspective is on things. What are their business problems and challenges? What are their priorities? It's the expression, before you fall in love with your own solution, try and fall in love with the customer's problem. And so, it's that kind of thing. The applications for the listening tour could be you're refining your brand strategy and positioning in the market, your messaging. It could be customer experience related. You could use a customer listening tour as a way to do a churn analysis or win-loss analysis. So, there are a lot of use cases for it. But as a marketer, it just sort of happened because I was talking to founders and CEOs as their marketing consigliere, if you will. And this conversation where I would ask them some questions that maybe we both thought there should be an answer to, like, who is your customer? Why do they sometimes— why do they buy from you? Why do they sometimes not buy? Why do they stay after a year? Why do they leave? What problem are you solving? During my discovery phase with this founder or CEO of, let's say, a B2B tech company, we would both realize very sort of candidly and authentically that there weren't crisp answers to those questions. And if there were, where did you get that answer? And often they were guessing. And so the listening tour just popped out of my mouth one day. I said, I don't want to be that guy who says, I know how to solve your problem because we haven't talked to the customer yet. So why don't I do a customer listening tour for you? And that was 2,700 discovery conversations ago. And it's, it's the passion of my professional life to do that kind of work now and get the better insights that come right from the customer's perspective.
I can't imagine a scenario where listening is a bad thing, right? Customers, prospects, you know, executives, just sitting down and processing what they're saying has to be the most undervalued skill we see in business these days.
All things.
That's true too. So, I love how, I love how you have kind of a colorful acronym, shall we say, that you use to challenge sales and customer success representatives to embrace silence after they ask a hard question. And we'll put it up on the screen, but maybe you can just share it with us.
Yeah. So, it's STFU. It doesn't stand for the typical definition. It is silence till you fully understand. And it's a way of, look, people have been talking about the importance of listening for a long time. And some, many people have said there's nothing new under the sun, but there are, it's important to find new ways to say things that engage the world and get them to change their behaviors and touch people. So that's what that is, is sometimes I spell STFU where the S is a dollar sign to remind people that it's all about growth. And bringing in money. But yeah, silence till you fully understand it. It is hard to keep quiet when you've been trained your whole career to present slides and keep talking and fill up the silence and address objections immediately without saying, let me make sure I understand you. Can you go on about that a little bit? I haven't really run into too many. I guess the people who are offended by STFU haven't reached out to me, but most people think it's either funny or clever or Or useful. So thank you for pointing that out.
Yeah, I mean, in its simplest terms, it just, it could maybe get the attention of some younger reps or people that are new to their career, because I do find that it tends to be something associated with nervousness, right? Not being patient enough to, like you're saying, be silent until you fully understand or perhaps ask a hard follow-up question. So I think the acronym itself might have a dual purpose in that it gets the attention of folks who you know, maybe are just starting out?
Well, and I think to that point, I love what you just said. I agree. And in my experience, when you're just starting out, you're, you're less confident in your knowledge base and therefore more likely to try and explain when you really should be listening. And again, in my body of work, customers love it when you're authentically curious about not just them, but their company. What are the priorities and challenges that their company is facing? And they really respect it when we as vendors, I include myself in that, become the student and they become the teacher. Customer becomes the teacher. So, I always tell folks earlier in their career, I understand it's nerve-wracking to try and listen and be silent or to ask a question you don't know the answer to, but customers really do appreciate that.
Let's continue on that vein because you talk about in your work asking Disruptive questions. And how does a question qualify as a disruptive question?
Thank you for asking that disruptive question of me. So, I will say that, let me start by saying, what is the enemy here? The enemy are boring cliché questions. For example, what keeps you up at night, customer? And one of my sub-missions is to eradicate the use of that in the B2B world especially. When you ask a cliché question, you're feeding into the normal, boring business patterns and conversational patterns that put people to sleep and don't result in insights. And when a customer has been asked that question 1,000 times over the years by many vendors, you're not going to get anything except a cliché answer. A disruptive question is one that speaks from the customer's perspective. And I'm happy to give you a couple examples. Where it taps into something that's going on in their world that's real. And it also has, so it has sort of a hook to it that they can relate to immediately. And it also has a twist, which is kind of shows some personality and some that we put some effort into the question. So a disruptive question wakes up a different part of the customer's brain, helps differentiate us as individuals, whether we're selling or supporting or help in customer success or managing the account. You know, let's think about, you know, how we're making them feel by— that we put some effort into the questions. And again, it's something customers, in my experience, really appreciate.
So I found this example and it really spoke to me. The example of a disruptive question you had mentioned, one was, what's happening at board meetings right now? Which is so insightful. That would really make me, if I was being, you know, if I was being approached by a seller, that would really make me stop and think, Okay, that's just not the typical question that I get.
Yeah. And I think being atypical helps us in this situation. And again, it's not the, oh, it's not how we've always done it. And that phrase is being the enemy of progress and innovation in too many instances. So, the way I ask that, and I do it in a very conversational way, and when I coach teams, I do it in this same conversational way. So, let me Let me start off with a big picture question. This is me to my clients, customer, or teaching. Let me ask, let me go up to the 30,000-foot level first before we get into anything about us. If I could sneak into your next executive leadership meeting or board meeting, what do you think is the top priority or challenge that you think I'd hear them discussing for like the next year or so? And boy, the number of times that the insights just start pouring out. You might think, oh, customers don't know what's going on. They're just a system admin. They don't know what's going on. No, they do know, and they have very crisp, clear answers. And you get insights that you can then tie to the value that you're trying to create for them. Is there a link between that top priority and the value proposition that you're espousing or trying to deliver on? And at a minimum, as you said, it's so engaging. Because the customer says, wow, this is going to be a different experience and I need to pay attention. Customers end up during what I call these radically authentic discovery conversations, they end up talking at least 70% of the time, sometimes 85% of the time.
Huzzah, right? That's exactly what we want. So that's great.
Well, it is exactly what I want people to do. I think customers would like to be able to share more about them and what's important to them. I don't know that we're giving them the chance. I don't know that we're carving out enough time and effort into the discovery and listening piece, which is, I think, what you and I have bonded about.
Right. Because you're like, hey, but I really need to show my slides. And it's like, well, maybe you really don't.
Oh, yes. One of the big rallying cries I have now is let's go deckless. Let's be bold and go deckless.
Here's another disruptive question. And I also love this one. You asking a customer what they would do or how they would respond if one of your competitors called them.
I can't tell you where these questions came from in my brain, except to say that when I did all these customer discovery conversations, I started trying to think about what happens in the customer's real world that we can tap into. They do get calls and outreach from competitors, not just sales calls, but they get invitations to webinars. They get They visit podcasts from your competitors. And so that question is, I'll just share that when I bring up that question, and maybe those in this audience are feeling the same way, like, whoa, why would we go there? Why? That's a Pandora's box. I don't want to ask about competitors. I don't want to give competitors any oxygen. The beauty of it is that is not a question that results in them talking about competitors.
That's right.
That is a question that gets them to reveal how they feel about the relationship with your product and your company. And you ask it on a scale of 1 to 5. So on a scale of 1 to 5, a 1 is you'd probably ignore the competitive outreach. A 5 is you'd pretty quickly get back to them to find out what they offer, what it costs, and just use the number as kind of a buffer, an easy place to start and say, oh, thanks for being so candid. Why did you say 5? Or 4. And often it's not because they're looking, it's because they're just trying to get some context as to the best way to do their job. And that's what content marketing is all about, right? They don't go to webinars because they're thinking of switching necessarily. They go to webinars to understand new use cases, best practices for what they're doing in their job.
I mean, this couldn't be more timely, Bob, as, you know, so many companies are looking at churn, right? And people, you know, businesses churn because they have potentially found another solution or a better So, just keeping a pulse on how your customers are engaging or not engaging with competitors is super vital right now.
Absolutely, 100%. And again, I think sometimes one of my favorite anecdotes is, you know, I think the day after I delivered a talk to a team, a CS team, I got a text from the team leader who said, we asked that competitor question. of one of our major customers, and we found out that they had a kind of a latent issue, and it's not good. But we wouldn't have known unless we had asked that question. So it's, it's good— it's bad that that's the case, but it's good that we learned it before the customer went out the door. We now have a chance to save them. So it's, it's not always going to save a customer. The point is to show the customer that you're willing to ask a courageous question that takes some—
Mm-hmm.
That's based in their reality and also to just to get them to open up. And so many times customers will say, I got a call from the competitor this morning, you know, and here's how I handled it. So it's very useful.
Absolutely. Bob, do you have another disruptive question you might want to share with our audience?
So I'll give you one that's also on the post-sale side, whether it's account management or customer success, and it's another kind of gutsy question to ask because you're asking a question you don't know what the answer is going to be. And the question is, so what's the one big thing that surprised you since you started working with us or signed the contract or the licensing agreement? And what you're really going for is the delta between their— the difference or delta between their original expectation and what they're actually seeing in real life. And that delta could be a positive surprise, like, we didn't realize how quickly you guys were going to hit the ground running, get up to speed, start delivering value, something like that. Or it could be a negative surprise where there's a negative gap that says, you know, based on what you told us originally, we were expecting X, that hasn't happened yet. You know, we were expecting a global capability, which you said was on the roadmap for 2023, and it never happened, you know, whatever that is. And And then you can gauge how important that surprise is, either the positive or negative surprise. But again, it comes from a place of we all— nothing is ever as it's promised. And it's not— there's nothing sort of— it's not the fake it till you make it sort of Theranos type of surprise. It's the, like, in the course of doing business, there were things they expected that we didn't deliver or things that we overdelivered on. I've had teams go out and ask this question and find out that an entirely new perception of the value proposition by asking 20 customers and then going back to marketing and saying, right now our website makes us sound like everybody else, but our customers are telling us this is what's special. And to see that happen and to accelerate a company's progress is really terrific.
Yeah, that's super insightful, especially if you could ask that question pretty early on, like perhaps shortly after onboarding, because You know, the data shows that churn really happens within the first 3 months of the contract, right? I mean, they're stuck with you for a year, but they've decided whether or not they're going to renew with you pretty early on. So asking that question and then giving your team the runway to maybe rectify it if it is a negative response just gives you so much more power to potentially create lifetime value.
I not only couldn't have said that better, I might steal what you just said. When I talk about this, that's exactly right. That really lands the plane, I think.
Awesome. Bob, that's all the time we have for this episode. And I think folks can visit your website if they want to learn more about those disruptive questions.
Yes, absolutely. It's boblondon.co. There's no M, so you can save time not having to type the M, but it's boblondon.co, and it talks about Everything I do, but also has a lot of insight about the tools and techniques that people can use right away.
And special thanks to all of you for listening today. If you'd like to support the Closing Time podcast, please consider leaving a rating or review on whatever platform you're using. As always, head over to insightly.com/closing-time to learn more about today's guests and find all the episode links and resources. That's all for this episode. We'll see you next week on Closing Time.
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