Closing Time

How to Teach CSM and Sales Reps to ask Disruptive Questions (and just $TFU)

What’s your talk-listen-ratio on sales calls? According to Gong Labs, the most successful reps only speak for 46% of the call.

If talking less and listening more is proven to increase win rates, why aren’t more sellers and CSMs doing it? 

Whether they lack patience or just have chatty personalities, sales leaders can arm reps with powerful questions to help them engage and better understand customers. The goal: Giving them more opportunities to acquire, keep, and grow revenue. 

In this episode of Closing Time, Bob London helps leaders empower their reps to ask disruptive questions and provides three examples that go beyond the cliche, “What keeps you up at night.He also provides a colorful acronym ($TFU) as a friendly reminder to embrace silence, allow the customer to speak, and listen intently. 

Watch the video:
Key Moments:
Embrace Silence and $TFU

Everyone loves a good acronym, especially those of us working in B2B sales or marketing—some are simply abbreviations (like CRM or ABM) while others are recall triggers for important best practices (like BANT or Sam McKenna’s #SMYKM).

Bob London has another one to add to the list, but don’t worry, it’s not a boring one. It’s called STFU, and it’s not in the way you might think. Instead of the usual meaning, it stands for “Silence Till you Fully Understand.” It’s a fresh take on the age-old advice about the importance of listening and serves as a friendly reminder for CSMs and sellers.

It’s tough for outgoing sellers to break the habit of constant talking, especially when they’ve spent their entire career presenting slides and addressing objections immediately. STFU encourages them to pause, understand, and then respond.

It’s not just a catchy phrase; it serves a dual purpose. For newer sales reps, it catches their attention and nudges them to be patient and listen. It’s a signal to be authentic and genuinely curious about the customer and their company.

Bob explains how starting in sales or customer success can be nerve-wracking, and the natural instinct is often to over-explain in situations where you’re not confident. However, the real magic happens when you, as a seller, become the student, and the customer becomes the teacher. Despite the initial discomfort, customers truly appreciate the authentic curiosity and the willingness to understand their priorities and challenges.

So, in a nutshell, STFU isn’t just a phrase; it’s a reminder to be silent, understand, and let the customer do most of the talking.

Your Questions Should Disrupt, Not Bore

Do you remember the conversation from last time someone asked, “how are you?” or “how’s work?” You probably don’t because you’ve been asked it a dozen times this week. If you want to be memorable to the people you speak with, you need to ask memorable and meaningful questions.

Bob refers to them as disruptive questions and emphasizes their importance in the world of sales and customer success.

Let’s start by answering the question, What makes a question disruptive? It’s the antithesis of the dull and overused clichés that plague sales conversations. They dive into the customer’s world, offering a fresh perspective and steering clear of the repetitive humdrum. A disruptive question has a hook, an element that immediately resonates with the customer, and a twist that injects personality and effort into the conversation.

Bob showing examples of questions.

Why does it matter? Because disruptive questions wake up a different part of the customer’s brain. Whether you’re selling, supporting, or managing accounts, it’s about making them feel heard and valued. It’s an art, putting thought into questions, and customers genuinely appreciate it.

Examples of Disruptive Questions for CSMs

Coming up with disruptive questions on the spot can be challenging. To get you started, Bob shares three examples of questions that can help sellers gain real, authentic responses from prospects and customers.

Disruptive Question 1: “Let me go up to the 30,000 ft level first before we get into anything about us. If I could sneak into your next 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?”

This clearly is not your run-of-the-mill question. Prospects are used to being asked, “What keeps you up at night?” not about the conversations happening among executives at their company. By shifting the focus away from the usual business chatter, it prompts customers to reveal relevant and current strategic priorities and challenges. It breaks the stereotype that customers lack a clear understanding of their organization’s big picture and gives them the floor to explain what they do know, which is likely more than you think they do. 

Disruptive Question 2: “On a scale of 1-5, 1 being you’d ignore the competitive outreach and 5 being you’d respond quickly, how likely are you to respond if a competitor reached out to you?”

Beyond the surface, this question isn’t about competitors; it’s about understanding the customer’s relationship with your product. Let’s face it, customers interact with your competitor’s content all the time, whether they download a research report or watch a webinar to hone their skills. This question is not just a competition check; it’s a journey into the customer’s mindset and the perceived value of your offering. 

Disruptive question 3: “What’s the one big thing that’s surprised you since you’ve started working with us?”

This question digs into the delta between expectations and reality. Whether positive or negative, the surprises reveal vital information for CSMs who are trying to gauge a pulse for the customer’s satisfaction with their product or service at a specific time. It’s a reality check, highlighting areas where you either exceeded or fell short of expectations. It’s not a gotcha moment; it’s an opportunity to fine-tune your approach and enhance the customer experience.

These questions collectively transform routine interactions into strategic conversations. They empower salespeople and customer success teams to uncover hidden issues, redefine their value propositions, and build stronger, more authentic relationships with their customers. Timing matters – asking these questions at the right moments ensures the insights gained are timely and impactful.





For more questions like these or to learn how you can continue to foster a culture of listening within your team, visit Bob’s website or follow him on LinkedIn


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 into 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 Ledergor from Gong.
And in that episode, he was sharing some great data
on talk listen ratios, on sales calls.
But we’re going to 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
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 have to could be,
you know, 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 consiglieri, if you will.
And you know, 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 you solving?
And 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’d 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 2700 discovery conversations ago.
And it’s the passion of my professional life
to do that kind of work now and get the the better insights
that come right from the customer’s perspective.
Yeah, 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.
That’s true, too.
Global Affairs.
Yeah, 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 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 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
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 racking 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.
Mm hmm.
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
my, one of my submissions is
to eradicate the use of that in the B2B world, especially.
When you ask a cliche 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 a thousand 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
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.
I think I think being atypical helps us in this situation.
And again, it’s not the oh, it’s how we’ve not how we’ve always done it.
And that phrase of being the enemy of progress and innovation
in too many instances.
So the way I ask that and it’s 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 team.
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 in to 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 the next year or so?
And boy, the number of, 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 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.
Right? Hazzah.
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.
Because you’re like, Hey, but I really need to show my slides
and it’s like, well, maybe, maybe you really don’t.
Oh, yes.
That’s one of the big rallying cries. I have now is let’s go deck-less.
Yeah, let’s be bold and go deck-less.
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 e-books, they visit podcasts from your competitors.
And so that question is
I’ll just share
that when I 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 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 one is you probably ignore the competitive outreach,
A five 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 five or four?
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 their use
cases, best practices for what they’re doing in their job, right?
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 solution.
So just keeping a pulse on how your customers are engaging
or not engaging with competitors is super vital right now.
And again, I think sometimes one of my favorite anecdotes
is, you know,. I think the day after I’d 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 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 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
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.
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,
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 get 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, we were, based on what you told us
originally, we were expecting X,. That hasn’t happened yet.
We were expecting a global capability, which you said
was on the roadmap for 2023, and it never happened, whatever that is.
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 the,
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 what 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, it’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 three months
of the contract, right?
I mean, they’re stuck with you for a year, but
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.
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.
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, there’s no M
so you can save time not having to type the M but it’s
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.
I love it.
Thanks so much for your insights
and thanks to all of you for tuning in to Closing Time.
Remember, you want to like this video, hit the button for notifications
and subscribe to the channel so you won’t miss an episode and we
will see you next week.

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