[Un]Churned · 9 Sep 2026 · From the week of 7 September
Stop Asking "Would You Renew?" Ask This Instead ft. Bob London
These are notes on the conversation, checked against its transcript. The episode itself has the full discussion.
In brief
Host Josh Schachter of Gainsight talks with customer discovery and listening expert Bob London, who ran a training engagement with Paycor's customer success team, about how to move CS and sales conversations from product talk to the customer's business. London lays out an inverted-pyramid conversation structure, a 'step back' setup, and a board-meeting question that he says disarms customers and sets the vendor apart. His main argument is that the standard 'if your renewal were tomorrow, would you renew?' question puts customers on the spot. He offers instead a 1-to-10 question about how the customer would react to a competitor's outreach, which he says several CS leaders call their best churn-risk signal. He also says these methodologies don't adopt themselves: leaders have to reinforce them through one-on-ones, keyword tracking and AI scoring of call transcripts before and after training, and the ROI case rests on catching a handful of surprise churns.
For founders
- Telling a team to 'be more strategic' without showing how is, in Bob London's words, pressure with no path; leaders have to name the mindset shift and supply specific questions and listening tools.
- Bob London says that when churn is diagnosed, sometimes as an autopsy after the fact, the cause is that the team simply didn't understand value the way the customer defines it.
- London argues that training only produces ROI if leaders reinforce it afterwards through one-on-ones, team meetings, recognition and keyword tracking in tools like Gong.
- London's ROI case for conversation training rests on preventing a few surprise churns: if four people on a 20-person team each catch one, he says the return is clearly positive.
- As a fractional CMO, London would not take on strategy, brand or positioning work unless customer interviews came first, because 'the answer is not in this room.'
For revenue leaders
- Bob London recommends replacing 'would you renew?' with: 'If one of our competitors reached out tomorrow, on a scale of 1 to 10, how would you react?' He says several CS leaders call it their best predictor of risk.
- London says the average answer to the competitor question is close to seven; he advises thanking the customer for their candor, asking what's behind the number, then asking what a competitor could say that would be a 'head turner.'
- London suggests opening calls and QBRs with a 'step back' setup and the question 'If I could sneak into your next board meeting, what would be the big topic?', then narrowing in an inverted pyramid to what's hard for them and where you fit.
- London says questions work best when they contain a trigger word from the customer's world, such as 'board', 'competitor' or 'finance emailed for a board bullet point', rather than the vendor's world.
- London measures behavior change by having a custom GPT trained on his methodology score 10 to 15 call transcripts before and after training.
What was said 25, most useful first
Introduce the big-picture part of a call by framing it as a 'step back' you take with your most successful customers; London says customers almost never refuse. Listen
London's suggested setup: 'We've found that with our most successful and longest-standing customer relationships, we periodically take a step back. We'll cover the day-to-day as always, but can we step back for five or ten minutes at the start?' He says the only time customers decline is when an unresolved problem makes them ask why you're stepping back while something is broken. In his view, the framing signals that you see the customer as a person trying to do a good job, not just a source of renewals and adoption.
“But can we just take a step back for five or 10 minutes here in the beginning? Sure. No one ever says no to that unless there's a problem that's unresolved”
Listen to the episode Retention & customer success Link to this
Asking 'If I could sneak into your next board meeting, what would be the big topic?' both disarms the customer and sets you apart from other vendors. Listen
London's opening question asks what topic would dominate the customer's next or last board or executive leadership meeting: a priority, challenge, mission or goal. He says it does two things. It disarms customers because they aren't being walked through adoption stats, and it sets you apart from other CSMs, sellers and vendors. The answer becomes 'the first dot' to connect to the value the customer needs you to deliver.
“If I could sneak into your next board meeting or your last board meeting or executive leadership meeting, what do you think would be the big topic of conversation that's being discussed?”
Listen to the episode Retention & customer success Link to this
Ask customers to rate from 1 to 10 how they'd react to outreach from a competitor; London says multiple CS leaders call it their best predictor of churn risk. Listen
London's renewal-stage alternative: 'If you got a call or outreach from one of our competitors tomorrow, on a scale of 1 to 10, how would you react?' A 1 means ignoring or deleting it; a 10 means making a point of getting back to them for any reason. The customer only has to give a number, and you don't name a specific competitor. London says he came up with the question by accident and that numerous CS leaders have told him it is the best risk predictor they have. He also says the answers have more to do with candor than with competition.
“Let's just say you got a call or an outreach from one of our competitors tomorrow, on A scale of 1 to 10, how would you react? A 1 is you would ignore it, delete the message.”
Listen to the episode Retention & customer success Link to this
The average answer to the competitor-outreach question is close to seven, and London says it usually doesn't signal intent to switch. Listen
London says that across roughly 3,000 discovery conversations and his teaching, customers answer close to seven on average, which scares most teams. His recommended response to a seven or eight is to thank the customer for their candor and ask what's behind the number. The typical answer, as he summarizes it, is that customers are not shopping around; as one person using one solution for one use case, they see competitors as a source of insight on other capabilities and best practices.
“It's close to a seven, but most teams are scared by that.”
Listen to the episode Retention & customer success Link to this
In user research, asking for the last time something happened gets more than asking how often it happens. Listen
Josh Schachter describes design-thinking user research from his time at BCG. Asking 'how often do you do X?' got thin answers like 'every other month'. Following up with 'tell me the last time that happened, give me that situation' put people in a concrete scene. He links this to London's hypothetical scenes, saying both let the person picture a situation.
“okay, great, well, tell me the last time that that happened. Like, give me that situation.”
London measures behavior change from training by scoring 10 to 15 call transcripts with AI before training and again afterwards, then comparing the two reports. Listen
London says AI has been 'a game changer' for measuring behavior change, though he notes this is not ROI. He batches 10 to 15 transcripts from before the training, runs an aggregated report on them, does the same after training, and compares the two. He concedes that showing the improvement in business numbers is harder.
“So by batching the transcripts before the training and running an abstracted report on 10 or 15 transcripts and then doing the same thing later after the training, you can get a pretty good sense of how things have improved.”
Listen to the episode Retention & customer success Link to this
Churn diagnoses, sometimes done as autopsies after the fact, show that the team didn't understand value the way the customer defines it. Listen
Asked how a leader knows the team struggles with above-the-line conversations, London says the first thing that comes to mind is unhealthy customers or predicted churn. He attributes this to CS and sales teams being trained to push what they offer and to define value the way internal training told them to. In his view, that training leaves no room for customers to say how they define value on their own terms.
“the diagnosis of that, which sometimes is an autopsy after the fact, is that we just simply didn't understand value the way the customer defines value.”
Listen to the episode Retention & customer success Link to this
Leaders should open the change by admitting they asked for strategic behavior without showing how, then name the mindset shift: customers engage more when asked about their business than when shown adoption stats. Listen
London says a VP of CS (or sales) should tell the team that 'be more strategic' was never accompanied by a how. The mindset he wants teams to take on is that customers are pleased and open when asked about their business and less engaged when the vendor pushes adoption stats, metrics or product updates. Leadership then supplies the tools: asking more strategic questions, pausing to avoid pivoting back to your own agenda too quickly, and staying anchored to the customer's company priorities.
“customers are actually really pleased and open when you ask what's going on in their business. And they're less enthused and engaged when you try to push adoption stats or metrics or product updates.”
Structure customer conversations as an inverted pyramid that starts broad and open-ended and narrows as it goes, whether it's a 30-minute discovery call or a 5-minute QBR opener. Listen
London teaches the same structure regardless of meeting length: the big, open-ended conversation at the top, getting more specific further down. He warns against jumping straight into a big-picture question, because customers aren't used to it, even though they like it. He sometimes tells customers explicitly that the conversation will follow an inverted pyramid.
“It doesn't matter if the conversation is a 30 minute discovery conversation or a 5 minute beginning of a QBR or other meeting. Inverted pyramid, big and open ended conversation at the top. It gets more narrow as you go down the question.”
Listen to the episode Retention & customer success Link to this
After the board question, narrow down by asking what makes achieving that priority hard for the customer and how the vendor fits into their equation. Listen
London's sequence is simple: the board-level priority, then 'what's difficult about your job in achieving that, what's in the way for you?', then 'how do we fit into your equation?'. To make it personal, he also suggests asking how the company-level priority has changed what the customer needs to deliver in the next six months.
“And then the next Question would be, what's difficult about your job in achieving that? Like, what's in the way for you? And then how do we fit into your equation? 1, 2, 3.”
Listen to the episode Retention & customer success Link to this
The board question works even when the contact doesn't attend board meetings, because it asks what they think you would hear. Listen
London anticipates the objection that many customer contacts don't sit in on board meetings. He says it doesn't matter, because the question asks for their view of what's being discussed. In his experience they generally give a relevant, insightful answer that can then be brought down to their own area.
“I know there are people listening who will say, my customer doesn't sit in on the board meeting. It doesn't matter. You're asking them what they think I would hear if I snuck in.”
Listen to the episode Retention & customer success Link to this
Painting a concrete scene gets more concrete answers than asking 'what are your top priorities?', and it also flatters the customer. Listen
Josh Schachter says the board question works because it puts customers in the room mentally rather than asking a generic priorities question. He adds that it raises their status: a director feels that the vendor thinks they have insight into what the board is discussing. London agrees and says it isn't manipulative, because the intent is to see the customer as a whole person.
“You're not just saying, what are the top priorities of the company right now?”
Listen to the episode Retention & customer success Link to this
Tell customers explicitly that you'll go into 'listen mode' and may be on mute, so they read your silence as focus rather than multitasking. Listen
London recommends being explicit about how the conversation will run, for example at the start of a QBR. He suggests saying you'd like to step back and go into listen mode, and that the customer may see you on mute because you want to focus on what they say and respond with relevant questions.
“you might even see me on mute. It's not because I'm multitasking. It's because I really want to focus on what you're saying”
Listen to the episode Retention & customer success Link to this
London has teams test questions in the field after a workshop to learn which questions fit which lifecycle stage. Listen
Asked which meeting types suit these questions, London says he runs a workshop and then sends the team out to use the questions and listening techniques with real customers. When they come back, they work out which questions work at which point in the lifecycle. He notes that some questions suit kickoff and onboarding and others suit renewal.
“we do a workshop and then the team is kind of forced to go out into the cold world and ask these questions and use the listening techniques. And once they come back, we get a better sense of which questions work at what parts of the life cycle.”
Listen to the episode Retention & customer success Link to this
Asking 'if your renewal were tomorrow, would you renew?' puts the customer on the spot and gets you little. Listen
Schachter offered the renewal-tomorrow question as what most people, and LinkedIn, would suggest. London rejects it. In his view it puts the customer on the spot and amounts to asking them to tell you what you want to hear or to confront you with the truth.
“I know that people use that question. You're putting the customer on the spot. You're saying, tell me something I want to hear.”
Listen to the episode Retention & customer success Link to this
Following up with a 'head turner' question reveals the gap between what customers have now and what they're curious about. Listen
After asking what's behind the number, London asks whether a competitor could bring up anything that would be a real head turner: a problem solved or a capability the customer hasn't heard of. He says not to lead them. His example answer: a customer expanding globally notes that the vendor's global capability was on the roadmap but they haven't heard about it in a while. He says customers often add that they'd bring what they heard back to their current CSM rather than switch.
“is there something a competitor might bring up in their outreach or in a conversation that would just be a real head turner for you”
Listen to the episode Retention & customer success Link to this
Questions open up when they contain a trigger word from the customer's world, such as 'board' or 'competitor', rather than the vendor's world. Listen
London says all his questions include a word that signals to the customer that the question is about their world. Board meetings happen in the customer's world. Competitor outreach does too: customers often start their answer with 'just happened yesterday', because they get calls, sit on email lists and attend webinars. He says this approach 'breaks open' a lot of insight.
“All the questions have a word in them that trigger something in the customer's brain that says, that question's about my world, not the vendor's world”
Listen to the episode Retention & customer success Link to this
Asking whether the customer has ever had finance email for a board-slide bullet point at the last minute surfaces their contribution to company priorities. Listen
Another board-level question London uses asks whether the customer has gotten an email from finance, the day before a board meeting, asking for a bullet point for a slide. He says customers recognize the situation strongly, which lets you ask what their bullet point would be about. He stresses that the scene must be the customer's scene, not one that leads toward the vendor, such as asking when they'd love to use a new feature.
“have you ever gotten an email from finance saying they need a bullet point for a slide for the board pre the next board meeting”
Listen to the episode Retention & customer success Link to this
A conversation methodology produces no measurable ROI unless leaders reinforce and track it after the workshops and coaching. Listen
London's proposals state that 'these methodologies do not adopt themselves.' He says leaders have to build the methodology into one-on-ones and team meetings, may add incentives or recognition for the behavior, and should track keywords in tools like Gong. He acknowledges this may feel like babysitting or handholding.
“So there will be no ROI or measurable unless you're doing things on the front end after the workshops, after the coaching to track and make sure people are doing it.”
Listen to the episode Retention & customer success Link to this
Preventing or catching a few surprise churns is enough to justify conversation training: if four people on a 20-person team each manage one, the ROI is clearly positive. Listen
London asks every client how their CFO would want ROI measured. He says he is most confident making the case by compiling anecdotes: avoiding about three surprise churns, rescuing at-risk accounts, or spotting risk and expansion opportunities. He admits that what he charges is 'not cheap' and that behavior change is hard to track in the numbers.
“So if a team is 20 people and four of them achieve one of those things, the ROI is going to be really positive.”
London uses a custom GPT trained on his methodology to score call transcripts, replacing roughly two hours of manual review per transcript. Listen
London built a custom GPT trained extensively on his 'radically authentic discovery' methodology to assess calls. It produces a coaching scorecard with a timeline in three columns: what the customer said, what the rep said next (for example, did they dig in or start a new thread), and a coaching point on what to say next time. He says doing this manually took him about two hours per transcript.
“it does would take me two hours per transcript and I'm not sure that's the work I actually want to do anyway.”
As a fractional CMO, London refused to do strategy, brand or positioning work unless customer interviews came first. Listen
London describes corporate meetings where eight people from the same demographic, in a conference room in Virginia, tried to work out how to market a product in Malaysia. He says he kept telling them the answer was not in that room. After being fired from a CMO-track role and going independent, he made customer interviews a precondition of his engagements and has since done about 3,000 of them.
“as a fractional cmo, I'm not going to do an engagement on strategy and brand and positioning unless we do that first.”
Telling a team to 'be more strategic' without showing them how is pressure, not direction. Listen
Bob London cites a LinkedIn post by Adnan Raman, head of global customer success and partner success at Paycor, who said that years of telling his teams to be more strategic had been a mistake. London says nearly every lead form he receives describes the same problem: teams are comfortable talking about products and solutions 'below the line' but are not confident or curious enough to talk about the customer's business. Paycor brought London in to train the team on more strategic, open-ended conversations as part of a value realization framework.
“That's not direction or leadership, it's just pressure with no path.”
Anchoring value to the customer's company and board-level priorities protects you when your individual contact leaves or changes roles. Listen
London says CSMs should try to stay tied to what the customer describes as company priorities, up to board level if possible. His reasoning is that this shows how your value aligns with the customer's business, not just with the person you happen to be speaking with, who may leave or change roles.
“so you can see how your value aligns not just with the person with whom you're speaking, the customer contact who may leave or change, but their business.”
Listen to the episode Retention & customer success Link to this
Once CSMs start having these business conversations, London says they tend to find it is the part of the job they wanted to do, and it pulls them out of firefighting. Listen
London reports hearing this from Adnan Raman and his team at Paycor. CSMs who adopted the approach said it was the part of the job they had wanted to do but had been too busy for. He adds that it also takes them away from some of the firefighting work.
“then they like oh yeah, this is the part of the job I really wanted to do, but I've been too busy.”
Listen to the episode Retention & customer success Link to this