The Conversation Your Competitors Aren't Having ft. Bob London

So you’ve asked your team to have more strategic customer conversations. Are you confident they know what that actually means? With over 3,000 customer discovery conversations under his belt, this week's guest has the answer.

Bob London, a strategic discovery expert, speaker, and coach, joined host Josh Schachter for this week’s [Un]Churned episode, “209. Stop Asking “Would You Renew?” Ask This Instead.” They covered the mindset shift from product-pushing to curiosity-led listening, the specific questions that open customers up at different stages of the lifecycle, and how leaders can reinforce the behavior change after the training ends.

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Listen on YouTube, Spotify, Apple Podcasts, and Gainsight.com.

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🎯 The [Un]Churned Take: “Would You Renew Tomorrow?” Is the Wrong Question to Ask

When you ask a customer if they’d renew tomorrow, their answer is usually just what they think you want to hear.

A customer who hasn’t spoken up in six months might say yes. One who’s been raising issues might say probably. But neither answer reveals what they’re really thinking, how their priorities have changed, or what might catch their interest from a competitor. “Would you renew tomorrow?” is a question makes vendors feel better, but it doesn’t get to the customer’s real thoughts.

Bob London, a coach, advisor, and Chief Listening Officer, has a different approach. Rather than asking customers to judge the relationship, focus on understanding their world.

From Easy Answers to Honest Ones

The question Bob recommends instead is this:

“If one of our competitors reached out to you tomorrow, on a scale of one to ten, how would you react? A one means you’d ignore it completely. A ten means you’d get back to them for any reason.”

After 3,000 conversations, Bob says the average answer is about a seven. Most Customer Success teams worry when they hear that, but the real value comes from digging deeper and finding out why the customer answered that way.

Chances are, it’s not because they actually want to switch. Customers see competitor outreach as a way to get information. They attend conferences, read emails, and want to stay informed. A seven just means they’re watching the market, not that they’re unhappy with you. Bob coaches his clients to use this follow-up:

“Is there anything a competitor might bring up that would be a real head-turner for you—something you haven’t heard anyone solve yet?”

That’s when you see the real gap between where the customer is now and where their curiosity has led them. Maybe it’s a feature that was promised but never delivered, or a workflow no one has solved yet. They aren’t looking to leave. They’re just waiting, sometimes anxiously, to see if their vendor will keep up.

The Leadership Implication: Begin in the Customer’s World

Bob’s competitor question is part of his broader coaching techniques around questions that focus on the customer’s world, not the vendor’s.

In this week’s UnChurned episode, “209. Stop Asking “Would You Renew?” Ask This Instead ft. Bob London”, he shared another example.

“If I could sneak into your last executive leadership meeting, what do you think the big topic of conversation would be?”

Customers don’t push back on these kinds of questions. They pay more attention because they see you care about what’s really happening at their company, not just checking off a renewal task. Adnan Rahman, who brought Bob in to work with the Paycor CS team, shared in his article, “The Unexpected Outcome of Paycor’s Value Realization Playbook”:

“For years I told my teams to be more strategic. It was a mistake.”

The problem wasn’t the goal itself, but that “be more strategic” isn’t specific enough. Bob points out that teams need a clear path, starting with broad, open questions about the customer’s world, and then staying focused there instead of shifting back to your own agenda.

Be a Good Listener, Even If AI Is Listening Too

Most of us have an AI notetaker humming along in the background of our meetings these days. But while AI might change how we capture and analyze conversations, it doesn’t mean we can stop listening altogether.

Technology shows us words and data, but listening intently, asking the right questions, and focusing on what matters to whoever is in the room with you is where your human-ness shines. You may uncover risks hiding behind the inflection in someone’s voice, or the unmet needs that show clear as day in the long pause they take to respond. In a world where AI makes data more accessible, it’s our willingness to ask, listen, and learn that turns customer relationships into lasting partnerships.

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🎧 Listen for These Moments

If your team is struggling to move beyond adoption stats and product updates, the full episode gives you the playbook. Three moments to listen for:

1. The lifecycle question map: which questions work at kickoff versus renewal, and why the right question at the wrong moment falls flat.

2. The scene-painting technique: how framing questions around a specific moment in the customer's world (a board meeting, a finance email) unlocks answers that generic questions never get.

3. The RAD coaching GPT: how Bob built a call assessment tool that produces a column-by-column scorecard for behavior change at scale.

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🔎 Where to Find the Speakers

• Bob London — LinkedIn: https://www.linkedin.com/in/boblondon/

• Josh Schachter — LinkedIn: https://www.linkedin.com/in/jschachter/

📎 Referenced in This Episode

• Paycor — HR software company where Adnan Raman leads global CS; the team Bob worked with on strategic conversation training

• Adnan Raman’s [Un]Churned episode — the prior episode where Adnan described the value realization transformation that led him to Bob

• JMI Equity — the private equity firm whose event introduced Bob to Jay Nathan and the CS world

• Jay Nathan — the CS operating expert at JMI who put Bob on stage and helped him understand the CS space

• Dale Carnegie — referenced by Bob as the original source of the “to be interesting, be interested” principle underlying his methodology

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Wrapping Up

The right question changes everything. You’d be surprised how many customers are just waiting to be asked.

See you next week 🧠