Bob London is the Founder & Chief Listening Officer at boblondon.co, and a member of Vitally’s Success Network. His insights on customer engagement and transparency are based on the 2,800+ B2B discovery conversations he’s conducted.

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I spent much of my corporate career as a serial interrupter, quick to jump in with objections and solutions. 

But over the course of several thousand customer discovery conversations, I’ve discovered that starting with a wide aperture, asking more interesting questions, and listening deeply are the keys to building trust, uncovering hidden customer risks and opportunities, and revealing profound market insights.

Let’s dive in:

1. Learning to Talk With — Not At — Customers

When I started doing customer listening tours 10 years ago as a fractional CMO to help clients better understand their customers, I found that Customer Success teams were hungry to learn the questions and listening techniques that would help them have more strategic, open-ended customer conversations. 

So I started giving them the advice that helped me unlearn my own bad communication habits: Shift your focus from talking at customers to talking with them.

One of the biggest game-changers was sending slides in advance. I’d record a two-minute Loom video giving a quick rundown and highlighting the key slides, so customers knew what to expect. If they had questions or feedback, we could dive into those areas directly during the meeting. It made our interactions smoother, more focused, and more valuable.

Here's another simple tip: You know that “questions/discussion” slide at the end of your deck? Move it to the beginning and say, “As we dive in we'd love to take a quick step back and hear how things are going in your world, your market."

2. Starting Conversations from 30,000 Feet

One of the most effective strategies I’ve developed is starting conversations by focusing on the customer’s bigger picture. I call it “opening your aperture.” Early in my consulting career, I realized that kicking things off with product metrics or account statuses was too narrow. Customers want to talk about what matters to them — and that usually starts with their company’s priorities and challenges, which are far above your specific product or service.

Now, I often begin with a simple, open-ended question:

"If I could sit in on your next board meeting, what do you think the top priority or challenge being discussed would be?"

This question catches people off guard — in a good way. It’s disarming and immediately shifts the conversation from a transactional exchange to something more strategic. Once we understand their priorities at a high level, it becomes easier to connect the dots between their business goals and how we can help achieve them.

3. Building Trust By Not Talking So Much

Building trust isn’t just about asking questions — it’s about listening deeply and making people feel truly heard. I’ve come to rely on a personal rule I call STFU: Silence Till you Fully Understand.

In practice, this means resisting the urge to jump in with solutions. Instead, I summarize what I’ve heard to confirm my understanding and ask follow-up questions like, “How does that tie into what your company’s priorities are right now?” or “What would your superior say about the significance of this?” This simple shift makes a huge difference. Clients feel respected, valued, and understood when they see you genuinely trying to grasp their perspective.

4. Uncovering Risks With Simple but Provocative Questions - About THEM

Over time, I’ve developed a tool kit of what I call “truth-sparking” questions that reveal risks by engaging the customer on their terms. One of my favorites is:

“If a competitor reached out to you tomorrow, how likely would you be to respond?”

Most clients respond with a number between 1 and 5. If they say 4 or 5, that’s a clear signal we need to dig deeper. I follow up with:

“What might a competitor say that would definitely cause you to respond to them?”

The insights I get from these conversations are invaluable. They help us identify risks early, understand unmet needs, and develop strategies to retain the client. Often, the answers aren’t about dissatisfaction but about their curiosity — things like global expansion capabilities or better reporting tools. These insights allow us to address concerns proactively before they become problems.

5. Turning QBRs Into UBRs: Putting the Customer at the Center

I’ve seen far too many Quarterly Business Reviews (QBRs) that feel like a chore for everyone involved. So, I created a new and much more curiosity-based and customer-centric concept: the UBR. The U simply stands for “You, the customer.”‍

In a UBR, the entire agenda is built around uncovering and deeply understanding  ultimate needs and priorities of customers — and their companies. Instead of walking them through product updates and metrics, we ask questions like:

• What’s the one thing you and your team need to get better at in the next six months?
• What’s the biggest thing that surprised you since you started working with us?

These sessions feel more like a conversation or a collaborative brainstorming session than a rigid meeting. They strengthen relationships, build trust, and often uncover valuable insights we wouldn’t get otherwise. Try replacing one QBR a year with a UBR and you’ll see growth in trust, engagement, and insights.

6. Aggregating Insights to Influence Product and Strategy

One of the unique strengths of CS teams is their ability to gather insights directly from customers. I encourage teams to treat every interaction as a chance to collect valuable feedback — and then aggregate that feedback to drive meaningful change.

It’s not enough to bring individual suggestions to the product team. I’ve found success in presenting trends and patterns backed by real-world examples. We use tools to analyze transcripts and feedback at scale, identifying recurring themes across multiple accounts. When we show product teams hard data along with customer voices, it’s much easier for them to digest and embrace.

This approach positions CS as the “ears of the vendor,” capturing the real-world voice of the customer and providing strategic insights that shape the product roadmap and align it with customer needs.

7. The Tangible Impact of Making Clients Feel Heard

Making clients feel heard and understood isn’t just a “soft skill” — it has real business impact. Here are some of the outcomes I’ve seen firsthand:

1. Builds Trust Quickly: When you focus on their needs, clients trust you more.
2. Aligns Value With Their Priorities: You deliver outcomes that matter to them, not just what you think is important.
3. Reduces Churn by Identifying Risks Early: Proactive conversations uncover issues before they escalate.
4. Unlocks New Revenue Opportunities: When you’re curious about their business, you find new ways to add value and grow the relationship.

Being Customer-Obsessed Is Your Secret Weapon

At the heart of Customer Success is the ability to make clients feel genuinely heard and understood. It took me years to unlearn old habits and embrace this mindset, but it’s been one of the most rewarding changes I’ve made.

By shifting the focus from your product to the customer’s business, asking thoughtful questions, and listening deeply, you can build stronger relationships, reduce churn, and uncover opportunities you didn’t know existed.

If there’s one thing I’ve learned along the way, it’s that every conversation holds opportunity. Whether it’s a quick check-in or a deep-dive strategy session, the way you engage with clients makes all the difference. When you make them feel truly understood, you’re not just managing accounts, you’re building partnerships that last!