In this interview, Bob London and a VP of Account Management (Speaker B) review a recent internal exercise where account teams were tasked with asking customers a set of disruptive, thought‑provoking questions. The conversation reveals that customers often responded with surprise—"no one's ever asked me that before"—which lowered conversational walls and yielded richer information about their needs. While the original goal was to deepen relationships, improve retention, and gain insight, the deeper dialogue sometimes uncovered untapped product opportunities, leading to new revenue prospects and follow‑up meetings. The VP notes that staff sometimes felt uneasy, fearing they had failed by steering the conversation toward sales, yet the disruptive questions ultimately facilitated more open, value‑adding exchanges. The discussion underscores the strategic value of curiosity‑driven questioning in account management, balancing relationship‑building intent with the potential for organic upsell opportunities.
Chapters
The team had at some point some homework. We asked them to go ask a couple of these more disruptive questions, which we'll show in a moment, to at least one or two customers. I think you were even on some of those calls. Like, what did you observe and what happened? Did you learn anything? Did customers open up? Were they sort of engaged in the process?
They were. Believe it or not, at least 2 or 3 times we heard people say, wow, no one's ever asked me that before. Right. And it's like it was, it took down a little bit of a wall because then they loosened up and gave us more information. And in some cases went off into a place where they were wanting to know more about a product that we have not sold them yet. Right. So it's not like these questions are intended to like try to upsell, it's more about us finding out more about them. But in some cases, it took us to a place of, well, we have something that could help you with that. And it spurred on more conversation and additional meetings to be set up. So I think there's some unintended things that come out of just conversations and that curiosity is that we found out that if we had not asked, we wouldn't have gotten to those.
I confess that, and we talked about this, when I started doing these workshops, I wasn't, positioning it as, oh, you can grow revenue. It was more about, as you say, relationship building and retention and more insights to understand the customer better and to serve them better, add value. But when we went around and talked about the homework people had done with your— on your team, several of them cited, if I remember correctly, potential new revenue opportunities based on just hearing more about what's going on with the customer. Is that accurate?
That's true. I, you know, one of the staff was upset. They said, I think I failed this, this, this mission, this assignment, because I asked the question, but then it turned into more sales and it was okay. It worked. You're on the right path. But just asking the question loosened up the whole conversation enough. The customer took her down that path, not her dragging the customer.
Oh my goodness.
But it's okay if it goes in that direction, but I do think when we did round 1 is that some of the staff were nervous, like, I'm afraid of the answers I'll get. And sometimes that prevents us from asking the question because what if they ask me to solve for X and when I can't. So there's this fear of we might hurt the relationship, but what we have found is that every one that we've done so far has been extremely positive. We've had good outcomes and we may not have found the information we wanted to find out. Like we may have found some bad news for us, but as you mentioned, I mean, to me, any insight is better than being ignorant. So once again, I, those are the things that I lose sleep at night about is the quiet customers that I, you know, that are just quiet. I'd rather have someone yelling at me and knowing they're in to fight for this relationship and we can solve for that versus someone quiet. Right.
