Instead of asking "what keeps you up at night?" and other cliches, try this instead.

Bob London explains why "What keeps you up at night?" gets generic answers. Instead, ask about the top three items on a board agenda or whiteboard to uncover what prospects actually care about right now.
Chapters
So when you're listening to customers and prospects, could be customer discovery, could be in a sales type environment, especially for a consultative sale, I want you to stop asking this question: "Hey, what keeps you up at night?" Now there's nothing intrinsically or inherently wrong with that question, but the fact is it's become a cliché. And when you ask cliché questions, questions that people get asked all the time, those people tend to give kind of automatic automatic cliché answers that they give all the time. That's not what you want. You want an insight. You want something that they haven't told other people. So you have to ask the question a different way. So instead of saying, "What keeps you up at night?" some suggestions are, "Hey, at the next board meeting, what are the top 3 priorities that everyone's working towards sort of for the next 6 months to a year or two?" Or you could even say to someone, if they don't have proximity to the board, it might be more appropriate to say, So what's, what's on your whiteboard right now? What are the 3 things that you're most focused on? And of course, the reason we start by asking these kinds of questions is because we want to understand where's the customer's head, where are they focused. They can't really focus on what we want to talk about or what we want to get out of them until we've looked at the world from their perspective. I'm going to start Googling the phrase "what keeps you up at night," and when I see blog posts and other things that recommend, I'm going to just flame them. Just kidding. But seriously, stop saying "what keeps you up at night," start asking other questions. You can download all the questions that I use and recommend and have developed over the last 5 years at chieflisteningofficers.com/free. That's right, absolutely free. You'll also get an entire process overview of how to conduct a listening tour, as well as listening tips—how to really hear what they're saying and go after the real insights. That's all for now. I'll keep you posted.
More from Bob

Matt Bowe, fmr. Senior Director of Member Success, Leading Hotels of the World

Beyond Words: The Art of Unveiling Customer Intent Ft. Bob London and Rijuta Bhagwat | Thinkly Talks

How to find out if your product or service is indispensable to customers. (Spoiler: Just ask them)

E21 | Uncovering the Secrets of Deep Listening: A Conversation with the Uh-MAYZING Bob London!






