What's Keeping You up at Night? 

Good morning and happy Q3. 


A new quarter kicking off brings new customers and discovery conversations. Today we’re talking about how not to start a discovery meeting. Let’s dive in.

“What's keeping you up at night?

If someone hasn’t told you already, let me be the first to say to stop asking this question— and others like this. Here’s why: 

  • It’s too informal: If you don't have an established relationship with the client, asking questions like this can easily be perceived as too casual for an initial business conversation. What’s keeping me up at night? My newborn son is keeping me up at night.

  • It’s lazy: It puts all the onus of the discovery process on your client. Show you did some research and are actually a thought partner. 

  • It might be too direct: Or intrusive. Neither of which are constructive if you haven't built rapport yet. Some clients might be uncomfortable sharing their deepest concerns early into a relationship.

  • It assumes awareness of a problem: The buyer might be perfectly content with the status quo and not have any (or be aware of any) immediate concerns.

  • It can make clients defensive: Clients may feel like once they confess a problem you’re going to try and force feed an offering as a “perfect solution” to their problem.

If you just love using the phrase “keep you up at night,” I don’t judge. But be more effective and consider saying:

“Based on my work with others in your industry, here's what should be keeping you up at night and why.” [knowledge drop]

Or

“Here's what will soon be keeping you up at night." [knowledge drop]

Discovery conversations aren’t just about you interviewing a customer about their business and what matters to them; they’re also about your customer discovering if you’re valuable or wasting their time. You’ve got to deliver value to your buyer from the first meeting— Do this by proving your expertise as the consultative seller who will help them make better decisions.

When joining your next discovery call, practice balancing 1) providing an educated point of view and an opinion with 2) being open minded as you ask questions.

Top performers’ discovery calls are 76% longer than those of average performers (source). While longer calls aren't necessarily better, it’s clear that if customers were hating the discovery conversation the call would be shorter. Bring an insight, an opinion, a strategy that’s worked for others, etc. on the discovery call— you'll be well on your way to building rapport. And all of a sudden your customer is more open to sharing the information you actually need to solve their problem.

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The Difference Between Being a Nuisance and Being Persistent