The Worst Question a Salesperson Can Ask

Joseph Abbott

Joseph Abbott, J L Abbot, LLC
January 2016

“What’s keeping you up at night?”

This one questions is probably asked by more sales people in a given day than any other. But while it seems innocuous - maybe even the right thing to ask a customer - it’s a question that simultaneously prevents sales while also destroying customer loyalty.

To understand what makes this question so destructive, we need to first understand where it comes from. For years, most sales training has focused on a single core principle: the shortest path to sales success is a deep understanding of your customer’s needs. If we understand what’s keeping customers up at night, we can build tight linkages between their problems and our solutions, the reby improving our chances of selling something.

As a result, companies have poured money into teaching their reps to ask better questions. But while it sounds great on paper, the approach suffers from two major problems. First, improving reps’ ability to diagnose needs on the fly proves colossally difficult - especially among average performers. Second, and more to the point, this approach is based on a deeply flawed assumption: customers actually know what they need in the first place.

But what if customers don’t know what they need? What if customers’ single greatest need, ironically, is to figure out exactly what they need? If this were true, the better sales technique might be to tell customers what they need.

High-performing, gifted reps (I call them “Challengers”) succeed by doing just this, revealing to customers problems - and solutions - that they don’t even see. This isn’t your standard solution-selling approach, focused on open ended needs diagnosis. A sales conversation with a Challenger provides valuable insight to customers instead of extracting it.

No supplier wants to be in the business of free consulting. They key is to teach in a way that leads customers to your unique benefits as opposed to leading with them. After reframing the way customers think about spending, your reps can create an opportunity to talk about a set of capabilities they can offer to better manage that spend, ultimately leading to higher-level sales conversations and bigger deals.

These conversations aren’t happen stance, there’s a specific art to getting them down right. I have found that insight-led sales conversations follow a distinct choreography that’s different from your standard sales pitch. Importantly, this isn’t something to leave to your individual reps to figure out. Marketing plays a critical role in identifying these teachable insights and equipping reps with the tools to deliver them to the customer.

Done well, this sort of sales approach creates a powerful differentiated interaction for customers because it leads with insight, not tiresome questions. And as it turns out, the difference really matters.