Asking Questions is an Underappreciated Art Form

April 19th, 2018 Posted by Discovery Questions, Sales Tactics 0 thoughts on “Asking Questions is an Underappreciated Art Form”

There was an excellent article in the May / June 2018 issue of Harvard Business Review entitled The Surprising Power of Questions.” The authors, Alison Wood Brooks and Leslie John, summarized many of the reasons that asking questions can add tremendous value to any conversation. This topic is highly relevant to every single one of your frontline employees who deal with customers, prospects, partners, etc.

When it comes to engaging with clients or prospects, frontline employees are typically told to ask “discovery” or “qualification” questions. That’s wonderful. It really is. Telling someone to ask questions is a great first step. The problem is, there is far too little focus placed upon teaching them how to:

  1. Ask the right questions, at the right time, to solicit the information they need to qualify a prospect and/or target their sales messaging
  2. Know how to ‘follow the breadcrumbs’ and dig deeper after receiving an answer
  3. Use a tone and approach that won’t spark defensiveness or be viewed as overly intrusive
  4. Identify the specific persona of the prospect / customer and understand their level of receptivity to engaging in a Q&A process
  5. Not be shy about asking questions that may, to some, feel uncomfortable (i.e. budgeting, decision-making authority, etc.)

Here’s the kind of story we often hear from our clients at pelotonRPM:

I can’t tell you how often my Reps come back from meetings feeling like they knocked the cover off the ball. They’re ready to break out the champagne. Then, I ask them what problem the prospect is dealing with that will motivate them to make a decision and make that decision soon. Crickets. I ask them about the prospect’s decision-making process and who needs to be involved. Crickets. I ask them about the prospect’s budget. Crickets. It scares me to think that they believe a good presentation equals a good meeting. It doesn’t. If they don’t walk out of that meeting knowing a lot more than they did when they walked in, it’s not a successful meeting!

Without asking the right questions, there is no way to target the value proposition in a way that will resonate with the prospect. Without asking the right questions, there is no way to know if the prospect has urgency, budget or the power to write a check. Without asking the right questions, there is no way to accurately handicap the probability of a sale closing or understanding the likely timing. To be successful, companies need their frontline teams to reframe how they define success when it comes to client / prospect interactions. Before stepping into a meeting (or onto a call), client-facing employees have to define a list of very specific objectives that they need to accomplish. Intelligence gathering will always be near the top of that list. Even the most eloquent sales pitch will fall on deaf ears if the person delivering the message lacks a full understanding of what is motivating, and limiting, the buyer’s behavior.

You can find the HBR article here:


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