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Six Tips To Re-Frame Boring Discovery Questions

Have you walked out of a discovery meeting with a prospect with incomplete information, unclear objectives or lack of direction? One reason could be the framing of questions used during the interview process. Here are six techniques to enhance your existing questions to prompt more insightful responses.

There is an art to interviewing, something we have all experienced when the practitioner is on the top of their game. If you've ever heard an episode of NPR's Fresh Air with Terry Gross, you know exactly what I mean. Terry is able to establish an instant rapport with her interview subjects using a combination of empathy, awareness and presence of mind. One key aspect of her arsenal is a series of questions that cut to the core of the subject's world, and they seemingly pour their heart out - in public, to a complete stranger.

It will be a monumental effort for a mortal like me to unpack what Terry does, but there are some quick and easy tricks you can use to re-frame your questions to solicit more compelling responses. At the end of the day, you want to establish a trusting relationship with the prospect and uncover key insights into their business problems - hopefully some of which you can address with your products or solutions.

Tip #1 - Start with a complement
"Flattery has an insidious ability to worm its way into the unconscious, where it creates persistent feelings that could affect the outcomes of all kinds of business interactions, from job interviews to sales to boardroom presentations." - Jaideep Sengupta, Professor of Marketing.

Flattery does not need to be fake. If you are a straight-shooter like me, then it may actually back-fire if the person detects you are being dishonest. However, if you have initiated this meeting, then you have basic respect for the individual and/or the company to warrant your time. You can easily uncover a worthy accomplishment to feature in your complement. If you insert a complement just ahead of a question, you are putting the other person in a more positive and agreeable state of mind, such that they might open up to further lines of inquiry. Example:

"I just read an article in CIO magazine that you are among the top 10 US companies when it comes to digital transformation. That was surely a challenging feat. Could you share what you did differently that allowed you to succeed where others are struggling?"

You have done yourself a lot of good with this one question. You have demonstrated that:

  • you did your research

  • you care about your prospect's success

  • you acknowledge their ingenuity and hard work

  • you are curious to learn from them

This type of question is ideally suited at the top of the meeting. It gets everyone in a positive vibe, and they are more likely to open up about what they are not doing well, later on in the discussion.

Tip #2 - Combine close and open ended questions effectively

A successful interviewer makes judicious use of both close and open ended questions. Close-ended questions are great to help qualify a particular line of thought or to gauge an issue. Open-ended questions help uncover the unknown - information that you are just not privy to. Both have their time and place during an interview.

Example of close-ended question to help qualify: "Are you looking to expand to international markets?" (yes/no)

Example of close-ended question to gauge or quantify: "On a scale of 1-10, how would you rate your level of readiness when it comes to international expansion?" (1-10)

Example of open-ended question to uncover unknown information (if answer to previous question was "3"): "What do you need to accomplish so your readiness level goes up from 3 to 8 or 9?"

Tip #3 - Ask for a story
"Storytelling reveals meaning without committing the error of defining it." - Hannah Arendt, Philosopher

We think and remember information in stories, not in bullet points. However, we often ask questions that can only be responded in bullet points. The problem with bullet point responses is that they are stripped of any context and it becomes difficult to convert the information into a useful insight.

An example of a question that will elicit bullet point responses:

"What are your key challenges when it comes to reliability of your hosting infrastructure?"

Instead, try:

"When was the last time you experienced down-time, or an extremely close call that was averted? What happened?"

Now, you have suddenly triggered every sensory faculty in the subject that puts them squarely in a very specific time and space in their life. It is a living memory, and they are able to respond in animated detail about the event, who was involved, what went wrong. There is emotional weight behind the response. Beyond the facts, you uncover what they really care about. The above question can be closely followed by "What did you learn from that experience?".

Tip #4 - Use extremes

On the theme of avoiding questions that elicit bullet points, another favorite sales question goes along the lines of -

"What are the top challenges you are trying to address with a CRM solution?" (if you are a CRM vendor).

There is nothing wrong with the question, and in fact you will get a lot of data that can be useful to identify an appropriate use case. However, there is danger of the response not providing you with the priority of the challenges or the significance of each challenge. This is critical information that you need in order to formulate a value proposition that will maximize the deal potential.

A powerful way to address this issue is to re-frame using an extreme hypothesis. Example of an "extreme" question:

"If there was only one thing you could solve with a CRM solution that would have an out-sized impact on your business, what would it be?"

Using extremes prompts the subject to give the matter a little more thought, to prioritize the issues and to clarify the reasons why they care. It also helps you focus the rest of the sales engagement to ensure you can tackle the most important client concerns.

Tip #5 - Don't ask "Why" (too much)

Nobody likes to be interrogated, especially your prospect who is evaluating multiple vendors simultaneously, and communicating the same information repeatedly. 5 Whys are appropriate when trying to establish root cause for a service incident. They are not appropriate or respectful in a discovery call. A 'why' question can often be interpreted negatively - as accusation or condescension. Too many "why" questions can put your subject in a defensive mode.

There are enough ways to use "what" and "how" to frame questions that can get you to the same information in a less threatening way - see previous tips for examples.

Tip #6 - Ask "What has changed?"

“What has changed?" is one question that should be part of every discovery call, taking a leaf out of David Field’s book “The Irresistible Consultant's Guide to Winning Clients”. The sub-text here is "Why now?". There is a specific reason this prospect took you up on your request for a meeting, at this moment in time. This question can unearth an important nugget that could be the hook to hang your entire sales opportunity on, like:

  • a challenge - "we had a series of poor quarters"

  • a change of direction - "we hired a new leader"

  • competitive intel - "our existing vendor/solution has failed to deliver"

  • financial context - "we were always interested, but we just got budget approval"

Even if the "need" has been clearly established, it is critical from a sales perspective to understand the compelling event behind it. It sheds light on the motivation and urgency behind the need, and how likely the prospect is to actually act on the need in the time frame that you want them to.

Hopefully you can use one or more of these techniques in your next discovery call. I would love to hear about your experience, or any suggestions for additional ways to re-frame discovery questions. Please contact me via email or LinkedIn.

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