Resource Logo

Hello, you are using an old browser that's not compatible and no longer supported. Please consider updating your browser to a newer version.

Contact Us Contact Us
4 minute read
Back To All

Challenger® Selling: “Courageous Questions” Differ from “Grenades”

Many sales leaders are urging their salespeople to adopt CEB’s Challenger Selling™ model to ask “challenging” questions to have effective sales meetings with prospects and clients.

The intent is to be more provocative, create differentiation in a crowded market, provide insight and hopefully add more value to the conversation. This post is designed to share some mistakes I have been seeing with this approach and to offer suggestions for properly asking “courageous questions” in an effective sales meeting.

Courageous Questions for Sellers

First, what is a courageous question? Many questions can take courage, including ones that are:

  • Direct
  • Delicate
  • Challenging to current thinking
  • Seeking commitment
  • Insightful
  • Thought-provoking

Courageous questions — relevant to the client and well asked — can take a relationship in a new and positive direction as part of an effective sales meeting. Yet, why are some received as “grenades?” The movie equivalent is Bruce Willis walking away from the villains’ hideout, pulling the pin on the grenade, tossing it over his shoulder … BOOM … causing a huge explosion in his wake. Throwing a grenade question on the table is not courageous, it’s a selling mistake.

On this topic, I have been seeing different problems from two categories of sales professionals. The first group of salespeople — long on confidence, armed with industry marketing intelligence and feeling empowered by their leaders — are more than willing to ask challenging questions in prospect and client meetings. Of course, challenging current thinking is likely to cause resistance. Instead of getting either mild resistance or the “wow” factor that they are expecting, they are met with significant blowback or stunned looks. Rather than marking an inflection point from which the relationship advances in a new and positive way, it now marks the fall-away point.

The second group of sales professionals, not as long on confidence and without a process to challenge thought, avoid asking the courageous questions. And, while competitors start to make inroads in the relationship, these salespeople wonder why the client relationship has stalled.

Avoiding Grenades

So, how do you ensure that your courageous question is received well and not as a grenade? Here are eight best practices for integrating courageous questions into an effective sales meeting:

  1. Know where you stand: If you are at all unsure that the foundation upon which your client relationship is built is solid, seek feedback and know where you stand. No assumptions, as courageous questions are best delivered from a position of strength.
  2. Establish trust: Look for signs in your interactions that trust has been established. These can include kudos for positive past dealings, an open exchange of information, responsiveness to calls and meeting requests and client-initiated calls.
  3. Establish credibility: This does not require you to be all-knowing on all subjects. It does mean that, because of your background, your work and the organisation behind you, the client sees value in engaging with you on this new topic.
  4. Prepare and practise: Preparing and then practising with a colleague tends to ground the over-confident and build conviction in the should-be-more-confident. Both language and delivery matter, so prepare to receive feedback on both prior to the client meeting.
  5. Choose an appropriate setting: Challenging a client’s thinking can feel awkward to you and threatening to the client, especially in front of others. Choose a meeting location and time that puts folks at ease rather than on edge. And, think carefully about how your question impacts not just the intended recipient but also others who may be present.
  6. Set the context: Courageous questions are relevant to the recipient. A relevant question reflects your knowledge about the client, as well as his/her organisation and the industry/market in which it operates.
  7. Structure the question skilfully: Combine a good preface, which expressly states why you are asking the question and/or why the customer should reply. Use an open-ended structure to invite discussion.
  8. Allow silence, and listen: It is not tough to tell when someone is genuinely interested in your thoughts. What is tough for many salespeople is taking a breath, engaging silence and listening, being attentive to language and cues and being curious enough to continue the dialogue by asking deeper questions based on the client’s reaction. The same guidelines go for colleagues who may join you at this meeting. Inform them about this part of the meeting, and, if they have a tendency to “ease the tension” and fill the silence, practise with them both the delivery and the silence that follows.

Remember the movie “Top Gun,” starring Tom Cruise (“Maverick”), the classic 1980s film that glamorised navy pilots? In a practise drill, Maverick locks onto an enemy fighter, and his flight instructor coaxes him to “take the shot.” Grenade questions ignore the best practices above, and taking the shot may result in a crash-and-burn, eroding trust and credibility. In cases where you’ve earned it, leverage the best practices above in an effective sales meeting, take the shot confidently and enjoy the new dialogue stream — and opportunities — created by your courageous question.

About the Author

In addition to facilitating highly interactive Richardson workshops for sales and sales management professionals in a variety of industries, Michael is also a highly skilled Executive Sales Coach who utilizes the practical insights and strategies that he has gained throughout his career to help sales teams strengthen customer relationships, increase qualified opportunities, and grow revenue. Prior to joining Richardson, Michael spent more than 20 years with State Street Global Advisors. Under his leadership, assets under management for the business he managed grew from $8 billion to more than $100 billion. He built, developed, and managed a team of professionals covering sales, relationship management, and client support.

Complimentary White Paper: Creating Trust With Buyers Through Selling with Insights