Reconnaissance selling

Ask strategic questions to gain valuable information

As a trainer, I’ve learned that sales professionals want to have a competitive edge. They want to help their clients succeed, and faster, but aren’t quite sure what to do differently.

Company onboarding programs are often ill designed, and by default, condition sales people to believe that selling is telling. Typical onboarding processes involve product and service training, as well as time to memorize and practice delivering the general capabilities presentation; but little information is provided regarding what questions to ask and what to do with the information that is received.


After graduation, sales people are directed to meet with prospects, qualify them and present some portion of the general capability presentation. Unfortunately, this makes for a nice company advertisement, but results in little sales traction. In fact, in some situations, this backfires when the buyer “tunes out” the sales professional and categorizes him as “just another salesman.”

Successful sales people know that to differentiate themselves, they must ask thought-provoking questions that cause the buyer to see his situation from a different perspective. This shifts the conversation from the standard sales-speak to focusing on operational bottlenecks, inefficient workflow processes, missed customer expectations and internal politics. The sales person gains important insights into the inner workings of the organization that may include:

  • What’s working well at the company?
  • Where is the business falling short of expectations?
  • Where are the bottlenecks in the organization?
  • What’s causing the bottlenecks?
  • Who will challenge a change to the status quo?
  • What solutions has the organization tried in the past?
  • What viable options have been or will be considered?
  • What does the organization need to move forward?
  • What is the budget?

Over the years, I’ve synthesized pages of questions into 10 simple categories.  I call these “Reconnaissance Questions” as they are designed to gather strategic information that helps the sales professional assess the situation. Here are the 10 reconnaissance categories:

  1. Assess the prospect’s business situation.
  2. Determine the scope of the opportunity.
  3. Define the desired outcomes.
  4. How willing is the prospect to change from what she is doing now?
  5. Where is he in the buying process?
  6. Who makes the decision and what is the approval process?
  7. What is her sense of urgency and timeline?
  8. Does your company have the capacity to deliver what the prospec wants/needs?
  9. Who else is the prospect talking to about this project?
  10. Has the project been funded? If not, when will it be?

Under each category, develop your list of questions. For example, under “Assess the Business Situation” you might write, “What top two business decisions will you need to make this year and how will this impact the organization?” or “If you could improve one aspect of your business that will immediately create value for your clients, what might that be?”

It’s advantageous for the entire sales team to complete this activity by themselves initially, and then come together as a group to share their respective lists. Simple case studies that reflect your range of clients will help turn this exercise into a realistic activity by asking them to create the list of questions that they would ask on the first call.

Then, working in smaller teams, ask the group to anticipate what responses they might receive from prospects and how to handle that response. If they are uncertain, the sales manager should offer guidance. This will help the sales person retain their cadence during a live prospect meeting.

By asking reconnaissance questions, sales professionals gain insider’s information, they learn the prospect’s language, and better understand how decisions are made. This leads to one of the most important outcomes, which is the speed in which trust is built. The refreshing and sometimes profound dialogue that unfolds can cause a buyer to assume your competency and even ask for assistance in how to position your offering to the committee and how to respond to committee member inquiries, resistance points and comparison to competitive offers. When possible, it’s good practice to conduct a dress rehearsal or mock discussion to prepare your buyer so he can respond with grace.

If your goal is to fill your sales pipeline with viable qualified prospects and accelerate the buying process, become a master at asking reconnaissance questions. You will differentiate yourself in the best possible way while getting the inside scoop on how your customer buys. This will help accelerate the sales process and position you as the true trusted advisor.

-Christine McMahon provides strategic sales and leadership coaching and training. She is co-founder of the Leadership Institute at Waukesha County Technical College’s Center for Business Performance Solutions, and can be reached at (844) 369-2133 or

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Christine McMahon helps leaders develop strategies and improve speed of execution by developing leadership talent, creating alignment between business functions and improving communications and accountability up, down and across a business. She is co-founder of the Leadership Institute and is in partnership with the WMEP. For keynote presentations, executive coaching, sales and leadership training, she can be reached at:

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