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10 Prospecting Questions to get you a Checkmate!

Casadee Wilson - Monday, June 20, 2016

A well known rule when working in sales is to ask questions. In sales roles we are told over and over that questioning is important, but WHAT questions are the ones that make the difference, and why?

10 Prospecting Questions 

Well the first thing to keep in mind is to think of questioning a prospect the same way you would when playing a game of chess. Each question needs to put you into a better position to play out the rest of the game.

So, let’s look at setting up the board, because before you can play, you need to know what to do with your pieces.

Ask yourself WHY someone would work with you specifically. Ask yourself what challenges they would be facing to have a need strong enough to be open to your company’s solution.

Then make your move. Keep the questions open, so you have room to move.

1. Tell me (NAME) what is the single, biggest frustration to you when it comes to your XXXXX?

  • REMEMBER to recap their answer, and respond to it - NEVER keep going. ACTIVE LISTENING is a HUGE part of ALL successful questioning strategies.

2. And what have you done to try to fix/solve that frustration?

3. How is that working for you? How will it work for you as long term solution?

  • You have now placed yourself into a position that will allow you to control the direction of the game. By having prospects identify their own problems, and reach a point of understanding that they are not in an ideal situation – via their own answers, you can start to dig deeper and get a real feel for what their next move needs to be.

4. So (NAME) tell me, what would be your ideal solution to XXX (your frustration)

5. What has stopped you from actively looking for that solution?

Use this question to identify their fears. Fears usually come from a mind frame of cost, time, or team.

MAKE SURE TO ADDRESS EACH FEAR, AND THEN FOLLOW UP WITH “What else has stopped you” until they have no more hesitations.

6. What would it mean to you, personally if (frustration) was no longer a problem for you?

(THIS IS PERSONAL – would they have more time for family and friends, would they sleep better, be less stressed etc..)

7. What would it mean to your company if (frustration) was no longer a problem for you?

(THIS IS BUSINESS – would they have more time for more clients/projects equalling more revenues, would they attract and retain more clients equalling more revenue etc..)

This is the point in the game where it becomes clear to both players who is in the lead. Remember, not every prospect will play a quick game. For many it’s better to play a longer game, whereas other times you want to go in for the quick moves to secure their king.

8. (NAME) from what you have told me (RECAP CONVERSATION) I’m sure we can both agree that it would be, at the very least, beneficial to get you some more information on how we could help you with this, yes?

(ONLY ask yes or no questions when you are sure the answer will be yes)

9. So if we could show you a solution that would solve (frustration) that was affordable to you, and would work for you long term, then that would be something worth looking at yes?

10. What would you prefer - To meet to discuss this tomorrow at (TIME), or (DAY AND TIME) next week?

And there you have it - Checkmate! Happy Gaming!