Asking Tough Questions

Module 8: Difficult Conversations Session Number: 52

Session Title: Asking Tough Questions

Session Overview:

Everything in this course builds upon itself and we’ll continue to work to build more value and gain more insight into our prospects and their challenges. 

During this session, you will learn:

  • Why you should ask tough questions in sales
  • When you should ask tough questions
  • Examples of tough questions you could ask

Training principle: 

Asking the proper questions will help your prospect move effectively through your sales process. Many sellers struggle with the idea of asking difficult questions because we worry that the prospect might get angry or choose not to do business with us. If they can’t put their confidence in us as a sales leader, then they won’t likely do business anyway. 

Step 1: Anticipate the wishy-washy things your prospects might say. 

  • Send me some more information
  • Let me get back to you on that
  • I will touch base with you in a week or so
  • Let me sleep on it
  • Let me think it over
  • I have to speak to my partner
  • I will reach out to you
  • Reconnect with me next week 
  • I will share this with (other decision-maker) and get back with you

You must challenge the status quo. Do not take these responses at face-value because your deals will likely die. 

Step 2: Ask for permission to make a counter-offer.

You need to get permission from the buyer to avoid making them angry. Consider responding with something like, “May I ask you a question?” 

Your tonality will make all the difference in how this question is received. 

Step 3: Share your concerns.

When your prospect says things like this in response to your information, these aren’t useful responses. You can’t present this response to your sales manager. You need something you can report back to your sales manager. 

  • “I have the impression this is not a high-priority item right now.” 

It’s better than you know now that this isn’t a good fit than to discover it later after you’ve invested your time in a deal that won’t close. 

  • “When someone tells me that, it usually means he isn’t interested but doesn’t want to hurt my feelings. Is that the situation here?”

If you aren’t sure of the objections you might encounter, talk to the seasoned sellers in your company to see what they have encountered. 

  • “I feel like you are shopping around right now and are more concerned about finding the cheapest price. Is that the situation?” 

No one can argue your feelings, so this is a good way to address some of these issues. Keep in mind, too, that you’ve built rapport by this time and you’ve gotten permission to ask these hard questions. 

  • “I feel like your current vendor is a sacred cow and no matter what I say, the team doesn’t want to change. Is that the case?”

Because the current vendor is a known entity and yours is unknown, this can present a challenge for you moving forward. 

Step 4: Use the prospect’s responses to address these issues.

Because you asked permission to present these hard questions, you’ll be able to use the information you’ve gathered from these responses to overcome the objections and build value. 

Step 5: If your prospect poses hard questions, be willing to hear them. 

I made the mistake early in my career of being fearful of these hard questions, but I’ve learned that there’s nothing to fear. It isn’t rude or pushy, and I don’t have to be subservient as a seller. If you’ve built rapport, they won’t be offended and they won’t hurt you. You’re the professional that the prospect is listening to. 

Step 6: Walk your prospect off the cliff

Prospects commonly encounter situations where they are unsure about making a purchase or moving forward. The best way to address these concerns is to address them head-on. 

  • “What are you unsure about when it comes to working with us?”
  • “Are there any other concerns?”
  • “Why is that an issue?”
  • “If we can address that issue, would that assist you in giving us an opportunity?”

Address those worst-case scenarios and help your prospect address those fears. Mitigate his risks by sharing previous experiences you’ve had with other prospects who had the same concerns. 

You can even provide an option for an opt-out with little risk because you know you’re going to provide amazing service. 

Step 7: Answer with a question.

If the buyer asks you a question that you don’t know the answer to or that puts you in a bind, you can respond with a question of your own. 

  • To the question, “How much does it cost?” respond with, “That depends… how many people in your organization will use the service?”
  • To the question, “What is your best feature?” respond with, “That’s different for everyone. What would you say is your biggest challenge?”
  • To the question, “What makes you better than our current vendor?” respond with, “They are a great company, and some people like us better but others don’t. What was it that made you choose them 3 years ago?”

Use the ammo you get from these questions to engage your prospects’ emotions. 

Tasks to Implement:

Practice these questions and do it in role-play. Use these questions to build more value as you move through your sales process. 

Session Recap:

Many sellers fear the tough questions their prospects might ask and they do their best to avoid them. Instead, use those tough questions to pose questions of your own and gather information that will help you build better value for your prospects.

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