Jack Daly and Caryn Kopp’s Favorite Sales Call Questions

In the world of Sales, most know they have to ask questions during sales calls, but not everyone knows which are the best questions to ask.

In the second episode of Sales B12 Season 2, sales experts Jack Daly and Caryn Kopp share their favorite sales call questions and provide insights on when to use these questions to gain trust, gain an advantage over competitors and also keep the sales process moving forward.

Customize Questions To Gain Trust

Selling is the transfer of trust and all questions and conversation in the sales call must work toward the goal of gaining trust. Jack recommends prioritizing building trust and securing a second appointment. Rather than delivering a pre-made presentation or diving into the specifics of the product or service, Jack advocates for spending time asking questions that uncover the prospect’s needs, opportunities, and problems. Create questions based on the homework done ahead of time from the website and LinkedIn profile. By doing this, you will differentiate yourself from competitors who don’t do this. In addition, it shows your prospect you have a genuine interest in this person’s unique circumstances. This creates a relationship of trust.

Two of Jack’s go-to questions include, “Our company works best when we provide solutions of which our clients are desirous. If I asked you what your pains are as a company, what would your answer be to that?” And, “When you think about your company, why would potential customers of your company choose your company over your competitors?” You can follow that up with, “Talk to me about those competitors.” Jack recommends spending very little time discussing your company and products/services in comparison to asking questions to learn about your prospect on the first meeting. Dig for the pains.

The Importance of Leveraging Time When Asking Questions

Caryn says there are different questions for different parts of the sales process. Asking the right questions at the right time helps move the sales process forward. Asking certain questions too soon or too late in the sales process can jeopardize a relationship or success in closing.

Further into the sales process, either at the end of the first meeting (depending on how the conversation progresses) or in the middle of the second meeting Caryn suggests her favorite 3 question sequence. which, when done properly, uncovers the path to working together including if there are others who need to be part of the decision process. This removes surprises.

Question #1: If what we discuss is nirvana for you, what is the road to us working together. What paperwork needs to be signed and who else needs to be involved?

The prospect knows the path internally to working with a new vendor. Asking early in the process allows you to follow that path, including involving others who need to be part of the decision (instead of having them show up as a surprise at the end). Many sellers are afraid to ask if a prospect’s boss needs to be involved. Instead, use the phrase, “who else” needs to be involved.

Question #2: By when do you want the work completed?

Use this question instead of asking, when will you make a decision. If you understand when the prospect wants the work completed, you can work backwards to identify when the decision needs to be made.

Question #3: Why is the timing important to you? Why is that timing important to your leadership team (aka your boss)?

If the sale stalls later in the sales process, you can leverage what the prospect told you about the importance of the timing to keep the sale moving forward. For example, “You told me that it was important for the work to be completed by x date because of y and z. If we don’t move forward together now, how will you achieve your timeline?

The Power of “Why”

Jack also touches on the power of asking “why” in the sales process. He frequently asks this question, even when it has been answered before, using it as a mechanism to dig deeper and get at the emotional aspects of the client’s decision-making process. Jack and Caryn recommend asking “why” 3 times times to the same question so you can get to the emotional answer.

The Importance of a Playbook

Jack says that most sports teams run better than most businesses. They have a playbook, they practice, their coaches are on the field working with the players. Most companies do not run this way but if they did, their players would have proven systems and processes to follow. They would be better prepared and would achieve greater success.


Knowing and using better questions at the right time during the sales process is crucial for sales success. By knowing which questions to ask and when to ask them, you can gain the trust of your prospects, keep the sales process moving and achieve your goal of closing more deals. Adopting the the sports team approach will also help – develop a playbook, refine if over time and use it as a roadmap for sales success. Caryn says, the seller with the best words wins!

Be on the lookout for Sales B12 Episode 3 and be sure to sign up to receive notification when new episodes are released.

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