How to Ask the Right Questions in Your Sales Conversation

It's incredibly difficult for even the most veteran salespeople to drive urgency and funding in their deals without attaching to a big business problem that your prospect is facing. Finding a big business pain is key.

That premise is one of the most basic sales principles. As our own John Kaplan would say, “It’s Egypt old.” It’s also the catalyst to selling on value over your product’s features. Finding a customer problem is the first step to winning the business and also the part of the sales conversation where many reps struggle.

Business issues and pains are the underpinnings of a value-based message. When you use your sales conversations to (1) tie your solutions to business problems and (2) show your differentiation — you create a captive audience that understands the importance of actively participating in their own rescue. How do you lay the groundwork for a value-based sales conversation? With effective discovery and trap-setting questions. 

Discovery Questions

If you can’t identify your customer’s most compelling pain points, you’ll struggle to sell your solutions. Deals are won and lost on effective discovery. If you want to sell on value, you have to ask questions that prompt prospects to verbalize their pain, in a way that gives you an opportunity to articulate the value of your solution. 

Asking open-ended discovery questions results in a two-sided conversation. Both, you and the customer learn from the answers. When customers hear themselves admit their problems, it creates buying momentum and gives you leverage to win the deal. Discovery questions create a sense of urgency, helping you move your customer through the buying cycle. When you successfully execute this approach, you get your buyer to come to their own conclusion that they have an urgent business problem that demands a solution. Then, they'll look to you for help defining the right solution.

Sellers who excel at helping the customers articulate their needs automatically have better knowledge about their customers. They’re able to better qualify opportunities while earning that coveted trusted advisor status that creates a successful customer/seller relationship.

[Dig deeper on improving your ability to ask great discovery questions]

Trap-Setting Questions

Discovery questions help you uncover customer needs, but they don’t necessarily provide the opportunity for you to demonstrate your differentiation. If you’re competing with other vendors in your sales cycle (and you most likely are), you won’t win the business without also using effective trap-setting questions as part of your customer conversations.

Trap-setting questions allow you to demonstrate how your solutions are better and different from the competition. They highlight the value that the customer will receive as a result of a differentiator that you have.

Just like discovery questions, trap-setting questions need to be open-ended and two-sided. They need to form a link in the customer’s mind between your differentiators and the ‘customer value’ that they just admitted was important, through your discovery questions.

In your sales conversations, think about the subject that you want to drive the conversation towards and work backwards. Begin with high-level questions and then use more detailed questions that allow you to use the customer’s answers to demonstrate your value.

At the end of a good round of trap-setting questions, customers should walk away believing that your line of questioning got them thinking about areas of value that they hadn’t yet fully thought about or comprehended. This will lead them to see that your company is tailor-made to address their needs and that the competition is not. Trap-setting questions draw the pivotal link between the value that customers want and the differentiators that your solutions provide. When executed correctly, these questions will help you get your buyer to anchor on required capabilities in a way that your competitors simply can’t measure up to.

[Dig deeper on how to trap competitors and pivot the deal in your favor]