How to Ask Insightful Questions

by | Apr 5, 2022 | Communication Skills

As a sales leader you want your sales team to consistently take their skills to the next level. One of the most critical sales training courses you need to provide is on questioning skills. This is one skill, when done effectively, will differentiate your sales team from the competition most of the time.

One of my favorite lines is:

“If your salespeople want better answers, they need to ask better questions.”

The primary purpose of questions is to open a conversation that develops trust. Questions will help your salespeople gain knowledge and understanding of what’s most important to the customer. When your salespeople gather information that their competitors don’t have, you can develop a solution that brings the most value. It also justifies the price of your solution.

For your salespeople to improve their sales skills they need to practice asking relevant questions. This requires strong listening skills. Listening with the intent to understand the customer’s situation means that you focus on the customer’s message and not your response. Stephen Covey said it best when he said, “seek to understand, then to be understood.” It takes discipline to stay focused since our mind will naturally wander during any conversation. You need to listen strategically. Not only what is said, the facts, but how it’s said, the feeling, and sometimes listening for what isn’t said.

What are the most relevant questions to ask?

There are many types of questions and some very good questioning models like SPIN Selling (Situation-Problem-Implication-Need/Payoff) questions. We know that open-ended questions build conversation and close-ended gain confirmation from the customer with yes-no responses. I’d like to share four types of questions that can improve your team’s success in gaining the most insights from the customer.

1. Strategic questions will get the customer to reveal what’s most important from their perspective. Some good strategic question examples include:

  • How important is that to you?
  • What’s preventing you from achieving your goals?
  • What’s the top challenge you’re facing today?

Strategic questions get to the heart of the matter for the customer. It will give you the most insight to their top priorities.

2. Provoking questions can take a deep dive into their most pressing goals and issues. This type of question gets the customer to consider their current state from a new perspective. You want to help them feel the gap between where they are today versus where they want to be. Some examples include:

  • Why do you think that occurs?
  • What would cause that to happen?
  • What are the consequences to your organization if this continues?

Provoking questions help the customer frame the intensity of their issues and to see the consequences of not taking action. Remember that customers make their decisions intrinsically not extrinsically. So, the salesperson with the right questions keeps the customer on the right path to consider what’s most important from their perspective.

3. Process question. At a former company, we called this the “in the day of the life” of the customer’s process. Process questions include:

  • Walk me through what happens when…”
  • Help me understand how you currently handle orders?
  • Can you tell me how your order fulfillment process works? I like to know the details behind the scenes of what occurs on a daily basis.

These questions help your salesperson get more involved in understanding how the customer operates their business. This will help you position how your products and services can best support what they are trying to accomplish.

4. What-Why-How questions. Here’s how best to use these in a typical sales discussion.

  • What questions focus on goals and results. They focus on the future. What is the customer trying to accomplish? Where would they like to be one year from now. “What” questions identify customer aspirations. Ask these questions first to help your prospect focus on their problems, their goals and their business.
  • How questions discuss ways of accomplishing goals and alleviating problems. “How” questions get into the details and the approach for the customer. Great salespeople gain understanding so that they can help navigate the customer in the right direction. This is the consultative approach that shows the customer the added value the salesperson brings to the table. It helps the salesperson to stay closely involved in the challenges the customer experiences. They have skin in the game and have the best intentions for the customer, leading to long-term relationships and repeat business.
  • Why questions focus on what has happened in the past. “Why” questions will uncover the root cause of a problem or issue the customer has been experiencing. “Why” questions help the salesperson lead the discussion to the best solution to alleviate the problem. It also helps the prospect better understand why problems have occurred and why your solution might be the best fit.

A great way to begin a What-How-Why question is to say:

“I’m just curious.”

This approach demonstrations that the seller is truly interested in alleviating the customer’s issues and delivering a solution that meets their needs.

A successful sales process starts with asking the right questions. Great sales teams will focus on improving these particular sales skills. Relationship selling is about the long-term. It’s building dialogue with the customer that gives you the insight you need to solve their problems better than any other provider. That is what sets great salespeople apart and it’s the reason why the profession of sales will never go away!

Good selling!

©Stu Schlackman


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