Skip to main content

The Strategy of Questioning Skills

Customer conversations

questions during sales meetings


Share on LinkedInShare on TwitterShare on Facebook

Great Questioning Skills Have Two Components: Part I - The Strategy: There are two essential components to questioning skills in a sales environment. The first involves strategy — the “what” to ask. The second is about the “how” of asking questions. The art of getting better at both begins with preparation.

This post will focus on the strategy of questioning skills. Part II will cover the skills involved in how to ask questions with proper empathy, pacing, and back-and-forth dialogue.

The first element in establishing an effective questioning strategy is to identify what you want to learn from the client. This means establishing clear objectives but not just those related to what you want to get out of the meeting. Think about what it is that you want to leave behind. This doesn’t mean a brochure or other information but, more importantly, what is the perception that you want to leave behind.

As for type of questions, at Richardson Sales Performance we often refer to the concept of a questioning funnel. At the top are big, overarching questions — such as the client’s goals and objectives — moving down to more granular questions about implementation and decision criteria.

Often, salespeople find it hard to start with big questions. They think too broad: “Tell me about the business and what you want to achieve.” If they have an existing relationship with the client, they usually start with what’s currently going on in the business at that moment. That’s an OK place to begin, but you typically don’t want to work your way down the funnel from there. Instead, take a step back and move to top-of-funnel questions, which will help in establishing the bigger picture and perhaps uncovering new opportunities. Then, proceed down the funnel with more focused follow-up questions.

One of the most frustrating questions that I hear salespeople ask is, “How’s business?” That’s something that they should know before going into the meeting. While some people say there’s no such thing as a stupid question, I have heard an awful lot of them. The stupid ones are questions that you could have and should have found answers to before meeting with the client. Research tells us that clients have less tolerance for questions these days, so salespeople need to make sure that they’re asking really good ones.

In consultative sales training sessions, when talking about what to ask, I tell participants they only get one shot to make an impact, but there are often opportunities to gather information over multiple meetings with the same person or from other stakeholders in the company. This helps with filling in the gaps. Plus, we must remember this is live information that we must be continually updating to be relevant in our solutions and ideas that we can bring to our clients.

It’s best to go into meetings with a list of questions prepared. This doesn’t mean starting at question one, proceeding through each one, and finishing at question 20. The list gives you flexibility to move about the conversation with the client, reacting in the moment to what’s most important to the client.

One trap that I see salespeople falling into is being too wedded to all of the questions that they want to ask. They might be on question three, but the client is talking about a subject related to question eight. If the salesperson isn’t actively listening and doesn’t hear what the client is saying, they’ll proceed down the list and still ask question eight. At that point, the client knows that the salesperson wasn’t listening and gets annoyed at having to repeat information that was already shared.

To have an effective questioning strategy, you have to be prepared but not be so tied to your homework that you can’t be flexible.

The key is to understand the client’s perspective so that you can determine if there are any opportunities for your organisation to be of help. You might uncover something that the client may not have considered, and there may be an opening for you to help create thinking or shape their existing thinking about possible solutions. In any case, being prepared and remaining flexible are part of a solid strategy for sales questioning.

Share on LinkedInShare on TwitterShare on Facebook
modern consultative selling approach white paper

White Paper: Elevate Your Consultative Selling Approach to Compete Today


View recent thought leadership

agile selling skills

Brief: How Agile Sales Professionals Use Sprints to Target, Message, and Engage Prospects

Download this brief to learn how Sprint Prospecting™ enables agility that quickly gets to the core of the customer’s needs.


evidence-based solution selling training for healthcare

Brief: Engaging Healthcare Professionals with Agile Messaging

Discover three ways sellers can deliver meaningful messaging to HCPs to gain access while staying in compliance.


successful virtual selling

Brief: Gaining Virtual Access to Healthcare Professionals

Download the brief to learn how healthcare sales professionals can front-load their efforts so their first outreach sparks interest.


Solutions You Might Be Interested In