The “How” of Asking Sales Questions

In Part I of this series, I focused on the strategy of questioning skills — the “what” to ask. In Part II, we’ll move on to the best way of  asking sales questions — the “how.” The elements involve proper empathy, pacing and back-and-forth dialogue.

The objective is to have a two-way dialogue with the client so that the meeting doesn’t feel like an interrogation. The skills for achieving this include acknowledging, little nods and paraphrasing back — “If I hear right, Mr. Client, what you’re saying is …” You become an active listener, being there in the moment instead of thinking about your next question or your next meeting. You demonstrate empathy.

I’ll share a true example of how not to do it. This comes from the time of the global financial crisis when a salesperson meeting with a client began the conversation by asking, “How’s business?” He said it more as a throwaway icebreaker as he was getting himself settled. The client was an entrepreneur who had grown the business to several hundred employees, including family members. The client responded, “To be honest, this has been the toughest of my 20-plus years in business. I nearly lost everything. I couldn’t even sleep at night, thinking about the impact losing the business would have on my family and employees.”

How did the salesperson respond? He said, “Oh OK, so what I wanted to talk to you about today was …” There was no empathy. No acknowledging. No sign of listening. I could almost see the client flinch and shut down. It didn’t matter what else that the salesperson said, he completely missed the opportunity to connect and ended up offending the client.

Empathy is about acknowledging when times are tough or when it’s an exciting time for growth. It’s about connecting first as a person before getting down to business.

When asking sales questions, other critical skills involve prefacing, trading, drilling down and pacing.

Prefacing: This is the sentence that you say upfront to explain to the client why you need to ask a particular question. Prefacing can often stop objections because now the client knows why certain information is important. If, for example, you want to determine the client’s budget for your solution, it can seem intrusive and aggressive to come right out and ask. Prefacing would allow you to say something like, “We would like to tailor our solution in a way that directly aligns our recommendation with your budget. Can you share how you have budgeted for this?” If the client says there is no current budget, you can take that one of two ways. It can be an early warning sign that this is not a good sales opportunity to pursue at this time, or it can signal the potential to align with the client and help them build a business case to win the budget.

Trading: This is similar to prefacing but refers to your willingness to share information if the client is willing to share in a similar manner. You might say, “We have worked with a number of clients who have achieved better results by combining solutions A and B. What are your thoughts around looking at a similar approach in your organization?” With this approach, you share that others have had success and ask for them to share their thinking. It also helps with what we call credentialing, providing subtle examples that you’ve worked with clients of a similar size or industry and have been successful. When done well, trading can open up the dialogue in meaningful ways.

Drilling down: We, as salespeople, often feel under time pressures to cover as much ground as possible in a meeting. Or, we fear appearing stupid and feel that we should already know what the client is sharing with us. As a result, we frequently are afraid to explore or question deeper. I am now seeing a very different approach from those who have a genuine curiosity about their clients. They are not afraid to enter into areas where they are not experts or know all the answers. They simply are interested in understanding the client’s perspective from multiple angles, and they use the drill-down skill to do this. When this happens, the client feels that the salesperson is sincerely interested and not just gathering data. The client is more likely to open up and share really important information that enables the salesperson to bring real relevance and value to the table.

Pacing: Salespeople tend to find pacing especially difficult. The idea is to ask one question, stop talking and listen. Instead, salespeople will often ask a question and, before the client responds, they’ll answer it themselves. Sometimes, salespeople offer a drop-down menu: “What’s your main concern here? Is it price? Is it location? Is it an issue around implementation?” The client might answer, “It wasn’t any of those, but they’re all concerns now.” Similarly, salespeople often ask two, three or four questions at once: “What’s your decision criterion? When are you thinking about making a decision? What’s your timing on implementation and rollout?” The client often only answers the last question because it’s the only one that they remember. So, pace the conversation. Ask your question, and let the client think about it and respond. Silence can be a salesperson’s best friend.