There's an old Sandler rule: no mutual mystification. Translated, it means don't assume you understand what your prospect means. Ask.
It sounds simple. In practice, most salespeople talk far more than they listen. They hear a prospect's first answer, assume they know the rest, and launch into a pitch. The result is a longer sales cycle, more objections, and proposals that miss the mark.
Asking better questions is the most reliable way to slow down the conversation and speed up the sale.
Why telling isn't selling
When you tell a prospect why they should buy, they evaluate your claims and look for reasons to doubt them. When you ask a question that leads them to their own conclusion, they believe it. People trust what they say far more than what they hear.
That's why Sandler encourages salespeople to aim for the prospect doing about 70% of the talking. Your role is to guide the conversation, not dominate it.
5 sales questioning techniques that move deals forward
1. Open-ended discovery questions
Closed questions get yes-or-no answers. Open-ended questions get information. Swap "Is budget a concern?" for "How have you thought about investing in a fix for this?" Start questions with what, how, and tell me about.
2. Reversing
Reversing is answering a question with a question. It's one of the core Sandler questioning techniques. When a prospect asks, "Do you offer a discount?", a rushed salesperson answers immediately. A Sandler-trained salesperson asks, "That's a fair question. Help me understand why you're asking." The answer reveals what the prospect really cares about, whether it's budget, a competing quote, or approval from someone above them.
Reverse with care. Always soften first, and never reverse so often that it feels evasive.
3. Softening statements
A string of direct questions can feel like an interrogation. Softening statements keep the conversation comfortable:
- "That's a great question."
- "I'm glad you brought that up."
- "I'm curious about something you mentioned earlier."
They lower the prospect's guard and make it easier to keep going deeper.
4. Clarifying questions
Words like soon, expensive, a lot, and better mean different things to different people. Clarify them. "When you say soon, what does that look like for you?" One clarifying question can prevent a forecast that's off by a full quarter.
5. Negative reverse selling
Sometimes the fastest way to get a prospect to lean in is to take a step back. "It sounds like this might not be a priority right now. Should we revisit it next year?" If the pain is real, the prospect will tell you why it can't wait. If it isn't, you've just saved yourself weeks of chasing.
Active listening in sales: the other half of questioning
Great questions are wasted if you don't listen to the answers. Active listening in sales means:
- Pausing before you respond. Silence often prompts the prospect to add the detail that matters most.
- Summarizing what you heard. "So if I understand you correctly..." confirms understanding and shows respect.
- Following the thread. Your next question should come from their last answer, not your call plan.
How questioning speeds up the sale
It can feel like questions slow things down. In reality, they remove the friction that stalls deals:
- Fewer surprises late in the cycle. Concerns raised early are easier to handle than objections at the proposal stage.
- Faster qualification. Good questions reveal quickly whether there's pain, budget, and a clear decision process.
- Stronger proposals. When you know exactly what the prospect needs, your proposal confirms what they've already agreed to rather than introducing new ideas.
Questioning is also what powers the Pain Funnel. If you missed it, read our previous post on how the Sandler Pain Funnel shortens your sales cycle. [Link to Post 1]
Make questions a habit, not a tactic
The goal isn't to memorize clever questions. It's to replace the instinct to tell with the instinct to ask. Start with one change on your next call: when a prospect asks a question, reverse it once before you answer. Notice how much more you learn.
In our final post this month, we'll look at the questions that matter most at the end of qualification: understanding exactly how your prospect will make a decision. [Link to Post 3]
Want your team asking better questions? Talk to your local Sandler trainer about building questioning skills that hold up under pressure.
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