You’ve covered the basics in your sales conversations. You understand the prospect’s needs, challenges, and goals. Now it’s time to go deeper.
In complex sales, the questions that move an opportunity forward can feel uncomfortable. That’s why many salespeople avoid them. But asking directly can help you understand how the decision will be made, what you’re up against, and whether your solution is truly a fit.
Here are five questions worth adding to your discovery conversations.
Who are the buyers and influencers?
The person you’re speaking with may not be the only person involved in the decision. Ask whether they’ll make the final call or recommend a solution to someone else. Find out who will use your product or service, and who inside the organization could champion or influence the decision.
When appropriate, ask to meet those people. The more clearly you understand the decision-making group, the better you can support the process.
Who else are you considering?
If the prospect is evaluating multiple providers, ask who else is in the running. You deserve to understand what you’re being compared against.
This isn’t about criticizing competitors. It’s about learning what matters to the prospect and how they’ll weigh their options.
Why might we be the right choice?
Ask what the prospect has learned about your solution that makes it a strong fit. Which parts of your approach address their needs? What value have you demonstrated that sets you apart?
Their answer can show whether your message is landing—and where you may need to clarify your value.
What could keep us from moving forward?
It can be just as useful to understand why you might lose. Ask what may be missing from your proposal or solution, or what could lead the prospect to choose another provider.
The answer may reveal an unresolved concern, a gap in your understanding, or a decision factor you haven’t discussed yet.
What have you learned from our conversations?
After several meetings, ask the prospect what they’ve learned about your product or service that they didn’t know before. What do they now understand about how your solution could help?
This gives you a chance to check whether the conversations have been useful and whether the prospect sees a clear connection between your solution and their needs.
Ask the questions that move the conversation forward
These questions can uncover decision dynamics, competitive risks, and the value a prospect sees in your solution. They may feel uncomfortable at first, but a direct, respectful conversation can help both sides decide whether there’s a good reason to move forward.
Don’t be afraid to ask.
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For sales teams looking to improve sales meeting questions, sales discovery, pipeline management, sales qualification, forecasting, prospecting, objection handling, and close rates, Scott Bliss, Sandler Jersey Shore, helps sales professionals and leaders build structured, repeatable sales processes.
Through proven Sandler sales training and sales coaching, teams can create more qualified opportunities, improve pipeline accuracy, increase productivity, and achieve more predictable results. Sales professionals can also strengthen B2B sales, consultative selling, opportunity management, discovery skills, and sales performance—while learning how to identify stalled deals and move them forward.
