Closer, are you looking to reach the real decision makers in your next sales meeting? The key might not be in your pitch, but in the sales questions you ask.
One common challenge sales professionals face is getting stuck with a single prospect who may not have the authority to move the deal forward. Often, this happens because we ask the same types of sales questions. The questions that the person in front of us can easily answer. This approach keeps the conversation going, but it doesn’t necessarily help us reach the real decision-makers.
Getting stuck with one contact is one of the most common reasons deals stall. The natural flow of a sales call rewards staying in comfortable territory, asking questions the person in front of you can answer – and avoiding the friction that comes with pushing for broader access.
The problem is that comfort at the contact level can create a false sense of progress. The conversation is going well, the prospect seems engaged, and the next steps feel solid. But if the person across the table can’t actually approve the deal, all of that momentum has a ceiling.
Knowing how to reach decision makers isn’t about bypassing your current contact or making them feel sidelined. The most effective path runs directly through them in order to gain buy-in from multiple stakeholders.
So how do you bring more voices to the table? Try this: start asking sales questions that your current POC can’t answer.
For example, if you’re speaking with someone in operations, ask a question that only someone in dev could answer. If you’re talking to someone in marketing, pose a question that requires input from the customer success team.
The goal is to create natural opportunities for your prospect to realize they need to loop in other colleagues.
When your contact says, “I’m not sure,” for the third time, you have the perfect opening to respond with: “That’s OK! Let me ask you this: who would know the answer? Would it make sense to bring them into our next conversation so I can understand the bigger picture and tailor this offer to fit your team’s needs?”
By strategically using sales questions to expand the conversation, you not only gather valuable insights but also increase your chances of getting buy-in from multiple stakeholders – moving your deal forward faster.
This technique only works if the questions are genuinely outside your POC’s wheelhouse. That requires some prep from you before the meeting.
Before each call, map out what you already know about the organization. Who else is likely affected by this purchase? What departments have a stake in the outcome? What would someone in finance, legal, or HR need to weigh in on that your current contact almost certainly can’t answer alone?
The more specifically you can tie a question to a function your contact doesn’t own, the more natural the handoff becomes. A question like “how does your HR team typically handle onboarding for new tools at this scale?” is specific enough that an operations contact will immediately recognize it’s outside their lane. That recognition is exactly what creates the opening you need.
This is also where your pre-call research on the organization’s structure pays off. The better you understand who owns what, the more precisely you can craft questions that point toward the right people.
Getting the meeting expanded is only half the job. When new stakeholders join, resist the urge to restart from the beginning or deliver a generic pitch to the broader group. That wastes the credibility your original contact helped you build.
Instead, use what you learned from your initial conversations to frame the discussion around the issues that matter to the people now in the room. Speak directly to why this solution is relevant to each stakeholder’s specific concerns, right now, rather than presenting a one-size pitch to a mixed audience.
One risk in this approach is making your initial contact feel bypassed or undermined. If they sense you’re trying to go around them, they can become an obstacle rather than an ally.
The language matters. “Who would know the answer to that?” is collaborative. It positions your contact as a guide rather than a gatekeeper. “I’d love to make sure I’m bringing the right solution to your whole team” signals that expanding the conversation benefits them, too.
So next time you’re in a sales call, rethink your approach. The right sales questions don’t just get answers. They get results.
Deals stalling before you can get to the right people? Explore the Work the Deal™ methodology for strategies to keep complex sales moving forward.