Importance of Follow-Up Questions in Negotiation

Assumptions are where sales deals go to die.. Yesterday, I was with the Intelligent Technical Solutions team for their 2025 sales kickoff, working through Breakthrough Conversations, focusing on how they can have better conversations with their buyers. One of the biggest challenges we discussed was how assumptions can derail the sales process. We know our product or service so well that we start to anticipate what buyers will say. We've heard the same questions and objections so many times that our brains fill in the gaps automatically and we rush. We pitch too soon. We propose too soon. We skip over the critical questions that help buyers truly understand their problems, the impact of those problems, and why solving them matters. It reminded me of something I learned in the Army. Assumptions are necessary for planning, but you don’t stop there. You send out reconnaissance to confirm or deny those assumptions. In sales, our reconnaissance is asking questions. Great questions. Follow-up questions. Questions that challenge our assumptions and uncover what’s really going on. When we do this, three things happen: 1. We show our buyers that we're actually listening. Asking the right follow up questions demonstrates that we care about what they’re saying and value their perspective. 2. We help them connect the dots. By answering our questions, they start to see the scope and importance of their problem in a way they hadn’t before. 3. We set ourselves up for success. Buyers who feel connected to us and who understand their own problem clearly, are far more ready to buy—and they’ll see us as trusted guides in the process. So here’s the challenge: Take a hard look at your sales calls and conversations. Are you letting assumptions run the show? Are you skipping the steps that help your buyers truly understand what’s at stake? If the answer is yes, stop. Start asking the right questions. Confirm and deny your assumptions. Because in sales—and in all communication—assumptions aren’t just a shortcut. They’re a dead end. #sales #salescommunication #salestraining #breakthroughconversations

When a prospect tells you they're struggling with something, they're handing you the keys to the kingdom. That moment of raw honesty is your opportunity to create real connection, demonstrate understanding, and actually SERVE them what they need (the whole point of sales). But so many reps rush past these golden moments. They hear the prospect mention a challenge and think, "Great, I can check that box and move on to the next question in my script." When someone identifies with a problem you've mentioned, that's your signal to dig deeper into that specific pain point... not move on to the next stage of the close. I recently watched a recording of a sales call where a prospect said: "Yeah, we're really struggling with lead quality right now." Instead of exploring that critical issue, the rep responded, "Great, and how many employees do you have?" There is no faster way to lose a deal than this. The prospect was practically begging to talk about their lead quality issues (a problem the rep's company could definitely solve). But the rep was so focused on completing their script that they missed the opportunity. In moments like these, you always need to double down. Ask follow-up questions like: "How long has that been a challenge for you?" "What impact is that having on your business?" "What have you tried to solve that problem already?" These deeper questions do two powerful things: They help the prospect fully articulate their pain (often revealing it's even worse than they initially suggested)... AND they position you as someone who genuinely wants to understand their situation (which you are). Next time a prospect identifies with a problem you've mentioned, resist the urge to move on. Go deeper. The sale is often hiding in those details.