Strategies for Addressing Client Concerns Directly

"Just checking in on that proposal." I sent this email the other day. My 4th "check-in" to this prospect. No response. Frustrated, I called my sales amigo: "I don't get it. Great demo, they loved our solution, but now they've gone dark." He asked a simple question: "What content have they engaged with since your demo?" I had no idea. The truth hit me: I was flying blind. I sent PDFs, presentations, and pricing. But had zero visibility into what they actually viewed. Were they showing it to others? Did they have concerns? Was anything resonating? I had no clue. Last week, I tried a different approach: After a promising demo, instead of attaching files to an email, I created a digital sales room. Inside: - Everything they needed to evaluate us - Organized by their specific priorities - Clear calls-to-action for next steps The difference was immediate: Day 1: The main contact viewed the ROI calculator twice Day 2: They shared it with their CFO (who I'd never spoken to) Day 3: The CFO spent 30 minutes on pricing information Day 4: They downloaded our security documentation Day 5: The main contact viewed implementation timeline 3 times I picked up the phone: "I noticed you've been looking at our implementation process. Any questions about that timeline?" Their response: "How did you know? Yes, actually, we're concerned about..." The objection surfaced BEFORE it killed the deal. Old school selling: Send content. Cross fingers. Guess what's happening. Modern selling: Share content. Watch engagement. Address concerns proactively. The hard truth: 90% of buying happens when you're not in the room. Are you still pretending those blind "check-in" calls are a strategy? Or are you watching how prospects actually consume information when you're not there? Stop asking prospects to update you. Start building systems that show you what's really happening. Agree?

This takes guts. Prospects often keep concerns to themselves. Why? There’s no trust. They’re afraid their concerns could be used against them or lead to manipulation. People are conditioned to be polite and avoid conflict. This can make it hard for prospects to openly express negative thoughts or skepticism. It can be uncomfortable to express doubts. The result? Stalled deals or ghosting. The way out? Call it out. By calling out what seems off, you encourage prospects to share what’s really on their mind, giving you the chance to address their concerns directly. Here are a few examples: “It seems like timing is off.” “It feels like you have some concerns.” “I’m sensing price might be a sticking point.” “You’re not sure this will work for you.” “Won’t there be internal pushback from your CFO?” “It seems like this might not be a priority for you right now.” “It feels like you might be concerned about implementation.” If you guess wrong, that’s okay. People like to correct, but they don’t like being corrected. Just because you don’t call out the elephants in the room doesn’t mean they’re not there. Unlocking truth is a good skill to learn and master. No truth, no trust. No trust, no transaction.

Objection handling done wrong causes buyers to say less. Objection handling done right encourages buyers to say more. (And let's be honest, it's hard to overcome objections if you don't truly understand what they are.) Quick story: (Internal conversation) "We should share our concerns with the seller." "There's no point, they'll just tell us we are wrong and try to convince us otherwise. I voce we just go with the competing solution and inform them they lost the deal next week." (If you're in sales or customer success, this conversation should worry you.) The best sellers I've worked seem to genuine want feedback in a way that leverages curiosity and transparency. Last year, I worked with a seller who got this right. We shared feedback on their proposal covering three main concerns: ability to meet technical requirements, self-serve capabilities, and pricing that scaled with our user base. Here's what they did so well in my opinon: 🔸 They listened instead of immediately refuting and problem-solving 🔸 They asked clarifying questions rather than getting defensive 🔸 They explored our use case instead of demanding to know the competition 🔸 They created space for more feedback rather than shutting it down At the end of the call, they said: "Thank you for sharing this. Here's what I heard you say [restated our concerns]. I'd like to address a couple of these points, but first let me touch base with our solutions consultant. Could we grab 30 minutes tomorrow? If it doesn't address your concerns, we'll graciously bow out. We don't want a bad fit. But based on what you shared, I think there might be some misunderstandings we can clear up." We agreed to the call. Turns out, there were misunderstandings. But here's the thing: admittedly we almost didn't share that feedback in the first place. Why? Because usually it feels like it falls on deaf ears or the seller will do anything to close the deal. I've shared this story before but encountered a similar situation last week so I thought it was worth sharing.