How to Engage Prospects Without Being Pushy

I just watched a rep lose a HIGH 6 figure deal in the first 5 minutes. Not because of price. Not because of product fit. Because of tonality. Here's what happened: Prospect: "Hi, nice to meet you. Just finished walking my dog..." Rep: "Great. What business priority brought you here today?" Prospect: "Um... we're just looking at options..." Call went downhill from there. The problem: Some reps have only one communication style. For instance: Direct and aggressive. But 60% of prospects need a softer approach to open up. Here's the framework I teach top performers: 1) Read the prospect in 30 seconds Fast talker, "let's cut to the chase" = match their energy Slow speaker, relationship-focused = dial it down 2) Adjust your questions accordingly Instead of: "Who's the decision maker?" Try: "Typically when companies evaluate new solutions, it involves a few people. In your organization, who would usually be part of that process?" Same information. Completely different response rate. 3) Practice the uncomfortable Yes, it feels fake at first. Your brain says "this isn't me." But you're not being disingenuous. You're adapting your communication style to connect better. The drill: Record yourself asking 5 discovery questions at different tonality levels for 20 minutes daily. Level 10 = drill sergeant Level 5 = curious colleague Level 2 = supportive friend When reps master tonality… Discovery calls run 40% longer Prospects share sensitive information earlier Close rates increase 30%+ One of my clients went from 23% to 31% close rate just by softening her delivery on budget and stakeholder questions. You can have the best discovery framework in the world, but if your tonality shuts prospects down, none of it matters. Sales leaders: This is coachable. Shadow your reps' calls and listen for tonality mismatches. Role-play different prospect personalities in team meetings. The reps who master this skill connect with every buyer type and consistently hit quota. P.S. DM me if you want to install this in your teams.

Someone asked me how many follow-ups I send to prospects who’ve shown interest but haven’t bought yet. My answer? I don’t stop. But I’m not “just checking in.” I’m making deposits. A deposit = information that makes people smarter about a topic they care about. (Like this post.) You can do this too. Create a Top of Mind sequence. Add prospects to it when they’re not ready yet. Not with “just bumping this to the top of your inbox.” Not with pressure. With perspective. With insight. With generosity. Start simple: Write down 5 questions your customers typically ask before they buy. Now turn each question into one email. One answer per message. You can even make it a video. Let your personality beam through. Don’t pitch. Don’t chase. Just teach. They may not buy now. But when the timing is right? You’ll be the first person they think of. Because you didn’t follow up. You followed through.

Ready to make your prospects the star of the show? Let me put you on to a play I used to run as a rep that still hits hard in trainings today “The Heros Trailer” video play Picture this Your prospect is the hero facing their big challenge (cue the dramatic music) Your job? Help them see how your product is the missing piece they need to overcome it Heres how you can run it 1. Highlight their journey In your video don’t make it all about you—make it all about them. Show that you understand their current struggle - “Here’s the challenge you’re likely dealing with and heres how we help heroes like you solve it” 2. Tease the solution Like any good movie trailer you’ve got to keep it intriguing. Don’t spill all the beans. Give just enough so they’re curious to see how it all plays out. This isn’t the full demo. it’s a teaser. “Imagine if you had a tool that does [X] you’d be able to achieve [Y]” 3. Back it up with credibility Drop in “reviews” from other heroes (aka testimonials) “Sara and Mike were in the same boat but after using [our product] they saw XYZ results” now you’ve got their attention and you’ve built trust without sounding pushy 4. The big CTA End with a cliffhanger “Let’s schedule a time for you to see the full picture” make it feel like a VIP screening they can’t miss 5. Get creative with distribution It’s not just about the video—it’s how you deliver it. Send it via email, LinkedIn DM or even a voice note follow up. Your goal is to cut through the noise and give them something different—something that makes them feel like you really get their journey The reason this works? You’re not just pitching you’re positioning yourself as the guide that helps them shine It’s all about their success story When SDRs in recent trainings tested this play they started landing meetings they’d been chasing for weeks The feedback? “This feels more like a conversation than a sales pitch—it’s engaging” So next time you’re setting up your outreach ask yourself How can you help your prospect see themselves as the hero in their story—and position your product as the tool that helps them get there? Give this play a shot and let me know how it goes 🤘