Tips for Engaging Prospects on Calls

Cold calling lesson: Don’t pitch. Poke. Let’s say I’m selling software that filters out fake AI-generated job applications. I could open the call like this: “Hey, we help talent teams eliminate AI-generated applications before they hit your ATS. We use advanced detection to save hours of recruiter time. The purpose of my call is to schedule time to show you how it works.” That’s a pitch. And when people feel pitched, they brace themselves. They get quiet. Guarded. Distrustful. Now let’s try poking the bear instead: “Not sure if you’re seeing this, but a bunch of companies are getting flooded with AI-generated job apps that look totally legit. How are you spotting those before they hit your ATS?” That’s not a pitch. That’s an illumination question. It surfaces a blind spot. It creates a little tension. It invites someone to think, not defend. Here’s the psychology: When you pitch, you’re telling them what their problem is. When you poke the bear, you’re letting them recognize it for themselves. That moment of recognition is where curiosity begins. And curiosity opens the door to conversation. So next time you’re on a cold call, ditch the pitch. Poke the bear. Buyers have the answers. Sellers have the questions.

You’re either talking AT your prospects or WITH them And trust me the difference is everything Heres a quick reality check One of the SDRs I worked with this week was using an opener like this on their cold calls “On a scale of 1-5 hows your experience with XYZ?” Its well intentioned but thats a dead end question that usually leads to a quick number and then silence right? Now you’re stuck trying to dig deeper without much context Instead we refined it like this “Saw you’re using XYZ for customer support. I was talking with Sara and Mike last week who said it’s about a 3.5 on a good day. Just curious hows the experience been for you?” This approach 👉 gives the prospect something real to work off of 👉 shows credibility by referencing peers in their space 👉 and opens the door for a genuine conversation If they say “It’s a 5! We love it!”- perfect! Now ask whats really moving the needle for them If they say “Yeah it’s about a 3 for us too” Awesome! Thats your chance to dig deeper “What’s holding it back from being a 4 or 5?” Now you’re not just grilling them with basic questions you’re guiding a conversation driven by real curiosity and insights As sales reps remember we get the chance to talk to a ton of folks in our ICP every week Use those conversations to refine your approach and bring real value into the next call It’s all about talking WITH them—not AT them But hey if you’d rather keep talking at your prospects… Well maybe cold calling is dying and you’ll end up like these guys ☠️📞

Problems sell deals—but leading with problems can backfire with outbound. Why? Because outbound is a game of first impressions. And you know what may not make a great first impression? Telling someone—who never asked you to reach out to them—about all the problems they have. Let me give you an example: ⛔️ Lead with problem Prospect: "Hello?" Rep: "Hi Samantha—it's Jason. I'm curious, how are you removing all the redundant work from your support team's workload to reduce support costs?" That's going right for the jugular. It takes a special kind of rep to be aggressive and pull off the tone to get the prospect leaning in. It's too assumptive for having met someone 10 seconds ago. ✅ Lead with priority, followed by problem This sounds more like this... Prospect: "Hello?" Rep: "Hi Samantha, it's Jason. I'm calling because we met with a support leader at a large retailer yesterday. They needed to scale more personalized customer interactions, but their team was bogged down with repetitive work that was driving up the cost to serve. Is that by chance top of mind for you as well?" ~~~ It doesn't seem like much, but you'll get prospects to open up way more when you— 1) Don't assume they have the problem 2) Lead with a goal or aspiration Try this in your cold calls this week and you'll get prospects to open up more.