Overcoming Call Reluctance: How to Stop the Mental Block of Interrupting Prospects (Ask Jeb)

Overcoming call reluctance starts with understanding why even seasoned sales pros freeze up when it's time to pick up the phone. They're paralyzed by one simple fear: interrupting a prospect's day. That's exactly what Kurt Roberts from Richmond, Virginia, brought to the table. Kurt's problem wasn't about not knowing what to say or how to pitch—it was the mental block around the very idea of interruption. He hated being interrupted by low-quality sales calls himself. And even though 99% of the time prospects were receptive to his message, he couldn't shake the feeling that he was being pushy just by dialing the phone. Kurt's got the skills. He knows what to say. His prospects love him once they're talking. But every time he reaches for the phone, his stomach knots up. Sound familiar? If you've ever stared at your phone, finger hovering over the dial button, worried about being "that pushy salesperson," you're not alone. The Projection Trap: Why Your Empathy Is Working Against You Kurt's challenge is rooted in something I call projection—deciding for your customer how they'll feel before you've even spoken to them. If you have a high level of empathy (and many great salespeople do), you naturally put yourself in the other person's shoes. You think: "I wouldn't want to be interrupted, so they won't either." Here's the brutal truth: That empathy is killing your pipeline. Because you don't actually know if your call will be an annoyance or the best thing to happen to them today. I've bought plenty of products from salespeople who "interrupted" me, because their timing and message were right. That wouldn't have happened if they'd let their fear of bothering me keep them from picking up the phone. The One Thing That Makes Interruption Welcome Nobody likes to be interrupted. But if you are going to interrupt, make it worth their time. Think about it: Would you rather get a cold call from someone who clearly knows nothing about you, or from someone who's done their homework and has a relevant, valuable reason for reaching out? There are two ways to make your outreach relevant: 1. Personalized Messaging for High-Value Prospects Do your research on the specific individual. Learn about their company, role, and current challenges. Use that to craft a tailored message that connects your solution directly to their world. This is essential for high-value, niche, or executive-level prospects. 2. Targeted Messaging for Scaled Outreach Build messaging that resonates with a clearly defined group—people who share the same role, industry, geography, or problem set. It's not as specific as personalized outreach, but it's still relevant to most people in your target list. Test it. If your calls fall flat, adjust the message until it clicks. Stop Confusing Prep Work with Prospecting Here's where most salespeople sabotage themselves: They spend their "prospecting time" researching LinkedIn profiles and crafting the perfect email instead of actually dialing. Let me be clear: Research is not prospecting. Building messaging is not prospecting. Prospecting is picking up the phone and interrupting people. Everything else is prep work. Block separate time for building your targeted or personalized messaging. Then protect your prospecting time like your mortgage payment depends on it—because it does. From Pushy to Helpful: Reframing Interruption Kurt's empathy makes him a sales rockstar once he's in conversation. But he was letting his concern for prospects' feelings rob them of the chance to work with him. That's not empathy—that's selfish. The shift is simple but not easy: You're not interrupting to take from them, you're interrupting to help them. You've earned the right to interrupt because you've done the work to make your outreach relevant. Missing a chance to help them because you didn't call? That's the real loss. 5-Step Action Plan to Crush Call Reluctance If you're struggling like Kurt,