How to Start Sales Calls with Confidence

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.

I analyzed 1,000+ cold calls and discovered why 87% of them fail in the first 10 seconds. The problem isn't your product or your pitch. It's that gatekeepers are programmed to instantly recognize and reject salespeople based on subtle cues most of us don't realize we're giving off. Let’s say the data is wrong in your tech stack and there’s no verified decision-maker name that you can find online that you can confidently call directly. Salesperson: "Hi, I'd like to speak with your CEO about our revolutionary software solution!" Gatekeeper: "What company are you with?" Salesperson: "I'm with TechBoost and we help companies like yours increase efficiency by 300%!" Gatekeeper: "We're not interested." Salesperson: "But you haven't even heard about our… " Gatekeeper: *click* Here's what works instead... Salesperson: "Hi Sarah, I'm hoping you can help me out..." [pause] Gatekeeper: "Sure, what do you need?" Salesperson: "My name is Marcus. It's my job to update our records as we help businesses with data security. Who's in charge of making decisions regarding that there?" Gatekeeper: "That would be Bob, our CTO." Salesperson: "Great, thanks. If you don't mind me asking (PAUSE)…who are you currently using for security?" Gatekeeper: "We use PaloAlto Networks but I think we’ve used them for 5 years now and are happy" Salesperson: "Appreciate that transparency. What's the best time to reach Bob?" Gatekeeper: "Mornings are usually better." Salesperson: "Perfect. Could you send me to his voicemail please?" Gatekeeper: "Of course, connecting you now." Here's the thing. Most sales reps are shooting themselves in the foot before they even finish their introduction. After coaching thousands of B2B teams, I've discovered three non-negotiable elements to mastering gatekeeper conversations: ➡️ PATTERN INTERRUPT Start with zero information. No company name. No title. Just a simple "I'm hoping you can help me out" with a pause. This instantly differentiates you from the 99% of salespeople who launch into a pitch. ➡️ INQUISITIVE TONALITY Not excited. Not aggressive. Not salesy. Think about how you'd sound if you were lost at a store looking for the cereal aisle. That's the tone that gets gatekeepers to lower their guard. ➡️ INFORMATION SEEKING APPROACH Your goal isn't to sell the gatekeeper. It's to gather intel. When you position yourself as someone updating records rather than pushing products, doors magically open. When you combine these three elements, something powerful happens: The gatekeeper starts perceiving you as one of the only types of callers they're programmed to help rather than block. I've seen reps go from 10% connection rates to 50%+ using this exact framework. You can't blow your numbers without qualified pipeline, and you can't build pipeline if you're getting blocked at the gate. Master this approach and watch your calendar fill with qualified meetings.

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.