7 cold calling mistakes I see sales reps make (& how to avoid them), according t...

I've made over 11,000 cold calls. I've booked 335 meetings, closed over $287k at a startup company and $40m in an enterprise multinational company, and saw what works. I've also seen what burns out reps fast. I remember one call early in my career that still haunts me - in a good way.

I dialed a prospect I'd researched for hours. I thought I had the perfect pitch. I started strong, hit all the value points, and delivered what I thought was a flawless opener. I was proud of it. But before I could even ask a question, I got hit with a brutal, "Not interested. Take me off your list."

I froze. I didn't push back. I didn't clarify. I just said "Thanks for your time" and hung up. I felt the rejection hard. I told myself I had failed. But instead of brushing it off, I replayed the call. I asked myself what went wrong. And, that's what I'll talk about here today.

Table of Contents

• My Time At the Phone
• Common Cold Calling Mistakes I've Seen Reps Make
• Pivoting From Mistakes to Success

My Time At the Phone

I've spent 17 years in the outbound sales trenches - and I mean the real trenches, the ones where your day lives and dies by that first 30 seconds on the phone.

I've made 11,519 cold calls. Sent over 650k emails. And I've learned that success doesn't come from talent. Instead, it comes from pattern recognition, consistency, and a willingness to get punched in the mouth and dial again.

I didn't start off great. I used to talk too much. I'd come in trying to prove value before earning the right to be heard. I thought I had to sound like I knew everything. But the truth? I didn't need to sound smart. I needed to be curious. I needed to make it about them, not me.

So I made the shift. I began opening with relevance, not rapport. I asked better questions. I focused on timing, context, and urgency. I wanted to learn why now, not just why us. From there, everything changed.

Over time, I started noticing patterns. I...