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.
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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 saw reps over-script and under-listen. I watched reps freeze when objections came up, or worse, avoid them entirely. I saw people mistake politeness for the pipeline.
I realized I didn’t want to be that rep. I didn’t want to manage feelings. I wanted to drive outcomes.
So I built a system. I tracked every metric. I A/B tested intros. I treated every “no” like a feedback loop. I turned cold calling into something structured, repeatable, and scalable.
That’s how I’ve booked 335 meetings, converted 69.1% into SQLs, kept my no-show rate below 18%, and closed over $287k in new business from cold outreach alone.
But beyond the numbers, what really matters to me is this: I’ve coached SDRs, AEs, and founders who felt stuck in their outreach, who were burnt out from the constant rejection, who were tired of the same empty scripts that didn’t reflect their voice or their value.
Together, we fixed that. We rewired their mindset. We redesigned their messaging. And we rebuilt their confidence.
I’ve done this across every continent I’ve worked in, from startups to corporates, across industries. I’ve supported teams in the USA, Brazil, LATAM, Europe, the Middle East, and Asia, helping them sharpen their outbound playbooks and land meetings with people they never thought would pick up the phone.
This isn’t theory. This is lived experience.
So if you’re making cold calls or leading a team that does, I’ve probably seen your exact challenge before. And, I’m here to tell you: cold calling isn’t dead. It’s just misunderstood.
Beyond that, cold calling is like science, meaning it’s always evolving. Today, the trend is a multi-channel approach plus hyper-personalization, using ABM (account-based marketing) strategies.
It’s like a sales funnel idea, when you have more opportunities of contacting that lead, you can increase the chances of having better conversations and conversions, so your KPI’s and sales improve with a solid strategy.
Common Cold Calling Mistakes I’ve Seen Reps Make
1. Pitching Too Early
I used to jump into the call like it was a 100-meter sprint. As soon as someone picked up, I felt this rush to pitch. I thought, “I have 30 seconds. I’d better say something brilliant before they hang up.” So I led with features, results, big client names, all the things I thought would grab their attention.
It didn’t work. Not because my pitch was bad, but because I hadn’t earned the right to give it yet.
People don’t want to be pitched. They want to be understood. They want to know why you’re calling them specifically, right now, and whether it’s worth their time to stay on the line.
Once I stopped trying to impress, I started to engage. I learned to open with context. I showed that I knew the company by mentioning a funding round they just raised, a new initiative their company launched, or a role they recently stepped into. Then, I asked a smart question, one that opened a door instead of slamming one shut.
That approach changed everything. When the first 10 seconds feel tailored, people stop bracing for the pitch and start listening for value.
2. Over-Relying on the Script
I’ve seen this play out across so many teams. The rep prints out a script, memorizes it word for word, and reads it like a customer service manual. No pauses. No personalization. No flexibility.
I used to do this too. Especially when I was new, the script gave me confidence. It felt safe, that is, until it didn’t.
The moment someone interrupted me or said something I wasn’t prepared for, I froze. The call derailed. I didn’t know how to recover, because the script didn’t give me permission to think.
That’s when I made a shift. I stopped treating the script like gospel. I started using it like a compass. Something to guide direction, not dictate every word.
I created frameworks instead, with openers that had modular parts. Objection responses that could be adapted. A structure that gave me freedom to be human, while still staying intentional.
The result? I sounded more natural. More confident. More in control. The person on the other end noticed, and they stayed on the line longer.
3. Mistaking Politeness for Pipeline
Early on, I celebrated every polite response.
“Interesting.”
“Send me more info.”
“Sounds like a good fit.”
But guess what? None of those people replied to my follow-ups. None showed up to meetings. None converted. I learned that these platitudes weren’t real signals. They were soft deflections — ways for the prospect to end the conversation without conflict.
I learned that politeness isn’t a commitment, and vague enthusiasm isn’t a pipeline. So, I started clarifying.
- “When you say interesting, what stood out to you?”
- “Is this something you’re actively exploring or just a general interest?”
- “Would it make sense to schedule something now, or is this not a priority?”
When you start qualifying early, you stop wasting time. Your calendar gets tighter. Your pipeline gets healthier. Most importantly, your energy stays focused on real opportunities, not on chasing ghosts.
4. Panicking at Objections
Early in my career, objections scared me. A “no budget,” or “we already use someone,” or “we’re not interested” would throw me off completely. I’d feel defeated. I’d try to defend or overexplain. Worse, I would just end the call and tell myself, “They weren’t ready anyway.”
Then, I realized something: Objections aren’t rejection. They’re engagement.
If someone pushes back, it means they’re thinking. It means they heard you. They care enough to have a perspective.
So I changed my relationship with objections. I tracked them. I studied them. I wrote down every common pattern and created responses to reframe pushback. Now, when I hear an objection, I lean in with curated responses.
- “Oh, that’s exactly why I’m reaching out.”
- “Totally understand. Can I ask you something about that?”
- “What would need to change for this to be more of a priority?”
Objections became my signal that I was getting closer, not further.
5. Talking More Than I Listen
In the beginning, I treated every call like a performance. I thought I had to drive the entire conversation, always have the next point ready, and sound confident.
Then, I realized that the more I talked, the less they did. The less they talked, the less I learned. The less I learned, the weaker my pitch became. In the end, I was pitching to assumptions, not real context.
So, I flipped it. I trained myself to ask, pause, and wait. I practiced listening to both their words and their tone. Their energy. Their timing. I used techniques like mirroring, summarizing, and layering my questions. Prospects opened up. They told me what they actually cared about. What was urgent? What was blocking them?
From there, it stopped being a pitch and started becoming a real conversation — one built on curiosity, not control.
6. Not Personalizing the Opener
I used to start every call with “How are you today?” or “Do you have 30 seconds?” And while it felt polite, it also felt … forgettable. Because, that’s what everyone says.
In cold calling, sounding like everyone else is the fastest way to get ignored. So, I stopped being generic. I started being specific. If they just hired a new CRO, I opened with that. If they announced a new partnership, I mentioned it. If they posted something on LinkedIn, I referenced it in the first line.
Personalization isn’t fluff. It’s friction removal. It shows you’ve done your homework and that this call isn’t just random. You came prepared to speak to them, not just a persona.
When you do that, people listen. Not because they owe you time. But because you’ve earned their attention.
7. Giving Up Too Soon
There was a time when every “not interested” felt like a wall. I’d thank them, hang up, and move on. I told myself, “They’re just not ready.” But in reality, I gave up too early.
Then I started treating every call, good or bad, as data. I tracked my tonality, my timing, my opener, even the time of day. I started noticing patterns.
- Sometimes, a quick “no” was actually a timing issue.
- Sometimes, I could re-engage the same contact two weeks later and get a yes.
- Sometimes, I wasn’t even getting rejected. I was just poorly positioned.
Now, I use every no to improve the next yes. I refine the script. I test new angles. I follow up smarter, not just harder.
In cold calling, you’re not looking for approval. You’re collecting intel. If you treat every objection as insight, your strategy sharpens with every call.
Pivoting From Mistakes to Success
Let me close this with something I wish someone had told me earlier in my career. It would’ve saved me from a lot of stress, burnout, and second-guessing.
The real difference between the rep who dreads cold calling and the one who turns it into a predictable pipeline machine? It’s not experience. It’s not talent. It’s not even confidence. It’s perspective.
Cold calling isn’t punishment. It’s power.
When I saw it as a grind, it drained me. When I saw it as a numbers game, I rushed it. When I treated it like a race to quota, I burned out faster than I hit my goals. But now? I treat cold calling like a craft. It’s a skill set I keep sharpening.
Cold calling, done right, is strategic. It’s personal. It’s one of the last places in business where real human connection still happens in real time. That alone makes it valuable, and rare.
That call I mentioned earlier — the one that crushed me at the time — taught me valuable lessons. The experience showed me that rejection doesn’t define you, but rather it redirects you. I learned that connection is always more powerful than performance. And, it reminded me that if you’re willing to pause, listen, and learn, every failure becomes part of your system.
So to every SDR, AE, founder, or sales leader reading this:
- Don’t just make dials, craft conversations.
- Don’t just chase pipeline, build momentum.
- Don’t just listen for gaps, listen for growth.
Because, cold calling isn’t just about getting the meeting. It’s about becoming the kind of rep who knows how to earn attention, build trust, and open doors that most people gave up on.
That’s what I’ve committed the last 17 years to. That’s what I teach. And if you’re serious about leveling up, just know, I’ve been where you are. I’m here to walk with you, call by call, pattern by pattern, breakthrough by breakthrough.
And, once you learn how to create that? You never look at the phone the same way again.
