Sometimes the universe delivers perfect teaching moments right to your doorstep. Today, within the span of one hour, I experienced two prospecting approaches that were so spectacularly awful, I had to write about them.
These weren’t just bad sales calls. They were masterclasses in how to ensure a prospect will never, ever buy from you. And the scary part? I bet the salespeople involved think they’re being persistent and professional. They’re not. They’re being desperate and tone-deaf. And there’s a huge difference.
Disaster #1: The Uninvited Calendar Terrorist
A few weeks ago, I had a LinkedIn message exchange with someone who sells some sort of program to help speakers raise their profile. There are thousands of these people out there, and most of them just separate speakers from their money, but I was polite. I told her I might be interested in a conversation at some point, but that this wasn’t that point.
Clear communication, right? Apparently not clear enough. The next thing I knew, I received a Zoom meeting invitation from someone who works for her. Not a request to schedule a call. Not a follow-up message asking when might be convenient. An actual calendar invitation for a specific time and date.
I never asked for this call. I never agreed to this call. Someone just decided to put a meeting on my calendar without permission. I responded and declined, explaining that I was too busy to even devote head space to this topic right now. His response? He’d send a different invitation for a month out. I told him more vehemently that I didn’t appreciate the tactic and had no interest because of it.
Today – weeks later – I received and declined yet another unsolicited Zoom calendar invitation from this same guy. Let me be crystal clear about what this approach accomplishes: It ensures I will never, under any circumstances, buy from this company. Ever.
Disaster #2: The Incomprehensible Cold Caller
While I was still shaking my head about the calendar terrorist, my phone rang. It was a cold call from some company promising to get me in front of thought leaders. I’ve heard this pitch a thousand times from a hundred different companies.
But here’s where it got interesting. The caller spoke with a very heavy accent and spoke very quickly. I couldn’t understand most of what she was saying. So I did what any reasonable person would do – I politely told her I couldn’t understand what she was saying and asked her to restate it more slowly. She repeated the exact same well-rehearsed pitch in exactly the same way.
I tried again. “I’m sorry, but I still can’t understand you. Could you please slow down?” Same pitch. Same speed. Same result. Finally, I told her the truth: “If I can’t understand what you’re saying, I’m not going to buy anything. It’s not my job to understand you – it’s your job to speak clearly.”
She hung up.
The Common Thread of Tone-Deafness
Both of these disasters share the same fundamental problem: complete disregard for the prospect’s communication preferences and boundaries. The calendar terrorist heard “not now” and interpreted it as “send me unsolicited meeting invitations until I give up and take the call.” The cold caller heard “I can’t understand you” and decided that repeating the same incomprehensible script was the solution. Neither one of them was actually listening. They were both just executing their processes, regardless of what the prospect was telling them.
This isn’t persistence. Persistence means continuing to provide value over time while respecting boundaries. This is just being pushy and annoying.
What These Approaches Actually Accomplish
Let’s be honest about what tactics like these really achieve:
They damage your reputation. Every unsolicited calendar invitation, every ignored request to slow down, every boundary you cross makes you look desperate and unprofessional.
They eliminate future opportunities. I might have been interested in that speaker program at some point. Not anymore. The approach killed any possibility of a future conversation.
They waste everyone’s time. How much time did that guy spend sending me multiple calendar invitations? How much more productive would it have been to respect my initial response and follow up appropriately later?
They reinforce negative stereotypes about salespeople. Every pushy, tone-deaf interaction makes it harder for professional salespeople to get the respect and attention they deserve. Honestly, this one makes me madder than any of them. Our profession doesn’t NEED any more negative stereotypes.
The Right Way to Handle These Situations
Here’s what should have happened in both cases:
Scenario 1: When I said “not now,” the appropriate response would have been, “I understand. When would be a better time to revisit this conversation?” Or even better: “No problem. I’ll check back with you in a few months to see if your situation has changed.”
Scenario 2: When I said I couldn’t understand, the appropriate response would have been to slow down, speak more clearly, or even suggest we continue the conversation via email where language barriers might be less of an issue.
In both cases, the salespeople should have adapted their approach based on what the prospect was telling them. That’s what professionals do.
The Bigger Picture Problem
These two disasters highlight a broader issue in sales today: too many people are following scripts and processes without thinking about the human being on the other end. Good prospecting requires reading the room, adapting to feedback, and respecting boundaries. It requires treating prospects like human beings with preferences and priorities, not just names on a list to be processed through your system.
When someone tells you “not now,” that’s valuable information. When someone asks you to slow down, that’s helpful feedback. When someone sets a boundary, that’s important data about how they prefer to be approached. Ignoring all of that in favor of your predetermined process isn’t persistence – it’s professional malpractice.
The Bottom Line
Both of these salespeople probably think they’re being diligent and thorough. They’re probably tracking their “touches” in their CRM and reporting to their managers about their consistent follow-up. What they’re actually doing is burning bridges, damaging their company’s reputation, and ensuring that prospects will go out of their way to avoid doing business with them.
Professional selling means adapting your approach based on what your prospects tell you. It means respecting boundaries. It means listening more than you talk. If you can’t do those basic things, you’re not in sales. You’re in harassment. And there’s a big difference between the two.
Your prospects know the difference, even if you don’t.
