Dear Elna,

It was more than 16 years ago, but I still vividly remember the first successful cold call I made for our business.

I’d mostly been sending cold emails. Much easier to type than to speak. No pressure, no cold sweats. No quivering voice or chance to stumble over my words.

I got the prospect’s number from someone who mentioned that this company occasionally commissioned market research. We had just started, brand new, no real street cred yet. And they were in an industry I knew nothing about.

We sat in our office, a small room, really (remote work was uncool back then) and I picked up the phone.

As I started speaking, my co-founder just stared at me. I was clearly breaking a slight sweat. I was nervous. I had already imagined the worst.

"Why did you call me?"
"Why are you so ridiculous?" 

But I just introduced myself, said what we did, and asked if they’d be interested in a meeting.

And the answer came: “Sure.” 

That was it. The end of the call and the start of a client relationship that spanned several years. The whole thing lasted less than 3 minutes.

Funny how we can so vividly imagine the worst-case scenario but rarely give equal airtime to the possibility of a good outcome.

So, I urge you: stop overthinking your outreach. 

In my home language, Afrikaans, there’s a saying: “Vra is vry en weier daarby.”  You’re free to ask, and they’re free to say no.

But they might also say yes. So ask.

Practically, it can look like this (for both calling & emailing):

1. Simplicity wins. No clever intros or cheesy hooks. Just connect the dots. Why are you reaching out? What made you think of them?
2. Don’t attach anything. Don’t ask for too much. No PDFs. No Calendly link (yet). No five-paragraph summaries.
3. Keep it to 3 sentences max: Who you are, why you're reaching out and what you’d love from them (a quick call, feedback, intro). This isn’t a pitch. It’s a doorway.
4. Use a casual tone. Like you would when chatting over coffee. And skip the "sorry to bother you", you’re not bothering anyone. You’re offering something helpful.
5. Think positively. Go in with a hopeful mindset. Imagine the best-case outcome.

Remember, you’re starting a conversation, not closing a deal. You’re helping, not just selling. This person could genuinely benefit from what you’re offering. And if they don’t take you up on it? That’s on them.

To quote Nike: just do it. Don’t overthink it. Action beats inaction every time.

And hey…What if they say yes? 

Yours in not overthinking it too much,
Elna

p.s. My course is live! Discover the fundamentals of B2B selling in my practical and relatable course. Currently available for just $1 as part of my birthday special: Find it here

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