03/25/25 12:11 am
Every sales organization needs to prospect. And prospecting means cold-calling, or — far more often these days — cold emailing. Many of us hate reaching out to folks we don’t yet know to pitch them on the products and services we have to sell.
Just this week, I spoke to a sales coaching client of mine, and he highlighted one of the key reasons he hates cold outreach: “The rejection is the worst.”

There are a few reasons I’m not a professional actor — this despite my charm, chiseled good looks, and comic timing. But one of those reasons is the endless rejections that actors get; most auditions don’t end with the auditioner scoring the role, and even being “the best” doesn’t mean you get every part. Audition rejections feel personal. You weren’t good enough. You weren’t right. Ugh.
I do not feel the same kind of personal rejection when I’m prospecting, and I’d like to encourage you not to, either. When you’re pitching what your company has to offer, it’s business, not personal.
That same client I was working with this week said something I loved — that when he’s cold pitching folks, he always starts with the mindset that they’d be lucky to have him.
The truth is, the hardest part of prospecting is that it’s hard to scale well. There are countless tools out there that leverage AI to write emails, or that can send your one email to hundreds or thousands of potential prospects. I’ve written before that I’m no fan of this approach.
Human-powered emails that express your originality and the fact that you’ve put personal thought into this prospect — even if 90% of your email is copy and pasted! — work so much better.
Another client of mine used an AI tool to reach out to hundreds of prospects over the past six months. The tool scored him more than a dozen meetings. Not one of those meetings yielded a true viable prospect.
Not one!
Human prospecting, where you’re you and you show that you’ve taken the time to research the person you’re writing, is slower. Time-consuming work is hard; it can take away from all the other work you have to do. But it’s far more rewarding, because it works so much better.
Think of prospecting as advocating for yourself and for your business. Remember how important shameless self promotion can be.
My son Liam is fourteen, and a musical prodigy. He’s massively talented at a slew of instruments: piano, bass, drums, saxophone, guitar…
He’s also worked hard to overcome shyness. There’s nothing intrinsically wrong with being shy, of course, but as a parent, I’ve felt it’s necessary to teach all three of my kids about the importance of advocating for themselves: That includes standing up for what’s right, asking questions when they need answers, seeking fairness for themselves and others.
And yes, sometimes advocating for yourself also includes shameless self-promotion.
Liam and I just released our fourth(!) album together. I love that he likes making music with me. Earlier this week, I asked Liam whether he would tell his friends at school about the new album, and he hesitated. And I pushed him on it: We’re proud of our growth in skill at songwriting, recording, mixing, and mastering; we wrote some ridiculous and silly but also GOOD songs — why wouldn’t he promote the album to his friends?
He thought about it and concluded that the idea of telling his friends about his albums FELT embarrassing, but that he couldn’t come up with a single reason why it WAS embarrassing. He came home from school Monday and told me that yes, indeed, he had told his friends about the album.
Shameless self-promotion, baby. No one knows about the great things you do unless you tell them.

So first of all, check out our new album. We’re proud to tell you about it.
But more importantly, reset how you’re thinking about prospecting. It’s not about making yourself vulnerable to potential rejection. It’s about celebrating your work and your company and what you do. You’re proud of what you have to offer. Even if it’s not the right fit for this particular prospect, that’s not a reflection on the value of what you do or what you’re selling.
Block out time on your calendar for prospecting. Block out time that you know you’ll actually use. If you block out two hours, it’s quite likely you’ll end up having other work that overlaps that time, and you’ll say to yourself oh it’s fine, I have so much time for this, plus it can wait— no no no. Tell that part of your brain to take a hike.
Block a reasonable amount of time. Start with even 15 or 30 minutes. Send the emails. Make them human. Schedule follow-ups. And don’t mind the rejections; better to get the “no” in email than to waste time on futile meetings or later follow-ups.
It sucks that rejection is part of sales. But so is closing, and those victories feel great. Aim to let those feel sweeter than the sting of any “no thanks” replies you get.