A friend who worked in sales with me for years was shocked when I admitted that after all these years, rejection still hurts me.
Not when a client churns or offer gets rejected, that’s just business.
But when you reach out to a stranger and they completely misunderstand what you do or treat you like an automated AI bot?
That stings. And it always makes me wonder:
Did I miss the mark explaining myself?
Was I too confident, too timid, or just caught them on a bad day?
For the longest time, I thought this made me a bad salesperson. The industry myth is that a great seller is a thick-skinned shark who doesn't care what anyone thinks.
But that's just not true.
Feeling the sting of rejection isn't a weakness—it's a sign of empathy.
And using that empathy as a guide is how I dealt with it.
The real weakness is when we get so insecure that we build this thick-skin by disabling the “person” part of a “salesperson”.
Where rejections come from
Most of the worst rejection comes when we forget to sound like actual humans and slip into “salesperson” mode:
“I saw you’re hiring a social media specialist, so clearly social media matters to you. Most managers can’t afford a whole team—that’s where we come in…”
This is what most modern AI-powered outreach sounds like. It assumes too much, says too little, and jumps straight to the pitch.
Now, what if you led with empathy instead?
“Saw you’re looking for a social media manager, so I thought I’d put myself on your radar—not for the hire, but in case the workload gets heavy.
So many new hires end up overwhelmed fast with posting, engaging, strategizing they leave or get fired as fast as they arrive.
If you ever want to lighten the load, that’s what we help with :)
I hope you find a great candidate. And if you need any recommendations, I know some stellar people!”
See the difference? Offer help, show you get it, explain what you do—without just pushing for a sale.
The too-chill mistake
The opposite mistake is trying so hard to be non-salesy that you become vague and waste people's time.
“Hi, I’m building my professional network in your industry, would love to connect and chat about common issues.”
Harmless with solo founders who actively build their networks out. With a C-suite exec, though? You’ll get burned. The move here is the opposite: skip the pleasantries and get right to the point.
“Hi, are you using Monday for ops? I’ve built an analytics tool using Monday data to cut operational costs by up to 10%.
Would love to show a demo, but not sure who owns this on your team. Sorry to go direct—I figured you’d know who to send me to.”
The last paragraph on it’s own ot me more meetings than I can count.
You can’t avoid every rejection
The less generic, the less painful the rejection. The more you understand their problems, the more likely you get a real response. And when you do get a “no,” it won’t keep you up at night.
That’s how I see it. It still stings sometimes, but you get used to it.
Oh, and for the love of all that’s holy, please don’t go the opposite route: automating and outsourcing everything so you don’t have to deal with the horror of sales. That will just turn your business into a horror show :)
A quick update
After a recent off-line LinkedIn event (thanks again to all of you that came!) and a string of conversations with founders, I’ve decided to do something new. I’m putting together a limited sales communication training program for full-cycle salespeople and founders.
If you:
juggle positioning, outreach, content, relationship-building, and closing all on your own?
have a high-ticket b2b product or service?
need meetings with decision makers?
It’s for you.
Testing the first round in September. Small group, small price—but I’ll want your help to shape the final version.
If you’re interested, reply and I’ll share the details.