This week I coached a salesperson who wanted to generate more meetings through LinkedIn.
He wasn't struggling because he lacked a good product or because LinkedIn "doesn't work."
His biggest challenge was something I see almost every week.
He didn't have a repeatable process.
Stop Trying to Sell. Start Conversations.
The biggest mistake most salespeople make on LinkedIn is treating every message like a mini sales pitch.
Prospects don't open LinkedIn hoping to be sold to.
They open it to network, learn and have conversations.
Instead of leading with what your company does, lead with curiosity.
Ask simple questions that are easy to reply to.
Questions create conversations.
Conversations create opportunities.
Voice Notes Beat Video
Video messages can work, but they're a high commitment for both you and the recipient.
Voice notes feel much more natural.
They're quicker to create, easier to consume and often feel more personal than a polished video.
For existing connections especially, they're massively underused.
Make Your Messages Feel Human
Most LinkedIn messages look like emails squeezed into a chat window.
Instead of sending one large paragraph, split your message into three short texts.
For example:
"Hi Sarah."
"I noticed you're hiring several SDRs."
"Curious... what's your biggest challenge ramping new hires?"
It feels like a real conversation rather than an automated sequence.
And the prospect gets 3 notifications. And they’ll be more inclined to send a brief response.
Your Follow-Up Doesn't Need to Be Clever
It’s just needs to happen.
Fortunes are in the follow up as they say.
Salespeople often overthink follow-up.
Some of the highest-performing messages I've seen are incredibly simple.
Worth a chat?
Any thoughts?
Curious what you made of this?
Don't disappear after one message.
Persistence, when done professionally, wins far more meetings than perfection.
Give Prospects Something to Be Curious About
One idea we discussed was creating a mock benchmarking report.
Using ChatGPT, you can build an example report showing the type of insights your platform could generate.
You're not pretending it's their data.
You're simply demonstrating the outcome your product delivers.
Curiosity is often a stronger motivator than another list of features.
Consistency Wins
We finished by setting a simple target.
Send 50 LinkedIn outreach messages over the next week.
Not because every message will become a meeting.
But because outreach is a numbers game.
If your process averages one meeting from every 50 quality messages, your job isn't to obsess over individual replies.
Your job is to execute the process consistently.
The best sales people are always consistant.
And that's usually what separates the reps who hit quota from the ones who don't.
