Most people treat LinkedIn like a cold email machine. That’s why their outreach gets ignored.  In this episode of the Close The Deal Podcast, Jack Hayes shares a completely different approach—one that starts with curiosity, feedback, and real conversations instead of a pitch.

Most LinkedIn outreach fails. Here’s why this one works.

Listen to the Close The Deal Podcast:

Why Most LinkedIn Outreach Fails

LinkedIn has become one of the most powerful platforms for B2B sales.

But there’s a problem.

Most people use it the wrong way.

If you’ve ever opened your LinkedIn inbox, you know exactly what this looks like. Someone connects with you… and five seconds later you get a pitch.

“Hi, great to connect. Here’s what I do…”

It’s predictable. It’s impersonal. And it rarely works.

That’s why Gen Z entrepreneur Jack Hayes built a completely different approach.

Instead of pitching prospects, he starts conversations.

And it starts with one simple shift.

Ask for feedback.

The Psychology Behind Asking for Feedback



Most sales outreach focuses on positioning the sender as the expert.

But Jack flips that approach.

Instead of trying to prove expertise immediately, he activates the expertise of the person he’s reaching out to.

When you message someone and ask for their feedback, several things happen instantly:

First, the conversation becomes collaborative.

Second, you respect the experience of the person you're reaching out to.

Third, you remove the defensive barrier people naturally build when they expect a sales pitch.

This small shift changes the entire dynamic of the conversation.

Instead of feeling sold to, the other person feels valued.

And that dramatically increases the likelihood they respond.

Why LinkedIn Is Built for This Strategy

LinkedIn isn’t like other social platforms. The platform itself is built around connections.

Not followers.

Connections.

That small detail reveals the real intent behind LinkedIn: professional conversations.

Yet most outreach strategies treat LinkedIn like an automated cold email machine.

Mass messages.

Generic pitches.

Volume over value.

Jack’s approach brings the platform back to what it was originally designed for: professional dialogue.

The Simple Outreach Framework

The strategy itself is surprisingly simple.

Step one is sending a connection request.

But instead of immediately pitching, the first message focuses on context.

You briefly explain:

• The problem you solve
• Who you help
• A quick example or proof

Then comes the key element.

You ask for feedback.

Not a sales call.

Not a meeting.

Feedback.

For experienced founders and executives, this immediately triggers curiosity. Their expertise is being acknowledged.

And that makes them far more likely to engage.

Automation Without Losing the Human Touch

Automation tools have become common in LinkedIn prospecting.

But many companies misuse them.

Instead of helping conversations happen faster, automation becomes a spam machine.

Jack’s rule is simple:

Automation should only support human conversations.

That means limiting follow-ups, avoiding aggressive message sequences, and always making sure messages feel like they came from a real person.

When automation respects the relationship instead of replacing it, it becomes a powerful growth tool.

The Real Meaning of Closing the Deal

When asked what “closing the deal” means, Jack gives a refreshingly direct answer.

Cash collected.

Not promises.

Not contracts.

Not performance projections.

Cash collected.

It’s a simple reminder that sales ultimately comes down to results. Conversations, relationships, and outreach strategies all matter—but at the end of the day, businesses run on revenue.

The Lesson for Entrepreneurs

The biggest insight from this conversation is simple.

People don’t want to be pitched.

But they’re always open to a conversation.

When you approach outreach with curiosity instead of persuasion, something interesting happens.

People respond.

Conversations start.

Opportunities open.

And sometimes, that single conversation leads to the deal.

Episode Summary

In this episode, Jack Hayes shares a modern approach to LinkedIn outreach built around asking for feedback instead of delivering sales pitches. By activating the prospect’s expertise and focusing on conversation rather than persuasion, founders can dramatically increase response rates and build stronger B2B relationships.

Key Questions This Episode Answers

• Why do most LinkedIn outreach messages fail?
• How can entrepreneurs generate B2B leads without sounding like a salesperson?
• What is the feedback-driven outreach strategy on LinkedIn?
• How should founders use automation without damaging their reputation?
• What role does Gen Z play in reshaping modern sales strategies?

Top 3 Jack Hayes Mindset Quotes:

“Instead of pitching someone, ask for their feedback.”

“LinkedIn is built on connection, but most outreach removes the connection.”

“Closing the deal means cash collected.”

Frequently Asked Questions