When Should You Pitch on LinkedIn? (Here’s the Only Rule That Actually Works)

If you spend any time on LinkedIn, you already know there’s one debate that never seems to die: when you should pitch after someone accepts your connection request.

Some people swear you should pitch immediately — no small talk, no warmup, just get to the point.

Others insist it’s the fastest way to get ignored or blocked.

And the post I saw recently captured that tension perfectly.

On one side, you have Matt Firestone saying:

“Rip the band-aid off and tell me what you’re selling. Nobody has time for fake relationship building.”

On the other side, Evan Hughes jumps in with the exact opposite take:

“Please stop pitching the second your connection request gets approved. I remove 3–5 connections a week because of this.”

They are on the ame platform, with the same feature but completely different expectations.

And that’s what makes this tricky, especially if you’re freelance writing, consulting, or trying to grow your business on LinkedIn.

So let’s break it down, because the comments under posts like this always reveal the real answer behind when you should pitch and how to do it without turning people off.

People Aren’t Arguing About Pitching

It’s not like content marketers, CEOs, or founders are walking around with a deep hatred for pitches (I hope not!).

Most of them understand pitching is part of doing business.

Some even expect it.

What they don’t like and what sparks all the frustration on LinkedIn are pitches that show up with absolutely zero context.

A cold message that lands in someone’s inbox without relevance, personalization, or any indication you know who they are feels like sleazy sales call that noone wants to answer.

It interrupts their day, and adds nothing of value. That’s the part people push back against — not the pitch itself.

A good writing pitch shows you took five seconds to understand the person. A bad pitch could’ve been copied and pasted to 300 people before you.

When there’s no context or no mention of something they posted, no hint you understand their role, or no clear reason why they, specifically, should care — the pitch lands wrong.

It feels like an ask without any effort. And that’s the kind of outreach that gets ignored and deleted.

So no, people aren’t anti-pitch. They’re anti-automation, and anti “Hey, want to hop on a call?” from someone who didn’t even glance at their profile.

And that’s exactly why Matt Firestone and Evan Hughes land on opposite sides of this debate.

Matt’s POV

Matt works in sales. His entire day is pitches, demos, and getting straight to the point.

He doesn’t want warm-up messages or “How’s your week going?” fluff. To him, a fast pitch is respectful and it saves time and gets right to the decision.

Evan’s POV

Evan, on the other hand, leads marketing at a fast-growing B2B company. He gets pitched constantly. Sometimes every hour.

And most of those messages? They’re irrelevant, automated, or sent by people who didn’t even bother to look at his profile.

So of course he’s tired of the instant pitch.

When you see both sides, it actually makes sense.

And once you start reading the comments under posts like this, you notice the same patterns over and over again:

People don’t mind a writing pitch when:

It’s relevant to their work
It’s clear you know who they are
It sounds like a human wrote it
It doesn’t jump straight to “Can we hop on a quick call?”

People absolutely hate a pitch when:

It’s generic
It’s a copy-paste script
It has nothing to do with their role
It pushes for a meeting before trust exists
It ignores the content they’ve already shared publicly

So the real problem isn’t when you pitch. It’s whether the pitch fits the person you’re sending it to.

Timing matters far less than relevance and once you understand that, the whole debate starts to feel a lot less dramatic.

So… When Should You Pitch? Here’s the Only Rule That Works

Pitch to potential clients when your message is relevant and earned and NOT when the connection is approved.

That might be 10 seconds after they accept you. That might be 10 weeks later.

Your timing depends on the context YOU create.

And here’s how to create that context without faking a relationship or wasting anyone’s time.

1. Personalize the Connection Request (Without Being Weird)

This is where most people overthink things.

Personalization doesn’t mean writing a paragraph.

It doesn’t mean studying their entire content history. And it definitely doesn’t mean pretending you’ve been following them for years if you discovered them five minutes ago.

A simple, direct line is enough:

“Saw your post on X — spot on. Would love to connect.”

That’s it. Seriously.

No pitch. No fake “value-first” angle. No trying to impress them with how thoroughly you stalked their profile.

Why does this work?

Because personalization signals intention.

It tells the other person you’re not connecting at random, and you’re not running some automated mass outreach campaign.

You’re showing a basic level of awareness, which is already more than what 90% of LinkedIn users do.

When someone sees a personalized request, they naturally assume any future message from you will also be relevant and thoughtful.

That’s the whole point. You’re building a context bridge that makes your follow-up feel appropriate instead of abrupt.

And here’s the best part: you only need one line to do it. When you do it this way there’s no fluff and everything is genuine and intentional.

Just a clear, human reason for hitting “connect.” That’s all people really want at this stage.

2. Engage Twice Before Pitching (Yes, Twice is Enough)

When trying to connect on LinkedIn for some future writing clients, you don’t need a long, drawn-out “relationship building” phase before you send a pitch.

Nobody has time for that, and frankly, most people can see through it anyway.

But you do need to show you’re a real human who actually understands who they are.

And that only takes two small touches and not a month of nurturing them (although, some people may need a bit more time than two touches).

Two genuine interactions can look like:

A post they shared
One real comment that proves you paid attention
Thoughtful reply to something they said

This helps you look less like a bot and more like a human wanting a connection (but also a writing job!).

When you show up even twice and it’s not performative, just simply and intentional, you signal that you’re different from the mass-pitchers filling their inbox.

And honestly? That alone puts you in the top 5% of LinkedIn communicators.

Most people skip this step entirely and go straight to “Hey, can we hop on a quick call?”

You doing the bare minimum already feels refreshing… and that’s what makes your eventual pitch feel welcome instead of intrusive.

3. When Pitching, Make it Clear Why You’re Reaching Out

This is the moment where most people lose the deal before it even starts.

Not because they pitched, but because the pitch has no context to anything the person said, posted, or cares about.

A great writing pitch isn’t long and it isn’t dramatic.

It simply answers one question:

“Why are you reaching out to me specifically?”

When you can answer that clearly, your writing pitch immediately feels relevant instead of random.

A great pitch sounds like:

“You mentioned [very specific pain point].
I help [very specific type of business] fix that with [simple solution].
If you ever want a quick breakdown, I can send it. No obligation.”

Short, respectful, and grounded in something they already expressed.

A terrible pitch, on the other hand, usually sounds like this:

“Can we hop on a quick call? I have an amazing solution that will transform your business.”

No context and no reason. It’s just a request for their time, which is the most expensive thing they have.

4. If No Response, Don’t Chase Them Down

This one always hits a nerve, but it’s the truth: once you’ve sent a clear, relevant pitch, the ball is officially in their court.

Your job is done.

Anything beyond that starts to look desperate… and desperation is exactly what gets people removed, muted, or blocked.

Nothing kills your credibility faster than follow-up messages like:

“Just bumping this to the top of your inbox!”
“Circling back on my last message!”
“Any thoughts?”

These phrases don’t make someone suddenly interested.

They just remind them that you’re prioritizing your need for a response over their bandwidth, timing, or interest.

But again, you need to make each pitch personal and if a circling back sounds like a good idea, then do it. Generally I will circle back about a week to two weeks and then one final time a month later.

I make my followups still highly personal and relevant and try not to “templatize” my response.

Realize this:

If someone wants your pitch, they will reply.

Maybe not today. Maybe not this week. But they’ll come back to it when the timing aligns with an actual need.

And if they don’t respond at all? That’s a signal too.

Professional outreach isn’t about chasing people, it’s about creating clarity and letting adults make their own decisions.

If the writing pitch was relevant, respectful, and well-timed, you’ve already done more than most.

The Real Takeaway: Pitching Isn’t Bad But Bad Pitching Is Bad

When you really break down this conversation about when to pitch, and the reactions, you start to see the bigger picture:

Both Matt and Evan aren’t wrong in their assessment.

They’re all reacting to the quality of outreach they receive and not the concept of pitching itself.

That’s the nuance most freelance writers skip right over. Instead of asking “Should I pitch?” the better question is:

“What kind of pitch experience do I want to create for people?”

Because on LinkedIn, you get to choose the reputation you build:

You can be the spam pitcher who blasts the same message to 200 people a day.
You can be the over-nurturer who engages for months and never gets to the point.
You can be the never-pitch-anyone-ever creator who posts daily but never actually asks for business.
Or you can be the intentional, relevant, respectful pitcher who reaches out with clarity, context, and confidence.

And here’s the surprising truth:

Out of all four, only one consistently books clients, the one who pitches with purpose and respect.

So, realize that pitching isn’t the problem it’s bad pitching is the problem.

Once you understand that, outreach becomes a lot less scary, and a lot more effective.

My Simple Rule for Freelance Writers

After a decade as a freelance writer online and having sent hundreds of pitches, I’ve boiled outreach and networking down to one rule I teach every WriteTo1K student — and follow myself:

Pitch fast when it’s relevant.
Pitch slow when you need context.

It sounds simple, but it solves almost every outreach problem freelance writers struggle with.

If your message is clearly tied to something the person posted, said, or is actively working on? You can pitch right away. It won’t feel abrupt because the context already exists.

If you’re connecting with someone new and you need a moment to understand who they are, what they do, or whether your offer fits? Slow down.

Give yourself time to gather the context so your pitch doesn’t land wrong.

This rule prevents you from sending random messages that get ignored.

And, most importantly, it helps you build a reputation on LinkedIn as someone worth connecting with — someone professional,and respectful of other people’s time.

That’s all you need to start landing clients without annoying the very people you’re trying to reach.