For those who spend any time on LinkedIn, you already know there’s one debate that by no means appears to die: when it’s best to pitch after somebody accepts your connection request.
Some folks swear it’s best to pitch instantly — no small discuss, no warmup, simply get to the purpose.
Others insist it’s the quickest solution to get ignored or blocked.
And the put up I noticed lately captured that pressure completely.
On one facet, you will have Matt Firestone saying:
“Rip the band-aid off and inform me what you’re promoting. No one has time for faux relationship constructing.”
On the opposite facet, Evan Hughes jumps in with the precise reverse take:
“Please cease pitching the second your connection request will get permitted. I take away 3–5 connections every week due to this.”
They’re on the ame platform, with the identical function however fully completely different expectations.
And that’s what makes this tough, particularly if you happen to’re freelance writing, consulting, or making an attempt to develop your corporation on LinkedIn.
So let’s break it down, as a result of the feedback beneath posts like this all the time reveal the true reply behind when it’s best to pitch and how to do it with out turning folks off.
Individuals Aren’t Arguing About Pitching
It’s not like content material entrepreneurs, CEOs, or founders are strolling round with a deep hatred for pitches (I hope not!).
Most of them perceive pitching is a part of doing enterprise.
Some even anticipate it.
What they don’t like and what sparks all of the frustration on LinkedIn are pitches that present up with completely zero context.
A chilly message that lands in somebody’s inbox with out relevance, personalization, or any indication who they’re seems like sleazy gross sales name that noone desires to reply.
It interrupts their day, and provides nothing of worth. That’s the half folks push again towards — not the pitch itself.
A great writing pitch exhibits you took 5 seconds to grasp the individual. A foul pitch might’ve been copied and pasted to 300 folks earlier than you.
When there’s no context or no point out of one thing they posted, no trace you perceive their function, or no clear motive why they, particularly, ought to care — the pitch lands flawed.
It seems like an ask with none effort. And that’s the type of outreach that will get ignored and deleted.
So no, folks aren’t anti-pitch. They’re anti-automation, and anti “Hey, need to hop on a name?” from somebody who didn’t even look at their profile.
And that’s precisely why Matt Firestone and Evan Hughes land on reverse sides of this debate.
Matt’s POV
Matt works in gross sales. His whole day is pitches, demos, and getting straight to the purpose.
He doesn’t need warm-up messages or “How’s your week going?” fluff. To him, a quick pitch is respectful and it saves time and will get proper to the choice.
Evan’s POV
Evan, alternatively, leads advertising and marketing at a fast-growing B2B firm. He will get pitched consistently. Generally each hour.
And most of these messages? They’re irrelevant, automated, or despatched by individuals who didn’t even trouble to have a look at his profile.
So after all he’s bored with the moment pitch.
Once you see each side, it truly is sensible.
And when you begin studying the feedback beneath posts like this, you discover the identical patterns time and again:
Individuals don’t thoughts a writing pitch when:
- It’s related to their work
- It’s clear who they’re
- It seems like a human wrote it
- It doesn’t leap straight to “Can we hop on a fast name?”
Individuals completely hate a pitch when:
- It’s generic
- It’s a copy-paste script
- It has nothing to do with their function
- It pushes for a gathering earlier than belief exists
- It ignores the content material they’ve already shared publicly
So the true drawback isn’t when you pitch. It’s whether or not the pitch suits the individual you’re sending it to.
Timing issues far lower than relevance and when you perceive that, the entire debate begins to really feel rather a lot much less dramatic.
So… When Ought to You Pitch? Right here’s the Solely Rule That Works
Pitch to potential shoppers when your message is related and earned and NOT when the connection is permitted.
That may be 10 seconds after they settle for you. That may be 10 weeks later.
Your timing is determined by the context YOU create.
And right here’s create that context with out faking a relationship or losing anybody’s time.
1. Personalize the Connection Request (With out Being Bizarre)
That is the place most individuals overthink issues.
Personalization doesn’t imply writing a paragraph.
It doesn’t imply finding out their whole content material historical past. And it undoubtedly doesn’t imply pretending you’ve been following them for years if you happen to found them 5 minutes in the past.
A easy, direct line is sufficient:
“Noticed your put up on X — spot on. Would love to attach.”
That’s it. Severely.
No pitch. No faux “value-first” angle. No making an attempt to impress them with how completely you stalked their profile.
Why does this work?
As a result of personalization alerts intention.
It tells the opposite individual you’re not connecting at random, and also you’re not operating some automated mass outreach marketing campaign.
You’re displaying a fundamental degree of consciousness, which is already greater than what 90% of LinkedIn customers do.
When somebody sees a customized request, they naturally assume any future message from additionally, you will be related and considerate.
That’s the entire level. You’re constructing a context bridge that makes your follow-up really feel acceptable as a substitute of abrupt.
And right here’s one of the best half: you solely want one line to do it. Once you do it this manner there’s no fluff and all the pieces is real and intentional.
Only a clear, human motive for hitting “join.” That’s all folks actually need at this stage.
2. Have interaction Twice Earlier than Pitching (Sure, Twice is Sufficient)
When making an attempt to attach on LinkedIn for some future writing shoppers, you don’t want an extended, drawn-out “relationship constructing” part earlier than you ship a pitch.
No one has time for that, and admittedly, most individuals can see by way of it anyway.
However you do want to indicate you’re an actual human who truly understands who they’re.
And that solely takes two small touches and never a month of nurturing them (though, some folks may have a bit extra time than two touches).
Two real interactions can seem like:
- A put up they shared
- One actual remark that proves you paid consideration
- Considerate reply to one thing they mentioned
This helps you look much less like a bot and extra like a human wanting a connection (but in addition a writing job!).
Once you present up even twice and it’s not performative, simply merely and intentional, you sign that you just’re completely different from the mass-pitchers filling their inbox.
And truthfully? That alone places you within the prime 5% of LinkedIn communicators.
Most individuals skip this step fully and go straight to “Hey, can we hop on a fast name?”
You doing the naked minimal already feels refreshing… and that’s what makes your eventual pitch really feel welcome as a substitute of intrusive.
3. When Pitching, Make it Clear Why You’re Reaching Out
That is the second the place most individuals lose the deal earlier than it even begins.
Not as a result of they pitched, however as a result of the pitch has no context to something the individual mentioned, posted, or cares about.
An awesome writing pitch isn’t lengthy and it isn’t dramatic.
It merely solutions one query:
“Why are you reaching out to me particularly?”
When you possibly can reply that clearly, your writing pitch instantly feels related as a substitute of random.
An awesome pitch seems like:
“You talked about [very specific pain point].
I assist [very specific type of business] repair that with [simple solution].
For those who ever need a fast breakdown, I can ship it. No obligation.”
Quick, respectful, and grounded in one thing they already expressed.
A horrible pitch, alternatively, normally seems like this:
“Can we hop on a fast name? I’ve an incredible resolution that may remodel your corporation.”
No context and no motive. It’s only a request for his or her time, which is the most costly factor they’ve.
4. If No Response, Don’t Chase Them Down
This one all the time hits a nerve, but it surely’s the reality: when you’ve despatched a transparent, related pitch, the ball is formally of their court docket.
Your job is finished.
Something past that begins to look determined… and desperation is strictly what will get folks eliminated, muted, or blocked.
Nothing kills your credibility quicker than follow-up messages like:
- “Simply bumping this to the highest of your inbox!”
- “Circling again on my final message!”
- “Any ideas?”
These phrases don’t make somebody immediately .
They only remind them that you just’re prioritizing your want for a response over their bandwidth, timing, or curiosity.
However once more, you might want to make every pitch private and if a circling again seems like a good suggestion, then do it. Usually I’ll circle again a couple of week to 2 weeks after which one remaining time a month later.
I make my followups nonetheless extremely private and related and check out to not “templatize” my response.
Notice this:
If somebody desires your pitch, they will reply.
Possibly not immediately. Possibly not this week. However they’ll come again to it when the timing aligns with an precise want.
And in the event that they don’t reply in any respect? That’s a sign too.
Skilled outreach isn’t about chasing folks, it’s about creating readability and letting adults make their very own selections.
If the writing pitch was related, respectful, and well-timed, you’ve already executed greater than most.
The Actual Takeaway: Pitching Isn’t Dangerous However Dangerous Pitching Is Dangerous
Once you actually break down this dialog about when to pitch, and the reactions, you begin to see the larger image:
Each Matt and Evan aren’t flawed of their evaluation.
They’re all reacting to the high quality of outreach they obtain and never the idea of pitching itself.
That’s the nuance most freelance writers skip proper over. As a substitute of asking “Ought to I pitch?” the higher query is:
“What sort of pitch expertise do I need to create for folks?”
As a result of on LinkedIn, you get to decide on the status you construct:
- You will be the spam pitcher who blasts the identical message to 200 folks a day.
- You will be the over-nurturer who engages for months and by no means will get to the purpose.
- You will be the never-pitch-anyone-ever creator who posts each day however by no means truly asks for enterprise.
- Otherwise you will be the intentional, related, respectful pitcher who reaches out with readability, context, and confidence.
And right here’s the shocking fact:
Out of all 4, just one persistently books shoppers, the one who pitches with goal and respect.
So, notice that pitching isn’t the issue it’s dangerous pitching is the issue.
When you perceive that, outreach turns into rather a lot much less scary, and much more efficient.
My Easy Rule for Freelance Writers
After a decade as a contract author on-line and having despatched tons of of pitches, I’ve boiled outreach and networking down to at least one rule I educate each WriteTo1K pupil — and comply with myself:
Pitch quick when it’s related.
Pitch sluggish if you want context.
It sounds easy, but it surely solves nearly each outreach drawback freelance writers battle with.
In case your message is clearly tied to one thing the individual posted, mentioned, or is actively engaged on? You possibly can pitch instantly. It received’t really feel abrupt as a result of the context already exists.
For those who’re connecting with somebody new and also you want a second to grasp who they’re, what they do, or whether or not your provide suits? Decelerate.
Give your self time to collect the context so your pitch doesn’t land flawed.
This rule prevents you from sending random messages that get ignored.
And, most significantly, it helps you construct a status on LinkedIn as somebody price connecting with — somebody skilled,and respectful of different folks’s time.
That’s all you might want to begin touchdown shoppers with out annoying the very folks you’re making an attempt to succeed in.
I Simply Made LinkedIn Outreach Simpler!
Nicely, I hope I did!
Let me know within the feedback beneath what you’re scuffling with on LinkedIn! I’ll attempt to assist.
Additionally let me know if you happen to’re going to make use of this pitching course of when connecting on LinkedIn!
I need to know.