I recently approached a stranger online without any agenda, just curiosity.
Seeing his steady stream of LinkedIn posts linking to articles across various publications, I was genuinely in awe. As someone who finds writing to be slow and difficult work, I could not figure out how one person could produce that much, that consistently.
So I left a comment on one of his posts asking about his writing routine, not expecting much, and then forgot about it entirely.
He responded. Writing, he said, comes easy to him and does not take long. I stared at that for a moment. I have heard well-known writers talk about fighting through blocks for years, and here was a stranger telling me writing is just… easy. My mild curiosity became something closer to urgency. I needed to understand how that was possible.
So I suggested a Zoom call, fully expecting a polite no or even no response which is the usual outcome when you ask something like that from someone you have never met. He said yes.
Afterwards, I started thinking about why the whole thing had been so effortless. No carefully crafted subject line, no credential listing, no formal ask. Just a genuine question left on a post, followed by a suggestion.
I had not been thinking about pitching at all, and yet that is exactly what I had done. Asking something of a stranger, especially on social media, is a form of pitching, and somehow this one worked.
Maybe he is simply an unusually generous person. Or maybe my understanding of pitching has been wrong. Somewhere between that comment and that Zoom call, I realized the pitch advice I had been following was answering the wrong question.
Here is what that interaction taught me about why pitches actually land.
Give Them Something to Think about and Pass to
Most pitch advice starts with you. Know your audience, sharpen your value proposition, lead with your strongest credential as people say. The assumption underneath all of these advice is that the receiver is evaluating what you bring to the table.
But there is usually something else happening on the other side of the inbox.
When someone reads a pitch, they are not only asking whether it benefits them directly (which we all do). But we also, often without realizing it, asking whether this is something worth mentioning to someone else. A useful idea to forward to a colleague, an interesting person to recommend to a podcast host they know, a perspective that would land well in a conversation they are already having.
People are constantly thinking what they share, and a pitch that fits naturally into that habit has a different kind of pull than one that is simply asking for something.
I believe my non-pitch pitch had that element. When I left that comment on his LinkedIn post, I was not offering credentials or explaining why a conversation with me would be valuable. I was just genuinely curious with his work, and that probably felt different from most of what we think and how we approach our ask.
I did not plan it that way…in fact, I did not have any plan. Looking back, it was probably the moment that made everything else possible, not because I gave him something to share, but because I was not asking for anything.
The uncomfortable part is that the moment you start thinking about what the receiver might want to pass along, you are back to strategizing, and it probably shows.
The pitches that create this kind of pull tend to come from genuine engagement, not from reverse-engineering someone’s sharing habits.
Timing Is Research, Not Luck
There is a version of pitch advice that tells you timing matters, send on Tuesday mornings, avoid Fridays, never pitch in December.
That kind of timing is about optimizing for attention, catching someone when their inbox is slightly less full. It is not wrong exactly, but it is also not what I mean.
The more useful version of timing is about catching someone in a moment of open need, and that is something you can actually read rather than guess.
A podcaster who just launched a new season is actively building a guest list. An editor who posted last week about a gap in their coverage is telling you exactly what they are looking for without knowing they are telling you. A publication that announced a themed issue has a specific hole to fill.
These signals are public and readable, but most people pitch without looking for any of them. They find a platform they like, write the email, and send it, which is essentially a volume strategy dressed up as outreach.
When I commented on his post, I showed up during his activity, on his content, while he was already in a sharing and engaging mindset. I did not engineer that, but it meant my comment arrived in a moment of openness rather than interrupting something else entirely.
Here is where it gets complicated though.
Reading these signals carefully is genuinely useful, but there is a version of this that tips into surveillance, studying and tracking posts, timing your approach to the minute. At that point you are no longer being perceptive, you are just being calculated with better data.
The difference between the two is probably whether you are reading signals because you are genuinely interested in the person’s work, or because you are optimizing for a response. People can usually feel which one it is.
Make Saying Yes Feel Effortless
By the time I suggested a Zoom call, the relationship had already built itself through small, low-friction steps. A comment, a response, a short exchange. The ask, when it finally came, did not feel like an ask at all because most of the weight had already been quietly removed.
This is the part of pitching that rarely gets discussed, probably because it is harder to package into actionable advice.
In a world where everyone is overcommitted and moderately overwhelmed, the pitch that requires the least effort to act on has a real advantage over the pitch that is merely compelling.
Compelling still requires the receiver to evaluate, decide, respond, and manage whatever comes next.
Effortless just requires a yes.
What effortless looks like in practice is a clear angle, an obvious fit with the platform or audience, and a sense that the person pitching has already thought through the details so the receiver does not have to.
It is the difference between an email that opens a conversation and an email that opens a project. Most people, when they are already stretched, will quietly choose neither over the second option.
Most pitch advice pushes in the opposite direction, be more compelling, more persistent, more thorough in explaining your value.
All of that adds weight to the yes. The better move, most of the time, is to make the yes feel like the easiest thing the receiver does that day.
But again, the paradox holds.
If you sit down to engineer an effortless pitch, you are already doing the opposite of what made my Zoom request work. The effortlessness came from the fact that I was not managing the interaction, I was just genuinely curious and the ask followed naturally from that.
You cannot really manufacture natural. You can only notice when it is already there and not get in its way.
Final Thought
That one-line comment on a stranger’s LinkedIn feed led to a Zoom call, which led to a coffee meeting, and eventually to a publication. None of it was planned.
I was not thinking about strategy when I left that comment. I was genuinely curious about how someone else was managing the work I find so hard, and that curiosity apparently came through even in a single sentence.
Whether he recognized something authentic in it, or whether he is simply the kind of person who says yes to everyone, I will never know for certain.
What I do know is that I was not angling. There was no calculated ask, no positioning, just honest interest in another person’s experience. And that is the uncomfortable thought I keep coming back to:
If the most effective pitching looks like genuine human curiosity, what does that say about all the tactical advice we follow?
We spend so much time perfecting the ask that we forget the other person has not agreed to listen yet.
I have also stopped calling him a stranger. Though I am still debating whether to pitch him on reviewing my pitch style, or whether he just really enjoys coffee with anyone who asks:-)
Life Outside of Design Studio 