LinkedIn: start a conversation, don’t pitch

Read this first

LinkedIn is your soft touch next to the phone. The goal is to start a conversation, not book a meeting.

One good question beats ten pitches.

The one rule

Never say you saw them looking at a competitor. Same rule as every channel. You know the secret, you never say it out loud.

One thing that confuses people here: if your opening question asks who they compete with, that's fine. Asking who someone goes up against is normal small talk. Telling them you know they're shopping is not. Asking is fair game. Knowing is the part you keep quiet.

The sequence

  1. Connect, no note. Blank requests get accepted more. A note screams “sales.”
  2. Not accepted in a few days? Don’t wait. Keep calling and emailing. A non-accept isn’t a dead end, it’s a nudge to try another door.
  3. A warm intro beats a cold connect. If someone at your company knows them, ask for the intro first.
  4. Have someone senior send it for exec-level people. It converts better, and it opens the warm path above.
  5. They accepted but ignored your question? Send a voice note or a video DM. Almost nobody does this, which is exactly why it works.
  6. Still not connected by the end of the week? Send an InMail. Last step on this channel. It lands in their inbox whether they accepted you or not.

Your profile is a landing page

They will click it before they reply. Make it read like a page about them, not your resume.

The first message

Once they accept, do not pitch. No link. No paragraphs. No “got 15 minutes?”

Send one open-ended question they can answer off the top of their head, short enough to read like a text. That’s the entire formula. It has to be about their world, not your product.

You’re not booking a meeting with this message. You’re getting a reply.

Here’s ours, so you can see the shape

What we send at Letterdrop

"Hey [Name], do you go up against [Competitor 1] or [Competitor 2] pretty often?"

This works for us because we sell competitive intelligence, so competitors are a natural thing for us to be curious about. Yours will be a different question. Don't copy this one unless you also sell into that conversation.

Now write yours

Ask what the equivalent question is for your category. It passes if it’s all five of these:

Some shapes that travel well across categories:

Steal the shape, swap the topic

"Hey [Name], how's your team handling [the problem] these days?"

"[Name], curious what you're using for [category] right now?"

"Hey [Name], is [the problem] still a headache for you or have you got it sorted?"

"[Name], who owns [the thing you sell into] on your team these days?"

Fill in the brackets with whatever is genuinely top of mind for the person you're calling. The best version names something they deal with on a Tuesday.

Not sure what yours should be? Ask ChatGPT to draft five and pick the one you’d actually send.

When they reply “yeah, why?”

Don’t dump a pitch on them.

Say this

"We help [teams like yours] [outcome]. Worth swapping notes for 10 min? Even if we never work together I can send you [the thing you're offering]."

Warm-up move

Leave a real comment on their recent post before you DM. Not “Great post!”, an actual thought.

Now you’re a friendly face instead of a stranger.

No reply? Send a voice note or a video

They accepted you and then ignored your question. Don’t send another typed message into the same silence.

Send a voice note or a short video instead. Almost nobody does this, so it doesn’t look like the forty other messages in their inbox. They can hear that you’re a real person having a normal day, which is very hard to fake in text.

How to actually send one

The beats

  1. Who you are, fast. (5 seconds)
  2. Acknowledge you’re following up, with zero guilt. (8 seconds)
  3. The real reason you’re bothering them: the problem, one proof. (20 seconds)
  4. The ask, which is not a demo. (8 seconds)
  5. An easy way out. (4 seconds)

Sample: 45 seconds

Voice note or video DM, roughly 45 seconds

"Hey [Name], it's [You] over at [Company].

I sent you a message last week about [the problem] and didn't hear back, which is completely fair, you're busy.

Figured I'd try this instead.

The reason I keep bugging you: I talk to a lot of [people in their job], and [the problem] comes up constantly. [Similar customer] had the same thing going on, and [what changed for them].

I'm not trying to book you into a demo. I'm just curious how you're handling it, because if you've got it sorted I'll leave you alone.

Either way, hope your week's a good one."

Just over 100 words, which is about 45 seconds at a normal talking pace. Time yourself out loud once before you send your first one, because everyone talks slower than they think. If you're running long, cut the proof line, not the easy out at the end.

If they reply, you’ve won the channel. Answer like a human, stay curious, and go back to the phone playbook for asking about the meeting.

Last step: the InMail

They never accepted. You’ve called, you’ve emailed, the week is up. InMail is your last swing on this channel, and it goes to their inbox whether they connected or not.

You get a subject line here, so use it. Same rules as everything else: no pitch, no link, one question, and never a word about the competitor.

InMail

Subject: quick question

Hey [Name], tried you a couple of ways so I'll keep this short.

Do you go up against [Competitor 1] or [Competitor 2] much? Curious how your team handles [the problem] these days.

No pitch, genuinely just curious. If it's not your area, point me at whoever it is and I'll leave you alone.

The "point me at the right person" line is doing real work. Even a no gets you a name.

You get a limited number of these a month, so spend them on high-priority accounts. If they don’t reply, the LinkedIn channel is done. Keep the phone and email going.

What NOT to do

Don'tDo
Pitch, link, or "got 15 minutes?" firstAsk one real question
Mention you saw them near a competitorAsk who they go up against
Stop calling because they didn't acceptKeep the phone and email going
Write a note on the connection requestSend it blank

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