LinkedIn playbook

LinkedIn runs alongside your calls, not instead of them. The goal here isn’t to pitch, it’s to start a conversation with one open-ended question that pokes the bear. Keep it light, keep it human.

The sequence

  1. Send a blank connection request (no note). Always.
  2. No accept after a few days? Switch channels. Don’t sit and wait, fall back to email, and keep dialing. A non-accept isn’t a dead end, it’s a signal to try another door.
  3. Look for a warm path first. If anyone at your company already knows them, leadership, a mutual connection, get that person to reach out instead. A warm intro beats the best cold message every time. Try the warm route before or in parallel with the cold one.

Connection requests

Your profile is a landing page

Before anyone replies, they’ll check your profile. Make it read like a sales page for your product, not a BDR resume.

The first message

Once they accept, do not pitch. No booking link. No paragraphs. No “hopping on a quick call.”

Send one open-ended question that piques their curiosity and pokes the bear, the tension someone in their seat actually feels. You’re inviting a reply, not asking for a meeting.

The question that works for us at Letterdrop is dead simple:

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

That’s the whole message. It’s casual, it’s specific to their world, and people answer it. Once they reply, take it from there: react to what they said, get curious, and run the same Diffuse → Discover → Sell-the-meeting logic as the phone playbook.

This isn’t the same as calling out their evaluation. You’re asking about their competitive landscape in general — fair game, and it gets people talking. You’re never saying “I saw you’re looking at X.”

Build your own version. The pattern that works: short, no pitch, names a real tension in their day, and answerable in one line. Ask yourself what the “do you go up against ___?” question is for your category, and lead with that.

What not to do

Channel guides: Phone · Email · Who works what