Outreach Cheat Sheet

There are lots of moving parts when it comes to outreach. And it's very easy to fall into the trap of saying the wrong thing. Keep this article in your back pocket - it's a quick cheat sheet that recaps the fundementals from the outreach playbook.

1. Your first message

Use the following formula to get the conversation going and increase the odds of a reply:

Hi [Name], [Icebreaker / Compliment]  
‍
[Qualifying Question]

The icebreaker / compliment‍

Humans are more open when they feel noticed and valued. A specific compliment proves you’ve done your homework and shifts you from “just another DM” to someone worth replying to. Skip it, and you’ll sound cold, automated, and easy to ignore.

Checklist:

1. Find something they actually care about (recent win, post, career milestone).
2. Keep it short (1–2 lines) and natural, write like you'd speak.
3. Avoid generic lines (“Great profile”) or over-flattery.
4. Where possible, find shared ground to build rapport.
5. If they don’t post, use career history or achievements.

Example: Hey John - huge congrats on winning the clutch award last month. That's an incredible achievement for you and the team. Congrats :)

The qualifying question

A clear, relevant question turns your opener into a conversation. Close-ended questions (“Is it going well?” or equivalent) are soft touch, personable and make it easy to answer and subtly reveal pain points. Without it, you leave them nothing to respond to.

Checklist:

1. Keep it short, ideally one sentence.
2. Tie it directly to the outcome you help clients achieve.
3. Use the “How’s [outcome] going for you - is it going well? :)” template.
4. Avoid selling in DMs Safe that for the call. Focus on uncovering pain.
5. Use simple language. Jargon read like AI wrote it.

Example: Hey John - huge congrats on winning the clutch award last month. That's an incredible achievement for you and the team. Congrats :)

Mind me asking how LinkedIn lead gen has been for you and the [company] team - is it going well?

2. Once they reply

After your qualifying question, prospects almost always fall into one of two camps:

(Path 1) They have a problem

If they admit things aren’t going well, they’ve just opened the door. Acknowledge their reality so it feels like a genuine conversation, then naturally invite them to a call - framed as help, not a pitch. Miss this, and you risk breaking the trust you just built.

Checklist:

1. Recognise what they said, use their own words where possible.
2. Keep the tone casual, empathetic, and human.
3. Frame the call as a quick way to explore solutions.
4. Keep it low-pressure (“worth jumping on for 20 mins?”).
5. Save your pitch details for the call, not the DM.

(Path 2) Things are “going great”

Many will say things are fine - even if there’s room for improvement. Don’t close the tab. Instead, pivot to their next goal. This keeps the conversation moving and gets them thinking things could be better - and about where they want to be - so you can position yourself as the one to help them hit their goal faster.

Checklist:

1. Acknowledge every response so it stays conversational.
2. Ask what their next goal is (make it specific to your expertise).
3. Offer 2–3 example goals to make answering easy.
4. If their goal aligns with your offer, invite them to a call.
5. Keep it curious and exploratory, not sales-y.

Formula

Replies that don't ackowledge the previous message feel transaction. Use this formula:

[Acknowledge what they said in their previous message]

[Ask the next question / position the call]

Managing Replies

Prospects will respond to your qualifying question in one of two ways:

• They have a problem → Acknowledge it and invite them to a call.
• They say things are fine → Acknowledge it, then ask about their next goal.

Give options so it’s easy to answer. e.g. "Mind me asking what your goal is or this quarter - more consistent pipeline / more enterprise leads?"

Checklist:

1. Always round off with a question (conversations die on statements).
2. Keep tone curious, not sales-y - like a doctor diagnosing, not pitching.
3. Objections/curveballs? Acknowledge + ask again (don’t “pitch dump”).

Positioning the Call

Once a problem or goal is uncovered, the next step is to book a call.

Checklist:

1. Keep it low-pressure (“worth jumping on for 20 mins?”).
2. Frame it as exploration, not a pitch (“curious if I can help”).
3. Give a clear next step (send a booking link once they say yes).
4. If not ready, keep the relationship warm don’t force it.

Follow-ups

No response ≠ not interested. If you nailed the above, assume they're busy.

Checklist:

1. 1–2 follow-ups is enough (space them out ~1 week).
2. Add value: comment on their recent post, share an insight, send a useful resource that expands on the issue you solve.
3. Avoid naggy bumps (“Just checking in…” or "John, thoughts?"). They scream low-skill salesman.
4. Try different formats (voice note, a video, and so on).
5. If still no reply, move them to “Not Interested” in your pipeline, and move on.

See examples

Need inspiration? We’ve pulled together screenshots of proven openers, qualifying questions, and follow-up messages based on the playbook. See the full set here → The Outreach Playbook

Using Agent Maya

Want to move faster? We built an AI Agent called Maya to prospect on LinkedIn, start conversations, and guide them to booked calls, all following this exact playbook. She handles the heavy lifting so you can focus on the calls. Join the private beta here.

Getting support

Don’t lose a warm lead because you weren’t sure what to say. If you're an exisiting client, share tricky replies or draft messages with your dedicated expert in Slack and get fast, proven responses that'll help get that prospect on a call.