Complete Guide to Creating High-Converting Messages & Follow-Ups for LinkedIn & Email Outreach

A messaging sequence is a pre-planned series of messages designed to start conversations and book appointments with cold prospects on LinkedIn or via email.

Instead of sending one message and hoping for the best, you create a strategic series of opening messages and follow-ups that you can use to engage prospects.

A typical outreach sequence includes:

Once you create these messages, your AI assistant on Conversifi handles the actual conversations, uses your messaging as a guide, maintains your tone, and moves prospects toward booking calls.

You create the framework, the AI does the heavy lifting.

Many replies come from follow-up messages 2, 3, or even later in the sequence.

People are busy, not uninterested. A good sequence gives them multiple chances to engage without being pushy.

Long messages feel like work. People skim on mobile devices, and big blocks of text get ignored.

Your opening message should typically be 3 sentences or less, around 70-100 words maximum.

Use plenty of white space. Make it easy to read in 10 seconds or less.

Short messages get higher reply rates because they respect the prospect's time and cognitive load.

Your opening message is not a sales pitch. It's a conversation starter.

Avoid talking about pricing, packages, or making big asks upfront.

The goal of your opening message is simply to spark a reply and show you understand their world.

Think of it like meeting someone at a networking event.

You wouldn't immediately launch into a full product demo. You'd ask a relevant question and see if there's mutual interest.

Personalization is what separates your message from the hundreds of spam DMs people receive every week.

Show you've done basic research by mentioning their role, company, or an industry challenge they likely face.

This doesn't need to be elaborate. A single sentence showing you understand their context is enough.

Example:

Messages that end with a specific, easy-to-answer question get more replies than messages that just state facts.

Your question should require minimal thought. Avoid anything that needs a long explanation or deep analysis.

Good questions:

Bad questions:

In your opening message, your call-to-action should be extremely small. You're asking for interest, not commitment.

Instead of "Book a 60-minute strategy call tomorrow at 10am," try "Open to a quick chat?" or "Worth exploring?"

Start with the smallest possible yes. Your AI will handle moving interested prospects toward booking once they engage.

You need messaging that clearly explains why prospects should care. A strong value proposition focuses on four elements:

Examples of concise value statements:

When creating your messaging sequence, you’ll need to choose one clear opening approach for the AI to follow.

The AI does not switch between styles automatically. Instead, it works from the messaging approach you set and applies it consistently across conversations.

In practice, we usually recommend testing different approaches in separate campaigns or sequences to see what performs best for your audience.

Below are the two approaches we most commonly use.

This approach focuses on starting a natural conversation before introducing your service.

The goal is to show relevance, ask a simple question, and build trust before moving toward a pitch.

This style works well when prospects are cautious, receive a lot of outreach, or need context before hearing about solutions.

This approach leads with clarity and value from the first message. You clearly state what you do, who it’s for, and ask if it’s relevant.

This works best in industries where people prefer efficiency and don’t want long back-and-forth conversations.

Choose one approach per messaging sequence.

If you want to compare performance, create separate campaigns and test each style independently.

This keeps your AI consistent, predictable, and aligned with your strategy.

The core principles above work for both sales and recruitment outreach. The main difference is what you emphasize.

Focus on business outcomes: revenue growth, time saved, risk reduced, efficiency gained, opportunities won.

Avoid pushy "buy now" language. Lead with curiosity and relevance. Your goal is to create interest, not force a sale.

Example Opening Messages (Sales):

Slow Build: "Hey Sarah, noticed you're VP of Sales at MarketPro. How are you handling outbound prospecting these days? Is LinkedIn something your team has explored much?"

Direct Pitch: "Hey Sarah, we help sales teams at companies like MarketPro book 20+ meetings per month while cutting outbound work in half. Open to exploring this?"

Focus on candidate benefits: career growth, role impact, company culture, flexibility, compensation (mention lightly if relevant).

Avoid sounding like spam or a mass blast. Show you've looked at their background and understand what might interest them.

Often best to ask a light question first rather than diving straight into the role details.

Example Opening Messages (Recruitment):

Slow Build: "Hey Marcus, saw you've been leading product at FinTech Solutions for the past two years. Impressive growth you've been part of. Are you generally open to hearing about senior product roles, or are you pretty settled where you are?"

Direct Pitch: "Hey Marcus, we're hiring a VP of Product for a Series B fintech that's scaling fast. Thought of you based on your background at FinTech Solutions. Open to learning more?"

Most people don't reply to the first message, not because they're uninterested, but because they're busy.

Research shows that many replies come from follow-up messages 2, 3, or even later. Each follow-up is another opportunity to catch someone at the right moment.

The key is to follow up without being annoying. Stay polite, stay helpful, stay low-pressure.

Keep follow-ups extremely short. Often just 1-3 lines.

Stay polite and low-pressure. You're simply checking if they saw your message and giving them another chance to engage.

You can add light humor in later follow-ups to stand out and show personality. Just make sure it's appropriate for your audience.

Simple, Professional Follow-Ups:

Humorous Follow-Ups (for later in the sequence):

Your last follow-up should leave the door open while providing genuine value with no strings attached.

The goal is to end on a generous note. Even if they never book a call, they should feel like the interaction was worth their time.

Structure of a final follow-up:

Example Final Follow-Ups:

"Hey Michael,

Maybe this slipped by, but if your board is still stretched thin and you want to explore how professional management could drive real growth for your association, we should connect.

You can check out a 2-minute video showcasing what we could achieve here: [video link]"

"Hey Sarah,

Last one from me! If scaling outbound is still on your radar, I put together a quick guide on how sales teams are booking 20+ meetings per month with AI-powered outreach.

Grab it here: [resource link]

No pressure at all, but if you ever want to chat: [calendar link]"

Get crystal clear on who you're targeting and the one main problem you solve for them.

Example: "VP of Sales at B2B SaaS companies struggling to scale outbound without adding headcount"

Create both a "slow build" and "direct pitch" version. Use this simple structure:

Slow Build Structure:

Direct Pitch Structure:

Design a variety of follow-ups your AI can use:

Before finalizing your sequence, verify:

Slow Build Opener: "Hey {FirstName}, noticed you're {Title} at {Company}. How's your team handling LinkedIn prospecting these days? Still doing it all manually?"

Direct Pitch Opener: "Hey {FirstName}, we help sales teams like yours at {Company} automate LinkedIn outreach in their exact tone and book meetings on autopilot. Most clients see 20+ meetings in their first month. Open to exploring this?"

Slow Build Opener: "Hey {FirstName}, saw {Company} in my network. What's tougher these days, keeping members engaged or keeping the board from burning out?"

Direct Pitch Opener: "Hey {FirstName}, we help associations like {Company} grow 20%+ annually while saving boards 100+ hours. Everything's flexible, month to month, no contracts. Open to a quick chat?"

Slow Build Opener: "Hey {FirstName}, saw you've been leading engineering at {Company} for the past two years. Impressive growth you've been part of. Are you generally open to hearing about senior engineering roles, or are you pretty settled where you are?"

Direct Pitch Opener: "Hey {FirstName}, we're hiring a VP of Engineering for a Series B SaaS company scaling fast. Thought of you based on your background at {Company}. Open to learning more?"

"Hey {FirstName},

Maybe this slipped by, but if {pain point} is still an issue and you want to explore how {your solution} could help {Company}, we should connect.

You can check out a 2-minute video showcasing what we've achieved here: [video link]"

The mistake: Your first message is 5+ sentences or includes multiple paragraphs explaining everything about your service.

What to do instead: Keep opening messages to 3 sentences maximum. One line of context, one line of value or question, one CTA.

The mistake: Using language like "I'd love to show you," "I'm reaching out because," "I wanted to introduce you to," or excessive exclamation points.

What to do instead: Write like you're texting a colleague. Casual, confident, direct. "Noticed you're doing X. We help with Y. Worth exploring?"

The mistake: "Book a 60-minute strategy call on Tuesday at 2pm" or "Fill out this questionnaire so we can assess your needs."

What to do instead: Start with the smallest ask possible: "Open to a quick chat?" or "Worth exploring?" Save calendar links and specific times for after they've shown interest.

The mistake: Ending with "Let me know your thoughts" or "Feel free to reach out" or "Looking forward to hearing from you."

What to do instead: Ask a specific, simple question: "Open to a quick call?" / "Worth exploring?" / "How does that sound?"

The mistake: Either sending 10 follow-ups in 3 days, or sending one message and giving up forever.

What to do instead: Plan 4-6 follow-ups spaced over 2-3 weeks. Stay polite and low-pressure. End with a generous value-drop message.

The mistake: Every follow-up is just "bump" or "just checking in" or "circling back."

What to do instead: Include humor, insights, or resources in at least some of your follow-ups. Make each message worth opening.

The mistake: "We leverage cutting-edge AI-driven solutions to optimize your omnichannel B2B go-to-market strategies."

What to do instead: Write like a human. "We automate your LinkedIn outreach and book meetings on autopilot."

The mistake: Generic blasts that could go to anyone: "Hi, I help companies grow."

What to do instead: Always include at least one personalized element: their role, company, recent activity, or relevant pain point.

If you want help generating opening messages and follow-ups based on your specific offer, you can use ChatGPT or Claude with this prompt:

I need help creating a LinkedIn/email outreach messaging sequence for my business.

Here's information about my offer and target audience:

[PASTE YOUR OFFER DETAILS, TARGET AUDIENCE, VALUE PROPOSITION, AND ANY RELEVANT CONTEXT HERE]

Please create:

1. Two different opening message approaches:

- Approach 1: "Slow build" (trust-first, question-based)

- Approach 2: "Direct pitch" (value-first, immediate offer)

2. 5-6 follow-up messages including:

- 2-3 simple, professional nudges

- 1-2 humorous/playful follow-ups

- 1 final value-drop message with a resource offer

Requirements:

- Keep all opening messages under 70 words and 3 sentences maximum

- Make follow-ups 1-3 lines each

- Use casual, conversational tone (like texting a colleague)

- Avoid jargon, buzzwords, and overly salesy language

- Include clear personalization variables like {FirstName}, {Company}, {Title}

- End opening messages with simple, specific questions

- Make sure the value proposition clearly covers: the outcome, why it works, speed of results, and ease of implementation

Format the output clearly so I can easily copy each message into my outreach tool.

Simply paste this prompt into ChatGPT or Claude, add your specific offer information, and it will generate a complete messaging sequence following all the best practices in this guide.

Before launching your outreach, run through this final checklist:

Opening Messages:

Follow-Ups:

Value Proposition:

Overall Tone:

Once your sequence is ready, your Conversifi AI assistant will use these messages as a foundation, adapt the conversation naturally based on prospect responses, handle objections, and move interested prospects toward booking calls. You create the framework, Conversifi does the rest.