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Crafting Effective First Message Prompts

This article explains how to create effective First Message prompts in Kakiyo to maximize your LinkedIn outreach success.

Ilan Asseo avatar
Written by Ilan Asseo
Updated over a month ago

What is a First Message Prompt?

While the Context Prompt guides the entire conversation, the First Message Prompt specifically instructs the AI on how to craft the initial outreach message to your prospects. This first impression is critical - it determines whether prospects will engage or ignore your outreach.

Important Clarification: The "First Message" is NOT the connection request, but the first message sent AFTER the prospect has already accepted your LinkedIn connection request.

Why First Messages Matter

The initial message has unique challenges:

  • You have only seconds to capture attention

  • LinkedIn users are bombarded with bad cold messages

  • A poor first message can permanently close the door

  • It's your first real opportunity to demonstrate value

First Message Prompt Structure

An effective First Message Prompt typically includes:

1. Task Definition

Clearly explain what the first message should accomplish:

# Task 

[Define what the first message should achieve and its core approach]

2. Constraints and Requirements

Set specific limitations and must-have elements:

# Constraints 

[List specific rules the AI must follow in crafting the message]

Key Elements to Include in Your First Message Prompt

Consider including instructions about:

  • Length: Most successful first messages are brief (~30 words)

  • Personalization: How to use prospect information effectively

Leveraging Rich Data for Personalization

One of Kakiyo's most powerful features is the AI's access to extensive data for personalization:

LinkedIn Profile Data

The AI has access to the prospect's complete LinkedIn profile:

  • Current and past positions

  • Company information

  • Education history

  • Skills and endorsements

  • Published content and activity

  • Mutual connections

Additional Imported Data

When you import your prospect list, you can include additional data:

  • CRM information

  • Previous interactions

  • Custom notes and tags

  • Industry-specific details

  • Qualification criteria

  • Any other data you've collected...

This wealth of information allows for truly hyper-personalized messages that go far beyond generic templates. The AI can craft messages that reference specific aspects of the prospect's career, recent accomplishments, shared connections, or industry challenges.

Testing Your First Message Prompts

The key to success is iteration:

  1. Create 2-3 different First Message Prompt approaches

  2. Compare the AI-generated messages for quality and impact

  3. Choose the most promising approach to start your campaign

  4. Refine based on actual performance

Common First Message Mistakes to Avoid

In your First Message Prompt, avoid instructing the AI to:

  • Use generic, templated-sounding openings

  • Make the message too long

  • Focus on your company rather than the prospect

  • Use buzzwords and jargon

  • Sound too formal or robotic

  • Make bold claims without evidence

  • Ask for too much in the first interaction

Balancing Personalization and Efficiency

The most effective first messages feel personalized without requiring extensive research:

  • Use the AI to create messages that reference specific details from the prospect's profile

  • Test approaches that can be personalized at scale using available LinkedIn data

  • Find the right balance between customization and template-based efficiency

Next Steps

Once you've crafted an effective First Message Prompt:

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