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Outreach Prompts for Leadership Candidates Who Usually Ignore You

Senior candidates don’t reply to cookie-cutter messages. This prompt helps you write peer-level LinkedIn outreach that starts real conversations with VPs, CPOs, and CTOs.

Harshita Gakkhar

5 Min Read

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This Prompt Makes You Sound Smarter Than 99% of Recruiters

The hard truth?
98% of leadership candidates won’t even touch your message unless you’re from FAANG or one of those top AI darlings. Senior folks like CTOs, CPOs, and VPs are flooded with LinkedIn messages, and most sound the same: templated, robotic, and easy to ignore.
If you think ChatGPT will make you sound more robotic, you’re wrong. With the right inputs, it becomes your secret weapon for crafting thoughtful, peer-level, personalized outreach that opens real conversations. Let me show you how.

The Prompt

Act as a senior LinkedIn communication expert with 20+ years of experience in executive messaging and leadership hiring outreach.
Your task: Help me write a LinkedIn connection message that gets accepted and opens a conversation about a leadership hiring opportunity.
My goal is to reach out to a senior leader (CTO / CPO / VP / CXO) for a potential leadership hire.
I will share:
The person’s [LinkedIn About section]
Their [most recent LinkedIn post]
A brief about the [role and company (e.g., “Hiring VP of Engineering for a Series B SaaS company backed by Sequoia”)]
Based on that, please generate:
1 personalized LinkedIn connection note (max 300 characters)
10 opening lines (1 sentence each) to grab their attention
10 closing lines (5 short questions + 5 soft statements; each under 5 words)
Tone: Peer-level, thoughtful, and human. Avoid buzzwords and recruiter-speak. Write like someone they’d respect, not ignore.

Always include the leader’s About section and a recent post they’re gold for personalization. This prompt shines when your input reflects their voice, not just your hiring need. That’s what makes your message stand out in a sea of sameness.

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