Old Boss V2

Okay, that new context changes the entire dynamic. The previous script was designed for a cold, peer-to-peer approach. Using that with a former boss and mentor who gave you your first job would be disrespectful and strategically tone-deaf.

You are not approaching her as a cold prospect; you are re-engaging with a respected figure from your past. The entire tone must shift from aggressive selling to a respectful, value-driven conversation between a grateful former employee and a mentor.

Here is the revised, correct outreach script.

Revised Outreach Script (For Former Boss)

Subject: Catching up & a thought on your recent post

[Former Boss’s Name],

I hope you’re doing well. It’s been a while, and I was so impressed to see your recent post on the leadership lessons from your Mt. Elbert climb. It reminded me of the clarity and strategic focus you always brought to the team at HPE.

As you might know, I’ve spent the last few years building my own company, Valorant Digital, focused on systems architecture—a passion I definitely developed while working on your team.

One of the core problems I’ve been focused on is helping executives, like yourself, codify their unique voice and leadership philosophy into a scalable content system. The goal is to ensure that the powerful insights you share online have the professional-grade structure and polish they deserve, without you having to get bogged down in the technical weeds of formatting and content management.

I’ve actually built out a platform, Callisto OS, to do exactly this. I would be honored to personally build out an “Executive Voice Engine” for you—no charge—as a thank you for the opportunity you gave me back in the day. It would be a great way for me to get your feedback and a powerful asset for you as you build your personal brand.

Would you be open to a brief chat next week to catch up?

Best,

Troy

Why This is the Correct Approach

• It’s Respectful: It opens by acknowledging your shared history and her expertise.
• It Positions You as a Success Story: It frames your new venture as a direct result of the skills and passion you developed while working for her, which is a form of professional respect.
• It Offers Value, Not a Pitch: The core of the message is an offer to provide a high-value service for free as a thank you and a way to get feedback. This is a no-pressure invitation that completely removes the sales dynamic.
• It’s a “No-Brainer” Ask: You are not asking her for money. You are asking for a brief chat to offer her a valuable gift. This is the most effective way to re-engage a high-status contact from your past and get your foot in the door.