Raise it because their situation changed. Leave a real way to say no.
A plan for raising an expansion with an existing customer, starting from the observable change that makes it relevant and ending with an easy exit.
An upsell fails when the customer can tell it exists for your quota. The pitch arrives with an invoice or a support reply, hinges on a limited-time offer, and tells them nothing about why now. Trust takes the damage.
Upsell Conversation tests your reason first: if you cannot name a change in the customer's world, it tells you to wait. When you can, it picks the setting, drafts an opening that asks about what you noticed, writes the offer for both answers, and ends with a line that keeps the door open.
What it produces.
- →A one-sentence test of why this customer, why now
- →A recommended setting for raising it
- →An opening question and offers for yes and no answers
- →A no-pressure exit and a revisit date
- ✦Account managers with customers who have outgrown their plan
- ✦Consultants with a client who has a new adjacent need
- ✦Founders who dislike pushing existing customers
- →upsell-conversation.zip: a native Claude Skill. Upload to Settings → Skills in Claude, or unzip to
~/.claude/skills/ - →upsell-conversation-skill.md: plain markdown. Works in ChatGPT Custom GPTs, Gemini, Claude Projects, agent system prompts, anywhere
- →A README inside the zip with install steps for Claude, ChatGPT, and Gemini
No subscription · free updates within v1.x
Works as a Claude Skill (.zip) and as a plain .md for ChatGPT, Gemini & every LLM
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Before you buy.
How is this different from just asking Claude directly?
Asked cold, Claude writes a persuasive upsell message. This first checks whether there is a real reason to raise one, then structures the conversation as a question with a real option to say no.
How is this different from a Tool?
Playbooks are systematically produced to a fixed template and priced accordingly ($12.99). Tools are hand-built, one at a time, and go deeper ($39 to $199). A Playbook gives you a reliable method for routine work; a Tool is for when the judgment matters more than the format.
Will this work with ChatGPT, Gemini, and other LLMs?
Yes. You get a native Claude Skill (.zip) that auto-invokes in Claude, plus a plain .md you can paste into a ChatGPT Custom GPT, a Gemini system prompt, or any LLM. The procedure travels with the file.
Can I share this with my team?
It's licensed for your own personal and professional use. The output it produces is yours to circulate. To put the Playbook itself in the hands of a whole team, email hello@authority.md about team licensing.
What if it doesn't work for me?
If the file hasn't been delivered, or arrives defective or empty, we refund in full: see our refund policy.