These are pulled directly from Appendix A. Paste them into your tool of choice, replace the bracketed sections, and use them this afternoon. The full playbook contains twenty.
A note before you start: every template is a draft to refine, not a finished product. The single most predictive habit of an executive whose AI use compounds is that they adapt these to their voice, their context, their stakes. Treat them that way and they will work for you for years.
For pressure-testing any initiative before you commit to it. The "imagine it has already failed" frame surfaces risks that forward-looking analysis tends to miss.
You are a strategy consultant with deep experience in [INDUSTRY]. Below is a brief on an initiative we are considering: [BRIEF]. Assume we proceed and twelve months from now the initiative has clearly failed. Working backwards, identify: 1. The five most likely causes of failure, ranked by probability. 2. The two warning signs that would appear early for each. 3. The single biggest assumption in our brief that, if wrong, would cause failure on its own. Be specific. Avoid generic risks like "execution challenges."
Before any meaningful negotiation — investor, customer, partner, hire. Run this the night before. Then run it again with one fact updated.
You are advising me in a negotiation. The counterparty is [DESCRIBE: stage, role, incentives, recent news]. I want to achieve [OUTCOME] and I am willing to concede on [CONCESSIONS]. Produce: 1. The counterparty's three likely top priorities, ranked. 2. The thing they care about that I have probably underweighted. 3. Two specific framings I should use matching their priorities. 4. The one thing I should NOT say, and why.
For the conversation you're putting off. Performance feedback, a withdrawn offer, a co-founder disagreement, a board update on missed numbers.
Roleplay [THE OTHER PARTY]. Background: [DESCRIBE]. I will tell them [THE MESSAGE]. They will likely react with [ANTICIPATED]. Stay in character. After three exchanges, drop character and tell me: 1. What I said that worked. 2. The one thing I said that escalated the conversation. 3. The single phrase I should have used instead.
For the email that needs to land with someone who doesn't know you and gets fifty inbound asks a week. Specificity is the only currency that works here.
You are writing on my behalf to [PERSON, TITLE, COMPANY]. I have never spoken with them. I want to [GOAL]. Public information about them: [PASTE OR DESCRIBE]. Write a four-to-six sentence email that: - Opens with one specific, non-flattering observation about their work or company. - States my reason for reaching out in a single clear sentence. - Proposes one concrete, low-friction next step. - Does NOT use the words "synergy," "leverage," or "ecosystem."
For decisions that are about to clear your approval. The six-perspective frame surfaces objections each role would raise — without having to convene the actual meeting.
Below is a proposal we are about to approve: [PASTE]. Review six times from different perspectives. Be brief. 1. As the CFO: financial risk and capital allocation. 2. As the COO: execution feasibility and operational drag. 3. As the CRO: customer and revenue impact. 4. As the General Counsel: legal and regulatory exposure. 5. As a competitor: what would I do if I saw this? 6. As a long-tenured cynic: the unspoken reason this might fail.
The full playbook delivers the 6-layer prompt anatomy, the CLEAR framework, before-and-after rewrites of real executive prompts, three case studies, and the 30-Day Executive AI Sprint plan.