Prompt of the Week: The Executive Voice Style Guide Builder

Hi Reader,

Quick heads up before we get into this week's prompt. I'm trying something new.

Starting next week, alongside the regular Prompt of the Week, I'm going to start including a Claude Cowork prompt. It's a more advanced version of that week's prompt, built for those of you using Claude's new Cowork mode (the desktop app that lets Claude actually do work on your computer, read your files, run your apps and automate multi-step PR/comms workflows end-to-end).

It's a different beast than ChatGPT-in-a-browser. And it's where I think comms work is heading.

If you want in, 👉🏽 click here to get the Cowork version each week.

One click. No form. No spam. I'll just make sure the Cowork prompt shows up in your inbox starting next Saturday, right next to the regular one.

Now, onto this week's prompt.

There's a line in this week's SAP and Anthropic announcement that stuck with me. It described enterprise teams using Claude to build a style guide from a CEO's prior writing, then to ghost-draft emails in the executive's voice.

That's the thing.

For 20 years, "writing in the boss's voice" has been the comms version of an apprenticeship. You read 50 of their emails. You sit in 30 meetings. You absorb it slowly, by osmosis, and then maybe you start to sound like them.

The new move is to systematically extract that voice. So you (or your EA, or your junior AE, or your agency partner) can draft it in on day one, not month six.

👇🏽 Here's the prompt:

Prompt of the Week

🎯 Expert Mode: The "Executive Voice Style Guide Builder."

Scenario: You need anyone on your team — or an exec's EA — to draft emails, posts, and press quotes that actually sound like your executive. Not "AI doing a bad impression." Their actual voice.

Instructions:

1️⃣ Pull together 10 representative writing samples from your exec: 3 emails (one short, one long, one defensive), 3 LinkedIn posts, 2 internal memos, and 2 quotes from past press coverage. Drop everything into one document.

2️⃣ Paste the document into Claude or ChatGPT and run:

"Analyze the writing samples below. Build a detailed style guide that captures: (1) typical sentence length and rhythm, (2) signature phrases and word choices, (3) what this person never says or never uses, (4) tone shifts across contexts — confident, defensive, congratulatory, urgent — and (5) how they open and close written communications."

3️⃣ Have AI generate three test drafts using the guide: a 200-word LinkedIn post on a current industry topic, a 4-line internal email announcing a team wins, and a 50-word quote for a press release. Send them to the exec.

4️⃣ Have the exec mark every line that doesn't sound like them. Paste their edits back into Claude with:

"Here are the executive's corrections. Update the style guide to reflect these patterns, then regenerate the three drafts using the updated guide."

5️⃣ Repeat the loop once more. Save the final style guide as a reusable system prompt your whole team (and EAs, and outside agencies) can call up whenever they're drafting in this exec's voice.

Suggested Tool: Claude or ChatGPT.

Why You'll Love It

It turns "writing in the boss's voice" from a 6-month osmosis project into a 90-minute, repeatable workflow.
Your EA, your junior team members, and your outside partners can produce on-voice copy from day one.
The style guide compounds. Every quarter you refresh it, the drafts get better, and the exec edits less.

This is the closest thing comms work has to real leverage. Build the guide once, and every person writing in that voice instantly gets better — without the executive having to be in the room.

Talk soon, Chris

Here are a few articles from the past week to help keep you up to speed:

Google I/O 2026: How the AI search update changes SEO and brand visibility
Launchcodex / Google Blog May 19, 2026 Google's biggest I/O announcement for PR pros: AI Mode has surpassed one billion monthly users, and brands cited inside AI answers earn 35% more organic clicks and 91% more paid clicks than non-cited competitors on the same query. For communicators, the metric is shifting — it's no longer about ranking, it's about being named.
AI backlash becomes a real business risk
Axios May 17, 2026 New polling shows consumer excitement about AI has dropped from 50% to 19% in just two years — and 54% of Americans say they're experiencing AI fatigue. For brand communicators, this is a strategic warning: how you talk about AI is now a reputational variable, and audiences are increasingly punishing companies that feel AI-heavy or tone-deaf.
How AI Has Changed the Rules for Content Creation
O'Dwyer's PR News May 15, 2026 Content is no longer scarce — credibility is. This sharp piece argues that AI floods channels with volume while real scarcity shifts to verifiable, consistently sourced, human-edited information. The communications teams that win will be those applying editorial judgment, not just output speed.
The State of AI Regulation for Brands: May 2026
EPR / PR News May 2026 A national brand campaign now crosses at least five different state AI compliance regimes. This deep-dive maps the patchwork — including New York's synthetic performer disclosure rules effective June 2026 and the EU AI Act's accelerated disclosure deadline of December 2, 2026. The strategic case: build to the strictest standard now, and roll it down.
2026 Report: Confidence Gap Hinders AI in Communications
Tech Intel Pro May 2026 Communicators rate AI as urgent (7.4/10) and valuable (8.1/10) — but their confidence in actually using it effectively lands at just 4.2/10. Access to tools isn't the bottleneck. Belief is. Worth sharing with your CMO when making the case for dedicated AI practice time.