The roast
The world has been behaving weird for a while now. Strategies written three months ago are reading like historical fiction.
Every organization has a gap between its strategy and its reality. Some are managing it. Most are losing to it. The Strategy Roast is built to diagnose which one you are.
Eight questions, no flattery, one honest read of your organization. It combines what you said, what you didn’t say, and what was already known going in. At the end comes the roast 🔥
The format: skill + website
No more thoughts that live and die as posts. A Substack post is a thought expressed once. A skill is a thought that runs every time someone needs it. (It’s a file you install into Claude that encodes a process, so it runs the same way every time.) A website makes the skill free (as a bird).
The Strategy Roast is available as a Claude skill and as a website. Because diagnostic intelligence that used to live in consultancies and workshops should be available to anyone, not just clients with budgets. And if you happened to have a budget, the tool gives you a solid nudge which way to use it. (Don’t be shy, be in touch.)
What it reads
Four dimensions: Meaning, Transition, Value, Momentum. Each one a different layer of organizational reality, each one due for an update when the world shifts.
The roast reads across all four at once. It finds where ambition and capacity haven’t been in the same room for a while. Where the audience moved and the identity didn’t. Where the offering peaked sometime around 2023 and nobody’s said it out loud yet. Where the future vision is the current-year press release.
Who is it for
Built from years of work with art institutions, tech companies, lifestyle brands, and public organizations. So the questions have teeth for cultural and creative orgs in particular.
But it works for anyone where strategy and reality have stopped talking to each other. Even if you’re between jobs. Even if you’re just starting out.
Your turn
The roast is available two ways.
As a website. No account, no setup, just eight questions and an honest read at the end.
As a skill file for Claude. For those who want to go deeper, tweak it, run it on multiple organizations, or build on top of it.
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