Short conversations that make founders think about the right things. Fast.
Each one runs in Claude, ChatGPT or your preferred harness, takes 5–15 minutes, and ends with something concrete you can act on.
| Skill | The question | Time |
|---|---|---|
| Founder Alignment | Are you and your team pointed at the same thing? | varies |
| Founder Replaceability Check | Could your business run without you, and if not, what would it take? | 5–10 min |
| AI Readiness Check | Where does AI actually fit in your business, and what should you leave alone? | 10–15 min |
| Your Next Hire | Money is no object. Who is your next hire? | 5–10 min |
| Why Oh Why | What are you actually trying to achieve, underneath what you just asked for? | 5–10 min |
| CEO Interview Prep | What's your story for this role, and where is it thin? | 5–15 min |
Every question is a plain-text set of instructions in a SKILL.md file. Claude can install it as a skill. ChatGPT and any other AI can run it if you paste it in. Nothing here needs code or an API key, a free plan should be enough, and the conversation works the same way wherever you run it.
- Download the
.skillfile from the skill's folder above - Install it in Claude: Settings > Capabilities > Install skill
- Open a new conversation and use the trigger phrase in the skill's README
- Have the conversation
If you use Cowork, open or create a project with a folder connected (Dropbox, Google Drive or similar) before you start. Otherwise your output has nowhere to save. If you are not in Cowork, skip this and just have the conversation. You can set up a project later when you want to go deeper.
- Open the skill's folder above and open
SKILL.md - Copy the whole file, using the Raw view on GitHub if you want it clean
- Start a new chat and paste it as your first message, followed by the trigger phrase from the skill's README
- Have the conversation
To run the same question repeatedly, paste the file into a Custom GPT's instructions, or into a Project's instructions, instead of pasting it each time.
Gemini, Copilot, Mistral, a local model or anything else that takes a long first message works the same way as ChatGPT. Paste the contents of SKILL.md as your first message or into the tool's custom instructions, then say the trigger phrase.
A capable current model should run these. A smaller model may skip steps or ask several questions at once. If that happens, tell it to ask one question at a time and follow the instructions in the file exactly.
Most questions end with a short written brief. Claude with a connected folder saves it for you. In ChatGPT or another AI, copy the output into your own notes or documents before you close the chat.
New to skills? You will need Claude (free or paid works) and about 30 seconds to install. How to install a skill.
Quick Questions are part of a larger system. If a question surfaced something worth working on, the next step is the BoS OS Bootstrap. It researches your company from public information and sets up a structured operating system you can run with AI, one that remembers your decisions, tracks your missions, and helps your team stay aligned.
Most people who run a Quick Question and then run Bootstrap find the two connect directly. The question names the problem. Bootstrap gives you a system for working on it.
Founders often know something is off but have not named it yet. Quick Questions surface that thing quickly, without ceremony. They are not a substitute for deeper strategy work. They make the deeper work easier by giving you a clear starting point.
Quick Questions are part of the BoS OS, built by Business of Software.