Short conversations that make founders think about the right things. Fast.
Each one runs in Claude, takes 5–15 minutes, and ends with something concrete you can act on.
| Skill | The question | Time |
|---|---|---|
| Founder Alignment Check | Are you and your team pointed at the same thing? | 5–10 min |
| 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 |
If you're in 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 and you'll lose it. If you're not in Cowork yet, skip this and just have the conversation; you can set up a project later when you're ready to go deeper.
- Download the
.skillfile from the skill's folder above. Quick Questions are small enough that there's no build step. You're downloading the file as it sits in the repo, not a packaged release. - 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
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.