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Tools for working out what's actually slowing your business down.

Three free tools for small business owners. Two are questions to sit with on paper. One turns the same attention on the owner rather than the business. No score-chasing, no marketing polish, no email capture.


Pick the one that sounds like you

All four are free. No email capture, no "drip." Take whichever one is loudest right now. Then, if you want to work on your answers, get in touch.

The Health Checks work on paper or with Claude, same twelve questions either way. Anything you run with Claude runs on your own account: your key, your folder, your files. Nothing is hosted here, nothing is sent to me, and any usage cost is billed to you rather than to me.

Health Check 01 · 6 pages · 12 questions · ~20 min

The Operations Health Check

Twelve questions about how your business actually runs day-to-day: what's in your head versus what's in a system, and where the friction is hiding.

If you've thought any of these: "I'm the bottleneck." · "Nothing happens unless I'm the one doing it." · "I haven't taken a real vacation in three years." · "I know we're profitable, but I couldn't tell you why."

Health Check 02 · 6 pages · 12 questions · ~20 min

The Transition Readiness Check

Twelve questions for owners thinking about what's next: selling, stepping back, handing off, or building something that doesn't depend on you being there every day.

If you've thought any of these: "I'd like to sell this in 5 years." · "What happens to this business if I step back?" · "Could I actually walk away?" · "I don't know what this is worth."

Tool 03 · Claude Skills · 3 in order · ~an hour

The Personal Readiness Check

The Health Checks look at the business. This one looks at the owner. Build the picture of what you actually have, work out what an hour of your life is really worth, then find the point where the numbers stop requiring you to work. Three skills, run in order: holdings, then hourly wage, then crossover.

If you've thought any of these: "I don't know what I'd live on if I sold." · "I take a salary but I've never worked out what I earn an hour." · "I'll deal with the personal side later." · "I don't actually know what I have."


What's actually in them

These aren't lead magnets. They're the same questions I'd ask in a real first conversation, and the same system I'd build sitting next to you.

12

Real business questions. A mix of 1–5 scaled questions and short open prompts. Designed to surface what's actually true, not what looks good on paper.

3

Files you keep and own. The System Builder leaves plain files in your own folder: how your business works, what it must never suggest, and two jobs running for real. Nothing hosted, nothing to renew.

0

Gate-keeping or sales pitch. No email wall, no score, no upsell at the end. If your answers point to operations work, I'll say so. If they point to a broker, an attorney, or a bookkeeper, I'll say that too.


Why I built these

Most of the small business owners I work with don't need to be sold on the idea that something's off. They already know. What they need is a clean, low-stakes way to put words to it, before any conversation about hiring help.

So that's what these are. The Health Checks are the questions I'd ask in a first call, written down so you can sit with them on a Sunday morning instead. The System Builder is the session I run with clients, written down so it runs without me. If something comes up while you're working through any of it, write me. You won't get an autoresponder.

— Marika Olson