The basics.
Who you are, what the company is, and how we reach you. Nothing surprising here — just the ground truth so we come to our first working session prepared.
Primary contact
Company
Billing
Scheduling
What’s stuck.
The honest version. Not the polished one. Where is the business getting in its own way, and what has that been costing you?
The one thing
If you could fix ONE thing in your business tomorrow — one thing that would make everything else easier — what would it be?
How long has this been a problem? What has it already cost you in time, revenue, or stress — and what happens if nothing changes in the next six months?
What have you already tried to fix it? Why didn’t it stick?
Time & bandwidth leaks
Walk us through a typical week. What tasks eat the most time that you know shouldn’t require your attention?
What would you stop doing entirely if you could — today?
Where do things fall through the cracks most often? (follow-ups, handoffs, invoicing, scheduling, reporting, client comms)
Operations & process gaps
Walk us through how a new client moves through your business, from first contact to delivered result. Take it step by step: what happens, who does it, and which tool it happens in. Where does it slow down or break?
Are there things your business does repeatedly that follow a predictable pattern — same steps, same decisions, every time?
What questions do customers ask you over and over, before they buy and after?
What does your team structure look like? Who does what, and where are the gaps you feel most acutely right now?
Are there functions you are currently doing yourself that you know should belong to someone or something else?
Which decisions can only you make today? Which ones get stuck waiting on you?
Tools & technology
What tools and software do you currently use to run the business? List everything — CRM, project management, billing, comms, scheduling, reporting.
Which of those tools actually work well for you? Which feel like a burden, a workaround, or something you just tolerate?
Are there places where data exists in your business but no one is really using it — customer records, sales data, operational logs?
Where it’s going.
Revenue reality, the dream state, and what a real win looks like. Don’t filter the ambition here — we need the whole picture.
Revenue reality
What does revenue look like over the last 12 months? Growing, flat, or declining — and what is driving that?
What is the single biggest obstacle keeping you from growing revenue right now?
Are there services, products, or revenue streams you could be offering but aren’t — because of time, capacity, or operational limits?
What does your sales or lead generation process look like today? What is working and what is not?
Describe your best customer and your worst one: what kind of customer, and why. No names needed.
How much of your revenue is recurring vs. project-based? Is that ratio working for you, or would you like to change it?
The dream state
If you had unlimited funds and could hire anyone — a full team, all the specialists, every role you’ve been missing — who would you bring in first and what would they do? Don’t be realistic. Dream team only.
Describe the ideal version of this company three years from now. Revenue, team size, client type, how you spend your days — all of it.
What role do you want to be playing in that future version? What do you want to stop doing entirely?
If this business ran exactly the way you want it to — what would change about your personal life?
What success looks like
If we looked back 12 months from today and this engagement was a smashing success in your eyes — what would have needed to happen for you to feel that way?
What number or sign would tell you it worked?
What does success look like in 90 days? What is the first thing you want to feel different about?
What number or sign would tell you it worked?
Rules and boundaries
What won’t you do, even when it costs you money?
Anything you’re required to say, or must never claim, to customers? Who signs off on anything said publicly?
Readiness for the shift.
Where the business stands with technology today — and where a well-placed system could actually move the needle.
Tech comfort & prior experience
How would you rate your own comfort level with technology on a scale of 1 (low) to 10 (high)? What about your team?
Have you experimented with any AI tools so far — ChatGPT, Notion AI, automation tools, AI writing, voice agents? What was that experience like?
Is your team generally open to learning and adopting new tools — or is there resistance? What does change look like inside this company?
Quick-win opportunity scan
Pick the areas that feel most alive right now — no need to fill in every row. Blanks tell us as much as filled cells. For the areas you do fill in, note how it works today, where the pain is, and whether AI or automation could help. We’ll fill in the rest together in our first session.
| Business area | How it works today | Where the pain is | AI opportunity? |
|---|
What’s already built.
Your brand guide, the current tech stack, and the accomplishments worth knowing about. So we can audit and build from what already exists rather than rebuild from zero.
Brand guide
Current tech stack
Digital presence
Worth knowing
The team and what you sell.
Who keeps the business running, and what customers pay you for. Short answers are fine — a name and a role go a long way.
The team
The people who keep this business running (usually 5–15). List key people, not necessarily everyone on payroll.
Accuracy depends on how your team page is built. Review before saving.
What you sell
Your main products or services, one per row.
Accuracy depends on how your services and pricing pages are built. Review before saving.
What do people ask you for that you don’t offer?