Read the 8 questions, then tap the record button below when you're ready.
Take your time. Feel free to ramble. Don't edit yourself. 30 minutes is normal.
Your browser will ask for microphone access — that's normal.
Q1. Tell me about your business in your own words.
What do you do, who are your customers, and how long have you been at it? How many people work with you (if anyone)? Walk me through a typical day or week — what are you actually doing Monday through Friday, and where do you spend most of your energy? Roughly what percent of your week goes to working IN the business (the actual work plus the admin around it) versus ON it (selling, planning, growing)? A rough split is fine. And if anyone works with you, who does what — not just how many people.
Q2. Right now, is your business growing, stalling, or a mix?
What's the trend on revenue, customers, or leads? If it's growing, what's driving it? If it's flat or shrinking, what do you think is the cause — competition, losing leads, not enough time to sell, something else? Trust your gut, even if you can't prove it yet.
Q3. Walk me through the last task that ate more time than it should have.
Pick something from the last couple of weeks. What was it, why did it take longer than expected, where did you get stuck, and who else was involved? If you could have just snapped your fingers and deleted that part of the task, which part would it be?
Q4. What are the numbers in your business that actually matter to you — and what do you actually know about them?
How much do you make in a typical month, and do you know where that money comes from? How many hours do you work in a week, and how much of that is billable versus admin or busywork? How many leads do you get and how many turn into customers? Tell me what you track, what you don't, and what you wish you knew if it were easy to see.
Q5. What repetitive stuff do you find yourself doing over and over — admin, writing, decisions, anything?
Emails, estimates, invoices, scheduling, follow-ups, social posts, customer service replies. Walk me through what you currently use to handle it — a spreadsheet, pen and paper, your head, some software — and how long does a typical one take? What would be worth your time to automate or outsource? And if you could write a check today to make ONE of these tasks completely disappear, which one would it be — and ballpark, what's it worth to you to never touch it again?
Q6. What have you already tried with AI, ChatGPT, or any new software — and did it actually help?
Have you played with ChatGPT, Claude, or any AI tools? Tried any software (Zapier, Calendly, project management apps, industry-specific tools)? Anything you signed up for and stopped using? What did or didn't work, and why? Separately from AI: list the actual tools and software you run day to day — for scheduling, estimating, accounting, project management, communication, anything. Even if the honest answer is spreadsheets, paper, or just your phone, tell me that.
Q7. What's your biggest frustration right now about running the business?
Think of the thing that makes you most frustrated or exhausted — the problem you know you need to fix but haven't. It could be a money problem, a time problem, a quality problem, something falling through the cracks, a tool that sucks, a process that's broken. What's the one thing that, if it were fixed, would actually free up your week or make you more money?
Q8. If you had a free assistant who showed up Monday morning and could do anything, what would you have them do first?
Doesn't have to be realistic or even within scope. Could be "answer my phone," "write all my emails," "handle every invoice," "find me better customers," "do all the stuff I hate." Just tell me the gut answer — not what you think you "should" say, but what would actually make your life better.