01
The Business
1. What is your business and what do you do? Give me the real description, not the elevator pitch.
2. How long have you been in business and what stage would you say you're in right now — early, growing, plateaued, scaling, or something else entirely?
3. What is your approximate annual revenue? And are you profitable?
4. How many people are on your team — employees, contractors, or otherwise?
5. What's working in the business right now that you never want to mess with?
6. What's not working that you keep hoping will fix itself?
7. What is the single biggest constraint on your growth right now — be as specific as you can?
8. What decisions have been sitting on your desk the longest?
02
The Founder
9. What's quietly draining you that you haven't said out loud yet?
There's what's draining you that's obvious, clear, right in front of you. And then there's what's draining you that you haven't let yourself say out loud. That's the one we're after here.
10. Where are you leading from your standards — and where are you leading from your guilt, your fear, or your generosity?
11. What role are you playing in this business that only you can play? And what role are you playing that you shouldn't be anymore?
12. What's the hard call you keep not making?
03
The Future
13. Three years from now — if everything goes right — what does your business and your life as a founder actually look like? Think vividly. How much is the business making? How much are you making? What does your day look like hour by hour? Who is on your team and what are they doing? Get detailed — feel free to write as much as you want here.
Can't quite picture the future yet? Start with what it definitely doesn't look like. Sometimes the clearest path forward begins with what we're done tolerating.
14. What are you most excited about — even if it scares you?
15. What do you keep talking yourself out of?
16. What are you most afraid growth costs you?
04
The Relationship
17. What do you need from this partnership to do your best work?
Think about how you receive support, what kind of accountability actually lands for you, and what being truly in your corner looks like.
18. How will you know this was worth it? Not the metrics — the feeling. What's different about you, your business, your day six months from now?
