1. What is your current role, what does your business or work involve, and how long have you been doing it?(Help me understand who I'm talking to and at what level you're operating. Be specific.)
2. You've worked with coaches before. List them — programs, coaches, masterminds, retreats, courses. For each, what did you pay, what was promised, and what actually happened?(Don't soften this. I want the real history. If you got mixed results, say so. If you got nothing, say so. The truth here matters more than looking good.)
3. What specifically are you wrestling with right now? Not the surface version — the real version. What keeps you up at night? Where do you feel stuck? What pattern keeps repeating that you can't seem to break?(Be specific. "I'm overwhelmed" tells me nothing. "I make decisions reactively, lose my team's trust, and then overcompensate by working 70-hour weeks to fix it" tells me everything.)
4. If you and I worked together for six months and it was a complete success, what would actually be different in your life and work?(This is the early version of your guarantee. Take your time. Be specific. "Make more money" or "feel better" won't be accepted. What does your day look like? How are you leading? What decisions are you making? What's the felt experience?)
5. Why now? What's making you reach out today instead of three months ago or three months from now?(There's always a reason. What is yours?)
6. What's your honest assessment of why your previous coaching didn't work? Be specific. What was missing — from them, from you, or from the dynamic?(I'm not asking you to badmouth other coaches. I'm asking you to take responsibility for your part. If you can't see your part, this work won't help you either.)
7. If we worked together and you didn't get the result you wrote in Question 4, what would you do? Would you blame me? Demand a refund? Walk away quietly? Look at your own behavior?(How you answer this tells me everything about whether you're coachable.)
8. What are you willing to invest — time, money, and energy — to actually get the transformation you've been chasing? Be honest.
9. Is there anything else I should know before I decide whether to book this session with you?