1. How often do you reschedule meetings due to calendar overload?

A. Rarely – My calendar is clear and strategic
B. Sometimes – I get overwhelmed but manage
C. Often – My days are chaotic
D. Constantly – My calendar runs me, not the other way around

2. How many hours per week do you spend managing your inbox, scheduling, or follow-ups?

A. Less than 2 hours
B. 2–5 hours
C. 5–10 hours
D. Over 10 hours

3. How often do you have uninterrupted time to think, create, or lead strategically?

A. Daily
B. A few times a week
C. Rarely
D. What’s that?

4. Are administrative tasks preventing you from launching key projects (e.g., book, board meeting, philanthropy)?

A. Never – I have support for that
B. Occasionally
C. Frequently
D. Always – I can’t seem to get to them

5. What kind of support do you currently have?

A. A strategic partner who anticipates needs
B. A reliable assistant for day-to-day
C. Some project-based help when I ask
D. None – I do it all myself

6. How confident are you in handing over mission-critical tasks?

A. Very confident – I trust my team
B. Somewhat confident
C. Nervous but trying
D. I don’t trust anyone to do it right

7. Are you on track to build something that outlasts you?

A. Yes – My legacy is already taking shape
B. Sort of – I have ideas, but I’m not executing
C. Not really – I’m too caught up in the day-to-day
D. I don’t even have the bandwidth to think about legacy