MASTER THE IoO™ SYSTEM

Exploratory Questions for Entrepreneurial Master Planning

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Exploratory Questions for Entrepreneurial Master Planning

1. Passion & Purpose

What inspired you to start your business or pursue your current venture?

Which parts of your work bring you the most energy and fulfillment?

How do your personal values show up in your business decisions?

Are there passion projects you’ve delayed or deprioritized that deserve a second look?

What legacy do you want this venture to leave?

2. Experience & Expertise

What core skills or experiences have most contributed to your current success?

Which of your past business ventures or roles taught you the most about leadership?

Are there talents or perspectives you’ve undervalued in yourself?

What key lessons from failure have informed your current strategy?

What industries or niches do you feel you could dominate with the right alignment?

Network & Influence

Who are the 5 most strategically valuable people in your network today—and why?

Where are the “gaps” in your network that, if filled, would unlock new levels of opportunity?

Are there legacy relationships or partnerships you’re under-utilizing?

How do you maintain and grow influence in your sector or community?

Who in your circle could hold you accountable to your boldest goals?

4. Resources & Optimization

What assets do you own or control that others in your market don’t?

How effective is your current technology stack at supporting scale?

Which internal systems or processes are slowing you down?

Do you have access to capital, facilities, or proprietary IP that could be repurposed or licensed?

What resources do you need but haven’t pursued—funding, talent, mentorship?

5. Business & Revenue Architecture

What is your current business model, and what are its most and least scalable parts?

How diversified are your revenue streams today?

Are there membership, subscription, or licensing models you've explored?

Which product or service delivers the highest ROI—and which drains the most resources?

What are your unit economics, and how do they align with your 12-month revenue target?

6. Vision, Growth & Execution

What does your business look like at its absolute best, 3 years from now?

Which opportunities fall into the Fast Impact, Foundational, and Future-Forward categories?

What is your 30-90-180 day roadmap for growth?

Are there strategic partnerships or joint ventures you’re actively pursuing or avoiding?

How often do you evaluate your progress against your IoO™ categories?

Bonus: Strategic Alignment Questions

Which of your strengths are underutilized in your current plan?

What does “winning” look like—and how will you know when you’ve arrived?

If capital and time were unlimited, what business move would you make first?