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Entrepreneurial Self-Assessment Questions

Category: Self Reflection Tool

Date Published: Q1 2019

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Overview

Many people find the idea of entrepreneurship glamorous and flashy. However, they soon discover the reality of the situation…

This is a list of questions I developed when I was teaching "Starting Your Own Business" with SPARK in Ann Arbor, MI. The questions are designed to help people think through whether they truly want to become an entrepreneur and, if so, what their goals are.

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Usage Instructions

Find a place that inspires you to get in the right headspace. For me, that's often a coffee shop—or a brewery when I'm feeling adventurous.

Prepare for some self-examination. A cold beverage can help loosen up your brain parts, allowing honest answers to flow as you ponder these questions.

I recommend documenting your answers. While pen and paper are classic choices, you could also use a computer, create a mind map, or even speak your responses aloud into a journal. If you opt for the latter, consider using one of the many AI tools available to transcribe your spoken words.

Limit yourself to about 90 seconds per question to avoid getting bogged down in details. Work through the questions one at a time, jotting down your main reflections on each topic.

For extra insight, consider reviewing your responses with a mentor or business coach.

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Success Story

I've had the opportunity to sit next to dozens of aspiring entrepreneurs and walk them through these questions over the years. The conversations are always very rewarding and usually lead to several aha moments.

If you find these questions to be helpful, or if you have an idea of a question to add, feel free to send me a note.

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15 Questions

  1. What is my true purpose and/or the goal I hope to accomplish with this business?
  2. Why am I doing this instead of being an employee?
  3. How will you know when you’ve been successful in your business?
  4. What is the financial goal I am seeking to achieve?
  5. What sacrifices and risks am I willing to take to be successful?
  6. Why do I want to start a business? OR Why am I in business?
  7. Why do I believe this type of business is sustainable?
  8. Do I have the necessary education, skill and experience to succeed in this industry? If not, can I obtain these qualifications before start-up; how?
  9. If I will need financing, do I have the resources and credit worthiness necessary to be eligible? [High credit score plus assets, collateral and good financial history.]
  10. What are my I unnaturally good at?
  11. What do I suck at?
  12. What is my physical, mental and emotional health and stamina?
  13. What knowledge and skills do I have to start and control the day-to-day operations of a business?
  14. Do I know and understand the technology necessary to be competitive in this business?
  15. Do I have good judgment in people and ideas?
  16. What will it take for me to balance personal life and business demands? </aside>

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