Stuck in a Rut? These 13 Questions Will Set You Free!

Rudyard Kipling once wrote: “I keep six honest serving-men, (They taught me all I knew); Their names are What and Why and When, And How and Where and Who.

This quote resonated with me deeply, and I reflected on it as I looked back on 2023. I realized that I too had my own set of serving-men, in the form of questions.

These questions guided me through the year, helping me navigate the complex world of entrepreneurship.

They had taught me to be my own savior, to find inspiration within myself rather than seeking it externally.

Some of these I created myself, while others I borrowed from wise mentors and sources of inspiration.

Here’s part #1 of my favorites from 2023, {{contact.first_name}}:

  • What is the PREFERRED learning style of my target market?
  • Trying to find answers to this one, will get you thinking about the mediums/platforms you should be focusing on with your marketing.
  • Who needs CHANGE but is NOT out of money?
  • That was a question I created for myself, trying to figure out my target market for my consulting services.
  • WHO are you as a practitioner and WHAT is your practice?
  • “We are what we repeatedly do. Excellence, then, is not an act, but a habit”. It helps you pinpoint your different roles in life and regular activities that support growth in these roles.
  • How do you design and structure a business that learns & adapts effectively to a changing environment… a learning organization?
  • From the book “The Fifth Discipline The Art and Practice of the Learning Organization” by Peter Senge. It’s a reminder that no matter how perfect of a “machine” we design for today, it will need to adapt and change tomorrow.
  • What was I doing OBSESSIVELY before I was 10? What has always been my WEIRD?
  • As the wise adage “Know Thyself” advises us to do, this question helps you re-focus on your gifts, in case you have forgotten which they are.
  • Where do I have a HIGHER risk tolerance?
  • Risk tolerance is supposed to be a good barometer of your talents and natural propensities. In my case, I thought of humor, travel, mountain trekking, talking to strangers, and cooking. That’s where I’m most loose.
  • What declaration of POSSIBILITY can I make that has the power to TRANSFORM the community and inspire me?
  • Gets you thinking about your company’s ‘vision’ in less abstract ways and helps you put it in writing. Credit to Peter Block, the author of “Community: The Structure of Belonging”.
  • What is my R.E.S.E.T. button? What activities help to re-align my mental state?
  • Feeling a little burned out? A little reminder to go back to doing what has rejuvenated us in the past. Fun fact: The word “restaurant” comes from the French word “restaurer” — “to restore” or “to renew”.
  • How may I fail faster both in business and in my marketing?
  • A reminder that our progress is largely related to the velocity of our failures. Velocity, not speed, because velocity is directional, and speed is not. So consequently, it does no good to run fast in the wrong direction. Yet you still have to run fast to outrun others.
  • How can you INTEGRATE both opposites so you can have the benefits of BOTH without the downsides of either one?
  • That’s the ULTIMATE innovation question. Innovation is the antidote to the saying “There are no solutions, only trade-offs” — which is true in most cases. Trade-off means EITHER / OR thinking. Innovation: BOTH / AND.
  • If I were to start from scratch (but take anything I want from existing) what would I do?
  • The essence of the Idealized Design process professed by Russel L. Ackoff. It’s a useful thought exercise when you get stuck and cannot seem to find your way out. When you find yourself in a hole— first stop digging.
  • What are my personal revenue-generating or time-saving activities?
  • It helps narrow down the FEW important activities you should be doing as the founder/CEO. Especially if you find yourself overwhelmed or confused, and you can no longer separate wheat from chaff.
  • What’s the #1 THING I’m trying to accomplish? HOW will I know when I’m done? What is the exception? How can I show it?
  • Personalized questions from the Kolbe A test to help me (and maybe you) re-align with instincts and act according to my strengths (instead of weaknesses). FYI: My M.O. is 5-2-9-3, leading with Quick Start.

Questions are more than just tools for problem-solving.

They are guides that lead us to deeper understanding and innovative solutions.

The questions listed above have served me well in my journey, and I hope they can do the same for you.

Remember: Average minds sit in answers. Great minds sit in questions.

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