15 Questions Guide for New Founders - coach yourself to success

I have recently tweeted that you can think about questions as dynamic and ever-evolving windows into the problems you're solving. Answers on the other hand, would be static snapshots at a given point in time.

I believe that's why experienced business founders, coaches and masters of any craft love asking questions and probing for new angles and new points of view.

That's what I'm doing with my entrepreneurial clients and that's what I invite you to do for yourself. Of course, there are many questions you should be asking when embarking on a new business venture.

The questions listed below are the essence and summary of the most important areas you need to cover in your thinking and they've proven to be often forgotten or ignored. Don't ignore them and take time to think through them. You can and should come back to them at least once every 3 months and see how your thinking and feelings about your new business evolve.

The fact that you should document all the answers in detail goes without saying. Write things down, record the voice or the video. It does not matter, but make sure you have evidence to review and compare.

If you're not sure about tools to use to document your journey - here's a page with my favorite list of tools. Don't worry, you don't need all of them! I'm a tools nerd, so I love exploring new tools + I worked with companies working on some cool tools.

Without further due, let me give you the tools to become your own best self-coach. By regularly asking and answering these 15 questions (+ a few bonus ones) you will gain new insights, self-confidence and you will expand your comfort zone:

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15 self-coaching questions (+ some bonus ones):

Personal Drive, aka Purpose & Vision:

• Why am I starting this business?
• What change or impact do I wish to create in the world?

Solving Real Problems:

• Have I, or someone close to me, experienced the problem I'm trying to solve?

Unique Value:

• How would I describe the unique value my product or service offers in one sentence?
• Did I ask (do I think) they'd pay for it?

True Market Fit:

• Have I spoken directly to potential customers who are not my friends and family?
• What did I learn from them?

Competitive Edge:

• Who's the one competitor I admire most, and why?
• What can I do differently or better?

Monetization Clarity:

• If I had to explain to a 10-year-old, how would I describe the way my business makes money?

Startup Costs:

• How much of my own money am I willing and able to invest before seeking external funding?

Building Team:

• Who's the first person I'd hire or partner with, and why are they the right fit for my business vision?

Culture Creation:

• What three words would I want my future employees to use when describing our company culture?

Technology and Tools:

• Which technological trends and tools am I most excited about integrating into my business?

Customer Feedback:

• How do I plan to gather direct, candid feedback from my first 10 customers?
• How can I delight my first 100 customers so much that they'll naturally want to refer others?

Mentorship Value:

• Who in my industry would I dream of having as a mentor, and what's one question I'd ask them?

Hitting Roadblocks:

• When I encounter a setback or failure, who is my go-to person for advice or a pep talk?
• Is there one challenge that keeps me up at night?

Adaptability:

• How would I pivot if I realized that my current business model isn’t working tomorrow?

Growth or Exit:

• 5-10 years from now, would I rather see my business scaled and booming or sold to a bigger player?

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Bonus questions 😀 to make you even better self-coach

Learning Gap:

• What's one skill or area of knowledge I lack, and how am I planning to address it in the next six months?

Celebrating Wins:

• How will I celebrate my business's small victories, not just the big milestones?

Personal Sacrifice:

• What am I willing to give up in the short term to ensure the long-term success of my venture?

Resilience Check:

• What personal mantra or belief will help me push forward when faced with a setback?

Staying Legal (is a good thing):

• Have I consulted with a legal expert about potential pitfalls or requirements in my industry?

Sustainability Check:

• Beyond profitability, how am I ensuring that my business positively impacts the environment or community?

That's it. Here you have it. Self-coaching is possibly the best way to start making daily progress on your ideas, self-confidence, and adaptability skills.

And as always, if you have any questions or comments, reach me on X (Twitter).