30 Questions Every Entrepreneur Should be Asked Before Starting a Business (Part II)
Continuing from last weeks article- Over the years I have noted a series of issues that face the Business Start-up. Very simple but costly questions that I wish someone had asked me when I set up my first business 30 years ago.
No.16 How do you evaluate RISK? Are you personally risk averse or can you be the opposite and reckless? With money, time, resources, conflict, challenges, relationships? In my book ‘The Entrepreneur; White Ball Thinking’ I define the 5th characteristic of the entrepreneur as ‘The Gambler’. Summarised by how you master or manage-
- Facing Fear
- Loss of Wealth & Respect
- Calculated Risk
- Certainty
- Leaps of Faith

No.17 Do you read and study the life stories of Great Entrepreneurs? Do you take advice from the book recommendations made by successful Business owners? Learn to be inspired, take notes, learn from their challenges, successes & failures. My top 10 book recommendations…………..
If you don’t like reading- Download Audible- I have listened to and completed 28hrs towards my Business Book Reading Goals for 2026.

No.18 Do you have all the necessary Qualifications, Certifications and Training? If you are currently employed, or in further education and planning to start a business what training opportunities and certifications is your current employer offering that would help you long-term. Ask how much added value, added services or profit could be generated by having that accreditation?
No.19 Are you entering a high growth sector? Will your business be like pushing a large bolder up a hill or rolling a large bolder down a hill ? Hopefully the latter! How can you alter the design and model of your business to be the latter? And leverage greater success and profitability?
No.20 What new technology or in today’s business world A.I tools should you be adopting? And if you don’t what advantage will your competitor’s gain?If you want to build a legacy business you need the 4th characteristic of the Entrepreneur ‘The Inventor; Ideas’

No.21 Are your prices too low? Many start-ups loose major sales leverage at the out set of their start-up journey due to mis pricing. Once you offer a customer a price it is twice as difficult to raise the price point. Do your market research, and remember starting high always allows you to discount.
No.22 Before spending money on marketing, advertising and social media-Do you have a clearly defined Avatar of your primary customer? Have you crunched down on their age, sex, interests, sector, values, likes, dislikes.
No.23 Cashflow? Have you ensured that you have projected the correct amount of start-up funds you need to keep everything moving forward. In addition to all the resources to getting you to the start line- what will you need month to month to keep the lights on, pay yourself, your staff and restock the shelves and keep the cash flowing.
- Could you negotiate better payment terms with suppliers? 30 days, 60 days?
- Should you spread payments over months rather than paying everything up front?
- Have you created a parallel business & finance strategy through restart, startup, launch to 1st year cash flows?
No.24 Do your work in Order or Chaos? At the start of most mentoring sessions, I ask business owners and CEOs a simple but revealing question: Do you live and work in chaos or in order? For those who admit to operating in chaos, my next question is just as important:
Is there a senior manager i.e. their business partner or P.A that creates the ‘Order’ in their business? If not I recommend that they attempt to quickly change their habits if they want to gain one of the most essential skills for business success and maximum efficiency. Learn more read my blog https://designovation.co.uk/how-to-design-a-high-performing-business-model-and-out-smart-your-competitors/
No.25 Who are your SNEEZERS & CHEERLEADERS (clients who spread the news about how good you are)? Once you start your business and you gain these clients value them- they will propel your business forward. When you gain Sneezers & Cheerleaders this is your first signal that you are doing something right, serving a need and a frustration. It will save you a fortune in marketing!
A LETTER TO YOUR FUTURE SELF
I would suggest that you write the answers to my last FIVE questions in a letter to your future self that you save for future reference.
No.26 Who is your toughest CRITIC? Who in your personal life, work life, career is not necessarily negative but honest? Who in your life will always share some tough love, and cares enough about you to tell you the truth when you need it?
Seek out and find someone like this in business that when you need some honest advice in business they will cut to the chase and give you critical feed back about your business, your ideas, your plans and big business decisions!
No.27 in everything we chose to do in life there is some level of compromise and sacrifice.
Before you start the journey as an entrepreneur what are you not prepared to risk? Keep a promise to yourself to honour this;
- Your Health?
- Your Family Time?
- Your Home?
- Your Ethics & Values?
- Your Pension?
No.28 Where do you gain your source of self- belief and confidence?
I ask this because every entrepreneur at some stage reaches a point where they have a crisis of confidence. And when you reach this point I want you to remember what your answer was to this question; the tools, the people and solution you need to reach for!
For every business owner the answer is different;
- A Person in your life- your business partner, spouse, mentor, parent, friend, old aunt, past colleague
- Books & Education
- Personal Development & Self Help programmes
- Faith- whether spiritual or religious
No.29 Why are you starting a business and leaving employment?
- To be your own boss
- Have more work life balance
- Have more family time
- To gain financial freedom and independence, wealth
- To create, innovate, build a legacy
- To fullfill your passion
- Specific goal, reason?
And if you ever fall out of love with your business (which is inevitable in the journey of every entrepreneur) use it as a reminder of why you started this journey .
No.30 Ask yourself what is your final objective?
What is the final destination?
What will the business look like when it is finally done? Your BIG vision?
And then what is the plan? To replicate & franchise? To sell? Keep it in the family?
Why am I asking you this at start-up?
Because if you can’t answer this now you may be designing a business, a brand, and foundations that don’t match or support your final objective.
If you haven’t read the first 15 questions check it out NOW! PART I