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500 questions to ask before starting, selling or investing in business

This book is written for people who are considering starting, selling or investing in a business.

It's easy to forget to ask even the most obvious questions, which in worst case scenarios can lead to bad decision making. So here you go: 500 questions that you should not forget to ask when starting, selling or investing in a business!


Table of content and examples of questions in each chapter:

  • Introduction
  • Questions To Ask Yourself Before Starting A Business 
    • Are you willing to put in long hours?
    • Are your family supportive about this decision?
    • Can you adapt to change?
    • What are you hoping to achieve?
  • Questions To Ask Yourself Before Investing In A Business
    • How does this fit with your overall investment plan?
    • What is your investment time frame?
    • What are your goals with this investment?
    • How often (and how much) will you be making financial contributions?
  • Questions To Ask Yourself Before Selling Your Business The Big Picture
    • Do you have a sales strategy?
    • How much of the business are you willing to sell?
    • What is your business worth and what valuation are you selling at?
    • Is the price of the business fixed or negotiable?
  • Big picture
    • How would you explain the business in in 15 words or less?
    • In short, how does the business make money?
    • Is it an established business or just an idea?
    • Is there an established turnover?
    • How does the business differentiate itself?
  • Strategy
    • Does the business have a clear and defined strategy?
    • Has the strategy been put into writing?
    • How long has this strategy been in place?
    • What are the main strategic goals? Eg. Expansion, Market entry, Product launch 
  • Vision And Mission
    • What is the vision?
    • Is the business capable of reaching its vision?
    • Where should the business be in 5 years?
    • What does the business want to achieve over the next 5-10 years (goals)?
    • What will the business look like once its goals are achieved?
  • Founders, Owners And Key Personnel
    • Who are the current owners and what are their backgrounds (profiles)?
    • What are the owners core competencies?
    • Are the owners also the founders?
    • Are the owners running the business?
  • Product And Services
    • What is the main product that the business is selling?
    • What product generate most revenue?
    • What are the highest, lowest and average profit margins on the products sold?
    • What are the best selling products?
  • Customers
    • Who is the business's primary customer and what does their profile look like?
    • How does the business segment their customer?
    • What new customers would the business like to have?
  • Competitors
    • How many competitors are there in the market?
    • Has the business made a list of competitors?
    • Which of them poses the biggest threat?
    • What are the trends among competitors?
  • Customer Service
    • How is customer service today and what is the aim for it to be in the future?
    • What does the customer service team look like and how many people does it consist of?
    • How high is customer services prioritized (and why)?
    • What are the top 5 typical questions asked to your customer service team?
  • Market Analysis
    • How is the market defined?
    • Who has conducted the market analysis?
    • How big is the market (customers and/or $)?
    • What other products/ services might customers be interested in buying from the business?
  • Marketing And Sales
    • How does the business market itself? 
    • What marketing initiatives have been tried?
    • What marketing initiatives work?
    • What marketing initiatives work the best?
    • How much does it cost to acquire a customer?
  • Financial Information
    • Can the business supply historical income statements?
    • Can the business supply historical balance sheets?
    • Can the business supply historical cash flow documents?
  • Human Resources
    • Can the business provide a current organizational chart?
    • If the business is expanding how would a future organizational chart look like?
    • Are there charts describing the organization in the past?
    • Can the business supply biographies of senior management (including employment history, age, service, years in current position etc.)?
  • Legal Matters
    • Does the business currently have any legal disputes against it?
    • Does the business expect to receive any legal disputes against it?
    • Has the business started any disputes against others?  
  • Partnerships
    • What/ who are the business’s most important partnerships?
    • What does the business do to keep good relationship with its most important partners?
    • Has the business ever terminated any partnerships - and why?
  • Investors And Funding
    • Is the business on the lookout for an investor?
    • Does the business any have current investors onboard?
    • Has the business ever been declined by investors?
  • Assets
    • What assets does the business own?
    • Does the business own any properties?
    • Has office equipment (computers, desks.  etc.) been leased or purchased?
  • Capital Structure
    • Is the business established as a legal entity?
    • Are there any subsidiary companies?
    • Has the business ever been through any debt restructuring plans?
    • Has the business issued any options to anyone?
  • Technology Used
    • Does the business have the proper technology to support its vision?
    • What software does the business use in its the daily operations?
    • How is the business using technology to keep track of its key performance indicators?
    • Are the current technology applications state-of-the-art?
  • Future Growth
    • Is the business being navigated by a clear set of goals (see Vision and Mission-chapter)?
    • What is holding the business back in order to reach those goals?
    • What will it take to launch in a new market? (i.e. new city, state or country)
  • Exit Strategy
    • In short, what is the exit strategy (if any)?
    • Do all shareholders agree to the terms of the exit strategy?
    • Who could the potential buyers be?
  • Other Miscellaneous Questions
    • What parts of the business have been outsourced? 
    • In what order does the business prioritize its shareholders, employees and customers?
    • Are there any conflicts of interest? Eg. Former employment or affiliation?
    • How does the business spur innovation?
  • Documentation For Execution
    • Business plan
    • A detailed budget
    • Letters of current debts
    • Current credits
    • Current and past guarantees

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