20 Questions to Develop Your Business

A few months ago a friend who owns a retail furniture store asked me to
help him develop his business. My first step was to understand his business, where he had gaps…and also find out what he didn’t know (but should). I
came up with this list of 20 questions.
As important as the answers are to these, it’s as important that you CAN
answer them. These aren’t all the questions that you could ask, but these were the ones that first lept to the top of the heap for me. There were key answers I was looking for under each of these to understand where his company was mis-prioritized, underutilized and ineffective. Also, with detailed information on some of these (by week or month) you can find interesting insights that lead you to understand the troubling trends.

For my friend’s business, a lot of these were not known…which was the first step…to determine strategy and capture data. For many other answer, there wasn’t a reason for the answer. Similar to many small business owners, decisions were made from the gut or habit, for years. This happens despite the fact that data and competition might lead them in a different direction.

Just asking the questions, digging in deep on some of these, and asking "why" after each answer will yield benefit in most businesses!


  1. What are your short term and long term goals (what time
    period are these goals)?
  2. How do you measure success?
  3. What do you think
    are the top three things keeping you from achieving success?
  4. What are your
    company’s exclusives? What do you have that your competitors can’t or wouldn’t


  1. What is the average order size and average order margin? How has this trended?
  2. How
    many customers buy each month? What is the mix of new vs. previous
  3. What is a customer worth over a lifetime? Have you calculated the
    NPV profitability of customers?
  4. What is the cost per acquiring a customer?
    i.e. Total marketing costs / new customers.


  1. How do you communicate to existing customers after the
  2. What is your monthly marketing spend, and what is the mix between
    the different vehicles? What is this marketing expense trend vs. revenue over
    the past 3 years?
  3. How do you measure your marketing? What tests have you run?
  4. How do your competitors market differently than you?


  1. What are the top 3 things customers are looking for when they
    come to the store / web site? And how do you know this?
  2. Where are most
    customers coming from or going to when they visit your store / site? And how do
    you know this?
  3. If I were a customer, what would my 20 second word of mouth
    ‘sound byte’ be if I were to tell a friend about you? What would I say?
  4. Who
    is your primary competition and how do you differentiate your customer service,
    shopping experience, and products from competition?


  1. What are the roles/responsibilities of the top management in
    the company? How are these made clear to each of them?
  2. What are your key
    performance indicators and how often do you review them as management, and with
  3. How are employees compensated? Are there performance-based incentives?
  4. What are the career paths? Are they clearly communicated to employees?

5 Responses

  1. Thom Singer says:

    This is a great post. I think too often we just do.. without ever asking any questions as to “why” (I am guilty of this!!!)
    Thanks for these, I have to give a 30 minute presentation in an internal meeting at work tomorrow…and I am going to use the “20 Questions” (not these exact ones) as my theme to reach my audience (team members).
    You never know when reading a friends blog is just the spark you need. Your post helped ping my creativity and finish my presentation.

  2. 20 questões para desenvolver os seus negócios

    Sam Decker escreveu brilhantemente as perguntas abaixo, e sugere que a cada leitura e resposta seja feita a pergunta “por quê?”. Ele partiu da premissa de mercado atual, onde as empresas, para serem bem sucedidas devem ser voltadas para o cliente e não…

  3. Sam,
    That’s a good questionnaire to start with!

  4. Three Meaty Posts

    I’d like to share three meaty posts with you. First up is a post from Sam Decker called 20 Questions to Develop Your Business. Whether we work internal to an organization or have our own business, these are excellent questions.

  5. Mary Schmidt says:

    Great list – and I’d add:
    Strategy: Were your employees involved in the planning? Are you having regular review meetings? (This should be working sessions not Powerpoint Pontifications by the big boss.)
    Measurements: Are you measuring the right things for the right reasons? (for example, depending on the business and location – amount of revenue per customer might be a better measure – versus measuring total revenues or revenues per store.)
    Employees: Do you have job descriptions for all positions? Do you have a regular and consistent method of communicating with all employees?

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