55 Good Questions to Ask Yourself!

Whenever I meet a prospective new client, I am curious about how they got into their business and how they make money at their business.

I ask a lot of questions for my own knowledge but also as it turns out for their benefit as well.  We sometimes get so caught up in the day-to-day activities that we don’t make the time to step back and think about what we really are trying to accomplish.

So below is my list of 55 good questions to ask yourself.  If we were ever to meet, I would ask many of these questions of you.

Answer them honestly and then follow your own advice, you might just be surprised at how much you already know.


  • What does retirement look like?
  • How many hours do you work each week? How many hours do you want to work each week?
  • What do you do when you are not working? What do you want to do when you are not working?


  • Why did you get into this business?
  • What does success look like?
  • What is your exit strategy?
  • What does your company do? What will your company do in 5 years?  10 years?  25 years?
  • Choose one word that best describes your company: “We are an Operations or Marketing or Financial or Sales or People or Customer or Insert Your Word driven business.”


  • What’s working?
  • What’s not?
  • Why not?
  • What’s next?


  • What is your company’s value proposition (why do people buy from you)?
  • What is your Unique Selling Proposition or what are you best in the world at?


  • What is your current Gross Profit Margin? What do you want it to be and what are you doing to change it?
  • What is your current Net Profit Margin? What do you want it to be and what are you doing to change it?
  • Which major expense categories on your P&L account for 80% of the cost of doing business?
  • Who is responsible for each of these major categories?
  • What are the key metrics that drive your business?


  • Do you have a Board of Directors (formal or informal) and what is the board’s role?
  • What is the make-up of the board members?
  • Who is on your company’s management team?
  • How many of them were promoted from within (versus hired from the outside)?


  • What is the biggest decision you face in the next 60-90 days? In the next year?  In the next 5 years?
  • How will you make that decision? Will it be based on need, financial performance, investment opportunity or something else?
  • Who will be involved in those decisions?
  • What is the biggest challenge you face this quarter and what are you doing about it?
  • What is the biggest challenge you face this year and what are you doing about it?
  • What is the biggest challenge you face in the next 5 years and what are you doing about it?


  • What is your sales process?
  • What are the metrics of sales (calls to make an appointment, appointments to make a sale, length of sales cycle, etc.)?
  • How many salespeople exceeded their goal by at least 10% last year? How many missed their goal last year?
  • What is the selection process for salespeople? What is the training process for salespeople?
  • Which of your salespeople are Hunters? Closers? Consultative Sellers? Qualifiers? Farmers? Ambassadors? Account Managers?


  • How do you market your business? What works?  What doesn’t?
  • What percentage of your sales do you currently spend on marketing and why?


  • What is your annual employee turnover rate? How much is voluntary turnover and how much is planned turnover?
  • Why do employees leave? Why do employees stay?
  • How much training do you do per year for each employee (hours or days / year and dollars / year)?
  • Is the training internal or external, skill development or knowledge, voluntary or mandatory?
  • What would your employees tell me about your company?


  • Who is your ideal customer?
  • How often do they buy from you?
  • What percentage of their business goes to you and what percentage goes to your competitors?
  • When you lose a customer is it usually because of Price, Quality or Service?
  • When you gain a new a customer is it usually because of Price, Quality or Service?
  • Which customers represent 80% of your sales (in rank order)?
  • Which customers represent 80% of your profit (in rank order)?
  • Who are your Top 10 prospective customers? What will you do to win their business?
  • What would your customers tell me about your company?


  • Among your competitors, where do you rank in Sales? Quality?  Service?  Price?
  • What would your competitors tell me about your company?
  • Which competitors would you like to acquire and why?
  • Which competitor is most likely thinking of acquiring you and why?
  • Who are your top five competitors? What is their market share and what will you do to take share away from them?


Dave Baney is the founder and CEO of 55 Questions, LLC and author of “The 3×5 Coach: A Practical Guide to Coaching Your Team for Greater Results and Happier People”, which is now available in Paperback or a Kindle version at https://tinyurl.com/y8ecykfy

At 55 Questions, we work with successful top executives with a driving ambition to crush their competition.  We help CEOs and Entrepreneurs improve alignment, communication and accountability throughout their organization. www.55Questions.com

Follow Dave on LinkedIn https://www.linkedin.com/in/davebaney55questions/