100 small business strategy questions

Many small businesses are fueled by passion. They start because an entrepreneur has an idea (or is sick of working for a boss), they grow because their ideas solve a problem and somehow that solution is communicated to the marketplace.

Unfortunately, many small businesses fail… even ones that are seemingly successful and make profitable sales. The reason is, they’re simply existing day-by-day, sale-by-sale, without any real strategy or long-term vision to give their existence any direction.

If you’re an entrepreneur, answer these 100 small business strategy questions. The answers will help you to highlight areas of opportunity that you can exploit and areas of concern that you can mitigate. Bookmark this page and come back to it regularly to work through these questions every 3 to 6 months.

With your answers, create a list of to-dos that you can act on until you come back to these questions again. [Note: Since publishing this list, I have written individual posts about some of these strategy questions so I’ve updated this list with the links to those other posts.]

  1. What does your business do?
  2. What does your business sell?
  3. What does your business stand for?
  4. What parts of your brand truly reflect your current business?
  5. What parts of your brand do not (or no longer) reflect your current business?
  6. What are the top 10 benefits your business provides?
  7. Who is your perfect customer?
  8. How are you adding value?
  9. What are your products’ or services’ biggest flaws?
  10. How do you define a lead?
  11. Where are your leads coming from?
  12. What demographic are your leads?
  13. How are you creating leads?
  14. How are your competitors creating leads?
  15. How will lead creation change for your industry in the future?
  16. How do you define a prospect?
  17. What is your lead-to-prospect ratio?
  18. What demographic are your prospects?
  19. How is your prospect demographic different from your leads demographic?
  20. How are you turning leads into prospects?
  21. How are your competitors turning leads into prospects?
  22. What objections do your prospects have?
  23. What objections do you NOT have an answer for?
  24. How do you define a customer?
  25. What is your prospect-to-customer ratio (close rate)?
  26. What demographic are your customers?
  27. How is your customer demographic different from your prospect demographic?
  28. How are you converting prospects into customers?
  29. How are your competitors converting prospects into customers?
  30. What has caused you to lose a sale?
  31. How do you define an evangelist?
  32. What is your customer-to-evangelist ratio?
  33. What is your evangelist demographic?
  34. How is your evangelist demographic different from your customer demographic?
  35. How is your relationship with your customers?
  36. What were your 3 most successful marketing campaigns?
  37. What were your 3 least successful marketing campaigns?
  38. What marketing and sales activities are you using in each stage of your sales funnel?
  39. How do you measure company-wide success?
  40. How do you measure personal and/or employee success?
  41. How are you improving your relationship with your customers?
  42. How can you improve the process for receiving and acting on feedback from customers?
  43. How are you encouraging repeat sales?
  44. How are you encouraging upsells?
  45. Who else can use your products or services that you aren’t currently serving?
  46. What is your business model?
  47. What other peer-businesses use the same business model?
  48. What can you learn from peer-businesses that use the same business model?
  49. What other businesses (in other industries) use a similar business model?
  50. What can you learn from businesses in other industries that use a similar business model?
  51. Who are your top 3 competitors?
  52. Who/what are your indirect competitors?
  53. What does the most successful businesses in your industry do that you don’t do yet?
  54. Why would someone buy from you instead of your competition?
  55. When should someone buy from your competition instead of you?
  56. What are your competitors doing differently?
  57. What are your competitors doing better than you?
  58. What are your competitors doing worse than you?
  59. How are your relationships with your suppliers/vendors?
  60. How can your supplier/vendor relationships be improved?
  61. What does your organizational chart look like and what strengths/weaknesses are the result?
  62. What are the next 3 roles you need to hire for?
  63. What was the last thing you tested in your business?
  64. When was the last time you tested a price change and what were the results?
  65. What political changes do you see affecting your business/industry?
  66. What economic changes do you see affecting your business/industry?
  67. What social changes do you see affecting your business/industry?
  68. What technological changes do you see affecting your business/industry?
  69. What financial best practices have you implemented?
  70. How have buying habits changed in your industry?
  71. What trends are influencing buying habits?
  72. How will buying habits change in the future?
  73. How has your industry innovated in the past decade?
  74. How has your business innovated in the past year?
  75. Where does your business plan to innovate this coming year?
  76. How are you investing in your business’ growth (i.e. innovation, new equipment, etc.)?
  77. What is your plan to scale up your business?
  78. If you had to get rid of 90% of your customers, what 10% would you keep?
  79. If you kept 10% of your most profitable customers, what would that demographic look like?
  80. How can you increase your ideal customer base?
  81. How can you decrease your less-than-ideal customer base?
  82. Where are people talking about your business online?
  83. What are people saying about your business online?
  84. What is your plan if your industry suddenly received a lot of bad press?
  85. What is your plan if your business suddenly received a lot of bad press?
  86. What is your plan if your marketing went viral and you suddenly had 10x the customers?
  87. What contingency plans do you a have in place for natural disasters?
  88. What would happen to your business if you were unable to work?
  89. What has changed about your business since you started?
  90. How has your income trended since you started?
  91. How has your profit margin trended since you started?
  92. What plans do you have to increase income next year?
  93. What plans do you have to increase profits next year?
  94. Where do you see your business in 1 year?
  95. Where do you see your business in 5 years?
  96. Where do you see your business in 10 years?
  97. What strengths/assets can you leverage for growth?
  98. Where are your blindspots?
  99. What are the top 3 problems keeping you from advancing to the next level in business?
  100. What about your business, industry, or customers keeps you awake at night?

Aaron Hoos

Aaron Hoos is a writer, strategist, and investor who builds and optimizes profitable sales funnels. He is the author of The Sales Funnel Bible and he's a real estate investor and a copywriter for real estate investors.

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