Tough Questions

The tough questions you receive as a presenter can often lead to undesirable results. Anyone can rehearse a presentation until it sounds flawless. However, the instant someone asks you a tough question, your answer might completely extinguish all of the good will, good rapport, and positive feelings you created for the listener during the presentation. 

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Below, is a list of some of the toughest questions received by entrepreneurs from primarily angel and venture capital investors. Feel free to take any or all of them and prepare yourself by rehearsing your answers in much the same way you rehearse your presentation. For those questions you do not know the answer for, simply say so and get back to them with an answer as follow up. It is quite human to NOT have all of the answers all of the time.

  1. What does your company, product, or service do?

  2. What is the real problem you are solving?

  3. How will you make money?

  4. Who cares? or So what! Why should I or anyone else care?

  5. If this is so great, why hasn't this been done before?

  6. This has been tried before and failed. Why is it going to work this time?

  7. Why you and your team?

  8. What about Slide 7? [while you are on slide 4]

  9. This sounds like a product in search of a problem, isn't it?

  10. I didn't ask you that. I asked you about...?

  11. What is your unique or biggest differentiation?

  12. I have a 3 part question. One... Two... Three...?

  13. How many customers do you have?

  14. How many customers have you validated your product/service with?

  15. Come on. Move on already. Aren't you stating the obvious?

  16. What is your go-to-market strategy?

  17. What are you replacing today with your solution?

  18. What are the most important issues you see facing in the next 3-6 months?

  19. Why should we invest in your company?

  20. Isn't this just a feature?

  21. Haven't we seen this before?

  22. Why will people fall in love with your product or service?

  23. How do you stack up against your competition?

  24. What barriers have you put in place to stave off the competition?

  25. How big is the market, really?

  26. How big is your total addressable market (your TAM)?

  27. Why is this technology defensible?

  28. How do you compare to _________?

  29. Who is desperate or dying for your solution?

  30. Aren't you leaving money on the table?

  31. What are your real barriers to entry?

  32. What are the top 3 risks you face in your business right now?

  33. What is your exit or acquisition strategy?

  34. How many companies have you raised money for?

  35. How long do you see yourself remaining in the CEO role?

  36. How did your investors make out in your last company?

  37. How long before I capitalize on my investment?

  38. What's in it for me (WIIFM)?

  39. What do you want to be when you grow up?

  40. How do you want people to feel after your pitch?

What tough questions are missing?