Questions an Investor Should Ask an Entrepreneur or Startup

For many new entrepreneurs, knowing what questions may be asked and how to approach the whole pitching process can be a bit confusing.  While investors don't often work from a script or want to make it like a survey, having a set of questions which entrepreneurs should be able to answer easily and fully, helps investors make the most of the pitching process.

Here's a selection from Ben Yoskovitz in the Instigator Blog:

  1. What drives you to do this?  This helps investors to understand the motivation of the entrepreneur.  Is this a whim, or fancy, or is it something they are in for the long haul with?
  2. How have you validated this idea?  This shows they have thought through their idea and understand the potential customer needs.
  3. What keeps you up at night?  A good question to help understand the specific challenges that founder is facing.
  4. What are the next steps? While it may be hard to get it right, having a well thought out, reasonable plan is essential.  
  5. Where do you see the biggest risks?  This shows how much the entrepreneur knows the market they are in, and how they will tackle those problems.
  6. Who is the competition?  The entrepreneur should be able to not only talk about competitors, but also be able to tell you how they are different than their competition.
  7. How can I help?  If the entrepreneur has done their research, they should understand who the investor is and what their strengths are.  

Ultimately, investors have to feel comfortable with the information they get from any entrepreneur, and have to set their own standards, and measure it against the success they have in investing.