Folks at startups have different levels of experience when it comes to working with customers.  At the early stages when you are identifying the problem to solve, the key features of the solution and the customer segments that are the right fit for the solution, you’re spending a lot of time with customers trying to tease out as much information as you can.  Last week I was asked by a new founder what types of questions he should be asking in these meetings.  Here are a few suggestions:

  1. What does your typical day look like? – This one is especially useful at the earliest stages when you are still trying to get a deep understanding of the space, the customers and what the key pain points are for those customers.
  2. If you could change anything at all, what would it be? – This is a good one to get at the most pressing problem that a person is experiencing with a particular task or process.
  3. What is the biggest pain you have today? – This will have to be framed within the context of the broader space you are looking at of course. The key with this question is to probe around the characteristics of the pain.  Why is it painful? What is the measure of that pain (time, effort, etc.)?
  4. How are you solving this problem today? – Again, try to ask a lot of open-ended questions around this one too.  When was the solution implemented?  Why was it done like that? Who made the decision?
  5. What is this problem costing you? (lost revenue, lost customers, increased service costs, etc.)? – This is your first indication of how the customer might measure ROI no a solution in this space.
  6. Who would you expect to solve this problem? – I like this one because it tells me a bit about how a customer would define the solution in terms of market space and also starts telling me something about channels.  For example, in a recent set of interviews I did the customers said they would expect their phone carrier to deliver the solution to the problem (vs. getting it directly from a software provider) or they would expect to get it from a local VAR.  In another set of interviews I did for a different product the answers were IBM, Oracle and Microsoft – with clearly a different set of expectations around that for service, price, etc.
  7. Who else has this problem? – This might be different groups in an enterprise or different groups of consumers.  It’s an interesting question to ask to see what else the customer is seeing in the space.

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