These GREAT questions disappeared from Tom Tunguz’s blog so I wanted to paste them here for posterity

1. How did you hear about the product? Clarifies which customer acquisition mechanisms are working, and if they are consistent with the company’s perceptions.

2. What process did you use to pick this product over the competition? Sheds light into the sales process, key stakeholders and ultimate decision-maker, and sales cycle length.

3. Why did you choose this product? Clarifies product differentiation, whether there are different customer segments in the market who might use a different product to satisfy unique needs.

4. Which teams in the company use the product, and how has that changed over time? Reveals the key users, potential for account growth and negative churn possibility.

5. How important is this product compared to other software? Validates that, in the words of Paul Graham, this is a hair-on-fire problem.

6. How much do you pay? Is it worth more or less than X product? Ascertains whether the customer believes the return on investment is wildly in their favor.

7. How quickly is the product evolving? How satisfied are you with customer support and working with the company? Indicates churn risk.

8. To whom would you recommend this product? Clarifies the breadth of potential customers the product can serve, and the vigor with which an existing customer would recommend.