Mentoring Entrepreneurs: Why Customers Don’t Purchase

I had a great mentoring conversation with Boyede Sobitan. He is the Co-Founder & CEO of a startup in the food delivery space, OJAExpress. His business offers food delivery for specialized grocery stores. It is a very interesting business idea for a number of reasons, including what should be a customer base with great word of mouth referral potential. Its pricing model is that they charge a transaction fee. So not a recurring revenue model. We talked about a few challenges, but his biggest challenge was that the sales cycle to convert grocery stores was too long. Once he had grocery stores onboard, OJA could monetize them. But Boyede wanted to speed up the process to convert the supply side of the network.

I asked him, “why are they not signing up?” He didn’t have a great answer. So my advice was to simply ask the customer. Crazy right? Why not just ask the customer why they are not signing up?

At Validately, we did customer research called Sales Win/Loss Analysis. It is a simply as asking customers who recently purchased your product, “Why did you purchase our product?” Or for prospects that didn’t purchase, “why did you not purchase our product?” We hired a User Researcher to conduct the customer interviews, which allows the customers to speak candidly. Note, this is research, not an extended sales process. However, we also asked other sales related questions (such as budget, competitors considered, sales approval process, etc.). And it was GOLD!

How can you do this? Follow these steps:

  1. Hire a researcher on an hourly basis to do this project. You can find one on freelance sites like Upwork. It is worth the investment of hiring someone that the customers/prospects will view as independent.
  2. Create a list of 15 customers who recently purchased and 15 who have not purchased. If they have been in your sales pipeline for a year, it is safe to assume they are not buying.
  3. Create a test script. Questions to consider:
    • What were the top reasons that you chose to purchase our product? (or the flip for losses)
    • What other options did you consider?
    • Why did you choose (or not choose) our product over those options.
    • Walk me through the decision process at your company. Who is involved?
    • What was the most important criteria in your decision?
    • There are many others that you can think of….but you should get the gist by now.
  4. Have the User Researcher reach out to the list of won customers and lost prospects with an email that you draft asking for 30 minutes of their time for a $50 gift card. Tell them that you want to conduct this research to make your product better. It is purely for research purposes. Also, note, you should NOT join the conversations. The goal here is to learn, not change minds. Which leads me to…
  5. Have the Researcher record the session and prepare a summary report of the key findings with video clips. Tools like Validately are great at that, but you can use cheaper tools if you are on a tight budget. Key is to make sure that they record the session for you to watch with your entire team.
  6. Share the videos with your entire team. Schedule a time to discuss their takeaways. It is worth the time to have them stop what they are doing and watch the customers/prospects speak.

Try it. I believe that you will be blown away at the candor that customers will have. They will tell you everything about their purchase decision. You can co-opt their words for marketing material. You can focus on their stated priorities on your home page/marketing material/sales calls. We used the information to change our messaging on sales calls too. Knowing what better to prioritize for new prospects. For customers we won, it was really valuable because it opened the dialogue on getting customer feedback in the future, which we wanted. In general, I have always found customers to be very willing to give feedback if you ask them. Don’t try to sell to them. Just listen. You will be amazed!


Published by v1again

I try very hard to be a great father, husband and entrepreneur. Founded and sold 3 companies. is my 4th startup.

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