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There is a question that, if answered, gives you the insight to make sales and win proposals.

I was invited to teach a class with Dr. Robert Frey, author of Successful Proposal Strategies for Small Businesses, at University of Maryland Baltimore County (UMBC) in association with TargetGov. During our class, Dr. Frey said that, when possible, he always asks future clients a very specific question (the wording is important), “How would you paint a picture of success on this task/project/program now and going forward?” 

It is a question that, according to Dr. Frey, uncovers a spectrum of critical information. I couldn’t agree more. The following are four reasons this question must always be asked:

  1. Asking the future client to “paint a picture” encourages them to visualize the solution. In doing so, emotions are heightened and there is a more profound understanding and communication of their goals and challenges. The future client’s deepest hopes (benefits) and biggest fears (risks) are often shared.
  2. The future client gives backstory and connects the dots. They may also share unstated needs and concerns. For example, an RFP may read, “The offeror shall include three examples of quality control (QC) measures that eliminated errors on similar programs.” When asked the “paint a picture” question, the future client may reveal that they had great pain in the past due to poor quality control. Specifically, the QC process was skipped. Therefore, the examples should demonstrate that the quality control process would be adhered to in any situation. The question uncovers the logic behind the RFP requirements and exposes what keeps the future client awake at night.
  3. The words success, now, and going forward included in the question help to reveal short and long term considerations in the answer. Has the future client thought months, years, decades ahead? How far into the future? Is the path from today to tomorrow clear? Now is the time to know.
  4. The answer to the question ensures the future client and the solution provider are on the same page. For example, if I asked you to think of an office chair, what do you picture? If I ask another person to think of an office chair, do you think they will picture the same chair? Unlikely. For this reason, it is wise not to assume anything. Remain curious and ask clarifying questions so you can visualize the picture your future client is painting. Most sales documents and proposals fall prey to two egregious errors. Practice the following to avoid making these mistakes:

    a) Never paint part of their picture. If they are stuck, help them paint it themselves. You want the future client to be 100% invested in their depiction of the solution, which you will deliver.

    b) Never paint your picture and hope that you can convince the evaluators or decision makers that your solution should be theirs.

Next, Dr. Frey recommends creating a graphic that clearly illustrates that vision. Use the future client’s exact words and ideas in the graphic. Use this graphic as your roadmap.

Dr. Frey has had great success asking this simple question. Follow his example, and you will as well.

Mike Parkinson, CPP APMP Fellow, is an internationally recognized visual communications expert. He is a partner at 24 Hour Company specializing in bid-winning proposal graphics. His Billion Dollar Graphics web site, “Billion Dollar Graphics” book, and Graphic Cheat Sheet share best practices and helpful tools with proposal professionals. Contact Mike at or call 703-533-7209.

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