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How to win proposals by reading the mind of the evaluator

25 questions that will give you insight into how proposal evaluators think

The best way to write a great proposal is to get inside the mind of the evaluator and make it easy for them to reach the desired conclusions. It helps to be able to read the proposal like an evaluator. This can be challenging when you don’t know who the evaluators are. But you can still anticipate what an evaluator has to go through and how they’ll approach looking at your proposal. You might also consider the culture of the customer’s organization and the nature of what they are procuring. 

The answers to the questions below can vary bid by bid based on these factors. The following questions are intended as a way to consider the customer every time you are writing a proposal, and not as a one-time exercise.

See also:
  1. Is the evaluator the end user of what is being proposed? How does that impact what they’ll look for in the proposals?
  2. What guidance has been given to the evaluator regarding their assessment? Are they free to consider whatever they want or reach their own conclusions? How does that impact how they’ll read the proposals?
  3. If the evaluator is not technical, when they read a proposal do they want an explanation of the technology or an explanation of why it is the best way to get the results they are looking for?
  4. Is the evaluator primarily concerned with the qualifications of the vendors (who has the most), or how their qualifications impact their ability to deliver as promised? How does this impact the way you should write about your qualifications?
  5. How does the evaluator assess experience? Do they quantify it and look for the vendor who has the most? Or do they look for vendors who explain how they apply their experience to achieving better results? How does this impact the way you should write about your experience?
  6. Does the evaluator want you to describe yourself, or do they want to know how those details will provide them with better results? How does this impact how you should present details about yourself?
  7. If the evaluator is not the decision maker, what do they have to do to justify their evaluation? What do they need to find in the proposals to accomplish this?
  8. What tasks does the evaluator have to perform in order to complete their evaluation? Will the way your proposal is presented make this easier or harder?
  9. If the evaluator has forms to complete, how will they approach reading your proposal and completing those forms?
  10. What is motivating the evaluator to take action and what does that imply? How will what they see in your proposal impact their motivation and the actions they take?
  11. What must the evaluator believe to accept your recommendations? Does the proposal have to change their beliefs or reinforce them?
  12. What does the evaluator fear? How will this impact their assessment? What can you present to avoid having their fears negatively impact how they assess your proposal?
  13. What are the evaluator’s aspirations and goals? Can you show them how to fulfill their process and still achieve their goals?
  14. What if the evaluator can't find something they are looking for? Have you anticipated what they'll need to locate in your proposal to perform their evaluation? Is it easy to find?
  15. Is the evaluator in a hurry? Does the level of detail and way your proposal is presented support the evaluator’s pace?
  16. How many proposals does the evaluator have to consider? How much attention will they give each one? Will they be motivated to disqualify proposals? Does your proposal focus their attention on the right things?
  17. Must the evaluator reach a decision at all? What alternatives do they have?
  18. Does the evaluator trust you? Does what they see reinforce trust or detract from it?
  19. If the evaluator is concerned about price, will they also be concerned about a company’s ability to deliver at that price?
  20. Does the evaluator see your proposal as more work or as an opportunity? Why? What can you do in your proposal presentation to change that?
  21. If you have a formal evaluation process, how would you set up your evaluation forms? How would they relate to the instructions and evaluation criteria?
  22. Will the evaluator start the proposal review with the RFP and look for how the requirements are addressed in the proposal? Or will they start from the proposal and then try to match it up to the RFP?
  23. If you were the evaluator, and you gave the vendors instructions in the RFP and vendors didn’t follow them, how might you react? How would you assess whether vendors followed the instructions? What would make it easy to determine this in some proposals, but hard in others?
  24. If you are evaluating proposals based on the RFP, but the headings and terminology of the proposals are all different, how do you react? 
  25. If you are the evaluator, how hard will it be to compare the proposals you’ve received from different vendors? Do you compare them to each other, or to the RFP? 

How should all this impact the way you write and present your proposal?

How does it impact the outline, headings, layout, text, and graphics? How does it relate to your strategies for winning? How does it impact the way you articulate things in writing?

When you sit down to write a great proposal, you must take the information you have to share and present it from the customer’s perspective. Answering the questions above can help you discover your customer’s perspective and present things in the way they need to see them in order to accept your proposal.

Let's discuss your challenges with preparing proposals and winning new business...

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Carl Dickson

Carl is the Founder and President of CapturePlanning.com and PropLIBRARY

Carl is an expert at winning in writing, with more than 30 year's experience. He's written multiple books and published over a thousand articles that have helped millions of people develop business and write better proposals. Carl is also a frequent speaker, trainer, and consultant and can be reached at carl.dickson@captureplanning.com. To find out more about him, you can also connect with Carl on LinkedIn.

Click here to learn how to engage Carl as a consultant.

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