How to win by reading the proposal evaluator's mind

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.

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? What training have they had? What procurement policies or procedures might apply? 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? What matters about the technology to the evaluator? What should matter about the technology to them?
4. Is the evaluator primarily concerned with the qualifications of the vendors, or how their qualifications impact their ability to deliver as promised? Will qualifications be evaluated on a pass/fail basis? How will they assess who has more or better qualifications? Will they even try? 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 do they consider relevance? Does project size or complexity matter? Do they check your references? 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? Put how you want them to think about you aside for a moment. Do vendors really matter to them? If so, what will they think matters about the vendors submitting proposals? What do the evaluators need to know about you to reach a decision in your favor?
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 they have forms to fill out? Rationales to write? Comparisons to make? Checklists to complete? Scores to assign and calculate? Will the way your proposal is presented make this easier or harder?
9. What is motivating the evaluator to take action and what does that imply? What do they care about? What gives them inspiration? How will what they see in your proposal impact their motivation and the actions they take?
10. What must the evaluator believe to accept your recommendations? Does the proposal have to change their existing beliefs or reinforce them?
11. 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? Can their fears help you win?
12. What are the evaluator’s aspirations and goals? How does what you are offering fulfill their goals? Can you show them how making a decision in your favor will help them achieve their goals? 
13. 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 everything easy to find?
14. Is the evaluator in a hurry? Does the level of detail and the way your proposal is presented support the evaluator’s pace? Will they appreciate how easy evaluating your proposal is, or will it be a time-sink and drudgery that slows them down?
15. How many proposals does the evaluator have to consider? How much attention will they give each one? Will they be motivated to disqualify as many proposals as possible to lighten their load? Does your proposal focus their limited attention on the right things?
16. Must the evaluator reach a decision at all? What alternatives do they have? What should you say to prevent them from selecting one of those alternatives?
17. Does the evaluator trust you? Does what they see reinforce trust or detract from it? Do they see claims or do they see proof? 
18. When the evaluator considers price, do they also consider a company’s ability to deliver at that price? Where do they draw the line between wanting the lowest price possible and the risk of nonperformance? How does that impact your pricing and what you say about it in your proposal?
19. When the evaluator considers price, do they also consider value? Are they willing to pay more to get something more? What do they need to justify a decision to pay more to get a better value? Must it be quantified? 
20. The evaluator is concerned about risk, because they are always concerned about risk. How do they assess risk? Are they risk tolerant when it comes to innovation? Or are they risk averse? Which risks are they the most (or least) concerned about? What do they consider sufficient risk mitigation to be? How does this translate into how they perceive strengths and weaknesses, and how they justify their decisions?
21. How does the evaluator define strengths and weaknesses? Is it a strength to meet an RFP requirement, or does it have to be something more? Will risk mitigation count as a strength? What about quality improvements? If you have qualifications that exceed the requirements, will they consider that a strength? If the evaluation is conducted based on an assessment of strengths and weaknesses this becomes critical customer awareness to have.
22. Does the evaluator see your proposal as more work or as an opportunity? Is it the means to get something they want or is it just part of their job? Are they thoughtfully considering or just processing your proposal? What can you do in your proposal presentation to change that?
23. If you were the one to evaluate this procurement and you were doing it formally according to the RFP, how would you set up your evaluation forms? How would the forms relate to the instructions and evaluation criteria? Is your proposal optimized to evaluate well when those forms are completed?
24. 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? This can change how you present your proposal.
25. 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? Would you still be able to perform your evaluation? How hard would you try to evaluate the proposals that didn't follow the instructions?
26. If you are evaluating proposals based on the RFP, but the headings and terminology of the proposals are all different, would that confuse you? How hard do you try to find things that don't match, even if they mean the same thing? If you are keyword searching based on the RFP can you find what you are looking for?
27. 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?

If your proposal is full of what you want to say, then no matter what great things you have to say about yourself, you may be at a competitive disadvantage to a proposal prepared in a way that matches how the evaluators think.

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.

If you were the evaluator and picking an important vendor, wouldn't you look for someone who thinks the same way you do?