Why what you learned about writing outlines in school may cause you to lose your proposals

Most of the examples of proposal outlines we see on the internet are bad. Really bad. And many of them are used in textbooks and taught as best practice! Here is a typical example:

Title
Summary/Abstract
Introduction/Background
Statement of the Project Problem
Recommendation/Solution
Objectives
Scope
Methods
Schedule
Budget/Pricing
Resources/Staffing
Conclusion
References

Now, forget you ever saw it and never use any of these headings. While this outline may get you a good grade on a lab report, using it in a proposal could result in a loss because:

• It forces the decision maker to read halfway through your proposal before they find out what exactly it is you are proposing. Do you really think they are going to work that hard?
• At best it creates extra reading for the decision maker and at worst it is patronizing, because it tells them about themselves and tells them what their problem is. Recitation does not show understanding or scope. It’s giving them information they already have when what they want is a solution that proves you understand because it addresses their concerns. Understanding is best demonstrated by showing your solution in insightful. 
• It saves the conclusion for the end, when that should be the place where a proposal starts. Proposals should make your points and substantiate them instead of building up to them. Readers don't read a proposal to find out how it ends. If they don't see something compelling up front, they skip ahead looking for something that is compelling.

You see variations on this bad outline all over the place, probably because it's what people learned in school. It might be easy for a teacher to grade, but it makes a buyer’s decision more difficult, and that will increase your odds of losing your proposal. This outline is not competitive against an outline that’s written to give the decision maker what they need.

The headings in your outline should tell the customer what they need to know

The best way to understand how to write a proposal is to put yourself in the shoes of the person making the decision. When someone sends you a document asking you to do something, what do you need to see to decide what to do? The decision maker starts with questions and looks for answers. They don’t read your proposal. They look for answers.

When you are the decision maker, your questions might include:

• What am I going to get or what will the results be?
• Have my expectations been fulfilled?
• Do I have sufficient information and have my questions been answered?
• What could go wrong?
• Why should I believe I’ll get what’s been promised?
• What does the vendor want from me?
• How much is it going to cost and is it worth it?
• Am I sufficiently motivated to move forward?
• If I accept the proposal, what do I have to do?

Now pretend that you are receiving a proposal from someone who wants you to do something, approve something, or buy something. Think about the first thing you want to read. If you weren’t expecting to receive a proposal, it might be “What do you want (from me)?” If you were expecting the proposal, then the first thing you'll probably want to know is “What am I going to get?” This is closely followed by “What do I have to do to get it?” and “Is it worth it?” If you agree that it’s worth it, you’ll want to dig deeper and find out what it will take to make it happen. At that point you start looking for things that could go wrong and will want to make sure you can trust the person or company who brought you the proposal to deliver what they promise. If this is what the decision maker is looking for, then that is what your outline should be. 

You can use the questions above to organize your proposal:

• Introduce what the customer is going to get
  Are you fulfilling their expectations?
• Explain how you will do or deliver the desired results 
  Are you answering all of their questions, addressing and mitigating any risks, eliminating obstacles, establishing value, and proving that your proposal is their best alternative? Have you credibly shown that they will get what you’ve promised? If you are basing that (at least in part) on your experience or track record, have you shown what they’ll get as a result of your having that experience or how it will impact this project?
• Describe the cost and explain how to move forward
  Have you made it clear what they need to do to act on your proposal (including both their procedures as well as yours) and given them sufficient motivation to take that action?

Converting what the customer needs to know into your outline

You should organize your proposal around the questions that you anticipate the customer will have. But to convert these questions into an outline you present the answers. Instead of words that define categories, you can use your headings to deliver a message. If your headings are answers instead of questions, they can tell a story on their own. 

They should all add up to proof that you are the customer’s best alternative.

When you answer the questions you anticipate the customer having, provide each answer as a heading and then substantiate them in the text. Each heading should provide one more reason why the customer should accept your proposal. After you do this, compare it to the outline at the top and ask yourself which best provides the buyer with what they need to know.

What about the RFP?

If you're writing a proposal in response to a written RFP that specifies how they want the proposal organized, you must follow their outline. If you are like me, you didn't learn in school how to parse the instructions in an RFP into an outline, let alone how to incorporate multiple sections of the RFP to create a compliant outline. And you definitely didn't learn how to create a compliance matrix.

However, the evaluator still has the same questions and they still need to find the answers in your proposal. An excellent way to exceed the RFP requirements without increasing the cost of your solution is to do a better job of answering these questions, especially the ones they forgot to ask. If the RFP permits it, you can usually add to the customer's required outline. This gives you a chance to create a proposal that does a better job of answering the customer's questions.

The primary goal of a proposal is not to inform or describe, it’s to persuade by helping the reader decide. To win your proposal, you need to provide the decision maker with the answers they need and then motivate them to accept your proposal. Your outline should be organized to meet their needs and not simply recite the problem or categorize information.