16 ways to organize a proposal outline

If there is no RFP, then it’s up to you to figure out how to organize your proposal. When there is an RFP, it sets the customer's expectations regarding how you should organize your proposal. But it may only do so at a high level, leaving you to organize things at the detail level (provided you remain compliant with the RFP).

Here are some ways to organize your outline when it is up to you:

1. Expectations.  By far, the most important consideration in organizing your proposal is to fulfill your customer’s expectations. If you don’t know what they are, you should ask. If you can’t find out, you should guess.
2. Questions and Answers. Q&A formats are often used because they are easy.  But it’s also easy to slip into formulating questions that are based on your perspective instead of the customers’.  It can also be difficult to formulate your questions consistently and to ensure that you address everything you should.
3. Results/achievements/goals. Since the customer is most interested in what they are going to get if they select you, organizing your proposal around the results you will deliver, what will be achieved by selecting you, or goals you will fulfill can reinforce the message.  This works best when there are deliverables, and not as well for on-going service or maintenance proposals.
4. Alternatives or Recommendations. If you are providing the customer with choices, you can organize your proposal around the alternatives.
5. Customer Concerns. If the customer is aware of issues and has concerns, you can organize your response around them. This can work well for high risk projects, or proposals where the customer may choose to do nothing instead of accept the proposal.
6. Customer Priorities. Organizing your proposal around the customer’s priorities can make it easy to see how your proposal matches up.
7. Graphically. Stop thinking about an outline, and draw a picture instead.  Then organize your proposal around it. If you can visualize your offering, then you can make a huge leap in the customer’s perception about your proposal using this approach.
8. Sequence. If there are steps or phases to what you are proposing, you can organize your proposal around the sequence.
9. Calendar. If your proposal revolves around a plan that is based on the calendar, then you can organize your proposal around the dates.
10. Work Breakdown Structure. If your offering will be based on a work breakdown structure, then it may make sense to organize the text that way too.  This works best if the customer understands what a WBS is and is expecting to see one. 
11. Participants. If your proposal is about what people will do, then you can organize it around the participants. This will make it very personal, which could be a good thing or not.
12. Resources. If your proposal is about resource allocation, then you can organize your proposal around the resources.
13. Geographically. If your proposal covers a lot of ground (whether physical or virtual), and what will happen at each location matters, then you can organize your proposal around the locations. 
14. Hierarchy. If there is a top-down structure to what you propose (whether chain of command, logical, general to specific, or anything else), then you can organize your proposal around it.
15. Functionally. If the proposal is about a process or doing things, then you can organize your proposal around the activities.
16. Problem/Solution.  If the proposal solves one or more problems or expects to encounter problems, then you can organize your response around them to reinforce the purpose of the proposal.

And a bonus tip

If you are not trying to match the wording of the RFP, then word your headings to your advantage. Don’t make them merely descriptive of the section.  Use them to say something about what the evaluator is going to read. Use them to state the conclusion you want the reader to reach. Word them so that the Table of Contents tells your story. Word them so that someone who skims your proposal will know why to select you just from reading the headings.