8 Tips to Creating a Winning Annotated Outline

The annotated outline. It is the single most important tool for any proposal. It sets the stage for a compliant proposal and sets the tone for a compelling response. And yet, many proposal efforts include a dispute over how the proposal outline is structured which, if not resolved, can derail a proposal. So, what is an annotated outline?

An annotated outline is the master proposal template, generally in Microsoft Word, that includes all the right styles, fonts, margins, and so on. But more than just a proposal template, it includes the proposal outline structure in the form of section and sub-section headings, along with all the information the authors need to write compliant proposal sections that reflect the win strategy.

How to Create an Annotated Outline That Will Ensure Success
1. Include Proposal Instructions, Evaluation Criteria, and PWS or SOW requirements.

Following each proposal section or sub-section heading, paste in the solicitation’s Proposal Instructions, Evaluation Criteria, and PWS or SOW requirements within the annotated outline. It doesn’t matter what colors you use, but we are fans of red for Section L, blue for Section M, and purple for Section C or other requirements.

2. Use Proposal Instructions as the main structure your outline.

The structure of the outline, reflected in the section headings, should follow the Proposal Instructions first. Use subheadings down to the second, third, and fourth levels to incorporate the Evaluation Criteria and PWS/SOW requirements.

3. Include page allocations and restrictions.

The solicitation tells us how long the entire response should be, but the annotated outline should take it a step further. Provide guidance and target page counts down to the second and third headings. This ensures that you do not produce a first draft that is way over page count or falls short of providing the full content needed.

4. Provide additional guidance and content beyond the RFP instructions.

If win themes and discriminators have been established, include them in the outline. But don’t just cut and paste them, think of where they should be addressed, and how. Are they best presented in the introduction? Should they appear in a callout box? Or does a features and benefits table best showcase these themes? Further, which section should they appear, and how much real estate should be given?

5. Provide suggestions for what should be included in the narrative response.

We always include this as Guidance to Writer (in green). There is nothing more daunting to a writer than looking at a blinking cursor on a blank page. Give them a head start. Include specific questions that, once answered, will help them build the narrative response. Some questions might include: “Why is this requirement important to the customer?” “What tools will you use to meet the requirement?” “What process will be used to meet the requirement?” “Who and How will the quality of the product or deliverable be ensured?” “Have you ever performed a similar requirement before?” “If so, was it is successful?”

6. Don’t rely on using boilerplate.

We all know that using existing content, often from prior proposals, is appealing. It’s essentially the easy button. But since every proposal is unique, material from a prior proposal is not tailored to the existing requirements or the specific customer. We don’t suggest ignoring existing content entirely, but writers should be shown how to use it and what needs to be updated. In your annotated outline, provide clear direction on what previous content can be used, what should not be included, and what material needs to be developed from scratch.

7. Use tables.

Some content is best presented in a table, such as risks and mitigations strategies, or features and benefits. Don’t just suggest putting the content in a table, include the table itself so that the writers can get a sense of how the table should be presented, and how much space should be given. Include an example of how to complete the table so that the content included is correct and relevant.

8. Don’t forget about graphics.

Include suggestions as to where and when a graphic might be of value. Include the type of graphic that should be included (process flow, infographic, or organizational chart, for example).

How to Always Ensure the Success of Your Annotated Outline
1. Get consensus on the outline right away.

Once you have developed a first draft, share the outline with the key players to get feedback and ensure that the entire team agrees on the approach of the outline. Be ready to defend it as soon as you walk into Pink and Red Team.

2. Remember the annotated document is a living document.

If the entire team agrees to make a change to the outline, that is okay, so long as it does not interfere with compliance. A change to an outline is not an indication that the initial outline was wrong, it is an indication that the team is thinking collectively and creatively for ways to best present the content to strengthen the evaluation. And that is good!

Done properly, an annotated outline helps you win by ensuring compliance with the solicitation, creating a link between the capture/win strategy and the proposal, and providing concrete writing instructions to authors. Think of the time you spend developing a complete annotated outline as an investment in winning.

This post was written by Meghan Slipka, senior consultant at Red Team Consulting.