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Proposal Management Best Practices, Part 3: Outline And Annotate The Proposal

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Cheryl Smith

10.12.2022

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2 min

When it comes to proposal management, there are a lot of moving pieces to manage, and organization shouldn’t be the thing that keeps your proposal from winning the bid. 

Proposals are persuasive documents; structured logical written arguments that lay out everything in favor of your solution. Most teams rely on their subject matter experts to write their proposals – experts who are used to writing materials that inform and explain, such as documentation or training materials, rather than persuade. Outlining and annotating your proposal before writing begins takes a lot of the doubt and hesitation out of proposal writing, and saves time to focus on improving content maturity and quality that persuades as well as informs evaluators. 

Proposal Content Decisions

Whether your team starts with a blank page or approved boilerplate, they have some decisions to make about each requirement before they start writing. The right decisions deliver compliant and persuasive content for a productive review and productive feedback for strengthening your proposal. The wrong decisions deliver a confusing review with feedback like, "this needs more" or "I don't understand this." 

When you identify your decisions about each requirement up front, you save the team time and confusion and a lot of rewriting effort. 

Proposal Section Outline

The primary goal of the proposal outline is to comply with the structure required. At a high-level, it is reflected in your compliance matrix and your table of contents. At a more granular level, it can give your experts and writers a sense of direction, and you much more productive reviews.

Begin your content outline with your compliance matrix, and annotate each section with strategy-driving details. Start annotating each section by focusing on the reader. In other words, what reviewers, followed by evaluators, intend to find in each section. For example:

  • Why is this section important?
  • Who is this section important to? Is a competitor whispering in their ear? 
  • Should the response be written with the tech team or the front office in mind?

Proposal Requirement Annotation

Now, consider each requirement, or relevant group of requirements. What do your experts, writers and reviewers need to know? Before they write, and before they review? Annotations give them important clues that put them in a strategic mindset. They also help your team dig deeper, uncover patterns, notice important words, and highlight main points or win themes. 

For example: 

  • How do we address a question where the solution falls short? 
  • Who is this section or question important to? 
  • What interesting facts and statistics might resonate with the reader?

One more thing; outlining also helps reviewers by updating them on what the writing team is focused on in each section. This helps focus the comments on how to improve content maturity, and identify gaps so they can be addressed early and minimize last-minute research and rewrites.

Next in our series on proposal management best practices: How can you set your proposal team's expectations, establish trust, and keep the chaos to a minimum?

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Cheryl Smith

Cheryl Smith is our Senior Content Writer. She has additionally been writing and managing proposals since 1998. Shipley trained, she has helped establish proposal centers and advised on capture strategy, coached orals teams and lead marketing, communications and knowledge management programs. Cheryl is a graduate of The George Washington University with degrees in Theatre, Communications and Literature. When she’s not sharing her passion for work, she loves drawing, writing, cooking and exploring the Virginia woodlands with her husband, their dog Chase and the fuzzy guests they host for Rover.

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