Strategies to Outline Your Proposal: How to be Compliant and Compelling—All in the Same Proposal
By Harley Stein, Partner, Tenzing Consulting

The first order of business at early color reviews – typically blue (outline/compliance) and pink (storyboards/early proposal draft) – is evaluating compliance and wondering if we are telling our story. At most reviews, reviewers quickly determine that we are not compliant and we are not telling our story.

There are only two strategies to help you craft compliant outlines while telling your story when bidding to the Government:

  • Draft an outline that slavishly addresses and follows section L (or whatever section contains proposal instructions). Where the instructions differ with the evaluation criteria, embed the evaluation criteria in with the instructions
  • Draft an outline that slavishly addresses and follows section M (or whatever section contains evaluation criteria). Where the evaluation criteria differ from the instructions, embed the instructions in with the evaluation criteria

If you use any other strategy for outlining – for example, ignoring both the proposal instructions and the evaluation criteria, because they are “not logical,” and deciding to tell your story your way – you have wasted your bid & proposal dollars because you have just started directly down the path to a loss.

Let me repeat this, because I’ve participated in far too many early color reviews where the outlines were remarkably non-compliant – and often deliberately so.

No matter how tempted you are, no mater how much the team protests, draft your outline to be 100% compliant with the proposal instructions or 100% compliant with the evaluation criteria, with the embedding noted above.

Regardless of which method you use, if you want to win, you must select a strategy that conveys your key messages in multiple ways and multiple places.

Strategy 1: Address and follow the proposal instructions
This is the easiest path because our job, in outlining, is to “address and follow the shalls.” Typical Government RFPs are filled with shall statements in many places, and the proposal instructions are one of the key places along with the Statement of Work. The challenge is how to make sure that we address all the shalls, and that challenge is really all about parsing the shall language.

Hint: Watch the commas when reviewing shalls. Paying close attention to commas can help clarify any issues in decomposing requirement, shalls, and instructions.

Sometimes the proposal instructions are a clear statement that is easy to follow. For example:  “The Offeror shall address their approach to identifying qualified personnel.” Our compliant outline should have a sub-topic titled “Approach to Identifying Qualified Personnel.”

Sometimes the proposal instructions are a bit more complex. For example: “The Offeror shall describe its approach to integrating information assurance considerations within infrastructure, systems development, and maintenance activities.”

Is this one topic? Maybe? Are these three topics? Maybe.

The most comprehensive approach is to parse each phrase. The above then becomes three sub-topics titled:

  • Approach to Integrating Information Assurance Considerations within Infrastructure Activities
  • Approach to Integrating Information Assurance Considerations within Systems Development
  • Approach to Integrating Information Assurance Considerations within Maintenance Activities

The reason you outline this as three topics is pretty simple: We want the most comprehensive answer and we want to absolutely, positively be compliant. Turning this into three topics accomplishes both. However … once you sit down with your IA subject matter expert, you might find that there are no real differences between the considerations for infrastructure, systems development, and maintenance activities, and that our approach is identical or nearly the same.

If that occurs, then combine your topic title back to its original phrases: “Approach to Integrating Information Assurance Considerations within Infrastructure, System Development, and Maintenance Activities.” You can combine them because now you know that your proposal will address each and therefore be compliant.

And sometimes the proposal instructions are even more complex. For example, suppose the shall statement is the following: “The Offeror shall describe its approach for providing project management support to include process management and control, project status and cost reporting, identification and tracking of program measures, and identification of problems and corrective actions.”

Yikes! Now what is the sub-topic titled? Surely not “Approach for Providing Project Management Support to Include Process Management and Control, Project Status and Cost Reporting, Identification and Tracking of Program Measures, and Identification of Problems and Corrective Actions.”

No. The tricky part is deciding if all the topics are really sub-topics or if all the topics are separate.

Are all of the above separate topics? No. Why not? Because of the italicized phrase: “The Offeror shall describe its approach for providing project management support to include …” The “to include” means that everything that follows is a subset of project management support. To outline this means that you have a topic titled “Approach for Providing Project Management Support” and you have several sub-topics under it: “Process Management and Control” and “Project status and Cost Reporting,” as well as two other sub-topics.

What about addressing all the proposal instructions, but changing the order? Why change the order? That’s the most important question to answer. If your answer is “Because our order is more logical,” forget that argument. Nobody cares about logic. Should you discuss the companies that comprise the team before we address the organization chart that is filled with teammates as key personnel? Logically, you probably should, but we’ve seen many RFPs that require us to address it in the opposite order …  and guess what, we still manage to be both compliant and get our key messages across.

The bottom line is simple: follow the proposal instructions, in order. If you are desperate to change the order, ask the customer the question – can we change the order – and wait for their response.  That question is straightforward enough that you will probably get a straightforward answer.

Note: Remember with regard to asking the Government a question: you might not get an answer; you might not get the answer you want; and your question and the answer will be published for all bidders.  The safest bet is to do your best to talk yourself and your team out of asking a question and simply follow the proposal instructions.

Strategy 2: Address and follow the evaluation criteria
There are some Government procurement agencies that specifically tell you to address the evaluation criteria; for example, the Acquisition Center of Excellence. The ACE has more than a half-dozen facilities across the nation and they have conducted more than 500 source selections, many in the intelligence community.

Their instructions are very clear: “The offeror shall ensure that all aspects of Section M, Evaluation Factors for Award are addressed in the proposal … the issues discussed in the proposal format Volume III Technical/Management Instructions shall also be addressed.”

The intent is unmistakable: Follow the evaluation criteria and, where necessary, embed the proposal instructions. Yes, there are plenty of “shall” statements in section L; however, they are all directly aligned with section M evaluation criteria.

Curious that more RFPs don’t take this path, given that we will win or lose based on our score against the evaluation criteria.

The guidelines with regard to outlining to be compliant with the evaluation criteria remain the same as noted previously when outlining to be compliant with the proposal instructions.

Strategy 3: Use multiple means and places to deliver your key messages
First, let’s be clear what we mean by story: it is the win themes and differentiators – the key messages – that we want evaluators to notice and remember and score. The best win themes and differentiators not only sell us – they also help us score against the evaluation criteria.

Within a compliant outline there is always room for the key messages. There are five good methods and places to tell our story.

The first and most obvious method is an Executive Summary. This is a great way to tell your story, your way, in a crisp format that has a terrific chance of being read by everybody who matters.

If an Executive Summary is required by the RFP, then of course be compliant and follow the proposal instructions for content. Often, however, the instructions simply tell us to address the key elements and highlights of our proposal. This is an invitation to lay the story out exactly the way we’d like to in a way that showcases our differentiators.

You can also use the Executive Summary to kill two birds with one stone: First, find a way to tell our story, and second, tell our story within the framework of the evaluation criteria. This will showcase why us, but it showcases why us within the context of why we should be highly scored.

There are four other methods to spell out our key messages:

  1. Highlight paragraphs: An intro paragraph that captures the key points of the section or sub-section to follow. This intro addresses the key features, differentiators, benefits, and value of a particular section or sub-section
  2. Call-out boxes: This typically appears near the opening of a section or sub-section and in a few bullets or a crisp sentence or two address the key features, differentiators, benefits, and value of a particular section or sub-section
  3. Captions: Uses the figure or table captions to highlight value statements
  4. Pull quotes: These are typically used in magazines where they enlarge representative quotes or text as a means to draw readers into a story. We use pull quotes in proposals to highlight key messages and to highlight customer quotes about the quality of our work.

These methods to highlight key messages are best when used consistently, which allows evaluators to learn what to look for. Sprinkling our key messages throughout the proposal improves the chances that they will be read and allows us to repeat them as appropriate. We want this redundancy because nobody – except good proposal managers – reads a proposal from front to back; it is shredded and read piecemeal, so there is no guarantee that a message planted in one section will be read by every evaluator.

The bottom line is straightforward: Address and follow the proposal instructions or address and follow the evaluation criteria. Whichever method you use, make sure that you remain responsive and compliant and convey your key messages so the evaluators know why you are their best choice.

TenzingHarley Stein is a proposal professional, professional oral presentation coach and Partner of Tenzing Consulting, specializing in strategies, proposals, presentations and coaching. Contact Harley at or 302-593-6718.  Visit

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