Proposal Management Best Practices

for Proposal Professionals

1: Proposal Management and Bid Qualification

As a busy proposal manager, you’re juggling a lot of different tasks, from writing and reviewing and monitoring and reminding to compliance and deadlines. To keep your team in sync on a large, complex proposal, you follow a predefined process or a process tailored for a specific proposal, comprised of a series of activities and milestones. All aimed at delivering a high-quality, high-scoring, and stand-out proposal.

Your success relies on how effectively you shepherd your team through this process. Leveraging best practices will help you improve the efficiency of that process, empower a productive team, and, most importantly, influence how well your proposal resonates and scores with evaluators.

Opportunity Qualification

The proposal management process begins where the business development and proposal management team meet in the sales cycle; qualifying an opportunity. There are a lot of things to consider when qualifying a bid. What are the customer’s pains and goals? How will your solution address them? What proof do you have that you can do the work? Is the RFP hard-wired for someone else? The goal is to share opportunity information and agree on whether or not to invest in the proposal.

Challenge: When the proposal manager is absent from this milestone, you establish a dangerous transition, or hand-off, gap. The gap lies between what the business development team knows and the details the proposal team needs to write a compelling proposal. As the team begins to write, this gap widens, causing confusion, lack of focus, and unproductive reviews that force additional review and revision cycles.

Best Practice: Include your proposal manager in this milestone. Your proposal manager is your strategic partner in getting the proposal project done, not just on time, but up to evaluator expectations. They are familiar with your solution and your approach to winning and can bring valuable insights to the qualification process.

When your proposal manager is armed with opportunity background and strategy details from the start they can more quickly identify resource and planning challenges. They can inform and educate the team and point them in the right direction on reusable content and valuable proof points. And they can keep misinformation to a minimum and the writing process advancing smoothly.

A lot of improvisation and innovation goes into developing a winning proposal, and what your proposal manager doesn’t know can hurt you, and the pursuit. If the proposal manager is responsible for helping you win, then they need to be part of the discussion about what it’s going to take to invest and win.

Capture Strategy Development

The capture strategy is an opportunity-specific document that carefully outlines exactly how the team will close the sale. It typically includes an opportunity assessment, a competitive assessment, a solution or services capability assessment, a teaming assessment, and an initial price-to-win analysis. It is drafted in support of the opportunity qualification, or the bid/no bid decision, and forms the basis of the proposal management plan. Once the bid decision is a go, the capture strategy is refined and honed into a roadmap focused specifically on what it will take to win.

Challenge: When the capture strategy document is simply served up to the team as-is you establish a dangerous precedent. When the team doesn’t have an opportunity to ask questions, questions about the strategy’s thoroughness or validity will arise as they write. When the team doesn’t understand, or can’t get on board with, the capture strategy, delays in the writing process will quickly impact reviews, proposal quality and win probability.

Best Practice: Invite the team to react, ask questions and discuss details as the capture strategy is refined. This discussion will build better understanding and acceptance, empowering the team to move more quickly to the writing phase. This understanding and acceptance will also eliminate questions and doubts that arise as they write, aid compliance across sections, and smooth the narrative between different writers. Plus, you might just identify solution or strategy issues that are better discovered now than deep in the writing and review cycles.

When everyone on the team understands the big picture, and where their piece of the puzzle fits, they are more likely to step-up, engage, and deliver.

Capture Strategy Discussion

A productive team dialogue is critical to effectual proposal management; it addresses differing opinions, resolves doubts, and aligns strategy. It is distinct from one-way communication exchanges, such as with email, in that it promotes a discussion with a center, rather than from all sides. As much as a “killer app” email is, it is not well suited to a productive team dialogue, especially when the goal is to get everyone on the same page with strategy

Challenge: Group emails are a good example of pushing email to do something that it's not really designed to do. It may be as every day and accessible as coffee and doorknobs, but it’s also where attention and clarity goes to die.

First, email requires attention, a never-ending triage as people respond and reply, distracting you from your task at hand. When it comes to scope, email can be a real time-suck as people reply to the wrong subject, the discussion moves off-topic and the discussion thread becomes convoluted and confusing. In the end, if the team can’t easily participate in the discussion they will simply ignore it.

Best Practice: Experience demonstrates that the more collaborative the capture strategy discussion, the more efficient the writing and reviewing phases of your process will be. When you centralize this discussion, you more quickly socialize the capture strategy with the team and empower their consideration and collaboration. The team visits the capture strategy online, reviews and comments on the details with their questions and concerns. Other team members chime in with their thoughts or explanations. If someone has missed the conversation, they can visit the capture strategy online, review and provide their thoughts, building on what’s come before.

As a result, the team quickly comes to consensus; identifying issues, clarifying questions, resolving differing opinions, and agreeing on the strategy details they’ll use to write the proposal. Plus, the team can always return to the discussion, sorting and filtering to understand how you arrived at a decision. When everyone on the team focuses on a centralized discussion, you save time. Valuable time the team can invest in the quality that resonates with evaluators.

Your success relies on how effectively you shepherd your team through your proposal process. Leverage these best practices to close the gap between what business development knows and the details the proposal team needs to advance the win probability of your next proposal.

2: Proposal Management Writing Collaboration

Proposal writing is a team sport, tasking experts from across your organization to collaborate and bring a compelling and persuasive capture strategy to life in the proposal. Together, their knowledge and experience is greater than the sum of their parts; together their writing establishes authority, demonstrates empathy, validates proficiency, and exhibits commitment. All things an evaluator hopes to find when reading and scoring your proposal.

Writing as a proposal team, however, presents a challenge; with more minds comes differing writing styles and conflicting information. If not diligently monitored and addressed, these issues can negatively impact your proposal win probability.

Pre-Writing Plan

Proposal writing can often feel like a race to the finish line; the majority of the team has a full-time job and everyone has conflicting deadlines and shifting priorities. Whether you decide to write a section together all in a single document or you decide to break down the section into different files, the goal is to get everyone on the same page so your proposal reads like it was written from a single, authoritative source.

Challenge: There are a lot of things to consider before writing a proposal section. What are the customer’s pains and goals? How does your solution solve their problem and achieve their vision for the future? What proofs do you have that you can do the work?

When your team is out of sync on these opportunity details, discriminators and win themes, hairline cracks begin to appear in the writing. Under pressure and deadline, these hairline cracks grow, creating glaring gaps in your narrative, making it difficult for evaluators to read and understand.

Best Practice: To bring greater accuracy and continuity to the narrative, gather and discuss the capture strategy, proposal outline and scoring criteria for the section. Ask questions and agree on overall proposition, style, voice, word choice, and quantitative supporting details.

Break down the high-level scoring categories into relevant questions that might be raised in the evaluator’s mind as they read. Answer each relevant question as part of the writing, breaking down the answers into simple steps and terms. And agree on the writing strategy.

Organizations rely on collaborative teams to ensure their proposals are correct, compliant, persuasive, and quickly compiled. Beginning with a pre-writing plan ensures everyone on the team is on the same page, delivering against capture strategy, and focusing reviews and revisions on improvement rather than correction.

Leverage, but Tailor

No one wants to start from a blank page, or spend time recreating the wheel. Existing, or reusable, content, either from a content library or a past proposal, can speed things up. It can help the team turn around a quick first draft or submit on a tight deadline.

Challenge: We’ve written this before. Can’t we just use that? Yes, but, there are dangers; when your proposal narrative feels “cobbled” together from different sources, evaluators begin to question your attention to detail. And when your proposal doesn’t speak to their specific needs, evaluators begin to question your real interest in their business.

Best Practice: So, leverage your previous content to build your first draft and identify your gaps. Then use these best practices to fill the gaps and tailor your content with a focus on context unique to the customer, and of course, the evaluator.

  • Start by separating the context from the requirement. The proposal may be similar, but tailoring content within the customer’s context, i.e., capture strategy, win themes, and evaluation criteria, will help engage evaluators, keep them reading, and keep them from skimming.

  • Focus tailoring on the “what’s in it for me” aspect of your solution. Focus more on the “what” and the “how” and not so much of the “why.” The more specific you are, the better you’ll build credibility.

  • Make it relatable. People make decisions based on emotions and emotion drives purchasing behaviors. Break content down into easily digestible chunks. Now, infuse each chunk with a relevant, real-life client success story to leave a lasting impression on evaluators.

It may take many drafts to achieve the level of proposal maturity and quality evaluators crave for the win. Tailoring your content will erase the taint of reusable content, and help evaluators better understand and accept your solution.

Collaborate with Reviewers

As the team writes, proposal reviews are a critical step in the process. It is here where reviewer reactions and insights advance proposal maturity and quality; where a choppy narrative becomes engaging, where more concise language builds credibility, and where added details drive a deeper understanding of the solution for a more lasting impression.

Challenge: Aren’t we done yet?

Best Practice: Revisions are typically a crossroads for the proposal team. Time is of the essence and the course of action chosen will significantly affect the proposal’s win probability. Experience demonstrates that the more collaborative this Improvement phase, the more productive the revisions.

  • Ask for Instructions, Not Feedback. This is a best practice first brought to light by Carl Dickson over at PropLIBRARY, and further explored in David Seibert's insightful book, Proposal Best Practices: A Practical Guide to Improve Your Win Rate When Responding to RFPs. Improve time spent in review by asking for specific instructions instead of generic feedback. This small adjustment in mind-set will transform a “this is weak” comment into an “add this proof point to strengthen the section” instruction. Make sure your reviewers understand how each review builds on the last – incrementally improving win probability – and how their reviews are the roadmap that helps the team get there.

  • Use Reviewer Time Wisely. If the review date arrives and the proposal is not ready, full of gaps and inaccuracies and boilerplate, it’s time to reschedule. When it is time to review, swap the frustrating email search for a centralized review. Reviewers will save time with direct access to the current version of the document. They’ll have visibility into what other reviewers are suggesting, eliminating redundant instructions. They’ll have access to previous reviews and their instructions for context and deliver more thoughtful instructions. Add smart phone and tablet access and on-the-go reviewers will never miss a review again.

  • Proposal Reviews are All about Consensus; identifying and agreeing on what needs to be fixed and what needs to be strengthened in the proposal. When reviewers have collaborative access to each other’s work real-time, they can build on ideas, discuss differing opinions, and come to consensus during the review. Proposal managers spend less time clarifying weak comments and mediating differing opinions, and the team spends more time on revisions that improve quality.

By harnessing the collaborative energy of your experts and writers during the writing or Interplay phase, teams avoid the pitfalls of differing writing styles and conflicting information and pave the way for faster, more productive reviews.

3: Proposal Review Inspection

Proposal reviews are a best practice for inspecting and improving content throughout the writing process. They are iterative, aimed at compliance and accuracy and focused on improving proposal maturity. When done well, proposal reviews provide a valuable deliverable; feedback on where the team may have blinded themselves to compliant issues and solution or strategy weaknesses, and recommendations on how to improve quality.

Your success relies on how well each proposal review is managed. Leveraging best practices will help you improve review team productivity, empower consensus among reviewers, and drive specific revision instructions, rather than just feedback, that raise your competitiveness and increase your win probability.

Pre-Reviewing Plan

A productive proposal review begins with independent, knowledgeable reviewers. Independent reviewers bring a fresh pair of eyes for distance and objectivity.

Knowledgeable reviewers provide expertise for accuracy and understanding that brings context and the voice of the customer to the proposal. The right number and mix of reviewers depends on the size, scope, and complexity of your pursuit, as well as the size and goals of your organization.

Challenge: Conflicting priorities and shifting deadlines mean reviewers work in a silo, leaving scope and perspective to the proposal manager. The result is feedback based on opinion, and conflicting opinions at that. When reviewers aren’t on the same page, they will struggle to provide the team with helpful, cohesive direction and instruction.

Best Practice: Whether you leverage Shipley Color Team Reviews or define your own review approach, don’t skip a writing plan review, or Shipley's Pink Team Review. Early buy-in on how the team will write to the capture strategy is one of the best ways to avoid rewriting, or worse, a massive, mid-proposal strategy course change.

Give your review team a game plan. Gather and discuss the capture strategy, proposal outline and scoring criteria. Highlight areas of compliance and identify specifically what needs to be validated. Agree on overall style, voice, and word choice.

If you are conducting multiple reviews throughout the writing process, assign each review a focus. For example, an early review might focus on confirming the proposed solution and validating win themes and proposal themes, while a later review might focus on customer focus and scoring.

Consider assigning each reviewer a specific review mandate, for example solution functionality vs solution technology or win themes vs customer voice.

It is easy to assume reviewers are all pulling in the same direction. Confirm this by discussing your aims together. Beginning each review with a brief pre-review game plan ensures reviewers are on the same page and focused on revisions that drive improvement, not correction or course change.

Instructions Not Feedback

Each review step in your proposal process may have a different focus (first draft, second draft, Pink Team, Red Team). Each reviewer may have a different assigned mandate, (compliance, solution, strategy). Yet, review teams all have one common, overarching goal; advancing proposal win probability. The results of each review are the roadmap that helps the team achieve this goal during revisions.

Challenge: Many of the reviewer comments are unhelpful or uninspired, such as “this is weak” or “this needs more”. Or they are unclear, such as “add more here” or “this doesn’t make sense”. They are mostly useless, and many went in the “round file.” Feedback like “this is weak” doesn’t help you. The team has invested valuable time for nothing.

Best Practice: When you ask a generic question like “feedback,” you should expect a generic answer like, “this is weak.” Instead, ask a specific question like “how can I improve this section” or “how can I support this win theme”? This small adjustment in reviewer mind-set will transform a “this is weak” comment into an “add this proof point to strengthen the section” instruction.

Take this specificity a step further by assigning each reviewer a highlight color. Their review instructions will appear in that color, making it easier to locate and organize revisions, especially when writers are organized by expertise. Have reviewers assign each instruction a category, such as win theme or deficiency.

This provides the proposal manager with a valuable post-review tool; hot washing, or sorting and prioritizing exactly what is incorporated into your proposal before the team takes action. If time is tight, you’ll want to assign instruction categories that prioritize “weaknesses” over “strengths” so you address those compliance issues first.

Above all, give your reviewers time; taking time to think, and provide good instructions, now saves wasted time trying to revise based on bad instructions later.

Proposal reviews are hard work and there is never enough time to review, or revise, everything. It would exasperate most reviewers to know how many of their comments end up in the “round file” due to lack of clarity. Being specific helps reviewers focus on the result you want; insightful instructions that help the team improve quality, i.e., helping evaluators understand, and accept, your solution at a deeper level.

Come to Consensus

Proposal reviews are all about consensus; identifying what needs to be fixed or strengthened, and agreeing on how to fix or strengthen it. It is the difference between one reviewer’s opinion or preference and what is right for the proposal. It requires active participation and a commitment to finding the best “fix” that advances proposal quality without impacting compliance. Conduct as many, or as few, reviews as necessary, just remember, consensus saves time and drives quality.

Challenge: While the friction between differing opinions or viewpoints is great for innovating solutions and strategies, win themes and proposal themes, it is deadly when trying to improve proposal quality. When reviewers have no visibility into what the other reviewers are thinking and suggesting, they cannot come to consensus on the instructions.

When reviewers fail to come to consensus, they deliver redundant, disjointed, and conflicting instructions. This means the proposal manager must spend time mediating different opinions before the team can dive back into writing, or risk confusion and delays among the writing team.

Today’s proposal team is often overwhelmed by electronically submitted comments. With no way to handle them all in a centralized way, many comments make it to the modern version of the round file, the recycle bin.

Best Practice: Rethink review access; email may have revolutionized the way we work, but online, centralized reviews have revolutionized the way we review together. Despite diverse geographic locations, and conflicting priorities and shifting deadlines, each reviewer will see each other’s work. They can discuss differing opinions and come to consensus real-time.

Whatever approach you define, consensus requires collaboration. Collaboration promotes a team conversation with a center, rather than from all sides, so that everyone is on the same page. It drives consensus so the team focuses on advancing proposal quality given the time available.

At the same time, if they review separately on their own schedule, they can see what others have suggested and build off differing opinions to come to consensus. Add the ability to toggle between past versions during the review and your reviewers will have the big picture context they need to provide more thoughtful and productive instructions.

This also gives the proposal manager a competitive, time-saving edge. While the team is reviewing, the proposal manager can monitor how they’re doing. They are alerted as new review instructions are published. They can view the review team's work to date and take steps to clarify instructions before the review window closes.

Finally, schedule a post-review debrief. A productive reviewer-to-writer dialogue collaboration aligns review instructions with revision execution, reducing confusion, and ensuring everyone, no matter where or when they work, is on the same page moving forward.

Crafting a winning proposal is a time-consuming business investment. And it may take many review cycles to achieve the proposal quality required to be competitive. Teams who adopt a more accessible, more collaborative review process will save time and deliver the instruction roadmap necessary to advance your proposal win probability.

4: Post-Proposal-Review Improvement

Post-review revisions, or proposal Improvement, are typically a crossroads for the proposal team; the course of action taken determines your proposal quality. The quality of your proposal, how it is read and scored against the competition, determines your win probability.

Narrative and Story

Proposals are purchasing vehicles. Where business writing, such as documentation, is designed to inform and instruct, proposals are designed to get inside the mind of the evaluator and bring them around to your way of thinking. Quality proposals use narrative and story to engage readers and communicate a clear message about you, your business, and your solution.

Challenge: The proposal was difficult to read and follow. I couldn't connect the dots between the prospects challenge and how we address it. 

Best Practice: Storytelling in proposal writing works the same way as creative storytelling. Except that most elements, such as characters, plot, and setting, are already clearly defined. Improve your narrative and story by focusing on three elements: 

  • Improve Setup. The Setup sets the stage for what business looks like right now; current process, structure, and systems. What is your prospect's Setup? Maybe they have a legacy system that is no longer supported. As with any engaging read, the Setup lays the foundation for Conflict and Resolution.

  • Improve Conflict. The Conflict embodies the events that pushed the prospect to put out the RFP; challenges they are experiencing in their current state. For example, aging technology and a mandate to improve constituent services. Speaking to each one of your prospect's Conflicts in context will lay the groundwork for clear and persuasive Resolution.

  • Improve Resolution. The Resolution presents your company as the solution to the prospect's Conflicts. It doesn’t focus on how great your business is. It focuses on how great you can make your client’s business. Address each Conflict with a Resolution - followed by a brief description of how. Add proof to elevate your solution above the competition. 

Strategic repetition plays an important role in narrative and story as an effective way to subtly remind evaluators about your proposition as they read. Targeting strategic repetition in your cover letter, executive summary, solution overview/approach boosts readability. It also helps evaluator's pick up the narrative no matter what page they start on. Revise by rephrasing the same point, swapping in a client story or quote, and adding a visual to reinforce your point. 

Intent and Context

Writing with intent means your team has an objective; use the win strategy details to send your message. Context is the background, or Setup, that couches your win strategy in the evaluator's circumstances to help them accurately interpret your message. Quality proposals use intent and context to help evaluators absorb and understand your solution.

Challenge: The proposal answers the questions but the answers are generic, they are not aligned with the prospect’s perspective.

Best Practice: The details of intent and context should be defined as part of the pre-writing, or Interplay, phase of proposal development. Enhancing intent and context is one of the goals of the Improvement phase of proposal writing. Improve by honing your intent with these three questions:

  • Why is the team writing this proposal? Obviously, you're writing this proposal to win new business. But your intent is to persuade the evaluator. Assume nothing. Revise so that every answer, headline, bullet point, and graphic clearly connects the dots between your prospect's Conflict and your Resolution. 

  • Why is the evaluator reading the proposal? Yes, sometimes it is as simple as information acquisition or a scoring checklist. But it's probably more about how you think, organize, and solve problems. Revise with a focus on what the evaluator wants to hear from you. Consider what questions will arise in their mind as they read and answer them. 

  • What's your walk-away? Whether the evaluator reads the entire proposal, or just skims it, you should have a clear walk-away message that compliments your win theme(s). Revise with a focus on "What impression do you want to leave with the evaluator?" and "What is the action you want them to take?" 

By clarifying your intent, context ensures evaluator's accurately interpreting your meaning. Context also helps forge a relationship between your team and the evaluator. There are different types of context, but for our purposes of proposal writing, we'll focus on the physical context; the environment in which your proposal story takes place, i.e. the prospects Setup and Conflicts. Here are a few ideas for adding context to your proposal:

  • Be creative. Review your win strategy for details. Dig into the sales team's conversations with the prospect. Read their website and town hall notes. Follow them on Social Media. If you're the incumbent, talk to client support and the delivery team. Leave no stone unturned for examples of how your prospect is feeling in their current state. 

  • Revisit your goal. Review each Conflict. Now, imagine your Resolution's context; what will the world look like when your Resolution addresses their Conflicts? Context can take many forms, however, it's defining characteristic is relatability. 

  • Be mindful. There is such a thing as too much context. It can slow down the read and muddy the message. Include only what is necessary to demonstrate your understanding of the Conflict. Include only what is necessary to help the evaluator understand, and feel the impact of, your Resolution. 

Intent and context give evaluator's a sort of framework for interpreting your Resolution. When proposal teams write with intent and context, evaluators are able to look at the proposal through the lens of relevant perspective.

Tone and Authenticity

Tone is the expression of your business attitude, and specifically, how your audience perceives your words. It begins with how your writers feel about the subject; self-confident and enthusiastic, yet relevant, candid and sincere. It is conveyed by your writers through diction (choice of words and phrases), viewpoint, syntax (grammar and how you put words and phrases together), and the level of formality.

What makes your proposal authentic is the meaning it has for the evaluator. Evaluators are, for the most part, reading your proposal as an inquiry; what is the best way to solve the challenges. Quality proposals use tone and authenticity to up the ante. 

Challenge: The narrative is choppy and the proposal feels “cobbled” together from different sources. I see how we solve the challenges, but it "feels" like documentation. 

Best practice: You need to harmonize your content within the context of your evaluator's perspective. The details of how to set tone should be defined as part of the pre-writing, or Interplay, phase of proposal development. Correcting and smoothing, or harmonizing, the tone and authenticity is one of the goals of the Improvement phase of writing. Improve proposal tone and authenticity by asking these questions:

  • Is it positive? You want your proposal to say, "your project is important enough for us to write a proposal that helps you understand our solution at a deeper level". And you want your proposal to say; "your project is important enough for us to write a proposal you want to read and defend".

  • Is it cooperative? Your word choice—used to evoke positivity and collaboration—uses the pronoun “we” work together to invite mutual participation toward a shared goal.

  • Is it tasteful? Every audience is different, even if you’re selling the same solution or service. Time to revisit the win strategy for evaluator and decision maker details. Keep in mind it’s your audience’s taste that matters, and taste is subjective. 

  • Is it assertive? Exude confidence and authority by being straightforward and mindful of too much context. An assertive tone is most often used to persuade an audience about a topic.

  • Is it encouraging? Being understanding and supportive provides evaluators with reassurance, helping them overcome their fears and take action.

Your proposal says a lot about you, your business, your people, your solution, and what you're like to work with. And your tone and authenticity are a powerful way to communicate the right message. Think of it this way, if your proposal was a person, who would they be? Would you want to work with you? The appropriate tone and authenticity are often remembered far longer than a solution description. 

Crafting a winning proposal is a time-consuming business investment. It may take many review and Improvement cycles to achieve the proposal quality today's evaluators crave for the win. At this crossroad, take the high road; revise to improve quality and elevate your win probability

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