How Making Proposals Easy to Score Will Improve Your Win Rate

Ashley (Kayes) Floro, CPP APMP • February 24, 2026

Winning proposals don’t just happen because the solution is strong—they happen because the proposal is structured to earn points. Too often, teams focus solely on what they want to say, rather than how evaluators will read, interpret, and ultimately score their response. If you want to increase your probability of win, you must first understand how proposals are evaluated and then write with that scoring process in mind. By aligning your content to evaluation criteria, highlighting clear strengths, and making it easy for evaluators to assign high ratings, you can transform a compliant submission into a high-scoring, competitive proposal.


Understanding Proposal Evaluation


Before we can really understand how to make proposals easier to score, we have to understand how proposals are being evaluated. The first thing to understand is that proposals are typically first reviewed for compliance with the requirements as outlined in the proposal instructions. Next, the proposals are scored based on the evaluation criteria. Customers frequently assign strengths, weaknesses, and deficiencies to back up their scores. To receive an “Exceptional” score, your strengths have to outweigh any weaknesses, and no major deficiencies can be present. When using this scoring method, a deficiency is typically defined as a material failure of a proposal to meet a customer requirement or a combination of significant weaknesses in a proposal that increases the risk of unsuccessful contract performance to an unacceptable level. A weakness is defined as a flaw in the proposal that increases the risk of unsuccessful contract performance. And significant strengths are defined as aspects of an offeror's proposal that have merit or that exceed specified performance or capability requirements in a way that will be advantageous to the customer during contract performance. In our proposals, we want to minimize any weaknesses and deficiencies and maximize our strengths and significant strengths.


Organize Content So It’s Easy to Score


Understanding that proposals are scored, it makes good sense that when we’re writing proposals, we need to present the information in a way that is easy for evaluators to score. Most evaluators do not volunteer for the job and do not particularly enjoy it. It takes time away from their regular job, so they want to get it over with as quickly as possible. Therefore, we should aim to make the evaluator’s job as easy as possible. To make your sections easy to score, structure your response to the proposal instructions and the evaluation criteria. Next map in other requirements, as required (e.g., elements of the statement of work). To facilitate evaluation, consider including relevant RFP references in your section heading titles; this helps evaluators understand the logic of your organization and map your responses back to their evaluation scoresheet.


Use RFP Language


When writing proposals, you should also strive to use the language in the RFP to make the evaluation easier. For example, if the RFP asks for a Program Manager, you should use the title, Program Manager, not Project Manager. You should also strive to use the customer’s terminology and lexicon in our proposal to gain the customer’s confidence. By knowing your customer and speaking their language, you demonstrate that we understand them, and you begin to establish trust. What’s more, your customer evaluators often do key word searches to find what’s important to them in your proposals. To support them in this endeavor, you should make sure all sections include key words from the instructions, evaluation criteria, and the statement of work.


Theme Statements


Another way to help evaluators to score you higher is to include theme statements or strength statements consistently throughout your response. Theme statements set the stage for the section and grab the evaluator’s attention because they address an issue that is important to them. The ideal theme statement not only presents a solution feature that addresses a customer hot button, it also articulates clear, quantified benefits. I recommend including a theme statement for every first-level section and second-level subsection and formatting those themes to stand out from the rest of the text. If you theme effectively, the theme statements will show up as identified strengths in the evaluation debrief from the customer.


Callout Boxes


Another way to arm evaluators with the ammunition they need to give you a high score is to use callout boxes to help your major proof points stand out. Be sure that your proof points not only highlight quantified metrics, but make sure to provide the “so what?” statement as well. For example, it’s not enough simply to state: “We have used our proven staffing process to staff programs with 3-, 7- and 14-day turnaround times, including the MNOP program, where we staffed 15 FTEs in two weeks.” Ask yourself, “So what? What does this mean for my customer?” This might prompt you to add, “Leveraging this staffing process, we provide Customer ABC with low-risk task order start-up and delivery for large, small, short-term, and long-term requirements.”


Feature and Benefit Tables


Feature and benefit tables are another great way to help evaluators find proposal strengths. Similar to theme statements, feature and benefit tables highlight major solution features—that ideally address customer hot buttons—and articulate clear, quantified benefits. Typically, customers want things cheaper, faster, and/or better, which we might express as low cost, low risk, high quality, efficient, and/or effective. Use feature and benefit tables in each major section introduction to highlight the key elements of your approach. This could be every first-level section for shorter proposals, but it may be extended to each second-level subsection for longer proposals.


Articulate Benefits Throughout


As touched on previously, benefits tell the customer why they should care about our solution or its features; they articulate the “so what?” But, it’s critical to remember that benefits should be things that the customer cares about. For example, if the customer doesn’t care whether the transition is completed in three weeks or six weeks, then expedited timeline is not a benefit to that customer. It’s also critical to remember that benefits should be highlighted throughout the proposal narrative. It’s not enough for benefits to show up in theme statements, callout boxes, and feature benefit tables—these benefits need to be articulated and reinforced throughout the proposal narrative as well.


Make the Response About the Customer


Another critical way to score higher is to make sure you are focusing on the customer. Two key signs that your proposal writing lacks customer perspective include: (1) the proposal mentions your company or team name more than the customer’s name; (2) the proposal is about your company’s offer instead of the solution and benefits the customer will receive. A great proposal is about the customer and the benefits they receive from the proposed solution.


One of the easiest ways to make our proposal content more customer focused is to put them first—literally. Instead of saying, “Team ABC’s solution delivers a low-risk transition,” flip the construction and write, “Customer A receives a low-risk transition with our comprehensive transition approach.” The two sentences convey the same overall message, but by putting the customer first in the sentence, we shift the focus onto what the customer is receiving rather than what we are delivering.


Another easy way to make your proposal content more customer focused is to use the customer’s name more frequently than your company or team name. To validate whether you are doing so, you can try this quick test: hit Ctrl-F and search for the number of times you mention your company and/or team name; then search for the number of times you mention the customer’s name. You should aim to mention the customer’s name more times than yours. If you find that you have mentioned the customer far less frequently, you should revise our text to focus more on the customer and the benefits they will receive by choosing your solution.


Final Thoughts


In this world of bids and proposals, we all certainly want to win more. However, there are so many factors that impact a company’s probability of win, and a number of things throughout the opportunity lifecycle can impact a company’s chances of winning (both positively and negatively). Although the capture phase has the greatest potential to positively impact your chances of winning, you can certainly take steps to help your proposals score higher during the proposal writing stage. These actions include organizing content so it’s easy to score; using RFP language, theme statements, callout boxes, and feature and benefits tables; articulating benefits throughout the response; and making the response about the customer. These critical components during the writing phase can go a long way in facilitating the evaluation process and increasing your overall score—and a higher score can easily translate to a higher probability of win!




Shows requests for information (RFIs) becoming more important
By Ashley (Kayes) Floro, CPP APMP May 5, 2026
In government contracting, the pre-solicitation phase is where requirements are shaped, vendor relationships get established, and acquisition strategies get set. Experienced teams know this, which is why they invest heavily in customer engagement, competitive intelligence, and capture planning long before a Request for Proposal (RFP) is released. But one pre-solicitation activity has historically been undervalued: the Request for Information (RFI). That's changing fast, and contractors who haven't noticed are already behind. RFIs: No Longer Just Market Research The traditional view of RFIs is simple: agencies issue them to gather information about industry capabilities before drafting a solicitation. That definition no longer captures what's happening in the current procurement landscape. Today, agencies use RFIs to define and refine requirements, test the feasibility of solutions, identify capable vendors early, and reduce the risk of poorly structured procurements. RFIs aren't just gathering information anymore, they're shaping the acquisition itself. Why Agencies Are Leaning into RFIs Several forces are pushing agencies toward deeper pre-solicitation engagement with industry, with a noticeable emphasis on RFIs. Increasing complexity. Emerging technologies and evolving mission needs mean agencies often don't know what the right solution looks like. The Government needs industry input to understand what's possible. Budget pressure. With tighter budgets and greater oversight, agencies must justify acquisition strategies earlier. RFIs let the Government validate assumptions before committing funds. Risk reduction. Poorly defined requirements lead to protests, delays, and costly rework. Getting it right before the RFP saves the Government time, money, and credibility. The result: more consequential work is happening before the RFP is ever released, and RFIs are holding more weight. The Strategic Opportunity Contractors Are Missing For contractors, this shift changes when and how opportunities are won. Responding to an RFI is no longer a courtesy or a branding exercise. It's a chance to shape how the problem is framed, introduce alternative approaches, position your capabilities as the benchmark, and influence evaluation criteria before they're finalized. Organizations that engage early often help define the playing field. By the time the RFP drops, those who sat out may find themselves reacting to requirements that already favor someone else. The Bar Is Rising RFIs are also becoming more structured. Agencies increasingly use standardized response templates, form-based submissions, and structured data collection—making it easier to compare vendors side by side. This raises the stakes for how you respond. Vague answers and marketing language don't land in structured formats. Clear, specific, well-supported responses stand out and are far more likely to influence the outcome. What To Do About It Organizations serious about win rates need to rethink how they treat RFIs: not as optional, but as strategic. This means being selective but intentional about which RFIs to pursue, aligning RFI responses with your broader capture strategy, and focusing on insight rather than just information. The goal isn't simply to answer the questions being asked: it's to shape the questions that will appear in the RFP. Final Thoughts RFIs are not new, but their role in government contracting is changing in meaningful ways. RFIs have become a critical touchpoint where agencies and industry collaborate to define problems, explore solutions, and reduce acquisition risk. For contractors, they represent one of the earliest, and most valuable, opportunities to influence an outcome. The organizations that recognize this, and act on it, are the ones best positioned to win.
By Ashley (Kayes) Floro, CPP APMP March 30, 2026
When was the last time your team truly examined why you won—or lost—a proposal? Every submission your team makes, win or lose, contains a roadmap for doing better next time. Yet many organizations treat each proposal as a standalone event, moving quickly from one bid to the next without pausing to reflect on what worked, what didn't, and why. This is a costly mistake. A structured lessons learned program, built into every stage of the business development lifecycle, is one of the most powerful tools a company can use to sharpen its competitive edge. What many organizations overlook is that some of the most valuable lessons come directly from the customer. Internal assessments are important, but they only tell part of the story. Customer debriefs provide a rare opportunity to understand how the Government evaluated your solution, what aspects of your proposal resonated, where evaluators perceived risk, and how your approach compared to the competition. When combined with internal lessons learned efforts, debriefs can uncover strategic insights that dramatically improve future capture and proposal performance. Conducting Lessons Learned Conducting lessons learned after each proposal submission is a critical part of the business development lifecycle. It helps companies understand where they are excelling and where they need to improve. To ensure the experience is fresh in everyone's mind, each member of the proposal team should document their impressions—both positive and negative—within the first week after submission. Sample questions to consider include: Was the proposal development schedule reasonable and realistic? Why or why not? Were there any bottlenecks or major issues? If so, what were they, and how could they be mitigated in the future? Did the team work well together? If not, how could team dynamics have been improved? How effective was communication among the team? What went well? What could have been improved? Did any unexpected problems occur during proposal development? If so, how could they be mitigated going forward? Did the team stay within its B&P budget? If not, what could have been done differently? What worked best during the capture and proposal effort? What areas require improvement? A practical way to gather and analyze this feedback is to send a survey to each team member using an automated tool, which makes it easier to collate and compare responses. Just as importantly, organizations should ensure lessons learned discussions extend beyond proposal operations and include capture, pricing, solutioning, staffing, and customer engagement activities. Many proposal losses are rooted in issues that occurred long before writing ever began. Request a Customer Debrief Too often, companies only request debriefs after a loss, missing valuable opportunities to learn from wins as well. Winning debriefs can reveal why the customer selected your solution, which strengths carried the most weight, and where evaluators still saw weaknesses or risk despite awarding your team the contract. Those insights can be invaluable for recompetes and future pursuits. When requesting a debrief from the Government, professionalism matters. Requests should be submitted promptly, kept concise, and focused on understanding the evaluation rather than challenging it. The objective is not to argue with the customer, but to gain insight into how the proposal was perceived and evaluated. During the debrief itself, the most productive teams ask thoughtful, strategic questions such as: What proposal strengths had the greatest impact on the evaluation? Were there areas where the Government perceived increased risk? How well did the proposed approach align with the agency’s priorities? What differentiated the winning proposal? Were there areas where the proposal appeared compliant but not sufficiently tailored? Did the Government identify any gaps in customer understanding? The best debriefs often reveal issues that are not immediately obvious in evaluation scores alone. A technically compliant proposal may still fail because it lacked clear differentiation, did not sufficiently address customer pain points, or failed to inspire confidence in execution. Those insights are essential for improving future capture and proposal strategies. Equally important, organizations should approach debriefs as relationship-building opportunities. Agencies remember contractors that engage professionally, ask intelligent questions, and demonstrate a genuine commitment to improvement. After Action Report Once the feedback has been gathered, the Proposal Manager should review the trends and prepare an After Action Report that details lessons learned, root causes, and recommended next steps. This report should be shared with the full proposal team to ensure that insights are carried forward into future efforts. The most effective After Action Reports do more than document tactical issues. They identify whether the team’s overall strategy aligned with the customer’s priorities. Did the proposed discriminators truly differentiate the solution? Did the proposal clearly communicate customer understanding? Were there areas where the team assumed the customer valued something that ultimately had little impact on the evaluation? Answering these questions helps organizations move beyond surface-level process improvements and make meaningful strategic adjustments. Lessons Learned Session Additionally, after contract award is announced, the team should conduct a formal Lessons Learned Session to document and discuss observations, findings, and conclusions—win or lose. This session should incorporate both internal feedback and customer debrief information whenever possible. By understanding where the team encountered roadblocks, where the customer found gaps in the response, and what elements of the solution resonated most strongly, organizations can strengthen both their processes and their competitive positioning. Equally important: identify what the team is doing well and make sure those practices are preserved and repeated. Analyzing Trends and Updating Standard Operating Procedures (SOPs) Conducting lessons learned after each proposal is valuable, but the benefit compounds when you step back and look at the bigger picture. On an annual basis, review your After Action Reports, customer debrief notes, and lessons learned sessions as a body of work, and analyze them for recurring themes and patterns. As the year wraps up, whether you follow a corporate fiscal year or the calendar year, ask your team: What challenges keep surfacing? Where does the team consistently perform well? What issues repeatedly appear in customer debriefs? Are evaluators consistently identifying the same weaknesses or risks? Are there gaps in capture execution, customer engagement, staffing, or pricing strategy? Discussing and sharing these trends with your team creates a culture of transparency and accountability, and helps focus improvement efforts where they matter most. More importantly, translate those findings into action by updating your business development and proposal SOPs. If internal feedback shows the team is consistently scrambling during production, adjust your SOPs to launch the production process earlier. If customer debriefs repeatedly cite a lack of customer understanding, take a hard look at your capture process and strengthen your call plan execution. If evaluators consistently identify transition risk or staffing concerns, revisit your solution development and recruiting strategies. Continuously refining your processes in response to real data, especially direct customer feedback, is one of the clearest paths to improved performance and more wins. Final Thoughts Every organization in this industry wants to win more, and win rates are often cited as the headline measure of a business development organization's health. While they are a useful starting point, win rates alone don't tell the whole story. Too many variables influence any single outcome. What matters more is building the discipline to learn from every effort, regardless of the result. A consistent lessons learned program, paired with customer debrief analysis, annual trend reviews, and a willingness to update your processes, creates a feedback loop that makes your team sharper over time. The companies that win consistently aren't just the ones with the best writers or the biggest budgets, they're the ones that systematically learn faster than their competitors. Every proposal, whether it results in a win or a loss, provides an opportunity to improve. The organizations that capitalize on those opportunities are the ones that steadily build stronger capture strategies, stronger proposals, and ultimately, stronger win rates over time.
By Ashley (Kayes) Floro, CPP APMP March 25, 2026
Tight page limitations are continuing to be a challenge as contracting officers streamline their acquisition processes. When faced with tight page restrictions, we often find ourselves struggling with trimming five pages of material into two pages of allocated space. However, sometimes the content we are working with is so long because it is simply overly wordy. In this article, I present six tricks for eliminating waste. 1. Use Active Voice With active voice, the subject of the sentence comes first and performs the action in the sentence. Active voice is more straightforward and concise than passive voice. It typically results in shorter, sharper sentences. So not only does it take up less real estate, it flows better and is easier to understand. Passive: It was decided by the Program Manager to streamline the program. Active, Strong Verb: The Program Manager streamlined the program. 2. Eliminate Redundancies Remove redundancies that take up extra space and don’t add value. I present some examples below.