5 Common Proposal Mistakes and How to Avoid Them

Ashley (Kayes) Floro, CPP APMP • February 12, 2026
Lightbulb bursting

Winning new business in today’s competitive market, whether in the commercial or government space, depends on the strength of your proposals. Even highly capable organizations lose out when their submissions are generic, unclear, or non-compliant.


Proposals that read like a generic product or service description fail to stand out among competitors. Maybe you have cut and paste boilerplate content and simply changed the customer’s name. Maybe you have had AI generate your proposal content but failed to tailor it. Maybe you simply know nothing about the customer because the capture effort fell flat. Maybe this was a pop-up solicitation that leadership insisted on bidding. Maybe you just didn’t have enough time to produce something stronger.


The good news? Most proposal failures stem from a handful of common mistakes that can be avoided with the right strategies. This article explores those pitfalls and provides practical guidance to help you write proposals that stand out, speak directly to the customers’ needs, and maximize your chances of success.


Mistake 1: Incomplete Capture Plan and No Customer Understanding


At the heart of every successful proposal is a deep understanding of the customer. When your proposal speaks directly to your customer’s pain points and priorities, it becomes a solution that resonates. Most often, this customer understanding will come from the person nurturing the relationship with the customer—the capture manager. However, sometimes, for one reason or another, we have a missing or incomplete capture plan—and nobody on our team can shed light on what keeps our customer up at night.


If you find yourself in this situation, one powerful shortcut you can use is generative artificial intelligence (AI). You can use AI tools like ChatGPT to analyze the customer’s issues and hot buttons so you can tailor your messaging with speed and precision. Just upload the solicitation to the AI tool (as long as it isn’t marked confidential, CUI, or something similar), and then include a prompt like the following: “What are the key issues and hot buttons that concern this customer?” The tool will quickly and effectively pull out tangible hot buttons and issues present in the solicitation that you can write to in your response.


You can take this a step further and have the AI tool draft some messaging or positioning points. Though these will be somewhat high-level, and may include solution elements you need to validate, they will be a good start, and you’ll get them quickly. After you get your list of messaging or positioning points, you’ll want to validate any solution elements with your team. Then, add necessary specifics to take them from generic to compelling. 


Here’s an example:


  • ChatGPT may come up with the following messaging point: Our implementation methodology with rapid prototyping and continuous customer feedback reduces risk and accelerates delivery timelines.
  • To take this from generic to compelling, you’ll want to add specifics and metrics: Our low-risk approach cuts delivery timelines in half with our proprietary Agile-based implementation methodology, which drives rapid prototyping and incorporates continuous customer feedback.


Mistake 2: You’re Not Articulating Your Value


Once you have a baseline customer understanding, you should take time to develop strong win themes—concise, compelling messages that explain why your offer is the best choice. Emphasize what makes your solution unique and how it directly benefits the customer. Win themes should:


  • Reflect the customer’s top priorities
  • Highlight your differentiators
  • Be repeated consistently throughout the proposal to reinforce your value


For example, a win theme might be: “Our proven technology reduces operational downtime by 30%, helping achieve uninterrupted service delivery.” Once developed, reinforce these themes consistently throughout the proposal.


Mistake 3: Your Proposal is Full of Unsubstantiated Claims


To go beyond the generic and cookie cutter, you’ll also want to support your claims with evidence, such as case studies, metrics, past performance, testimonials, certifications, or pilot results. For example, after indicating that our advanced analytics enable the customer’s team to make faster, data-driven decisions that improve efficiency and reduce costs by 30%, we might include a proof statement of where we have achieved this success in the past: “For example, on XYZ contract, our advanced analytics enabled the customer to cut decision times in half and resulted in cost savings of $15 million.”


By adding proof statements as evidence and backing up our claims with facts and figures, we provide the necessary proof to substantiate our solution with the evaluator. Quantifying our proof points will make our content even more credible. Additionally, demonstrating past success reduces the perception of risk and helps the customer gain confidence in your capabilities, especially when you tie your capabilities back to positive outcomes for the customer.


Mistake 4: Overloading with Jargon and Technical Terms


Subject matter experts sometimes write proposals using internal jargon or overly technical language that evaluators may not understand. If this is the case, you’ll want to take time to rewrite their inputs in clear, concise, and customer-focused language. Ensure your proposal tells a story that resonates with both technical and non-technical readers.


Remember, evaluators often review dozens of submissions under tight deadlines, so complex wording, jargon, or filler language can slow them down—or worse, obscure your key messages. Every sentence should be easy to understand and tied directly to the customer’s priorities.


But being concise doesn’t mean oversimplifying. It means distilling your ideas into their most impactful form. Replace long-winded explanations with direct statements and eliminate buzzwords that don’t add substance. For example, instead of saying, “Our innovative, cutting-edge, next-generation platform leverages advanced synergies to optimize mission outcomes,” you might write, “Our platform improves mission performance by reducing downtime by 50% and streamlining workflows.”


Some tips for clear writing include:


  • Use plain language: Write as though you’re explaining to a smart colleague outside your industry.
  • Cut redundancy: If you’ve already made a point, don’t repeat it unless you’re reinforcing a win theme.
  • Prioritize active voice: “We deliver results” is stronger and clearer than “Results are delivered by our team.”
  • Use short sentences with strong verbs: Keep sentences focused and avoid unnecessary modifiers.
  • Test readability: Read your proposal out loud to catch errors or awkward sounding sentences, and use the tools built into your word processing program to check sentence length and grade-level clarity.


Concise, clear writing respects the evaluator’s time and ensures your strengths stand out without distraction. When every word adds value, your proposal communicates confidence, professionalism, and customer focus.


Mistake 5: Missing or Buried Compliance Elements


Proposals that fail to meet mandatory requirements or submission formats risk rejection or disqualification regardless of content quality. To avoid this mistake, create a compliance matrix early in the process to track all requirements. Include compliance as a key focus during color team reviews and consider assigning a specific reviewer to cross-read for compliance. Create a proposal production checklist that includes major compliance elements, and verify page limits, font size, document format, attachments, and signatures before submitting. Make sure to submit the proposal following the exact method required (e.g., online portal, email, hand delivery, courier, etc.).


Additionally, to help make sure that evaluators can find all the required information, we also want to make sure our proposal is easy to score. Structure your response to the proposal instructions and the evaluation criteria. Next map in other requirements, as required. To facilitate evaluation, consider including relevant solicitation references in your section heading titles. Additionally, evaluators often do key word searches to find what’s important to them. Make sure all sections include key words from the instructions, evaluation criteria, and the statement of work/performance work statement. To make your proposal narrative even more evaluator-friendly, leverage feature and benefit tables and highlight proof points using callout boxes.


Final Thoughts


Strong proposals are the result of planning, discipline, and a clear focus on the customer. By avoiding common mistakes like generic content, jargon, missing compliance elements, or weak themes, you can transform your proposal from a basic response into a persuasive, customer-centered solution. Every submission is an opportunity not just to compete, but to build credibility and strengthen relationships. Approach each one as a chance to prove your value—and win with confidence.


Originally posted on the Proposal Reflections Blog

Shows requests for information (RFIs) becoming more important

RFIs Have Changed. Has Your Strategy?

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.

From Submission to Success: How Lessons Learned Drive Better Proposals

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. 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. After Action Report Once the results are in, the Proposal Manager should review the feedback and prepare an After Action Report that details lessons learned and recommended next steps. This report should be shared with the full proposal team to ensure that insights are carried forward into future efforts. 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. By understanding where the team encountered roadblocks, and where the customer found gaps in the response, the team can address those issues and strengthen both the process and the final product on future efforts. 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 and lessons learned debriefs 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 yourself: What challenges keep surfacing? Where does the team consistently perform well? 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. Continuously refining your processes in response to real data 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 annual trend analysis 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 treat every proposal, win or lose, as an opportunity to get better.

Six Strategies to Tackle Tight Page Limitations

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.