You've spent weeks crafting what you believe is a winning proposal. Your team has poured over every discriminator, polished every win theme, and carefully positioned your solution as superior. Yet when the debrief arrives, the feedback feels alien: "significant weaknesses," "unclear benefits," "insufficient evidence."
Sound familiar? You're not alone. According to recent industry data, over 53% of proposal teams report disconnects between their perceived quality and actual evaluation scores.
The answer lies in a fundamental disconnect between how we write proposals and how evaluators actually score them. We're asking evaluators to do too much cognitive work—to translate our corporate storytelling into their evaluation criteria. And every time we force them to make these connections, we're gambling with our win probability.
The Hidden Translation Tax Killing Your Win Rate
Picture an evaluator at hour six of their review day. They've reviewed four proposals already, they're running on fumes and coffee, and now they're staring at your section about cloud infrastructure. You've written eloquently about your "innovative cloud-first approach" and your "proven track record of digital transformation."
But their evaluation sheet doesn't have checkboxes for innovation or transformation. It has specific columns:
Requirement compliance
Technical approach
Customer benefit
Risk assessment
Supporting evidence
Now they must translate. They must parse your prose, extract the relevant facts, mentally reorganize them, and map them to their scoring criteria. This translation work—this cognitive load—is what proposal professionals rarely discuss but what often determines outcomes.
Bruce Morton, a capture director and self-described rocket scientist turned proposal expert, frames it bluntly: "We're depending on the brilliance and motivation of the evaluator to make these connections. And I'd like to make them for the evaluator so that I don't have to depend upon them to do all this stuff."
The Harsh Reality of RFP Evaluation (That Nobody Tells You)
Here's what actually happens during evaluation. An evaluator doesn't read your proposal like a novel. They're completing a structured assessment, often using a spreadsheet or evaluation tool with specific fields to complete. For each requirement, they need to identify:
What the requirement asked for (with specific reference)
What you're proposing (clear and specific)
How your solution meets or exceeds the requirement (explicit connection)
The tangible benefit to the customer (not just features)
External evidence that you can deliver (proof beyond promises)
Miss any of these elements, and what you thought was a strength becomes a weakness—or worse, a deficiency. The evaluator isn't being difficult. They're working within a system, and that system demands clarity.
The UX Principle Your Proposal Team Is Ignoring
In user experience design, we obsess over reducing friction. We eliminate unnecessary clicks, simplify navigation, and present information exactly when and how users need it. Yet in proposals—documents with million-dollar stakes—we routinely violate these principles.
Consider how we typically structure RFP responses. We lead with our company's capabilities. We describe our methodology in detail. We showcase our past performance. Then, somewhere in this narrative, we expect the evaluator to extract the specific proof points they need for their scorecard.
That's like building a website where users must visit five different pages to complete a single purchase. The cognitive load compounds, patience wears thin, and even motivated users—or evaluators—give up.
One proposal manager at a Fortune 500 technology company shared: "We lost a $12M contract last year because our technical solution was 'unclear.' When we saw the winning proposal, I realized they weren't better—they were just clearer about connecting their solution to the evaluation criteria."
How to Build Strength-Based Win Themes That Evaluators Can Actually Find
So how do we reduce this cognitive burden and improve our RFP win rate?
Morton advocates for what he calls "strength-based win themes"—but these aren't your typical marketing messages. They're structured statements that pre-package information in the exact format evaluators need.
Instead of writing "Our cloud solution leverages industry-leading technology," you structure your response like this:
Requirement 3.2.4: [Exact requirement text]
Our Solution: Trampoline's FedRAMP High cloud infrastructure provides dedicated, air-gapped environments with 99.99% uptime SLAs.
How We Exceed Requirements: Our solution not only meets the baseline security standards but exceeds them with additional SOC 2 Type II controls and real-time threat monitoring.
Customer Benefit: You gain 43% faster deployment times with zero security incidents, allowing you to meet your aggressive program timeline without compliance risks.
Evidence: Our identical implementation for [Similar Agency] received a "Superior" CPARS rating in 2023, and our current FedRAMP authorization letter is included in Appendix C.
The evaluator shouldn't have to hunt, interpret, or guess. Every element they need for their scorecard is present and obvious.
But here's where most proposal teams stumble: evidence.
"Everyone has problems with evidence," Morton notes. "You're really good at this and you have no evidence from anyone that says this except you? I don't believe it."
Evidence isn't your own claims about excellence. It's external validation: customer testimonials, CPARS ratings, letters of commendation, contract renewals, award recognitions. Without evidence, even the strongest technical solution reads as unsubstantiated claims.
The Collaborative Challenge Most Proposal Tools Miss
Creating these evaluator-friendly proposals isn't a solo act. The technical expert who understands the cloud architecture might not know about the commendation letter from last year's similar project. The program manager who has the performance metrics might not understand the specific technical requirements.
This is where traditional proposal development breaks down. We assign sections to subject matter experts and expect them to independently create comprehensive responses. But comprehensive responses require collective knowledge.
Think about Morton's example: for a cloud requirement, the technical person knows the solution, but the program manager might have the evidence from five similar implementations. The contracts person understands the risk mitigation. The project lead knows the actual customer benefits realized on past projects.
Who makes these connections if not a deliberate, structured process or collaborative proposal management software?
The 5-Minute Test to Identify Hidden Cognitive Load in Your Proposal
How do you know if your proposal has a cognitive load problem? Morton suggests a revealing test: conduct your red team review using actual evaluation criteria, not general quality assessments.
Ask your reviewers to fill out the same evaluation sheets the customer will use. Watch where they struggle:
Where do they have to flip pages to find information?
Where do they have to interpret or assume?
Where can they simply not find what they need?
"Sometimes it's a shock to the writer who writes a really good thing, but it comes back as a deficiency because they didn't answer all the five elements," Morton observes. Better to face that shock internally than in a customer debrief.
The Competitive Edge of Clarity in RFP Responses
Here's what's fascinating about this approach: it's not about being dramatically better than your competition. It's about being dramatically clearer.
Morton recounts competitors telling him, "We almost won, we almost beat you. You just had a few more strengths than we did." Those extra strengths? They weren't necessarily superior solutions. They were solutions presented in a way that made the evaluator's job easier.
In a tie—and many competitive proposals are essentially ties on technical merit—the proposal that requires less cognitive work to evaluate wins. The evaluator can clearly see your strengths because you've presented them as strengths. They understand your benefits because you've explicitly connected them to their needs. They trust your capabilities because you've provided external evidence, not just internal assertions.
Making the Invisible Visible: A New Approach to Proposal Management
The real shift here is philosophical. We need to stop thinking of proposals as persuasive documents and start thinking of them as usability experiences. Every section, every paragraph, every sentence should reduce the cognitive distance between our solution and the evaluator's scorecard.
This might mean:
Sacrificing some of our narrative flow
Being more explicit than feels natural
Repeating information in different contexts to ensure it's found where needed
Using clear, structured formats with consistent labeling
Providing direct evidence where claims are made
Cross-referencing requirements explicitly
But isn't that a small price for clarity? For wins?
Your evaluators aren't your enemy. They're overworked professionals trying to make fair assessments under time pressure. When we make their job harder, we're not being strategic—we're being self-defeating.
So ask yourself: Are you writing the proposal you want to write, or the proposal they need to evaluate? Are you showcasing your story, or are you answering their questions? Are you making them work to understand your value, or are you making your value impossible to miss?
The choice—and the cognitive load—is yours to manage.
If you want to lower cognitive load at the source, structure your work the way the evaluator scores it. Trampoline does this by turning any RFP into a board with one card per requirement. Each card has simple fields for approach, compliance, benefit, risk, and evidence. Work is auto-assigned to the right SMEs.
The AI side panel pulls past answers and proof points from your library so writers can add real evidence fast. Red teams can score cards against the actual criteria. The system flags gaps before delivery. When finished, the Writer extension compiles the validated cards into the final doc, slides, or sheets.
The result is a proposal built in the evaluator’s format, not ours. Clearer for them. Calmer for you.