TL;DR
Government contractors face over 70 AI solutions, each claiming to revolutionize proposal work. But the real question isn’t “AI or no AI?” It’s “Which technology for which job?”
The answer:
- Deterministic software: Your compliance guardian (use when 100% accuracy is non-negotiable)
- Generative AI: Your creative partner (deploy when you need speed and innovation)
- And it is possible to have the best of both worlds!
This guide, built on insights from VisibleThread’s CPO Fergal McGovern, helps you make the right call every time.
Skip the Spreadsheet: How to Actually Evaluate Proposal Tools
Most enterprise technology selection processes are theatre. You know the drill:
- Week 1: Leadership announces a “comprehensive evaluation”.
- Week 2: Surveys flood inboxes asking for feature lists.
- Week 3: Responses pile up – genuine needs mixed with wishful thinking.
- Week 4: Someone compiles a Frankenstein requirements document.
The result? A contradictory 47-tab spreadsheet where Page 1 wants CRM, Page 5 demands contract management, and Page 9 requests features that contradict Page 2.
The Core Problem
People confuse frustrations with requirements, and requirements with solutions:
- “I need better version control” becomes “We must have blockchain”.
- “I want faster compliance checks” morphs into “The system needs machine learning”.
There’s a Better Way
Forget elaborate scoring matrices. Here’s what actually works:
1. Test-Drive, Don’t Demo
- Get hands-on access to the actual tool
- Use your messiest proposal with the impossible deadline
- Pay attention to how it feels (your instincts matter)
- Verify every vendor promise in real-time
2. Run the Dual-Task Challenge
Give every vendor the same test:
- Compliance task: “Verify our response addresses all 47 requirements in Section L”.
- Creative task: “Draft an executive summary highlighting our three differentiators”.
Watch for:
- Red flag: Struggles with both tasks and fails compliance confidently.
- Yellow flag: Handles one well but requires awkward workarounds.
- Green flag: Excels at both using the right approach for each.
3. Ask About Failure Modes
The best vendors show you how their tools fail and what safeguards prevent disasters:
- “What happens when your AI misses a compliance requirement?”
- “Can I see the AI draft something wrong? How obvious is the error?”
- “What prevents me from using the wrong tool for the wrong task?”
Understanding the Two Types of Proposal Technology
Deterministic Software: Your Compliance Guardian
What it is: Rule-based systems that follow precise, programmed logic like a smart checklist that never gets tired.
When to use it:
- Compliance matrix verification
- Legal risk identification
- Readability scoring
- Requirement traceability
- Format validation
- Acronym validation
- Document comparison
Why it works: Some things demand perfection. A 99% accurate compliance check means you missed something that could disqualify your entire proposal.
The trade-off: Zero creativity. It won’t write, innovate, or suggest better storytelling.
Generative AI: Your Creative Partner
What it is: Neural networks trained on massive datasets that create new content and adapt to context – like a brilliant writing partner who reads everything but needs guidance.
When to use it:
- Drafting narrative sections
- Executive summaries
- Tone harmonization
- Win theme development
- Content repurposing
Why it works: Creativity and speed matter. Going from blank page to decent draft in minutes instead of hours is game-changing on proposal deadlines.
The trade-off: It hallucinates. It makes things up and sounds confident when wrong. Never trust it unsupervised on compliance-critical work.
The Decision Framework: Matching Technology to Tasks
For every proposal task, ask two questions:
What’s the Cost of Error?
- High cost (disqualification, legal risk, compliance failure) → Deterministic Software
- Lower cost (stylistic choices, first drafts, brainstorming) → Generative AI
What’s the Primary Goal?
- Accuracy and verification → Deterministic Software
- Creation and innovation → Generative AI
When Deterministic Software Is Non-Negotiable
Deploy deterministic tools whenever a “guess” could result in disqualification or legal disputes.
| Task | Why Deterministic Software | Risk of Wrong Tool |
| Compliance matrix generation | Must capture every “Shall”, “Must”, and “Will” with perfect accuracy | Missing requirements = disqualification |
| Legal risk identification | Finding clauses like “liquidated damages”, “indemnification”, “termination for convenience” demands exact pattern matching | Missing legal tripwire = contract disputes |
| Readability scoring | Objective metrics based on sentence length and syllable count require deterministic logic | Unreliable scores you can’t defend in gate reviews |
| Acronym validation | Every acronym in a 500-page proposal must appear in the glossary – binary verification | Inconsistent documentation = unprofessional appearance |
| Document comparison | Identifying precise changes between the original RFP and amendments | Missing changes = non-compliance |
| Dictionary-based search | Finding specific win themes or keywords in past performance databases | Contextual approximations miss exact matches |
The pattern: When precision is mandatory and mistakes create compliance risk, deterministic tools are non-negotiable.
A Real-World Proposal Workflow
Here’s how to use both technologies effectively:
Stage 1: Kickoff (Day 1)
- Generative AI: Draft outline and initial win themes
- Deterministic Software: Build a compliance matrix
Stage 2: Writing (Days 2-8)
- Generative AI: First drafts of narrative sections
- Deterministic Software: Verify you’re addressing every requirement
Stage 3: Review (Days 9-12)
- Generative AI: Harmonize tone across sections
- Deterministic Software: Validate readability scores and identify unsupported claims
Stage 4: Final QA (Days 13-14)
- Deterministic Software: Final compliance sweep
- Generative AI: Polish executive summary
The pattern: Deterministic software bookends the process with verification. Generative AI accelerates creative work in between.
Building Your 2026 Proposal Tech Stack
Three Non-Negotiable Requirements
1. Get Both Tools in One Platform
Switching between six different tools creates integration nightmares and context-switching headaches. Look for platforms offering both deterministic precision and generative creativity.
2. Resist the “AI All the Things” Trap
Some vendors slap “AI-powered” on features that work perfectly with deterministic logic. Don’t pay for unnecessary complexity.
3. Let GenAI Do What It Does Best
If you’re manually drafting every proposal section when you have proven content libraries, you’re leaving time on the table. GenAI should accelerate drafting by learning from what’s already won.
What You’re Actually Buying
Don’t buy technology. Buy capability enhancement.
The right proposal tech stack should:
- Free your people for human judgment, strategy, and creativity
- Make processes precise in accuracy, consistency, and compliance
- Reduce cognitive load while increasing space for winning thinking
If a tool doesn’t deliver all three, keep looking.
The Bottom Line
Seventy-plus AI solutions compete for your budget. Most make the same promises with different logos.
Cut through the noise with two questions:
- What type of technology is this? (Deterministic or generative?)
- What task am I trying to accomplish? (Accuracy-critical or creativity-driven?)
Then apply this framework:
| If you need… | Use this… |
| 100% accuracy, zero hallucinations | Deterministic Software |
| Creative variations, speed, ideas | Generative AI |
| Both (and you usually do) | A platform with both capabilities |
The real question isn’t “Should we use AI?”
It’s “Which technology, for which job, at which stage of our proposal process?”
Answer that clearly, test ruthlessly, and you’ll build a tech stack that helps you win – not one that just looks good in procurement meetings.
Take Action
Test this framework: Map each task in your next proposal to the right technology type. You’ll know within one proposal cycle whether your current tools match your actual needs.
Security note: Whatever you evaluate must demonstrate appropriate security posture data protection, access controls, compliance with government requirements. If a vendor can’t immediately prove their security credentials, end the conversation.
Want to explore the full conversation? Check out Fergal McGovern’s complete article: The 12 Vibes of Tech Selection: Are You Building on Sand or Stone?
