AI Bid/ No Bid Assessment: Complete Prompt Guide
Transform your bid qualification process from hours to 20 minutes with AI.
The total session should look like this:
- Upload RFP → Use Phase 1 Master Prompt
- Interactive Assessment → Work through Phase 2 prompts conversationally with AI
- Challenge Session → Apply Phase 3 critical thinking
- Get Recommendation → Generate Phase 4 decision summary
The goal is to pull out key issues & strengths and reach a preliminary decision point faster.
Happy prompting!
Phase 1: Initial RFP Analysis
Prompt:
"I'm a bidding manager evaluating a new opportunity. I'll upload the RFP and background materials. Please analyse these documents and provide:
1. **Key Requirements Analysis**: Identify the 5-7 most critical project requirements
2. **Evaluation Criteria Breakdown**: Highlight which criteria carry the most weight (technical, commercial, experience, etc.)
3. **Red Flags Assessment**: Flag any concerning elements, unrealistic timelines, or unusual terms
4. **Resource Implications**: Estimate the complexity and resource intensity based on scope
After your analysis, I want you to guide me through an interactive assessment to determine if we should bid. Structure this as a conversation where you ask me targeted questions across 5 key areas: Capabilities, Competition, Relationships, Financials, and Strategic Fit.
Ready to start the interactive assessment?"
Phase 2: Interactive Assessment
Capability Deep Dive Prompt:
"I need you to assess our technical and delivery capabilities for this opportunity. Ask me targeted questions about our ability to deliver, then probe deeper based on my responses. Cover these areas:
1. Walk me through how we'd deliver the specific requirements you identified in the RFP analysis
2. Challenge me on our confidence level for the key technical capabilities they emphasise
3. Reality-check our ability to meet their timeline given our current workload
Ask me one question at a time, and don't let me give vague answers. Push for specific examples and evidence."
Competition Analysis Prompt:
"Now help me analyse the competitive landscape realistically. I want you to:
1. Ask me who else is likely bidding and make me explain why each competitor does/doesn't have advantages
2. Challenge me to articulate what makes us different and whether evaluators would actually see that difference
3. Force me to think like an evaluator - what would concern them about choosing us over competitors?
Don't accept generic answers. Push me to be specific about our competitive position and make me defend my assumptions."
Relationship & Intelligence Assessment Prompt:
"Let's evaluate our customer relationship and market intelligence. I need you to:
1. Ask me how we found this opportunity and what our actual relationship is with decision-makers
2. Probe our history with this client and how it positions us for this bid
3. Identify gaps in our knowledge about this opportunity and how those gaps might hurt us
Based on my answers, assess whether our relationship and intelligence give us a real advantage."
Financial Viability Prompt:
"Time for a financial reality check. I want you to:
1. Ask me what I think the customer's budget is and challenge how I arrived at that number
2. Test our pricing strategy - what's our ideal price and what happens if we need to go 15% lower
3. Push me on minimum acceptable profit margins and whether the project still makes sense
Don't let me be overly optimistic. Challenge me if the numbers seem unrealistic or if I'm not accounting for real costs."
Strategy & Resource Fit Prompt:
"Finally, let's assess strategic value and resource allocation. Please:
1. Ask who would actually lead this project and whether they're truly available for the timeline
2. Challenge me on why this project matters beyond revenue - is the strategic value real?
3. Force me to identify what we'd have to sacrifice to pursue this opportunity
Help me understand the true opportunity cost and whether the strategic fit justifies the resource commitment."
Phase 3: Critical Challenging
"Based on our conversation so far, I need you to act as a tough, skeptical advisor and challenge my thinking. Don't let me be overly optimistic. I want you to:
1. **Identify inconsistencies**: Point out where I seemed confident in one area but uncertain in another, especially if this creates risks I'm not seeing
2. **Stress-test my competitive position**: Challenge my assumptions about competitors - if my main competitor bids, force me to explain exactly how I'll overcome their advantages
3. **Reality-check my resources**: Push back on my timeline and resource allocation - what happens if key people aren't available or my assumptions prove wrong?
4. **Financial pressure-test**: Make me walk through worst-case pricing scenarios - what if I'm forced to bid 20% lower than planned?
5. **Challenge my evidence**: For anything I claimed as a strength, demand specific proof and examples
Be skeptical, ask tough follow-up questions, and don't accept vague or overly positive answers. I need you to find the holes in my thinking before I commit to bidding."
Phase 4: Final Decision Framework
"Based on our entire conversation, provide your final recommendation using this exact format:
## **BID RECOMMENDATION: [GO/CAUTIOUS GO/NO-BID]**
### **Scoring Summary** (1-5 scale):
- **Capability Match**: [X/5] - [specific justification]
- **Competitive Position**: [X/5] - [specific justification]
- **Customer Relationship**: [X/5] - [specific justification]
- **Financial Viability**: [X/5] - [specific justification]
- **Resource Fit**: [X/5] - [specific justification]
- **Strategic Value**: [X/5] - [specific justification]
**Overall Score: [X/30]**
### **If Proceeding, Focus On**:
1. [Key success factor to emphasise]
2. [Critical risk requiring mitigation]
3. [Competitive advantage to highlight in proposal]
### **Red Flags to Monitor**:
- [Specific concern from our conversation]
- [Timeline/resource risk identified]
- [Financial or competitive threat]
### **Outstanding Questions for Sales Team**:
- [Information gap requiring customer clarification]
- [Technical requirement needing validation]
- [Commercial term requiring negotiation]
Please provide this as a one-page summary I can share with my team."
Tips For Best Use
Be specific: The more detailed your responses, the better the AI’s assessment.
Upload Everything: Include RFP, client background, competitive intelligence, internal capacity docs.
Push back: If the AI isn’t challenging you enough, ask it to be more critical.
Iterate: If the recommendation doesn’t feel right, dig deeper into specific areas or add more questions to the prompt.
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