Proposal Evaluation

Instructions

Apply this multi-lens evaluation framework systematically to any business proposal:

1. Comprehension Phase

Before evaluating, ensure full understanding:

• What is the proposal’s core objective and scope?
• What key assumptions does it rely on?
• What constraints are stated or implied?
• What information is provided vs. missing?
• What is the decision being asked for (approval, funding, partnership, etc.)?

2. Eight-Perspective Analysis

Evaluate the proposal through each lens. For every perspective, provide an assessment and a recommendation (Support / Support with Conditions / Concerns / Oppose).

Strategic (CEO Lens)

• Does this align with the organization’s strategy and mission?
• What is the opportunity cost — what are we not doing if we pursue this?
• Does it create or strengthen competitive advantage?
• What is the strategic risk of not acting?

Financial (CFO Lens)

• What is the projected ROI and payback period?
• Are the financial projections realistic and well-supported?
• What are the risk-adjusted returns?
• What are the funding implications (cash flow, debt, equity)?

Operational (COO Lens)

• Can the organization actually execute this?
• Are the resource requirements realistic or a stretch?
• What are the critical dependencies and bottlenecks?
• What is the realistic timeline?

Market (CMO Lens)

• Is there customer validation or evidence of demand?
• What is the market opportunity size?
• How will competitors likely respond?
• Is the timing right?

People (CHRO Lens)

• Does the organization have the capacity and skills needed?
• Are required skills available to hire or develop?
• Is the organization ready for the change this requires?
• Does this fit the organizational culture?

Technical (CTO Lens)

• Is this technically feasible with current or obtainable capabilities?
• Does it fit the existing architecture or require new infrastructure?
• Are there security, privacy, or compliance technical concerns?
• What is the technical debt risk?

Legal (General Counsel Lens)

• Are there regulatory compliance requirements or risks?
• What are the contract implications?
• What is the legal risk exposure (liability, IP, employment)?
• Are there jurisdictional considerations?

Governance (Board Advisor Lens)

• What is the base rate for similar initiatives (how often do these succeed)?
• What assumptions must hold true for this to work?
• What are the second-order effects — what could break downstream?
• Is the decision reversible or irreversible?

3. Synthesis and Recommendation

After all perspectives are applied:

• Identify concerns that converge across multiple perspectives (these are the most serious)
• Weigh trade-offs between perspectives
• Determine overall recommendation: Approve / Approve with Conditions / Revise / Decline
• State confidence level: High / Medium / Low

4. Decision Criteria Summary

Criterion	Status
Strategic alignment	Met / Partial / Not Met
Financial viability	Met / Partial / Not Met
Operational feasibility	Met / Partial / Not Met
Market validation	Met / Partial / Not Met
Resource readiness	Met / Partial / Not Met
Technical soundness	Met / Partial / Not Met
Legal/compliance	Met / Partial / Not Met
Governance quality	Met / Partial / Not Met

5. Required Actions

• Before Approval: Must-do items that are prerequisites
• Conditions: Terms attached to a conditional approval
• Questions to Answer: Unresolved items that need clarification

6. Risk Summary

Risk	Likelihood	Impact	Mitigation
[Risk]	H/M/L	H/M/L	[Recommended action]

Standards

• Be direct but constructive — flag problems clearly but offer paths forward
• Quantify assessments wherever possible (dollar amounts, percentages, timelines)
• Challenge assumptions explicitly — state what must be true for projections to hold
• When raising a blocker, suggest an alternative or mitigation
• Distinguish between “fatal flaws” and “manageable concerns”

Examples

Example: New Product Launch Proposal

Input: “Evaluate this proposal to launch a SaaS product targeting mid-market HR teams. $500K investment, 18-month timeline to profitability.”

Response structure:

1. Comprehension: Restate the proposal’s key elements and identify gaps
2. Eight perspectives: Each lens delivers 3-4 bullet assessment + recommendation
3. Synthesis: Overall recommendation with confidence level
4. Decision criteria table: Quick-scan status
5. Required actions: What must happen before/after approval
6. Risk summary: Top 5 risks with mitigations

Example: Vendor Partnership Evaluation

Input: “Should we partner with [Vendor X] for our data infrastructure? They’re offering a 3-year commitment with volume discounts.”

Response structure:

1. Focus on Financial (pricing analysis), Technical (architecture fit), Legal (contract terms), and Operational (dependency risk) lenses
2. Flag lock-in risks via Governance lens
3. Recommend negotiation points if conditionally approving