Pick your phase. Pick your prompts.
Vendor decisions move through four phases. Each one needs a different lens. Match the phase to the prompt set below.
Who's even on the table?
Competitive Intelligence + Cost & Contract Analysis prompts.
Will it actually work for us?
User Experience Validation + Implementation Reality Check.
Make the case internally.
ROI & Value + Stakeholder Alignment prompts.
What happens when it breaks?
Scenario Stress Testing + Future-State Planning.
Three prompts. Every vendor. Always.
If you only ever use three prompts from this library, use these. Run them on every vendor that makes it to your shortlist. The pattern is "Act like {role}. {Specific ask}. Return {N concrete things}."
The CFO's analyst.
The EX researcher.
The PM.
💰 COST & CONTRACT ANALYSIS
What does this really cost?
Act like a CFO's analyst. Review this vendor's pricing page and identify 3 potential hidden costs or unclear pricing terms.
Act like a procurement specialist. Compare the contract terms of {Vendor A} vs {Vendor B}. Highlight red flags.
Act like a budget analyst. Calculate the 3-year TCO including licenses, implementation, training, support, and API overages.
Act like a vendor negotiator. Based on {Vendor}'s position, suggest 3 negotiation strategies.
🔧 IMPLEMENTATION REALITY CHECK
Will it actually go live by Q3?
Act like an implementation project manager. Create a realistic timeline and identify 3 potential roadblocks.
Act like a change management expert. Analyze the tool's learning curve and create a user adoption strategy.
Act like an IT security officer. Review {Vendor}'s security documentation and flag gaps.
Act like a systems integration specialist. Map out integrations and identify potential data flow issues.
👤 USER EXPERIENCE VALIDATION
Will my team like using this?
Act like an employee experience researcher. Identify the top 3 frustrations with {Vendor} and suggest demo questions.
Act like a UX analyst. Compare the mobile experience of {Vendor A} vs {Vendor B}.
Act like an HR business partner. Translate this feature list into employee benefits.
Act like a frontline manager. How will {Vendor} change my daily workflow?
🕵️ COMPETITIVE INTELLIGENCE
What does the market actually think?
Act like a market researcher. Analyze news, funding, and leadership changes for {Vendor}.
Act like a vendor analyst. Is {Vendor} prioritizing enterprise or SMB market?
Act like a due diligence specialist. Search for compliance violations or breaches in the last 24 months.
Act like a market intelligence analyst. Compare {Vendor A} vs {Vendor B} on innovation speed.
📈 ROI & VALUE REALIZATION
Make the case to the CFO.
Act like a finance partner. Identify 3 measurable KPIs to track post-implementation.
Act like a people analytics lead. Compare engagement metrics pre- and post-deployment.
Act like an HR transformation lead. Break down short-term vs long-term cost offsets.
Act like a productivity analyst. Calculate time savings across the organization.
👥 STAKEHOLDER ALIGNMENT
Get the team on board.
Act like an internal communications lead. Draft an announcement highlighting WIIFM for employees.
Act like a skeptical manager. Identify resistance points and address them with data.
Act like an HRBP. Translate strategic benefits into team-level value.
Act like an employee advocate. Draft FAQ responses on security, workload, and job-security concerns.
🧪 SCENARIO STRESS TESTING
What if it breaks?
Act like a business continuity planner. Map out impact if {Vendor} goes down for 48 hours.
Act like a global HR lead. Identify gaps for our geographies and time zones.
Act like a tech audit committee. Simulate a quarterly review and surface red flags.
Act like a crisis management lead. Draft an incident response plan.
🔮 FUTURE-STATE PLANNING
Will it still serve us in 18 months?
Act like a future-state planner. Evaluate scalability as our headcount doubles.
Act like a vendor relationship manager. Identify negotiation leverage we'll have at renewal.
Act like a technology strategist. Align {Vendor}'s roadmap with future HR-tech trends.
Run the play.
Start with the Power Trio
Every vendor. Always. Three prompts, three answers, ten minutes.
Pick 2-3 per phase
Don't run everything. Match the lens to where you are in the decision.
Add your context
Swap {Vendor} for the name. Swap {size/complexity} for yours. Paste in the pitch deck.
Chain for depth
Feed one prompt's output into the next. Surface what one pass misses.
Take the full prompt library.
35+ prompts · 8 stakeholder lenses · ready to paste into Claude, ChatGPT, Copilot, or Gemini.