Mock Vendor Evaluation Exercise

Slide 1: Mock Vendor Evaluation Exercise

On-screen

Mock Vendor Evaluation Exercise

Stress-test your buying process before money leaves the bank

Narration

Slide 1 — Mock Vendor Evaluation Exercise
Anna: Picture procurement as a dusty kettlebell. Everyone nods at it, no one lifts. Tonight we do.
Greg: But why mock evaluations instead of just diving into real ones?
Anna: Because the last team that skipped rehearsal picked a charming helpdesk, then mid-migration learned it synced five integrations. Fixing that cost double.
Greg: So this is our flight simulator: real decks, fake money, permission to stall safely.
Anna: Exactly—structured reps, a dash of humour, time to flag hype before the next “this will revolutionise your workflow” email.

Slide 2: Exercise objectives

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Exercise objectives

Give founders and operators a safe sandbox to practice structured vendor evaluation.
Surface hidden assumptions about pricing, risk, and cross-functional approvals.
Build confidence communicating trade-offs to leadership using data and storytelling.
Produce reusable artefacts: scorecards, escalation templates, and negotiation talking points.

Narration

Slide 2 — Exercise objectives
Anna: Our scoreboard tonight isn’t “pick Zendesk” or “pick Intercom.” It’s “can we run evaluation without drama?”
Greg: We test how well we surface hidden assumptions, negotiate respectfully, and document decisions like adults.
Anna: Exactly. When the Series A board call asks why you chose Vendor A over B, you’ll have receipts instead of vibes.
Greg: And we leave with artefacts—scorecards, negotiation scripts, reference-call checklists—that seed the procurement playbook.
Anna: Plus the muscle memory to brief execs in plain English instead of jargon bingo. That confidence is the real win condition.

Slide 3: Scenario setup

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Scenario setup

Context: A fast-growing startup must choose a customer support platform within two weeks.
Trigger: Current tool cannot handle integrations or analytics demanded by new enterprise clients.
Constraint: $120K annual budget cap, SOC 2 requirement, and migration must finish before peak season.
Outcome: Team recommends a vendor to the CEO with documented rationale and risk mitigations.

Narration

Slide 3 — Scenario setup
Anna: Context—our support queue has outgrown a scrappy inbox plug-in. We’re weighing Zendesk versus Intercom for the next growth spurt.
Greg: Leadership wants a recommendation in two weeks.
Anna: Ouch, two weeks? That's startup speed for you! We ship releases while running vendor due diligence.
Greg: Budget caps at $120K, SOC 2 is non-negotiable, and migration must land before the holiday spike. It’s like switching planes mid-flight.
Anna: So we document the “why,” not just the “who.” If turbulence hits, the logbook shows our trade-offs and the backup parachute plan.

Slide 4: Roles and personas

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Roles and personas

Evaluation lead (Ops/IT): Facilitates the process, consolidates findings, owns final brief.
Finance partner: Probes total cost of ownership, discount structures, and contract flexibility.
Security & compliance: Challenges data residency, access controls, and incident response posture.
Business sponsor (Support lead): Champions feature fit, adoption risk, and change management needs.
CEO/Board observer: Joins debrief to test clarity of recommendations and executive readiness.

Narration

Slide 4 — Roles and personas
Anna: The evaluation lead conducts the orchestra—sets tempo, invites dissent, keeps the scorecard honest.
Greg: Finance plays skeptic, probing cost, discount ladders, and what happens when usage blows past the tier.
Anna: Security and compliance are our “department of no, but.” They bring veto power plus mitigations so the plane still flies.
Greg: The support lead guards adoption, change management checklists, and whether onboarding beats last quarter’s fiasco.
Anna: The CEO observer is the storytelling boss. If they can retell your recommendation without notes, you’ve cleared the level.

Slide 5: Preparation checklist

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Preparation checklist

Circulate two real vendor dossiers: pricing page, security summary, implementation guide, reference quotes.
Share a common evaluation scorecard template (weights pre-filled but adjustable by the team).
Provide discovery call notes highlighting must-have integrations and stakeholder priorities.
Assign pre-work: each role drafts 3 deal-breaker questions and captures assumptions about budget or effort.

Narration

Slide 5 — Preparation checklist
Anna: Prep starts with two vendor dossiers—pricing pages, security briefs, a HubSpot implementation guide if we’re stacking it against Salesforce Service Cloud.
Greg: Everyone gets the same scorecard so debates hit weighting, not whether “reporting” belongs at all.
Anna: Discovery notes keep us anchored in customer pain instead of vendor bingo squares. They’re the antidote to “trust me, it scales.”
Greg: Pre-work matters: each persona brings deal-breaker questions and logs assumptions in the shared doc.
Anna: That discipline keeps the live session on decisions, not rummaging through Slack for missing context.

Slide 6: Live role-play flow

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Live role-play flow

Kick-off (10 min): Evaluation lead frames goals, decision deadline, and scoring method.
Breakout analysis (25 min): Pairs review vendor packets, annotating risks and opportunities.
Negotiation simulation (15 min): Finance and vendor rep role-play discount and term negotiations.
Security challenge (10 min): Compliance lead interrogates breach history and data segregation.
Executive pitch (10 min): Team presents recommendation and backup option to CEO observer.

Narration

Slide 6 — Live role-play flow
Anna: Phase one, kick-off—evaluation lead sets the clock, states decision criteria, and assigns who plays the vendor rep.
Greg: Phase two, breakout analysis—we pair up, annotate dossiers, and log gaps in shared notes instead of sticky pads.
Anna: Phase three, negotiation sprint—finance haggles on payment terms while the “vendor” guards implementation scope. Fifteen minutes, zero table-flipping.
Greg: Phase four, security challenge—compliance probes breach history, data residency, and redlines they’d refuse.
Anna: Phase five, executive pitch—we regroup, deliver a tight deck, and field curveballs about migration risk and change management support.

Slide 7: Discussion prompts by phase

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Discussion prompts by phase

Kick-off: What assumptions are we making about migration effort or internal staffing?
Breakout: Where do vendor roadmaps align or diverge from product strategy in the next 12 months?
Negotiation: Which concessions matter most—price, implementation support, exit clauses, or SLAs?
Security: What evidence do we need to validate their incident response claims post-contract?
Executive pitch: How will we monitor success in the first 90 days and trigger escalation if needed?

Narration

Slide 7 — Discussion prompts by phase
Anna: Kick-off prompt: what assumptions are we making about migration effort or weekend coverage?
Greg: Follow-up: who owns reference calls and what answers would make us walk away?
Anna: Breakout prompt: how does each roadmap support the bets we just pitched investors?
Greg: Negotiation prompt: would we trade a 10% discount for guaranteed onboarding hours or stronger exit clauses?
Anna: Security prompt: show pen-test summaries, breach notices, and data residency maps.
Greg: Executive prompt: how will we track adoption in 30, 60, 90 days without creative spreadsheet fiction?

Slide 8: Scorecard and documentation

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Scorecard and documentation

Use 5 weighted dimensions: functionality, security/compliance, total cost, implementation effort, vendor viability.
Require quantitative scores plus qualitative commentary and cited artefacts for each dimension.
Capture decision matrix in the shared workspace with version history to model governance discipline.
Flag open risks with owners, mitigations, and required executive decisions before contract signing.

Narration

Slide 8 — Scorecard and documentation
Anna: The scorecard anchors weighted dimensions—functionality, security, total cost, implementation effort, vendor viability.
Greg: No random numbers. Each score needs a quote, link, or screenshot so future you can retrace the decision.
Anna: Breadcrumbs help when a new CFO asks why HubSpot beat Salesforce or why we skipped the flashy AI add-on.
Greg: The decision matrix lives in a shared workspace with version history. Governance isn’t glamorous, yet auditors adore it.
Anna: Open risks get owners, mitigation dates, and escalation paths. No orphaned yellow flags—documentation becomes insurance when memories fade.

Slide 9: Debrief structure

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Debrief structure

What worked: Highlight behaviors that drove clarity, cross-functional alignment, or stakeholder empathy.
What puzzled us: Surface conflicting data, unclear responsibilities, or missing inputs.
Action commitments: Document process improvements, follow-up research, or policy updates.
Close with reflective prompts: How did each role experience the exercise? What would we change next time?

Narration

Slide 9 — Debrief structure
Anna: Debrief starts with “what worked” so we reinforce behaviour to repeat—transparent notes, quick risk spotting, vendors kept honest.
Greg: Then “what puzzled us.” Perhaps Intercom’s security appendix contradicted the sales pitch or our change management plan felt thin.
Anna: Every insight lands in the shared doc—no hallway wisdom vanishing before Monday.
Greg: Action commitments need names and dates. Who’s refining the scorecard? Who’s booking reference calls for the evaluation?
Anna: Close with feelings check-ins by persona. Did finance feel heard? Did support believe the adoption plan? Reflection locks in trust.

Slide 10: Success criteria and follow-through

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Success criteria and follow-through

Team delivers a concise recommendation memo with a go/no-go decision and quantified impact.
Executive observer can articulate trade-offs without referencing the team in the room.
Updated templates and lessons learned stored in the procurement playbook within 24 hours.
Schedule the next mock evaluation or live vendor review to keep muscle memory active.

Narration

Slide 10 — Success criteria and follow-through
Anna: Success is a memo you’d hand the CEO without sweating—recommendation, quantified impact, clear risks, and a backup plan.
Greg: The executive observer should retell the story unaided. If they need us nearby, we didn’t simplify enough.
Anna: Templates, negotiation notes, and reference-call scripts land in the procurement playbook within 24 hours.
Greg: Then we book next drill or live evaluation. Procurement is the vegetables of business—better when routine.
Anna: Finally, assign owners for vendor relationship management: quarterly health checks, roadmap reviews, and change management follow-ups so momentum sticks.