Mock Vendor Evaluation Exercise =============================== Slide 1: Mock Vendor Evaluation Exercise 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. On-screen text Mock Vendor Evaluation Exercise Stress-test your buying process before money leaves the bank Slide 2: Exercise objectives 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. On-screen text 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. Slide 3: Scenario setup 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. On-screen text 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. Slide 4: Roles and personas 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. On-screen text 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. Slide 5: Preparation checklist 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. On-screen text 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. Slide 6: Live role-play flow 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. On-screen text 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. Slide 7: Discussion prompts by phase 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? On-screen text 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? Slide 8: Scorecard and documentation 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. On-screen text 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. Slide 9: Debrief structure 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. On-screen text 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? Slide 10: Success criteria and follow-through 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. On-screen text 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.