Slide 1 — Mock Vendor Evaluation Exercise
Speaker 1: Picture procurement as a dusty kettlebell. Everyone nods at it, no one lifts. Tonight we do.
Speaker 2: But why mock evaluations instead of just diving into real ones?
Speaker 1: Because the last team that skipped rehearsal picked a charming helpdesk, then mid-migration learned it synced five integrations. Fixing that cost double.
Speaker 2: So this is our flight simulator: real decks, fake money, permission to stall safely.
Speaker 1: Exactly—structured reps, a dash of humour, time to flag hype before the next “this will revolutionise your workflow” email.
Slide 2 — Exercise objectives
Speaker 1: Our scoreboard tonight isn’t “pick Zendesk” or “pick Intercom.” It’s “can we run evaluation without drama?”
Speaker 2: We test how well we surface hidden assumptions, negotiate respectfully, and document decisions like adults.
Speaker 1: Exactly. When the Series A board call asks why you chose Vendor A over B, you’ll have receipts instead of vibes.
Speaker 2: And we leave with artefacts—scorecards, negotiation scripts, reference-call checklists—that seed the procurement playbook.
Speaker 1: 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
Speaker 1: Context—our support queue has outgrown a scrappy inbox plug-in. We’re weighing Zendesk versus Intercom for the next growth spurt.
Speaker 2: Leadership wants a recommendation in two weeks.
Speaker 1: Ouch, two weeks? That's startup speed for you! We ship releases while running vendor due diligence.
Speaker 2: Budget caps at $120K, SOC 2 is non-negotiable, and migration must land before the holiday spike. It’s like switching planes mid-flight.
Speaker 1: 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
Speaker 1: The evaluation lead conducts the orchestra—sets tempo, invites dissent, keeps the scorecard honest.
Speaker 2: Finance plays skeptic, probing cost, discount ladders, and what happens when usage blows past the tier.
Speaker 1: Security and compliance are our “department of no, but.” They bring veto power plus mitigations so the plane still flies.
Speaker 2: The support lead guards adoption, change management checklists, and whether onboarding beats last quarter’s fiasco.
Speaker 1: The CEO observer is the storytelling boss. If they can retell your recommendation without notes, you’ve cleared the level.
Slide 5 — Preparation checklist
Speaker 1: Prep starts with two vendor dossiers—pricing pages, security briefs, a HubSpot implementation guide if we’re stacking it against Salesforce Service Cloud.
Speaker 2: Everyone gets the same scorecard so debates hit weighting, not whether “reporting” belongs at all.
Speaker 1: Discovery notes keep us anchored in customer pain instead of vendor bingo squares. They’re the antidote to “trust me, it scales.”
Speaker 2: Pre-work matters: each persona brings deal-breaker questions and logs assumptions in the shared doc.
Speaker 1: That discipline keeps the live session on decisions, not rummaging through Slack for missing context.
Slide 6 — Live role-play flow
Speaker 1: Phase one, kick-off—evaluation lead sets the clock, states decision criteria, and assigns who plays the vendor rep.
Speaker 2: Phase two, breakout analysis—we pair up, annotate dossiers, and log gaps in shared notes instead of sticky pads.
Speaker 1: Phase three, negotiation sprint—finance haggles on payment terms while the “vendor” guards implementation scope. Fifteen minutes, zero table-flipping.
Speaker 2: Phase four, security challenge—compliance probes breach history, data residency, and redlines they’d refuse.
Speaker 1: 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
Speaker 1: Kick-off prompt: what assumptions are we making about migration effort or weekend coverage?
Speaker 2: Follow-up: who owns reference calls and what answers would make us walk away?
Speaker 1: Breakout prompt: how does each roadmap support the bets we just pitched investors?
Speaker 2: Negotiation prompt: would we trade a 10% discount for guaranteed onboarding hours or stronger exit clauses?
Speaker 1: Security prompt: show pen-test summaries, breach notices, and data residency maps.
Speaker 2: Executive prompt: how will we track adoption in 30, 60, 90 days without creative spreadsheet fiction?
Slide 8 — Scorecard and documentation
Speaker 1: The scorecard anchors weighted dimensions—functionality, security, total cost, implementation effort, vendor viability.
Speaker 2: No random numbers. Each score needs a quote, link, or screenshot so future you can retrace the decision.
Speaker 1: Breadcrumbs help when a new CFO asks why HubSpot beat Salesforce or why we skipped the flashy AI add-on.
Speaker 2: The decision matrix lives in a shared workspace with version history. Governance isn’t glamorous, yet auditors adore it.
Speaker 1: Open risks get owners, mitigation dates, and escalation paths. No orphaned yellow flags—documentation becomes insurance when memories fade.
Slide 9 — Debrief structure
Speaker 1: Debrief starts with “what worked” so we reinforce behaviour to repeat—transparent notes, quick risk spotting, vendors kept honest.
Speaker 2: Then “what puzzled us.” Perhaps Intercom’s security appendix contradicted the sales pitch or our change management plan felt thin.
Speaker 1: Every insight lands in the shared doc—no hallway wisdom vanishing before Monday.
Speaker 2: Action commitments need names and dates. Who’s refining the scorecard? Who’s booking reference calls for the evaluation?
Speaker 1: 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
Speaker 1: Success is a memo you’d hand the CEO without sweating—recommendation, quantified impact, clear risks, and a backup plan.
Speaker 2: The executive observer should retell the story unaided. If they need us nearby, we didn’t simplify enough.
Speaker 1: Templates, negotiation notes, and reference-call scripts land in the procurement playbook within 24 hours.
Speaker 2: Then we book next drill or live evaluation. Procurement is the vegetables of business—better when routine.
Speaker 1: Finally, assign owners for vendor relationship management: quarterly health checks, roadmap reviews, and change management follow-ups so momentum sticks.
Narrative Outline — Mock Vendor Evaluation Exercise Tasks - [x] Set up the role-play using real SaaS pricing pages. - [x] Include prompts for explaining backup costs to the CEO. - [x] Define success criteria for the exercise debrief. Notes - Outline the vendor evaluation role-play structure and discussion prompts. - Narratives emphasise role immersion, documentation discipline, and executive-ready storytelling.