WEBVTT 1.1 00:00:00.000 --> 00:00:02.800 Slide 1 — Mock Vendor Evaluation Exercise 1.2 00:00:02.800 --> 00:00:09.200 Picture procurement as a dusty kettlebell. Everyone nods at it, no one lifts. Tonight we do. 1.3 00:00:09.200 --> 00:00:13.600 But why mock evaluations instead of just diving into real ones? 1.4 00:00:13.600 --> 00:00:22.400 Because the last team that skipped rehearsal picked a charming helpdesk, then mid-migration learned it synced five integrations. Fixing that cost double. 1.5 00:00:22.400 --> 00:00:28.000 So this is our flight simulator: real decks, fake money, permission to stall safely. 1.6 00:00:28.000 --> 00:00:35.600 Exactly—structured reps, a dash of humour, time to flag hype before the next “this will revolutionise your workflow” email. 2.1 00:00:35.600 --> 00:00:37.600 Slide 2 — Exercise objectives 2.2 00:00:37.600 --> 00:00:44.000 Our scoreboard tonight isn’t “pick Zendesk” or “pick Intercom.” It’s “can we run evaluation without drama?” 2.3 00:00:44.000 --> 00:00:50.000 We test how well we surface hidden assumptions, negotiate respectfully, and document decisions like adults. 2.4 00:00:50.000 --> 00:00:58.400 Exactly. When the Series A board call asks why you chose Vendor A over B, you’ll have receipts instead of vibes. 2.5 00:00:58.400 --> 00:01:03.600 And we leave with artefacts—scorecards, negotiation scripts, reference-call checklists—that seed the procurement playbook. 2.6 00:01:03.600 --> 00:01:12.000 Plus the muscle memory to brief execs in plain English instead of jargon bingo. That confidence is the real win condition. 3.1 00:01:12.000 --> 00:01:14.000 Slide 3 — Scenario setup 3.2 00:01:14.000 --> 00:01:21.600 Context—our support queue has outgrown a scrappy inbox plug-in. We’re weighing Zendesk versus Intercom for the next growth spurt. 3.3 00:01:21.600 --> 00:01:24.400 Leadership wants a recommendation in two weeks. 3.4 00:01:24.400 --> 00:01:30.800 Ouch, two weeks? That's startup speed for you! We ship releases while running vendor due diligence. 3.5 00:01:30.800 --> 00:01:39.200 Budget caps at $120K, SOC 2 is non-negotiable, and migration must land before the holiday spike. It’s like switching planes mid-flight. 3.6 00:01:39.200 --> 00:01:48.000 So we document the “why,” not just the “who.” If turbulence hits, the logbook shows our trade-offs and the backup parachute plan. 4.1 00:01:48.000 --> 00:01:50.400 Slide 4 — Roles and personas 4.2 00:01:50.400 --> 00:01:55.600 The evaluation lead conducts the orchestra—sets tempo, invites dissent, keeps the scorecard honest. 4.3 00:01:55.600 --> 00:02:02.000 Finance plays skeptic, probing cost, discount ladders, and what happens when usage blows past the tier. 4.4 00:02:02.000 --> 00:02:10.000 Security and compliance are our “department of no, but.” They bring veto power plus mitigations so the plane still flies. 4.5 00:02:10.000 --> 00:02:16.000 The support lead guards adoption, change management checklists, and whether onboarding beats last quarter’s fiasco. 4.6 00:02:16.000 --> 00:02:23.600 The CEO observer is the storytelling boss. If they can retell your recommendation without notes, you’ve cleared the level. 5.1 00:02:23.600 --> 00:02:25.600 Slide 5 — Preparation checklist 5.2 00:02:25.600 --> 00:02:34.000 Prep starts with two vendor dossiers—pricing pages, security briefs, a HubSpot implementation guide if we’re stacking it against Salesforce Service Cloud. 5.3 00:02:34.000 --> 00:02:40.000 Everyone gets the same scorecard so debates hit weighting, not whether “reporting” belongs at all. 5.4 00:02:40.000 --> 00:02:48.400 Discovery notes keep us anchored in customer pain instead of vendor bingo squares. They’re the antidote to “trust me, it scales.” 5.5 00:02:48.400 --> 00:02:54.000 Pre-work matters: each persona brings deal-breaker questions and logs assumptions in the shared doc. 5.6 00:02:54.000 --> 00:03:00.000 That discipline keeps the live session on decisions, not rummaging through Slack for missing context. 6.1 00:03:00.000 --> 00:03:02.400 Slide 6 — Live role-play flow 6.2 00:03:02.400 --> 00:03:09.200 Phase one, kick-off—evaluation lead sets the clock, states decision criteria, and assigns who plays the vendor rep. 6.3 00:03:09.200 --> 00:03:16.400 Phase two, breakout analysis—we pair up, annotate dossiers, and log gaps in shared notes instead of sticky pads. 6.4 00:03:16.400 --> 00:03:23.600 Phase three, negotiation sprint—finance haggles on payment terms while the “vendor” guards implementation scope. Fifteen minutes, zero table-flipping. 6.5 00:03:23.600 --> 00:03:28.800 Phase four, security challenge—compliance probes breach history, data residency, and redlines they’d refuse. 6.6 00:03:28.800 --> 00:03:36.400 Phase five, executive pitch—we regroup, deliver a tight deck, and field curveballs about migration risk and change management support. 7.1 00:03:36.400 --> 00:03:39.200 Slide 7 — Discussion prompts by phase 7.2 00:03:39.200 --> 00:03:44.400 Kick-off prompt: what assumptions are we making about migration effort or weekend coverage? 7.3 00:03:44.400 --> 00:03:49.600 Follow-up: who owns reference calls and what answers would make us walk away? 7.4 00:03:49.600 --> 00:03:54.800 Breakout prompt: how does each roadmap support the bets we just pitched investors? 7.5 00:03:54.800 --> 00:04:01.200 Negotiation prompt: would we trade a 10% discount for guaranteed onboarding hours or stronger exit clauses? 7.6 00:04:01.200 --> 00:04:05.600 Security prompt: show pen-test summaries, breach notices, and data residency maps. 7.7 00:04:05.600 --> 00:04:12.000 Executive prompt: how will we track adoption in 30, 60, 90 days without creative spreadsheet fiction? 8.1 00:04:12.000 --> 00:04:14.400 Slide 8 — Scorecard and documentation 8.2 00:04:14.400 --> 00:04:19.200 The scorecard anchors weighted dimensions—functionality, security, total cost, implementation effort, vendor viability. 8.3 00:04:19.200 --> 00:04:26.400 No random numbers. Each score needs a quote, link, or screenshot so future you can retrace the decision. 8.4 00:04:26.400 --> 00:04:34.000 Breadcrumbs help when a new CFO asks why HubSpot beat Salesforce or why we skipped the flashy AI add-on. 8.5 00:04:34.000 --> 00:04:41.200 The decision matrix lives in a shared workspace with version history. Governance isn’t glamorous, yet auditors adore it. 8.6 00:04:41.200 --> 00:04:48.400 Open risks get owners, mitigation dates, and escalation paths. No orphaned yellow flags—documentation becomes insurance when memories fade. 9.1 00:04:48.400 --> 00:04:50.400 Slide 9 — Debrief structure 9.2 00:04:50.400 --> 00:04:57.600 Debrief starts with “what worked” so we reinforce behaviour to repeat—transparent notes, quick risk spotting, vendors kept honest. 9.3 00:04:57.600 --> 00:05:05.200 Then “what puzzled us.” Perhaps Intercom’s security appendix contradicted the sales pitch or our change management plan felt thin. 9.4 00:05:05.200 --> 00:05:10.000 Every insight lands in the shared doc—no hallway wisdom vanishing before Monday. 9.5 00:05:10.000 --> 00:05:16.800 Action commitments need names and dates. Who’s refining the scorecard? Who’s booking reference calls for the evaluation? 9.6 00:05:16.800 --> 00:05:24.800 Close with feelings check-ins by persona. Did finance feel heard? Did support believe the adoption plan? Reflection locks in trust. 10.1 00:05:24.800 --> 00:05:27.600 Slide 10 — Success criteria and follow-through 10.2 00:05:27.600 --> 00:05:34.800 Success is a memo you’d hand the CEO without sweating—recommendation, quantified impact, clear risks, and a backup plan. 10.3 00:05:34.800 --> 00:05:41.600 The executive observer should retell the story unaided. If they need us nearby, we didn’t simplify enough. 10.4 00:05:41.600 --> 00:05:47.200 Templates, negotiation notes, and reference-call scripts land in the procurement playbook within 24 hours. 10.5 00:05:47.200 --> 00:05:53.600 Then we book next drill or live evaluation. Procurement is the vegetables of business—better when routine. 10.6 00:05:53.600 --> 00:06:01.200 Finally, assign owners for vendor relationship management: quarterly health checks, roadmap reviews, and change management follow-ups so momentum sticks. 11.1 00:06:01.200 --> 00:06:25.200 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.