What pulled you into this conversation today?

• What's the single event or insight that prompted you to explore a new procurement solution now? Options: Internal audit revealed high maverick spend, AP team overwhelmed with invoice exceptions, CFO flagged forecasting gaps, New CPO or finance leader mandate, Compliance or regulatory concern, Other
• How long have you been noticing the procurement issues we're discussing? Options: Less than 3 months, 3–6 months, 6–12 months, 1–2 years, More than 2 years
• Who first raised the problem internally and what did they say was most painful?
• If you had to describe in one short sentence why solving this matters to the CFO or CPO, what would you say?
• What would be the most damaging outcome if nothing changes in the next 12 months? Options: Worse cash forecasting, Rising invoice fraud or errors, Increased AP costs/headcount, Supplier disputes and churn, Regulatory or audit penalties, Other

Are we quietly tolerating rogue orders?

• What would it cost your organization if a large share of purchases continued to bypass procurement — in dollars, risk, or lost control?
• What is your best estimate of current purchase order compliance today (percent of spend that follows approved procurement process)? Options: <40%, 40–60%, 61–80%, 81–90%, >90%, Unsure
• How do purchases most commonly bypass procurement in your org? Options: Email to supplier rep, Phone orders, Direct invoicing to AP, Shadow cards/corporate cards, Manual offline approvals, Other
• Which types of purchases or categories are most likely to go rogue (examples: suppliers, spend categories, ad-hoc services)?
• Tell us about a recent incident where a rogue purchase caused a material problem—what happened and who felt the impact?

Who actually holds the keys?

• Who do you think truly approves or authorizes spend day-to-day — and how often are those people bypassed?
• Which roles are required in your approval matrix (select all that apply)? Options: Requester, Line manager, Budget owner, Sourcing/procurement, Finance/AP, Legal, CFO/VP Finance, Other
• How consistent is your approval matrix across business units and countries? Options: Fully standardized, Mostly consistent with some local exceptions, Significantly different by BU/region, No formal approval matrix, Unsure
• When approvals are skipped, what typically explains it—speed, relationships, lack of enforcement, tools, or something else?
• How confident are you that approvers understand the financial and compliance impact of approving off-system purchases? Options: Very confident, Somewhat confident, Not very confident, Not confident at all

Why is an email still easier than the system?

• What makes emailing or calling a supplier feel faster or more attractive than using your procurement tool?
• Which parts of your current procurement experience do users call 'friction'? Options: Slow catalog search, Missing suppliers or SKUs, Cumbersome approvals, Poor mobile experience, Complex invoicing or matching, Other
• What is your average requisition-to-PO time today? Options: <4 hours, 4–24 hours, 1–3 days, 3–7 days, >7 days, Not tracked
• What percentage of POs are typically issued within 24 hours of requisition? Options: <20%, 20–40%, 41–60%, 61–80%, >80%, Don't track
• Share a specific story where a buyer chose the 'rogue' route—what motivated them and what did they risk bypassing?
• What would need to change in the buying experience to make your users pick the platform over emailing a rep?

If invoices matched every time, how would your world look?

• Imagine AP stopped seeing exceptions—what would change in day-to-day operations, team focus, and morale?
• What percent of invoices currently exception out due to PO/match issues? Options: <10%, 10–20%, 21–30%, 31–50%, >50%, Unsure
• What are the top root causes of your invoice exceptions today? Options: No PO exists, PO/invoice quantity mismatch, Price variance, Partial shipments/receipts missing, Duplicate invoices, Other
• On average, how many hours does AP spend resolving a single exception? Options: <1 hour, 1–2 hours, 2–4 hours, 4–8 hours, >8 hours, Don't know
• How does the current exception volume affect your finance team's ability to forecast and close the books?

What would a successful 60‑day pilot actually prove?

• If the pilot is a clear success in 60 days, what three measurable outcomes convince you to expand?
• Which of these metrics would you hold as primary acceptance criteria (select up to three)? Options: PO compliance >80%, Requisition-to-PO <24 hours, Invoice exceptions reduced by X%, User voluntary post-pilot adoption, Time AP spends on exceptions reduced, Improved cash forecasting accuracy
• Which business units would you choose for the pilot and why? (pick up to two) Options: Operations, IT, Facilities/Real Estate, Marketing, Sales, Finance/AP, Procurement/Sourcing, Other
• Who will own pilot success day-to-day and who is the executive sponsor? Options: CPO/Head of Procurement, VP/Director of Finance, Head of BU, Procurement Program Manager, Other
• What governance cadence will you commit to for the pilot (review frequency and stakeholders)? Options: Weekly core team, Bi-weekly steering, Monthly executive review, Ad-hoc as needed

What's most likely to block you from saying yes?

• What single organizational barrier has historically stopped procurement projects from getting traction here?
• Which of these will require explicit approval before a pilot can start? Options: Budget reallocation, Legal & commercial terms, IT/security signoff, Supplier consent/punchouts, Data sharing agreements, Executive sponsor signoff
• How ready are your systems for integrations (catalog import, punchout, invoice history)? Options: Fully ready, Mostly ready with minor work, Requires moderate IT effort, Major IT project, Unsure
• Who owns the data responsibilities and who needs to approve data sharing for the pilot?
• What assurances or mitigations would make procurement, IT, and legal comfortable to move forward?

If we built the smallest possible pilot that could still prove value, what would it include?

• If you had to launch with the absolute minimum to demonstrate impact, which elements are non-negotiable and which can wait?
• Which catalogs or supplier types must be in the pilot (select all that apply)? Options: Office supplies, MRO/Facilities, IT hardware/software, Professional services, Marketing services, Single-use strategic suppliers, Other
• Do you require punchout integrations or are hosted catalogs acceptable for the pilot? Options: Punchouts required for key suppliers, Hosted supplier catalogs acceptable, Mixed approach, Unsure
• Can you provide a sample approval matrix, 30–90 days of invoice history, and sample catalogs within the pilot prep window? Options: Yes, within 1 week, Yes, within 2–4 weeks, Yes, in 1–2 months, No, would need support
• Roughly how many pilot users would you want to onboard and what roles will they have? Options: 5–10 requesters, 10–25 requesters, 25–50 requesters, Multiple approvers and AP users, Other

Who will notice the wins — and who needs convincing?

• Who in your organization will be the first to notice and celebrate pilot wins, and who will be the first to push back if it struggles?
• Who is your executive sponsor and what will they need to see to greenlight scale? Options: CPO/Head of Procurement, VP/Finance or CFO, COO, CEO, Other
• Which internal KPIs or dashboards will be used to communicate pilot progress to stakeholders? Options: PO compliance (%, Requisition-to-PO time, Invoice exception rate, AP time spent on exceptions, User adoption rates, Cash forecast variance
• What incentives or communications would encourage voluntary continued use after the pilot?
• How will you collect qualitative feedback from buyers and approvers during the pilot (channels and frequency)? Options: In-app surveys, Weekly user interviews, Support tickets analysis, Manager check-ins, Other

Next steps — what would make this an easy yes?

• Given everything we've discussed, what would a simple, low-risk next step look like from your perspective?
• What timeline would you be comfortable with for pilot kickoff? Options: Within 2 weeks, 2–4 weeks, 1–2 months, Longer than 2 months, Unsure
• What information or assurances do you still need from us to make a decision?
• Who else should be part of our discovery conversations going forward? Options: Head of AP, IT/Security lead, Legal/Compliance, Business unit lead, Finance Controller, Other
• If we agree a pilot today, what would success look like at the end of week two, week four, and day 60?

• Solution Experience Kickoff — Current State & Success Criteria
• Data & Access Prep — Build the Simulation Sandbox
• Scenario Simulation Workshop — Live Purchasing Flows
• Invoice Exception Reconciliation Lab
• Validation, Acceptance & Pilot Commitment

• Demonstrate a measurable reduction in manual exception cases after AI matching and rule tuning.
• Surface and agree the concrete business consequences we must address.
• Introductions & Meeting Objectives
• Agree an import validation checklist and test dataset to use during simulations.
• Ensure access and test users are available for scheduled scenario sessions.
• Customer to correct and resend any missing or malformed catalog fields and approval rules.
• Platform team to import data into sandbox, run validation checks, and post import report.
• Provision two BU test environments and create named test users for the simulation workshop.
• Restate One-line Current State, Consequence & Future State
• Prove with live evidence that the platform delivers the defined future state for core purchasing scenarios.
• Tie each simulated behavior back to the customer's stated problems and quantify expected operational delta.
• Force customer validation after each scenario to remove ambiguity about fit and ease-of-use.
• Identify any configuration gaps or UX concerns that would hinder adoption.
• Platform to capture scenario logs, timings, and screenshots and share a session report with measured outcomes vs acceptance criteria.
• Customer to review and confirm whether each scenario's outcome satisfies their operational definition of 'better'.
• Platform to implement agreed rule tweaks and re-run any failed edge-case scenarios as scheduled.
• Recap Exception Types & Business Impact
• Produce a single-line current state statement that all parties accept.
• Agree on rule thresholds and which exception types can be permanently automated for the pilot.
• Document the expected AP time savings and acceptance metrics to include in pilot success criteria.
• Customer to provide the agreed set of historical exception invoices and supporting PO/receipt records.
• Platform to run matching, produce before/after metrics, and deliver a reconciliation summary with tuned rules.
• Both teams to decide which exception types will be included in the pilot automation scope.
• Summary of Simulations & Key Metrics
• Validate that simulated outcomes meet the predefined acceptance criteria or surface precise remediation steps.
• Agree and document the pilot scope, timeline, success metrics, and owners for execution.
• Obtain clear mutual commitment to proceed to the 60-day pilot with a governance plan.
• Platform to produce a Solution Experience report summarizing scenarios, metrics, logs, tuning decisions, and unresolved gaps.
• Customer and seller to sign or acknowledge the pilot statement-of-work and responsibilities document.
• Schedule pilot kickoff date, assign governance cadences, and publish the pilot measurement dashboard owner.
• Define one-sentence future state with measurable acceptance criteria (PO compliance, cycle time, exception reduction).
• Agree on simulation scope and required pre-work items with owners and deadlines.
• Customer to deliver catalog extract, supplier list (including punchout endpoints), approval matrix, and representative invoice/exception samples.
• Assign sandbox and data owners (customer and platform) and share contact details.
• Schedule Data & Access Prep session and provide timeline for imports.
• Review Pre-work Deliverables
• Confirm all required data is available and correctly mapped for accurate simulation.
• Provision a sandbox environment that mirrors customer decisioning and approval flows.
• Gap Review & Risk Mitigations
• Catalog & SKU Mapping
• One-sentence Current State
• Scenario 1 — Catalog-approved Purchase (Happy Path)
• Import Historical Exception Samples
• Validation Checkpoint 1
• Quantify Consequence
• Run AI Invoice Matching & Review Decisions
• Approval Matrix & Routing Mapping
• Agree Pilot Scope, Timeline & Acceptance Criteria
• Scenario 2 — Rogue Supplier / Email Attempt
• One-sentence Future State & Success Metrics
• Rule Tuning & Re-run
• Governance & Communication Cadence
• Supplier & Punchout Configuration Plan
• Validation Checkpoint 2
• Scope of Simulation Scenarios
• Sandbox Access, Test Accounts & Roles
• Measure Results & Acceptance Check
• Decision & Commitments
• Import Validation & Test Dataset
• Scenario 3 — Partial Shipment & Invoice Mismatch (AI Match)

• Import and normalize supplier catalogs
• Load supplier contracts and pre-negotiated pricing
• Activate punchout and cXML supplier integrations
• Configure approval matrix and routing rules
• Deploy buyer storefront with search and cart
• Enable mobile goods-receipt capture and receiving
• Activate AI-powered three-way invoice matching
• Configure exception rules and price/quantity tolerances
• Integrate ERP for PO, AP, and GL synchronization
• Enable PO compliance and cycle-time dashboards
• Provision single sign-on and role-based access
• Deliver end-user training and adoption workshops
• Automate PO issuance and supplier notifications

Import and normalize supplier catalogs

• Do you have existing supplier catalogs to import? Options: Yes - CSV/Excel, Yes - Punchout/cXML, Yes - API/Hosted, No
• How many supplier catalogs will need to be imported and maintained? Options: 1-10, 11-50, 51-200, 200+
• Which catalog file formats or endpoints do your suppliers provide? Options: CSV/Excel, cXML, OCI, REST API, Other
• Do SKUs need mapping to your internal part numbers or taxonomy? Options: Yes, No
• Do catalogs require normalization for currency, unit-of-measure, tax, or lead time? Options: Yes, No
• Will you need ongoing automated catalog syncs (frequency)? Options: One-time import, Daily, Weekly, Near real-time/API

Load supplier contracts and pre-negotiated pricing

• Do you have supplier contracts with negotiated pricing to load? Options: Yes, No
• Approximately how many active contracts should be ingested? Options: 1-10, 11-50, 51-200, 200+
• What pricing structures are present in contracts (select all that apply)? Options: List price only, Tiered/volume discounts, Rebates/bonuses, Contract-bound catalog
• Are contracts available in machine-readable form or only as PDFs/scan images? Options: Machine-readable, PDF/scan only, Mixed
• Do you require fallback/pricing precedence rules when multiple prices exist? Options: Yes, No
• Who owns approval for contract price overrides (procurement, finance, supplier)? Options: Procurement, Finance, Supplier, Other

Activate punchout and cXML supplier integrations

• Do you plan to use punchout/cXML integrations for any suppliers? Options: Yes, No
• How many suppliers require punchout or cXML integration for the pilot? Options: 1-5, 6-20, 21-50, 50+
• Which supplier integration protocols are needed (select all that apply)? Options: cXML, OCI, REST API, EDI, Other
• Will your suppliers manage integration configuration or will you require platform-led build? Options: Supplier-led, Customer-led, Platform/Third-party build
• Are there firewall/IP allowlist or credentialing requirements for supplier punchouts? Options: Yes, No
• Do you need real-time basket sync (prices/availability) from punchout suppliers? Options: Yes, No

Configure approval matrix and routing rules

• How many approval levels or tiers should be configured? Options: 1-2, 3-4, 5+
• What triggers should determine routing (amount, category, supplier, project)? Options: Amount threshold, Commodity/category, Supplier, Project/Cost center, Custom attribute
• Do you require parallel or split approvals for certain transactions? Options: Sequential, Parallel, Split/Shared approval
• Do you need delegation rules for out-of-office or proxy approvals? Options: Yes, No
• Should approval thresholds be tied to GL account or cost center? Options: Yes - GL, Yes - Cost center, No
• Is an auditable approval trail and automatic notifications required for all steps? Options: Yes, No

Deploy buyer storefront with search and cart

• Do you want a catalog-driven storefront, curated merchant pages, or both? Options: Catalog-driven, Curated storefronts, Both
• Should storefronts be customized per business unit, region, or a single global view? Options: Single global, Per BU, Per region
• Which search and navigation features are required (select all that apply)? Options: Full-text search, Faceted filters, SKU search, Supplier filter, Image/spec search
• Do you need approval gating or spend limits enforced at cart checkout? Options: Yes - approval gating, Yes - spend limits, No
• Will you require rich content on product pages (images, spec sheets, lead times)? Options: Yes, No
• Is native mobile app functionality required or is responsive web sufficient? Options: Responsive web, Native mobile, Both

Enable mobile goods-receipt capture and receiving

• Do you require mobile receipt capture for PO receiving? Options: Yes, No
• Which receiving methods should be supported (select all that apply)? Options: PO receipt, ASN/advance shipment notice, Partial deliveries, Lot/serial capture
• Is photo or document capture at delivery required for auditability? Options: Yes, No
• Do receiving users need offline/off-grid capability (no internet)? Options: Yes, No
• Should mobile receiving integrate with warehouse systems or TMS? Options: Yes, No
• Is barcode or QR code scanning required for fast receipts? Options: Yes, No

Activate AI-powered three-way invoice matching

• Do you currently perform PO-Receipt-Invoice three-way matching today? Options: Yes - automated, Partially, No
• What invoice mismatch types are most common in your environment? Options: Quantity variance, Price variance, PO missing, Partial shipment, Tax/discount differences
• What is your average monthly invoice volume? Options: Less than 1,000, 1,000-5,000, 5,000-20,000, 20,000+
• Do you want the AI to learn from historical exception resolutions (supervised learning)? Options: Yes, No
• What default tolerance bands would you accept for auto-match (price/quantity)? Options: Strict (0%), Low (1-3%), Medium (4-10%), High (>10%)
• Who will own review of exceptions (AP, Procurement, Buyer)? Options: AP team, Procurement, Purchaser/BU, Other

Configure exception rules and price/quantity tolerances

• Do you have existing exception thresholds and SLAs to replicate? Options: Yes, No
• Should tolerances be global or vary by BU/supplier/category? Options: Global, Per BU, Per supplier, Per category
• Which escalation paths should exceptions follow (select all that apply)? Options: AP, Procurement, Purchaser, Finance/Controller
• Do you want auto-resolution rules for small variances (e.g., auto-approve <1%)? Options: Yes, No
• Should the system automatically notify suppliers about exceptions? Options: Yes - auto notify, No - manual only
• What SLA target should apply for exception resolution? Options: 24 hours, 48 hours, 5 business days, Custom

Integrate ERP for PO, AP, and GL synchronization

• Which ERP system(s) must be integrated? Options: SAP, Oracle EBS, Workday, NetSuite, Microsoft Dynamics, Other
• What integration scope do you require (select all that apply)? Options: PO export, AP invoice sync, GR/receipt sync, GL posting, Master data sync
• Preferred integration method? Options: Real-time API, File-based batch (SFTP), Middleware/iPaaS, Other
• What is the expected frequency for PO/AP/GL synchronization? Options: Real-time, Hourly, Daily, Weekly
• What internal IT resources are available for integration work? Options: Dedicated integration team, Some support, Limited support, None
• Are there data residency, compliance, or custom field mapping constraints? Options: Yes, No

Enable PO compliance and cycle-time dashboards

• Which KPIs do you want surfaced in dashboards (select all that apply)? Options: PO compliance %, Requisition-to-PO cycle time, Invoice exceptions, Adoption rate, Spend under management
• Who are the target audiences for dashboards? Options: Procurement team, Finance/AP, Business unit leaders, Executives
• Do you require real-time dashboards or scheduled reports? Options: Real-time, Daily, Weekly, Monthly
• Do you need role-based views or the ability to restrict KPI visibility by BU? Options: Yes, No
• Should the platform push alerts when KPIs breach thresholds (e.g., PO compliance <80%)? Options: Yes, No
• Do you need export/connectors to external BI tools (e.g., Power BI, Tableau)? Options: Yes, No

• Non-Disclosure Agreement (NDA)
• Master Services Agreement (MSA)
• Statement of Work (SOW)
• Order Form & Pricing Schedule
• Pilot Commitment & Acceptance Agreement
• Data Processing Agreement (DPA)
• Security & Compliance Addendum
• Implementation & Integration Plan
• Service Level Agreement (SLA) & Support Terms
• Governance & Cadence Agreement
• Change Order & Scope Management
• Termination, Renewal & Exit Plan
• Liability, Indemnity & Insurance Schedule

• Pilot Outcomes Validation Review
• Adoption & Voluntary Use Confirmation
• Exceptions, Invoice Matching & Root Cause Retro
• Shared Backlog Prioritization & Implementation Plan
• Governance & Scale Decision Workshop

• Publish the prioritized backlog to the shared workspace with owners, due dates, and impact scores.
• Produce a named list of users/BUs who committed to voluntary use and any conditions tied to that commitment.
• Create and assign remediation tickets for top 5 adoption frictions with resolution owners and target dates.
• Schedule targeted refresher trainings or job‑aids for cohorts with low repeat usage.
• Current State of Exceptions (one sentence)
• Validate how many exceptions were solved by platform logic vs manual intervention and quantify residual risk.
• Agree on concrete root-cause remediations owners and timelines to lower invoice exception rates.
• Establish short experiments to demonstrate % reduction in exceptions after fixes.
• Deliver a ranked list of exception root causes with sample transactions and proposed remediation per cause.
• Owner to schedule AI‑matching tuning runs and report back with before/after metrics within 14 days.
• Create supplier or catalog tickets to correct systemic data issues discovered during retro.
• Backlog Overview & Scoring Criteria
• Produce a prioritized backlog with owners, impact scores, and target delivery windows.
• Align on SLAs and dependency mitigations to reduce schedule risk for fixes required to meet acceptance.
• Agree a public cadence and transparency mode for backlog updates for pilot stakeholders.
• Opening & One‑Sentence Current State
• Owner to create minimal scope tickets for high-impact items with clear acceptance criteria for QA.
• Schedule weekly 15-minute backlog syncs during remediation window to track progress and unblock items.
• Recap: One‑Sentence Future State and Pilot Verdict
• Reach a documented decision on whether to scale, and if conditional, list required conditions and owners.
• Establish a governance cadence and clear ownership for rollout and escalation once scaling begins.
• Agree a phased rollout timeline per BU that reflects pilot learnings and backlog readiness.
• Publish the official Scale Decision document with required preconditions, owners, and baseline timeline.
• Set up the agreed governance meetings (steering and working group invites) and distribute charters.
• Create a rollout risk register and assign owners to each mitigation item with review dates.
• Confirm whether the pilot met each acceptance metric with evidence and stakeholder sign-off.
• Surface any measurement gaps or disputes and create a short remediation list.
• Capture an explicit decision record for pilot acceptance or next remediation steps.
• Export and attach the raw metric datasets and dashboard snapshots used in the meeting.
• Owner to produce a one-page Decision Record noting accepted metrics, contested items, and required evidence with owners and due dates.
• Instrument missing telemetry identified in the meeting and schedule a short re-check within 7 days if needed.
• One‑Sentence Desired Future State
• Verify which BUs and user cohorts will continue using the platform voluntarily after pilot.
• Identify and prioritize adoption friction points with owners and timelines to address them.
• Agree on immediate reinforcement actions (training, comms, UX tweaks) to sustain adoption.
• Consequence Summary (Why this mattered)
• AI Matching Performance Metrics
• Behavioral Evidence Review
• Readout: Metrics & Voluntary Use Summary
• Review & Score Top 10 Items
• Assign Owners, SLAs, and Release Targets
• Root Cause Deep Dive (Top 3 Categories)
• Top Adoption Frictions (data + anecdotes)
• Risk & Mitigation Heatmap
• Acceptance Criteria Checklist
• Governance Cadence & Roles
• Data-Driven Proof: Dashboard Walkthrough
• Process & Policy Remediations
• Integration & Data Cutover Dependencies
• User Feedback & NPS/CSAT Snapshot
• Force Validation
• Mitigation & Reinforcement Plan
• Proof-of-Fix Plan
• Scale Timeline & Phasing per BU
• Communication & Pilot Backlog Transparency
• Outstanding Measurement Gaps
• Voluntary Use Confirmation Rollcall
• Final Decision & Action Register
• Next Steps & Decision Record