Quick Introductions — Who’s in the Room?

• To get us started, who are the people we should know about for this initiative? Please list name, title, and function for each primary stakeholder.
• Which of these roles exist on your side? (select all that apply) Options: Chief Procurement Officer (CPO), VP / Head of Procurement, Category Manager, Finance / CFO, Head of Accounts Payable, IT / CIO, Supplier Operations / Supplier Management, Legal / Contracts, Business Unit Leader, Shared Services Lead, Other
• Which of the named stakeholders would you expect to be directly involved in day-to-day pilot decisions (names or roles)?
• Is there anyone who must be kept informed but won’t be making decisions? (names/roles)

Who's Really Calling the Shots?

• If this effort stalls, whose signature or objection has historically stopped similar programs from moving forward? Options: CPO/Head of Procurement, CFO/Finance Leader, CIO/IT Leader, Head of Supplier Ops, General Counsel/Legal, Business Unit Head, CEO/Executive Sponsor, Other
• Who has final approval authority for running a pilot and green-lighting a rollout in your organization? Options: CPO, CFO, CIO, Procurement Council/Steering Committee, Legal, Shared Services Leader, CEO/Board, Other
• Which stakeholders must be convinced that savings are real before finance will reflect them on the P&L? Options: Procurement, Finance, Business Unit Leaders, Supplier Ops/Onboarding, Legal/Contracts, IT/Integrations, Other
• Who will be accountable for measuring and certifying outcomes at pilot close (name and role)?
• Have these groups collaborated on cross-functional procure-to-pay pilots before, and if so, what worked or failed in that collaboration? Options: Yes, and it worked well, Yes, with notable friction, Tried but failed, No prior cross-functional pilots, Not sure
• Describe a recent example where lack of alignment between procurement, finance, and IT caused a project delay or loss of savings.

What Would 'Good' Actually Look Like for Them?

• If Procurement were to tell their leadership the project succeeded, what three measurable changes would they point to? Options: Realized $ savings, Higher contract compliance (%), Increased catalog coverage, Reduced maverick spend, Faster sourcing cycle time, Higher buyer adoption, Other
• In one sentence, how would your Procurement lead define ‘good’ for this initiative?
• If Finance is skeptical today, what specific evidence would cause them to accept that negotiated savings actually hit the P&L? Options: Validated P&L impact ($), Improved PO-to-invoice match rate (%), External audit confirmation, Automated contract enforcement shown in logs, Other
• What numeric success signal does Finance require to call the pilot a win? (e.g., $ realized, % reduction vs baseline) Options: <$500k, $500k–$2M, $2M–$10M, >$10M, % improvement target (enter below)
• For Supplier Ops, what outcome would make their day-to-day easier and worth supporting the change? Options: Fewer invoice disputes, Simpler catalog updates, Faster supplier onboarding, Clear supplier pricing enforcement, Reduced PO exceptions, Other
• Please articulate a one-line acceptance criterion from Procurement, Finance, and Supplier Ops (three separate lines).

Timeline Pressure — What’s the Real Deadline?

• If leadership asked for demonstrable results in 90 days, what would that force you to deprioritize?
• What target dates should we plan against for pilot kick-off and pilot validation? Options: Immediate (30 days), Near-term (30–60 days), Short (60–90 days), Quarter (3 months), 90–180 days, 6–12 months, 12+ months
• Are there immovable external milestones tied to this timeline (fiscal close, merger integration, board review)? If yes, list them. Options: Yes, No
• Who has authority to rebaseline the timeline if dependencies slip? Options: CPO, CFO, Program Manager/PMO, Steering Committee, Other
• What are the consequences if the pilot misses the preferred acceptance date? Options: Other, Reprioritization, Loss of funding, Extended timeline without penalty, Executive escalation, Program cancellation

Where Trust Breaks Down — The Real Reasons Finance Questions Procurement

• Why does Finance doubt that procurement’s negotiated savings are flowing to the bottom line? Pick all that apply. Options: Buyers ordering off-contract, Contract terms not machine-readable, Catalogs out of date, Invoices not matching POs, ERP posting differences, Incentive misalignment, Lack of end-to-end traceability, Other
• Share a concrete example where claimed savings didn’t reconcile to Finance’s numbers—what sequence of events caused the gap?
• How is sourcing-to-savings reconciliation currently performed? Options: Manual spreadsheets, ERP cost center reports, BI/dashboard with integrated data, Third-party reconciliation/audit, Not reconciled systematically, Other
• Approximately how long does it take to produce a validated reconciliation report today? Options: Same day, 1–3 days, 1–2 weeks, 2–4 weeks, Longer than a month, Not tracked
• Who signs off on the reconciliation results before Finance will accept them (name/role)?

Power, Process, and Pain Points — The Tightly Held Systems

• Which systems house your sourcing, contract, purchasing, and AP records? Please list system name and owner for each (e.g., Sourcing: X owned by Procurement).
• Which system is currently treated as the system of record for negotiated prices? Options: ERP, Contract repository, Procurement system (e-procurement), Catalog system, Supplier portal, No single source of truth, Other
• Which of these areas do you consider most likely to leak negotiated savings at the last mile? (select up to 2) Options: Catalog maintenance, Buyer override behavior, Invoice matching exceptions, Supplier non-compliance, ERP posting variance, Contract extraction inaccuracies, Other
• Which existing integration (if any) enforces pricing at PO creation today? Options: Catalog-to-PO integration, Contract-to-PO link, ERP price master, No enforcement exists, Other
• Tell us about a recent purchase where the negotiated price failed to flow to payment—what system step broke?

Decision Rules, Escalation, and Governance — Who Decides Exceptions?

• If a buyer needs to purchase off-contract, what happens today? Is there a formal exception path or is it handled ad hoc? Options: Formal exception process, Ad hoc approvals via email, Manager approval in system, No formal process, Other
• Who approves exceptions and at what dollar thresholds? Please capture role and threshold where possible.
• How are exception volumes tracked and reported (system, cadence)? Options: Automated dashboard, Manual log/spreadsheet, Ad hoc reporting, Not tracked, Other
• What governance cadence would be realistic for review during the pilot (choose one)? Options: Weekly, Bi-weekly, Monthly, Quarterly, Ad-hoc as needed
• What specific report or KPI would make governance meetings constructive for you (name the top 3)?

Readiness & Change — People, Data, and Signals

• If adoption stalls among buyers, what is the real cost you fear most (pick one primary consequence)? Options: Lost savings, Increased operational cost, Program cancellation, Reputational damage, Longer ROI period, Other
• Which groups will need formal enablement and approximately how many users in each (Procurement, Buyers, AP, Finance, IT)?
• Rate the current data readiness for contracts, supplier master, and catalogs on a 1–5 scale (1 = poor, 5 = ready). Options: 1, 2, 3, 4, 5
• Describe the largest data gap you expect during integration (e.g., missing price tables, inconsistent supplier IDs, scanned PDFs without structure).
• Who will be the operational owner on your side during the pilot (name, title, email if available)?
• What communication cadence and format do you prefer for stakeholder updates during pilot (select all that apply)? Options: Weekly status call, Bi-weekly executive summary, Shared dashboard access, Ad hoc email updates, Monthly steering committee

Risk Appetite & Political Reality — What Won’t Change Easily?

• Which internal process or tool is most politically protected and unlikely to change even if it costs savings?
• What level of change management effort do you consider feasible for this pilot (light, moderate, heavy)? Options: Light (awareness + brief training), Moderate (training + champions), Heavy (process redesign + incentives)
• Are there stakeholder incentives or compensation that could conflict with enforcing contracted behavior? If yes, describe. Options: Yes, No, Not sure
• What political risks or organizational sensitivities should we be mindful of when designing the pilot?

Commitments & Next Tangible Steps — What Will Prove Momentum?

• What is the smallest, clearly scoped pilot you would accept to prove the end-to-end value (choose one)? Options: Single category, single BU, Single category across multiple BUs, Category + supplier cohort, Category with full contract enforcement, Broader multisite pilot
• Which single metric would cause leadership to demand scaling the program? (pick up to 2) Options: $ realized savings, % increase in contract compliance, % improvement in PO-to-invoice match, Reduction in invoice exceptions, Time to contract-to-order closure, Other
• Who needs to sign the pilot charter or statement of work (names/roles)?
• What is your preferred target kick-off window for the pilot? Options: Within 30 days, 30–60 days, 60–90 days, Next fiscal quarter, Flexible / TBD
• List any immediate blockers we must resolve before scheduling kick-off (systems access, data extracts, legal terms, resource availability).
• What would you like us to deliver as the next artifact after this alignment conversation (pilot charter, data checklist, stakeholder RACI, proof-of-concept plan)? Options: Pilot charter, Data & integration checklist, Stakeholder RACI, Proof-of-concept plan, High-level commercial terms, Other

Quick Grounding: Where Are We Mapping Today?

• Which business unit, region, or legal entity are we focusing on for this current-state map? Options: Global enterprise consolidation, North America, EMEA, APAC, A single business unit, Other
• Rough scale — what is the annual procurement spend for this scope (approx)? Options: Under $500M, $500M–$1B, $1B–$2.5B, $2.5B–$5B, Over $5B, Unsure
• Who on your team should be the primary point of truth for system and data details during discovery?
• Do you have a recent org chart or RACI for sourcing → purchasing → AP we can reference? Options: Yes - up to date, Yes - needs updating, No, but we can create one, No and not planned
• Please describe one recent example (month/quarter) where a sourcing decision did not translate to expected spend results.

If Your 'Savings' Vanish, Where Do They Go?

• How often do you see a material gap between negotiated sourcing savings and what Finance recognizes in the P&L? Options: Quarterly or more often, Once or twice a year, Occasionally, Rarely, We haven't measured
• Walk me through a recent example where negotiated price or supplier awards failed to be enforced—what broke and why?
• Where do you believe the majority of leakage comes from today? Options: Sourcing not capturing key terms, Purchasing uses non-contracted suppliers, Catalogs not maintained, Invoices not matched to POs, Rebates/allowances not claimed, Other
• How do you currently measure contract compliance and realized savings (tools, frequency, KPIs)?
• Estimate the order: which stage causes the largest percent of leakage (Sourcing / Purchasing / AP)? Please explain briefly. Options: Sourcing, Purchasing, AP / Invoice, Split evenly / unclear

Are Your Systems Helping—or Hiding—the Problem?

• If your systems were honest, would they show the true path of a negotiated price to a paid invoice—yes or no, and why? Options: Yes — end-to-end traceable, No — partial visibility, No — siloed systems, Unsure
• Which transactional and contract systems are in use across sourcing, procurement, catalog, and AP for this scope? Options: SAP ECC / S/4HANA, Oracle EBS, Oracle Cloud ERP, Coupa, Ariba (SAP), Ivalua, Jaggaer, Workday Procurement, Basware, PeopleSoft, Homegrown / Custom, Other
• Where are contracts stored and how are prices captured today (structured CLM, ERP fields, scanned PDF repository, spreadsheets)? Options: Central CLM with structured pricing, ERP contract fields, Scanned PDFs / shared drive, Spreadsheets, Embedded in sourcing tool only, Other
• Which purchasing channels do buyers most often use (catalog/punchout, non-catalog PO, procurement card, manual supplier invoices)? Options: Catalog / punchout, Non-catalog PO, Procurement card, Direct invoice (no PO), Supplier portal, Other
• Can you attach or point us to a representative sample of a contract, PO, catalog item, and invoice mapping for the chosen category during intake? Options: Yes - can provide immediately, Yes - after legal review, No - but can create redacted samples, No

Who's Really Responsible When Compliance Breaks?

• If a buyer orders off-contract, who currently owns the exception—procurement, the business, finance, or IT—and how often are exceptions approved? Options: Procurement owns and approves, Business unit approves, Finance owns approval, IT/Systems team enforces, No clear owner
• Describe how approval workflows work today for off-contract spend and who can override price or supplier fields.
• How are buyers incented or penalized around compliance—are there scorecards, bonuses, or informal norms? Options: Formal scorecards / incentives, Informal feedback, No incentives, Penalties exist, Other
• Who is accountable for master data (suppliers, SKUs, pricing) and how often is it reconciled? Options: Procurement, Finance, IT / Data Team, Shared Governance, Suppliers (via portal), Other
• Tell us about a time an enforcement rule caused business friction—what happened and how was it resolved?

Integration Reality Check — Trivial vs. Nightmare

• What integration methods are acceptable or preferred by your IT/security team for connecting sourcing, procurement, and AP systems? Options: REST APIs, SOAP, cXML / punchout, EDI, SFTP / batch flat files, Direct DB replication, Middleware (Mule, Boomi), Other
• Do you have existing middleware or an iPaaS we must use, or are point-to-point integrations acceptable? Options: Must use existing iPaaS/middleware, Point-to-point acceptable, Open to either, Unsure / need IT input
• What non-functional constraints matter most for integrations (security standards, data residency, SLA, encryption, audit logging)? Options: SOC2 / ISO requirements, Data residency / GDPR, Encryption in transit & at rest, Change window limitations, Low-latency / real-time, High availability SLAs, Other
• Is there a test environment or sandbox with representative data for integration testing? Options: Yes — fully provisioned, Yes — limited / needs work, No, Unsure
• What is a realistic timeline your team expects for a basic integration (catalog sync + PO writeback + invoice visibility)? Options: 4–8 weeks, 2–3 months, 3–6 months, 6+ months, Unsure

Show Me the Data: Visibility, Accuracy, and Trust

• Which transactional fields are reliably available at invoice line-item level today (supplier ID, contract ID, PO line, SKU, unit price, taxes, GL code)? Options: Supplier ID, Contract ID / clause ref, PO number, PO line / SKU, Unit price, Tax line, GL / cost center, None reliably available
• How far back does your clean, transaction-level data go for this category (months/years)? Options: 12+ months, 6–12 months, 3–6 months, Less than 3 months, No reliable history
• Rate the quality of supplier master data (completeness, duplicates, correct IDs): Options: High quality, Moderate — needs clean-up, Poor — many duplicates/inaccuracies, Unknown
• Can we get a scheduled extract or API access to a sample set of POs and invoices for the chosen pilot category to map matching success rates? Options: API access available, Scheduled extracts (SFTP/CSV), Manual extracts only, Not available
• What manual reconciliation or downstream spreadsheet work must be done today to reconcile negotiated vs paid prices?

When Enforcement Breaks: People, Process, and Habits

• Why do buyers choose non-contracted suppliers or prices—habit, availability, speed, catalog gaps, or something else? Options: Habit / convenience, Catalog missing items, Supplier availability, Speed of approval, Pricing complexity, Other
• How long have those buyer behaviors been tolerated before becoming 'standard practice'? Options: Months, 1–2 years, Several years, Decades / cultural
• What training, governance, or change levers have you tried to shift buyer behavior and what worked or failed?
• Are exceptions logged and reviewed (and if so, how frequently and by whom)? Options: Yes — centrally reviewed, Yes — reviewed by BU, No formal logging, Partial logging
• If we could reduce exception approvals by 50% in the pilot category, how would that feel for your teams and leadership? Options: Very impactful, Meaningful but manageable, Marginal, Not sure

Pick the Right Category to Make the Point

• Which category are you most motivated to use as a pilot to validate end-to-end enforcement? Options: Indirect MRO / Facilities, IT hardware & peripherals, Office supplies / furniture, Professional services, Logistics / freight, Raw materials, Other
• What makes this category a strong test case (volume, high contract maturity, repeatability, supplier concentration)? Options: High transaction volume, Mature contracts, Standard SKUs, Few suppliers, Complex pricing / rebates, Other
• Estimate the expected annualized realized savings if enforcement worked perfectly for this category (ballpark). Options: Under $500k, $500k–$2M, $2M–$10M, Over $10M, Unsure
• Are there contractual complexities (tiered pricing, rebates, volume discounts, freight terms) that need special extraction logic? Options: Tiered pricing, Rebates / retroactivity, Volume discounts, Freight / incoterms, No special complexities, Other
• Who are the top 3 suppliers in this category we should treat as priority during extraction and catalog sync?

Non-Negotiables: Risks, Compliance, and Timing

• What regulatory, audit, or internal compliance constraints could block our ability to access or process the data required for verification? Options: SOX / financial controls, GDPR / data privacy, Export controls, Supplier confidentiality, Internal audit concerns, None
• Are there procurement or legal terms that would prevent automated enforcement (e.g., exclusivity clauses, negotiated exceptions)? Options: Yes — several, A few minor, No, Unsure
• What is the latest acceptable pilot start date and the date by which you need demonstrable results? Options: Start in 1 month, Start in 1–3 months, Start in 3–6 months, No fixed date
• Which stakeholders must sign off to run a pilot (titles and teams)?
• What would constitute a 'show-stopper' risk that would stop the pilot from proceeding?

If We Move Fast Together: Practical Next Steps

• From 0–10, how ready is your organization to provide the access and samples needed for a one-category pilot? Options: 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10
• Which of these can you commit to supplying within two weeks to accelerate scoping? Options: Contract samples, PO / invoice extracts, Supplier master file, Approval workflow diagrams, Sandbox access, None of the above
• Who will be the day-to-day liaison during pilot setup, and what is their availability (hours per week)?
• What success metrics would make the pilot a clear ‘win’ (examples: %PO-to-invoice match, realized savings captured, %catalog adoption)? Options: PO-to-invoice match rate, Contract compliance %, Realized savings $, Catalog adoption %, Invoice match exception reduction, Other
• One last practical ask: what concerns would stop you from sharing redacted data sets for initial analysis, and how can we help mitigate them?

Quick Context — How we got on the call

• In one sentence, what triggered this review right now (e.g., audit finding, CFO question, merger, category review)?
• Which single spend category would you prioritize for an end-to-end proof? (name the category and why)
• Roughly how much is your enterprise annual procurement spend (USD)? Options: <$500M, $500M–$1B, $1B–$2.5B, $2.5B–$5B, >$5B
• Who will be the executive sponsor for this evaluation (title)? Options: CPO, CFO, SVP Procurement, Head of Finance Ops, Other
• What is your target decision timeline for choosing a partner for the pilot? Options: <30 days, 30–60 days, 60–90 days, 90–180 days, Unsure

When Procurement’s 'Savings' Don't Show Up on the P&L — What's Really Happening?

• When procurement reports negotiated savings, what evidence do you actually use today to show finance that those savings flowed to the P&L? Options: Contract register vs spend analysis, PO-level enforcement reports, Invoice match reports, Ad hoc reconciliations, We don't have consistent evidence, Other
• Tell me about a recent example where procurement claimed savings but finance disagreed — what was the gap, and how did it feel to stakeholders?
• Which of these best describes where you believe the disconnect lives today? Options: Sourcing optimization -> awards, Contract terms not extracted, Catalog/Punch-out mismatch, PO creation not enforcing contracts, Invoice matching failures, Supplier master data issues, Other
• How confident are you in your current measurement of 'realized savings' (procurement claim vs finance-validated)? Options: Very confident, Somewhat confident, Not confident, We don't measure consistently
• If I asked your CFO what would convince them the savings are real, what would they say (specific KPIs or evidence)?

Where Value Quietly Slips Away — Follow the Chain

• Which single moment do you suspect leaks the most value: award, contract authoring, catalog mapping, PO creation, invoice matching, or payment? Why? Options: Sourcing award, Contract creation/extraction, Catalog ingestion/mapping, PO creation/enforcement, Invoice matching, Payment/finance reconciliation, Other
• Walk me through a typical purchase in the prioritized category from need -> payment. Where do exceptions most often occur?
• How often do buyers select non-contracted suppliers or non-catalog SKUs for this category? Options: Almost always, Often, Sometimes, Rarely, Never tracked
• What percentage of invoices in this category require manual intervention before payment (e.g., price disputes, PO changes, unmatched lines)? Options: <5%, 5–15%, 15–30%, 30–60%, >60%, Don't know
• Who maintains catalogs and contract price lists today, and how often are they updated? Options: Procurement team, Category manager, Shared services, Suppliers, ERP team, Other
• Share one story where a contract clause (rebate, pricing tier, lead-time) wasn't enforced — what happened and why?

Who Holds the Real Decision Power When an Order Is Placed?

• When a buyer places an order, who actually chooses the supplier and price in practice (role/team)? Options: Category managers, Buyers in business units, End-users, Shared services, Sourcing team via catalog, Other
• Who has final sign-off on changes to supplier lists, catalogs, or contract price tables? Options: Procurement leadership, Finance, IT/ERP, Category owner, Shared services, Other
• Describe any delegated buying authorities or capping rules that routinely let non-contracted purchases through.
• Which stakeholders must be engaged for a pilot to change buyer behavior in this category? Options: Procurement, Finance, IT/ERP, Business unit leaders, Supplier enablement, Legal/Contracts, Other
• How do internal incentives or KPIs for buyers and approvers align (or conflict) with using contracted suppliers?

If We Could Make Your CFO Proud — What Would They See?

• What specific metrics would convince leadership the pilot 'worked' (e.g., realized savings %, contract compliance %, invoice match rate)? Options: Realized savings ($), Savings as % of spend, Contract compliance %, PO enforcement %, Invoice match rate %, Cycle time reduction, Other
• What time window should we use to validate impact (e.g., 30/60/90/180 days)? Options: 30 days, 60 days, 90 days, 180 days, Other
• Who will be the official sign-off authority for pilot success in procurement and in finance (title and expected acceptance criteria)?
• How much deviation from expected savings would be tolerated before stakeholders want to halt or redesign the pilot? Options: <10% deviation, 10–25%, 25–50%, >50%, Unsure
• If the pilot shows positive savings but adoption is uneven, which outcome matters more: absolute dollars saved or demonstrable, repeatable process change? Options: Absolute dollars, Repeatable process change, Both equally, Unsure

Are Your Systems Ready to Talk — A Data Reality Check

• List the primary systems involved in the source-to-pay chain for this category (ERP, eProcurement, Contract repo, Ariba/Coupa, AP automation, supplier portal).
• Which of these platforms does your organization use? (select all that apply) Options: SAP ECC/S4HANA, Oracle E-Business Suite/Cloud, Workday, Coupa, Ariba, Jaggaer, Ivalua, Custom/Legacy, Other
• Do you have extractable sample data we can share during scoping (e.g., PO lines, contract clauses, invoice PDFs)? Options: Yes — ready now, Yes — available with approvals, Partially — some extracts exist, No — would need to create extracts, Unsure
• What format do the contract sources typically take (structured contract repo, scanned PDFs, Word templates, email attachments)? Options: Structured repo (database), Scanned PDFs, Native Word/PDF with structured fields, Emails/attachments, Other
• Who owns providing system access and data extracts for integration (title/role)?
• Are there security, legal, or supplier confidentiality constraints we should expect when ingesting catalogs and contract texts? Options: Standard NDA needed, Data classification restrictions, Supplier restrictions, No major constraints, Unsure

What Usually Breaks Adoption — Where Should We Watch Closely?

• When you've tried process change before, what single human behavior was the hardest to shift?
• How do procurement, finance, and business users currently react when a new enforcement or catalog is introduced? Options: Eagerly adopt, Cautious but cooperate, Resist and workaround, Ignore until forced
• What existing governance or change management programs can we leverage to accelerate adoption? Options: Procurement governance board, Finance steering committee, Change management COE, Training teams, None, Other
• Who are likely early-adopter teams or regions that can show quick wins?
• What incentives or KPIs could we align to reward buyers for using contracted suppliers and catalogs? Options: Buyer scorecards, Incentive compensation, Manager dashboards, Approval gating, Other
• Describe the biggest organizational risk that would cause this pilot to stall (e.g., competing priorities, supplier pushback, IT backlog).

Designing a Pilot That’s Impossible to Disagree With

• If we run a pilot for the chosen category, what is the smallest scope that would still prove end-to-end value (e.g., single BU, region, supplier set)? Options: Single business unit, Single region/country, Top suppliers by spend, Specific supplier type, Other
• Which success signals must we collect daily/weekly versus monthly to convince stakeholders? Options: PO enforcement rate, Catalog adoption rate, Invoice match rate, Realized savings, Cycle time, Other
• What sample data (PO lines, contract PDFs, invoice batches) can you commit for an initial 30-day validation?
• Who would be the day-to-day contact on your side to resolve data questions and validate results?
• What would be a minimally acceptable duration for the pilot to be statistically persuasive? Options: 30 days, 60 days, 90 days, 180 days, Depends on volume
• If the pilot meets targets, what is the expected next step and who approves the rollout (title)?

Final Alignment — Practical Next Steps and Risks to Close Now

• What approvals or internal milestones must be in place before we begin integrations and data ingestion? Options: Executive sponsor approval, Legal/NDA, IT security sign-off, Finance validation, Supplier agreements, Other
• List three critical dependencies we should resolve before scheduling the pilot (people, data extracts, IT access, supplier commitments).
• What would make you say 'not ready' to start a pilot (specific blockers)?
• How would you like us to present pilot findings — format and cadence (e.g., weekly dashboard, executive summary, joint review)? Options: Weekly dashboard, Bi-weekly checkpoint, Executive summary at end, Live walkthroughs, Other
• Who should be invited to the initial scoping workshop from your side (name and role if possible)?
• On a scale of 1–10, how urgent is solving the leakage between sourcing and payment for your organization? Options: 1, 2, 3, 4, 5, 6, 7, 8, 9, 10

Start: One-Minute Snapshot

• Which spend category should we evaluate for this pilot? Options: Indirect/MRO, IT Hardware & Peripherals, Software / SaaS, Professional Services, Facilities & Utilities, Marketing & Media, Logistics / Freight, Other
• Roughly how much do you spend in this category each year? Options: <$5M, $5M–$25M, $25M–$100M, $100M–$500M, >$500M
• What triggered this category review—select all reasons that apply Options: CFO questioned realized savings, Category review found high off-contract spend, Post-merger consolidation, Supplier performance issues, Audit or compliance finding, Other
• Who is the primary sponsor for this pilot (name and role)?
• How confident are you that existing contracts actually cover current buying behavior in this category? Options: Very confident, Somewhat confident, Unsure, Not confident

Are You Comfortable with Negotiated Savings Walking Out the Door?

• When procurement says they negotiated X in savings, how often do you see those savings reflected on the P&L? Options: Almost always, Often but not always, Sometimes, Rarely, Never
• By approximately what percentage do you estimate negotiated savings are leaking before they reach payment? Options: <5%, 5%–10%, 10%–20%, 20%–40%, >40%
• Tell us about a concrete example where a negotiated price or supplier award failed to be enforced—what happened and who raised it?
• Which teams raise the loudest concerns when realized savings don’t show up: procurement, finance, supplier ops, or others? Options: Procurement, Finance, Supplier Ops, Business Unit Buyers, Audit/Compliance, Other
• What is the emotional impact on the team when these discrepancies surface (e.g., credibility loss, firefighting, stakeholder tension)?

Who’s Running the Playbook?

• Where do decision rights feel most unclear today — contract terms, PO approvals, invoice disputes, or supplier setup? Options: Contract terms, PO approvals, Invoice disputes, Supplier setup/onboarding, Catalog ownership, All of the above
• Which people or roles need to be involved for a pilot approval (select all that must sign off)? Options: CPO / SVP Procurement, CFO / VP Finance, Head of AP, IT / Integration Lead, Legal / Compliance, Category Manager, Supplier Operations
• Who currently owns contract extraction and maintenance for this category? Options: Procurement COE, Category manager, Legal, Third-party admin, No dedicated owner, Other
• Who is responsible today for enforcing contracted suppliers and prices at PO creation? Options: Buyer manager, Procurement policy engine, ERP controls, No one/enforcement gap, Other
• If a buyer repeatedly bypasses the contract, what is the existing escalation path and typical consequence?

Where Does the Money Actually Leak — Be Brutal

• Where do you believe most leakage happens in your flow: sourcing awards not applied, buyers ordering from non-contracted suppliers, manual price overrides, catalog mismatches, or invoice exceptions? Options: Sourcing awards not applied, Non-contracted suppliers used, Manual price overrides, Catalog out-of-date, Invoice price/quantity mismatches, Supplier rebates not applied
• Which systems are involved across sourcing → PO → invoice today (select all that apply)? Options: SAP ECC/S4, Oracle EBS/Cloud, Coupa, Ariba, Workday, Homegrown procurement system, Spreadsheets/Shared drives, eProcurement bolt-ons
• Approximately what percent of POs in this category are created from a catalog vs. created ad hoc? Options: 0%–10%, 11%–30%, 31%–50%, 51%–75%, 76%–100%
• Give one or two concrete recurring exception types (e.g., price variance because catalog outdated; buyers use local supplier for speed). Why do these exceptions persist?
• How often do suppliers send invoices that don’t match the PO and require manual intervention? Options: Rarely, Monthly, Weekly, Daily, Multiple times per day

If We Could Rewind the Transaction, What Would Success Look Like?

• Imagine a perfect closed-loop where sourcing, contracts, POs, and invoices are linked — what outcome matters most to you emotionally and financially?
• Which measurable signals would prove the pilot succeeded (select up to three)? Options: Contract compliance %, Realized savings $, PO-to-invoice match rate, Number of manual exceptions, Catalog freshness / hits, Time-to-pay or days payable
• What minimum threshold would you require to consider the pilot successful: target contract compliance percentage? Options: >90%, 80%–90%, 70%–80%, <70%
• What invoice match rate would you expect after enforcement is in place? Options: >95%, 90%–95%, 80%–90%, <80%
• Which single KPI, if it moved to your target, would unlock executive support for full rollout?

What’s Stopped Past Fixes From Sticking?

• When prior initiatives to improve compliance fell short, what was the primary reason — people, process, data, or tech? Options: People / adoption, Process gaps, Poor data quality, Integration limitations, Lack of executive sponsorship, Commercial/legal constraints
• Which change levers have you tried before (select all that apply)? Options: Buyer training, Sourcing incentives, Supplier enablement for catalogs, ERP configuration changes, Policy enforcement through approvals, Penalty clauses
• How much internal bandwidth (FTEs or % of team) can you allocate to a 3–6 month pilot for integration, testing, and enablement? Options: <0.5 FTE, 0.5–1 FTE, 1–3 FTEs, 3–5 FTEs, 5+ FTEs
• What incentives or governance change would most likely shift buyer behavior for the long term?
• Who would be the change champion responsible for driving buyer adoption day-to-day?

Can We Trust the Data?

• How mature is your contract and invoice data for extraction and mapping (contracts digitized with structured pricing, partially scanned, or mostly PDFs)? Options: Fully structured (contract database), Partially structured (mix of PDFs and fields), Mostly scanned PDFs, No centralized contract data
• Which of these data extracts can you provide for an initial pilot (select all you can provide within 30 days)? Options: Contract PDFs, Sourcing award outputs, PO history (last 12 months), Invoice history (last 12 months), Supplier master data, Catalog files/CSV
• What is the typical SLA for granting system access or secure export of sample data to an integration partner? Options: <1 week, 1–2 weeks, 2–4 weeks, >4 weeks, Depends on legal/data approvals
• What formats and sample size are easiest for you to share for pilot validation (e.g., CSV of 3 months PO lines, 100 contract PDFs)? Options: CSV / database extracts, XML / EDI, PDFs only, AP system native export, Other
• Are there any obscure or localized ERP forks, country-specific processes, or suppliers that will require special handling?

What Would You Be Comfortable Committing To?

• If the pilot delivers the agreed success signals, how quickly could procurement and finance commit to a phased rollout decision? Options: Immediately (within 30 days), Within 60–90 days, Within 3–6 months, Undecided / needs executive review
• Which pilot duration would you be comfortable with to validate savings and enforcement: short proof-of-concept or full quarter? Options: 4–6 weeks (fast POC), 90 days (quarter), 180 days (extended validation), Depends on sample volume
• What budget range is allocated or available for running this pilot (integration, data work, enablement)? Options: <$50k, $50k–$150k, $150k–$500k, >$500k, Not yet budgeted
• Do you have legal/data constraints we must honor during pilot (e.g., DPA, SOC2 vendor requirements, data residency)? Options: Yes—DPA & security controls required, Yes—data residency restrictions, Minimal constraints, Unsure / need to check
• What specific governance gates must be in place to move from pilot to rollout (e.g., finance sign-off, SLA, legal approval)?

Designing a Pilot That Will Actually Prove Itself

• If we design a tightly scoped pilot, how many suppliers would you want included to prove enforcement works? Options: 1–5, 6–20, 21–50, 50+
• What monthly transaction volume (PO lines or invoices) would you expect the pilot to process to be statistically meaningful? Options: <500 transactions, 500–2,000, 2,000–10,000, >10,000
• Are you willing to route POs through a validation layer during pilot (temporary policy enforcement) to test real-time price/supplier checks? Options: Yes—fully route through, Partially—sampling or % of POs, No—we need non-invasive validation only, Unsure
• What measurable deliverables do you expect at pilot close (examples: validated savings $, increased compliance %, reduced exceptions)?
• Who will provide day-to-day access and a sandbox environment for testing integrations (name and role)?

Before We Close — How Does This Feel?

• What is your single biggest fear if we run this pilot and it doesn’t show the expected benefit?
• What is your biggest hope or upside you tell your executive sponsor about if this pilot succeeds?
• How ready are you to begin work on a pilot from a resourcing and executive support perspective? Options: Can start immediately, Can start in 1–2 months, Need 3+ months, Unsure—need internal alignment
• What blockers remain before you can commit to a pilot (legal sign-off, budget, data access, stakeholder alignment)? Options: Legal sign-off, Budget approval, Data access, Stakeholder alignment, Integration calendar, None
• What would you like our next agreed step to be? Options: Schedule technical discovery call, Share data extract template, Draft pilot scope and SOW, Executive briefing with finance and procurement, Other