Let’s Begin: Who You Are and What Success Looks Like

• In one sentence, what is the primary outcome you want this EDI/connectivity project to deliver?
• Which of these best describes your primary role in this initiative? Options: IT Manager/Director, Supply Chain/Logistics Lead, Operations Manager, E-commerce/Marketplace Lead, Finance/Revenue Protection, Other
• Tell us briefly about your organization (industry, estimated annual transaction volume, and ERP/WMS in use).
• How urgent is a solution for you right now? Options: Critical — must fix within 1 month, High — 1–3 months, Medium — 3–6 months, Longer term — 6+ months, Undetermined
• Who needs to sign off on budget and go-live (select all that apply)? Options: IT leadership, Supply chain/operations director, CFO/finance, Business unit owner, Security/compliance, External partner/vendor

Are You Settling for ‘Good Enough’—and What That’s Costing You

• If we added up the cost of onboarding delays, failed transmissions, and chargebacks over the last 12 months, how would you characterize that number? Options: Significant and measurable, Noticeable but not tracked closely, We track some metrics but unclear total, Minimal — not a current issue, Unsure
• Describe the most recent incident that resulted in a retailer chargeback or lost sale — what happened, why did it happen, and how long did it take to resolve?
• What compliance failures recur most often for you (syntax errors, missing acknowledgements, mapping mismatches, timing windows, ASN/invoice mismatches, other)? Options: Syntax/formatting errors, Missing functional/technical acknowledgements, Incorrect or missing mapping logic, Late transmission / timing SLA breaches, ASN vs invoice discrepancies, Other
• How do recurring EDI issues affect internal teams (time spent, morale, overtime, diverted projects)?
• Which cost or impact would make fixing this a top priority (chargebacks, lost revenue, customer relationships, audit/compliance risk, operational overhead)? Options: Chargebacks, Lost or delayed revenue, Customer/retailer relationship risk, Audit/compliance exposure, IT resource drain, Other

What’s Actually Breaking — Tell Me a Real Story

• Think of a partner that gives you the most trouble — what is the single repeatable failure they cause that frustrates your team?
• How often do you discover a partner-related failure proactively versus being alerted by the trading partner or a chargeback notice? Options: We detect first (automated monitoring), Detected by internal teams manually, Alerted by the trading partner/retailer, Detected only when finance flags chargeback
• When a failure occurs, what’s the usual fix path and who ultimately owns remediation (IT, operations, third-party integrator)? Options: IT remediates, Operations/Warehouse remediates, Shared IT + Ops, Third-party/vendor handles, No clear owner
• How long does a typical mapping or integration error take to diagnose and correct, from first alert to validated fix? Options: Hours, 1–2 days, 3–7 days, More than a week, Varies widely/unsure
• Which technical layer do most problems trace back to — connection/protocol, translation/mapping, master data, ERP integration, or partner spec changes? Options: Connection/protocol (AS2/SFTP/API), Translation/mapping, Master data (SKUs/pricing), ERP/WMS integration, Trading partner spec changes, Other

What Would ‘No Surprises’ Actually Feel Like?

• Imagine zero chargebacks and predictable partner onboards for the next 12 months—what immediate business changes would that enable?
• What target onboarding velocity would be transformative for your business (partners/month or time-to-first-trading-document)? Options: < 1 week per partner, 1–2 weeks, 2–4 weeks, More than a month, Varies by partner complexity
• What uptime and delivery SLA would you need to feel confident (choose the minimum acceptable) Options: 99.9%+, 99.5%, 99%, We need SLAs by document type/time window, Unsure — need guidance
• Which metrics will you use to evaluate ROI for a new platform (chargeback reduction $, onboarding time saved, headcount change, error rate, partner satisfaction)? Options: Chargeback $ reduction, Onboarding time per partner, Error rate decline, IT/Ops FTE hours saved, Partner satisfaction/retention, Other
• If we reached those targets, who in your organization would view the project as a clear success and why?

Who Really Has to Be Aligned — Let’s Map the Decision-Makers

• Where do you currently see misalignment between IT, operations, supply chain, and finance when it comes to EDI priorities?
• Which stakeholders must be engaged during discovery, implementation, and acceptance (select all that apply)? Options: IT integration lead, ERP application owner, Supply chain/operations lead, Warehouse manager/WMS owner, Finance/accounts payable, Compliance/security, Customer success/retailer relations
• What are the non-negotiable acceptance criteria each stakeholder group insists on (examples: SLA hours, audit logs, mapping accuracy, data retention)?
• Who will be the single point of contact for escalation and approvals during onboarding and cutover?
• How does finance prefer to see chargeback risk mitigated — reserve, SLA credits, insurance, or operational controls? Options: SLA credits/penalties, Operational controls and checks, Financial reserves, Insurance/risk transfer, Combination/other

How Fast Can We Realistically Move? Windows, Constraints, and Hidden Timelines

• If I told you we could onboard a typical retailer in X days, what timeline would you immediately reject as unworkable—and why?
• What blackout or peak periods (sales events, inventory freezes, fiscal close) restrict migration or cutover windows for your teams? Options: Holiday peak season, Monthly/quarterly close, Major promotions (e.g., seasonal sales), ERP upgrade windows, No major blackout periods
• What internal resources will you commit to onboarding (FTEs, hours/week) and which must remain focused on BAU?
• Do you have accessible test environments and data extracts for ERP/WMS and sample trading-partner data? If not, what’s missing? Options: Full test environment and data ready, Partial — some data unavailable, No test environment, Unsure
• Which communication protocols and handshakes must we support out-of-the-box for your partners? Options: AS2, SFTP, VAN, API/REST, FTP, Other

Put Us to the Test: Use Your Real Partner Scenarios

• List the 3–5 trading partners that cause the most onboarding headwinds or highest chargebacks, and why each is challenging.
• For each partner above, which document types and volumes are most critical (POs, ASNs, invoices, inventory, remittances)? Options: Purchase Orders (PO), Advance Ship Notice (ASN), Invoices, Inventory feeds, Remittance/advice, Other
• Which of these mapping/validation behaviors would you like us to demo using your data: strict rejections, auto-correction suggestions, conditional transforms, or human review workflow? Options: Strict rejection with error details, Auto-correct and suggested fixes, Conditional/partner-specific transforms, Human-in-the-loop review workflow, All of the above
• Do you consent to share sanitized examples or sandboxes of your partner specs and failure logs for a joint proof-of-concept? Options: Yes — we can share sandboxes/specs, Yes, but only redacted data, No, not yet — need legal review, Unsure
• What would count as a successful proof-of-concept for your team (criteria and duration)?

What Would Make You Confident to Commit — Risk, Commercials, and Acceptance

• What is the single biggest barrier that would prevent your team from switching vendors or approving this project today?
• Which commercial model aligns most with your procurement preferences? Options: Subscription per trading partner, Volume-based per transaction, Fixed implementation + support retainer, Managed services (fully outsourced), Hybrid
• What acceptance criteria must be met before your finance team will release final payment (examples: partner-by-partner validation, reduction in error rate, documented SLAs)?
• Which support model would make your operations team sleep better at night (24/7 managed service, business-hours support + escalation, dedicated TAM), and why? Options: 24/7 managed service, Business-hours with escalation, Dedicated Technical Account Manager (TAM), Ad-hoc support as needed
• If there were one proof point we could deliver in 30 days to shift internal sentiment, what should that be (reduce chargebacks, onboard 1 key partner, automate reconciliation, other)? Options: Reduce chargebacks, Onboard 1 high-value partner, Automate reconciliation/reporting, Demonstrate end-to-end SLA adherence, Other

Quick Snapshot: Who's Running Your EDI Today?

• Who in your organization is primarily responsible for EDI operations and day-to-day partner issues? Options: IT / Integration team, Supply Chain / Logistics, E-commerce / Operations, Finance / Billing, Outsourced Managed Service Provider, Shared / Matrix team, Other
• Which ERP, WMS, or commerce platforms are the primary sources or targets for your EDI messages? Options: SAP ECC / S/4HANA, Oracle (EBS / Cloud), Microsoft Dynamics, NetSuite, Shopify / BigCommerce / Magento, Custom / Homegrown, Multiple / Hybrid, Other
• How many active trading partner relationships do you currently exchange EDI with? Options: 1–10, 11–50, 51–200, 201–500, 500+
• Approximately how many EDI transactions (POs, ASNs, invoices) flow through your systems per month? Options: <1,000, 1,000–10,000, 10,000–50,000, 50,000–200,000, 200,000+
• If you had to name the single biggest thing about your current setup that keeps you awake at night, what would it be?

Why Do Chargebacks Still Catch You Off Guard?

• What is the most surprising or recurring source of chargebacks you've learned the hard way?
• How many chargebacks do you receive in a typical month? Options: None, 1–5, 6–20, 21–100, 100+
• Roughly how much do chargebacks cost you in a typical month (direct and indirect impact)? Options: No measurable cost, < $1k, $1k–$10k, $10k–$50k, $50k+
• When chargebacks happen, which internal team typically owns remediation? Options: Finance, Supply Chain / Operations, IT / EDI, Customer Service, Cross-functional task force, Outsourced partner, Other
• What percentage of your chargebacks do you believe are caused by mapping/format errors versus operational issues (late ASN, wrong quantities) versus transmission failures? Options: Mostly mapping/format, Mostly operational (ASN/qty), Mostly transmission/protocol, Evenly mixed, Don't know / not tracked

What's Living Under the Hood? Mapping Your Topology

• Which legacy habit, component, or vendor in your EDI topology is silently multiplying risk every month?
• Which communication protocols are in use today (select all that apply)? Options: AS2, SFTP, VAN / FTP, API / REST, EDIINT, Partner web portal / manual upload, Other
• Where do you perform translation and mapping today? Options: On‑prem translation server, Hosted VM / colo, Cloud SaaS EDI platform, Mix of on‑prem and cloud, We rely on partner portals, Unsure
• How complete is your documentation of partner configurations, contacts, and SLAs? Options: Complete and centralized, Mostly documented, Patchy / spreadsheets, Mostly tribal knowledge, None
• How often do you change mappings, partner configs, or protocols and who approves those changes?

Which Trading Partners Drain the Most Energy—and Why?

• Which trading partner or partner type monopolizes your team's time today, and why do they keep getting priority?
• Please categorize your top trading partners by type (select all that apply). Options: Large national retailer (e.g., big-box), Regional retailer / chain, Distributor / wholesaler, 3PL / carrier, Marketplace (e.g., Amazon), Direct-to-consumer / dropship retailer, Supplier / vendor, Other
• How long does onboarding a typical new partner take from kickoff to production today? Options: <1 week, 1–4 weeks, 1–3 months, 3–6 months, 6+ months
• For partners that are slow to onboard, what are the most common blockers? Options: Complex mapping requirements, Poor source data quality, Backlog in compliance testing, Partner unresponsiveness, Internal resource constraints, Legacy protocol issues, Other
• Which three partners have the strictest compliance specs and what specifically makes them difficult?

Walk Me Through a Recent Failure Like a Story

• Tell the story of a recent EDI failure—what happened, who noticed, and what felt different about it?
• How was the issue first detected? Options: Automated monitoring alert, Partner notified us, Retailer chargeback/notice, Finance reconciliation, Customer or operations reported, Manual audit, Other
• From detection to resolution, how long did that incident take on average? Options: <1 hour, 1–8 hours, 8–24 hours, 1–3 days, 3+ days
• Who had the hardest time during the incident (roles/teams) and what was the real human cost?
• Did that incident trigger a financial penalty, lost sale, or other measurable harm? Select all that applied. Options: Financial penalty / chargeback, Lost sales / delayed shipments, Operational overtime / extra staffing, Customer escalation / SLA breach, No measurable impact, Unsure

Where Do Your Monitoring and Alerts Let You Down?

• If your monitoring could only fix one blind spot tomorrow, what would you ask it to surface that it currently misses?
• Which monitoring tools, dashboards, or reports do you rely on today to surface EDI failures? Options: Homegrown scripts / scheduled reports, ERP error logs / alerts, EDI gateway / VAN dashboards, Third‑party monitoring tool, Partner portals, No centralized monitoring, Other
• How often do you get false‑positive alerts versus missed incidents? Options: Mostly false positives, Balanced, Mostly missed incidents, Rare alerts, We don't track
• How are escalations handled when an incident is identified—formal on‑call, ad‑hoc, or something else? Options: Formal on‑call rotation, Ad‑hoc emails / calls, Manager escalation only, Escalation to outsourced provider, No formal escalation process, Other
• What manual troubleshooting or repeatable tasks consume the most of your team's time when failures occur (list top 3)?

If Chargebacks Disappeared Tomorrow, What Would Change?

• Imagine zero chargebacks and frictionless partner onboarding—what would that change in your day‑to‑day and in business outcomes?
• Which KPIs would you use to prove success within 6–12 months? Options: Onboarding time per partner, Chargebacks per month, Transaction success rate (PO/ASN/Invoice), Mean time to detect (MTTD), Mean time to resolve (MTTR), Cost to manage EDI / month, Other
• What uptime or delivery SLA would truly satisfy your trading partners and internal stakeholders? Options: 99.9%, 99.95%, 99.99%, Four 9s+ (99.999%), Unsure / depends on partner
• What ROI or payback timeframe would make a migration or platform change a no‑brainer for your leadership? Options: <3 months, 3–6 months, 6–12 months, 12–24 months, Longer / strategic investment
• Who in finance or the business must be convinced to approve investment, and what evidence would move them?

What's the Smallest Change That Could Reduce Risk in 90 Days?

• What's the one small, minimally disruptive change you haven't tried because it felt risky—but that could materially cut chargebacks in 90 days?
• Which internal decision‑makers would need to sign off to run that change or a pilot? Options: CIO / VP IT, SVP Supply Chain / Logistics, VP Operations, Head of Finance / CFO, Procurement, Managed Services / MSP, Other
• What technical or access constraints would block fast progress (select all that apply)? Options: No test environment, Limited ERP access, Security approvals pending, Partner unresponsiveness, Insufficient staff bandwidth, Legacy middleware limitations, Other
• How ready is your team to start a pilot or proof‑of‑concept in the next 60–90 days? Options: Ready immediately, Ready with minor prep (1–2 weeks), Need 1–2 months prep, Need 3+ months, Not ready
• For a short pilot, what specific measurable outcomes would define success?

Quick Intro — Who Are We Working With?

• Who will be the primary day-to-day owner of EDI/trading-partner onboarding at your company? Options: IT Manager, Supply Chain Director, E‑commerce/Marketplace Ops Lead, Finance / Accounts Payable, Logistics / Warehouse Manager, Third‑party integrator, Other
• In one sentence, what is the business goal you want this onboarding work to deliver?
• Roughly how many internal people will participate in onboarding activities (project, mapping, testing, ops)? Options: 1–2, 3–5, 6–10, 11–20, 21+
• Which backend systems are in scope for connections (select all that apply)? Options: SAP, Oracle/EBS, NetSuite, Microsoft Dynamics, Manhattan/WMS, Shopify/Magento/BigCommerce, Custom ERP, Other
• What is your preferred communication cadence and primary channel for project updates? Options: Weekly project call, Bi‑weekly call, Ad‑hoc email, Slack/Teams channel, Ticketing system (JIRA/ServiceNow), Other

Are We Truly Aligned (Or Just Agreeing to Get Started)?

• If we asked IT, Supply Chain, Operations and Finance to describe 'what good looks like' for EDI, how different would their answers be? Options: Almost identical, Some differences, mostly aligned, Mostly different, We haven't asked them
• For each stakeholder group above, what single metric would make them say the project succeeded? (list by role → metric)
• Who has final sign‑off authority on vendor selection, SLA commitments, and budget for this work? Options: IT Director/VP, Supply Chain Director/VP, CFO/Finance, Cross‑functional committee, CEO/COO, Other
• Are there fixed budget windows, procurement cycles, or approval gates we must plan around? Options: Yes — procurement window, Yes — quarterly budget cycle, Yes — fiscal-year constraints, No strict windows, Unsure
• How urgent is this initiative on your company’s priority list right now? Options: Critical — must deliver in 0–3 months, High — 3–6 months, Medium — 6–12 months, Low — 12+ months

Where the System Actually Breaks — Tell Us the Worst Stories

• Tell us about the single most damaging EDI incident you’ve had in the last 12 months — what happened, which partner was involved, and what was the business impact?
• How frequently do you experience chargebacks, penalties, or rejected documents from trading partners? Options: Weekly, Monthly, Quarterly, Rarely, Never
• Estimate the annual financial impact of chargebacks, remediation, and manual reconciliation (ballpark if exact unknown). Options: < $10k, $10k–$50k, $50k–$250k, $250k–$1M, > $1M, Unsure
• Which document types create the most exceptions for you today? Options: 850 — Purchase Order, 810 — Invoice, 856 — Advance Ship Notice (ASN), 846 — Inventory, 820 — Payment/Remittance, Other
• When an exception occurs, how quickly is it typically detected and how long until resolution? Options: Detected within minutes, resolved within hours, Detected same day, resolved within 1–2 days, Detected within days, resolved in a week, Detection/resolution time varies widely, We lack consistent detection
• Who currently owns exception management and escalation when a partner fails compliance? Options: IT support/Integration team, Supply Chain/Operations, 3PL or Managed Services, Finance/AP, Shared responsibility, Other

What Hidden Rules Are We Ignoring?

• Which trading partners have undocumented quirks or one‑off rules that keep causing repeat problems?
• How many active trading partners are you transacting with today (including retailers, distributors, marketplaces, and 3PLs)? Options: 1–10, 11–50, 51–200, 201–1000, 1000+
• How many partner‑specific maps/configurations do you maintain in house versus how many are standardized across multiple partners? Options: Mostly custom per partner, Mix of custom and standard, Mostly standardized templates, We don't track this
• Which communication protocols do your partners require (select all that apply)? Options: AS2, SFTP, API/REST, FTP (legacy), VAN, Other
• Do you maintain a single source inventory of partner specs, test cases, and failure histories? Options: Yes — centralized and up to date, Partially — some partners documented, No — documentation scattered, No — we rely on tribal knowledge
• For partners causing the most friction, what are the top three recurring failure modes (e.g., missing PO numbers, unit-of-measure mismatches, ASN timing)?

If We Could Snap Our Fingers — What Would Change?

• If leadership declared this project an unambiguous success in 6 months, what specifically would look and feel different?
• What onboarding velocity do you need to hit to meet business demands (partners onboarded per month)? Options: 1–2, 3–5, 6–10, 11–25, 25+
• What uptime, delivery, or processing SLA do you require for critical document flows? Options: 99.99%, 99.9%, 99.5%, 99%, Lower / flexible, We don't have a target
• Which compliance threshold would eliminate most chargebacks for you (error rate target)? Options: <0.1%, <0.5%, <1%, <2%, Other / unspecified
• What ROI timeframe would make this investment compelling (months to break‑even)? Options: 0–6 months, 6–12 months, 12–24 months, 24+ months, ROI not primary driver
• Which 3 KPIs will you insist on tracking post‑deployment to judge success? Options: Onboarding time per partner, Document error rate, Chargebacks ($), Operational FTE hours saved, Transaction throughput, System uptime

Who Needs Access — And Can They Give It?

• If we can’t immediately access the ERP/WMS test environment, how likely is onboarding to stall? Options: Very likely — critical path, Possible delay but manageable, Unlikely — we have workarounds, Unsure
• Can you provide the following test/data extracts for mapping and validation (select all you can provide now)? Options: POs (current and historical), Invoices, ASNs, Inventory snapshots, Shipping manifests, Master data (items, UOM, GL codes), None available yet
• Do you have separate test/dev environments for ERP and WMS that we can use for end‑to‑end validation? Options: Yes — full test environments available, Yes — limited data/test access, No — only production, Unsure
• Which credential types will we need to integrate with your systems (select all that apply)? Options: SFTP keys, AS2 certs, API tokens/keys, VPN credentials, OAuth, Username/password, Other
• Who are the named technical owners for ERP, WMS, and EDI (role + best contact) we should coordinate with?
• Are there known data quality issues (missing SKUs, inconsistent UOMs, duplicate IDs) we should account for before mapping? Options: Yes — many issues, Somewhat — a few known issues, No — data is clean, Unsure

What Would Make Cutover Fail — Let’s Name Those Risks Now

• What single predictable failure during cutover would cause leadership to call the project a failure?
• Are there blackout dates, peak sales periods, or retailer blackout windows when cutover is prohibited? Options: Yes — fixed seasonal peaks, Yes — periodic billing cycles, No — flexible timing, Unsure
• Which partners require synchronized cutover with the retailer/3PL (i.e., cannot be cut over independently)?
• What rollback or backout constraints do we need to design for (e.g., cannot reverse invoices in ERP, inventory timing issues)?
• Who has authority to approve go‑live on the day of cutover (role and contact)? Options: IT Lead, Supply Chain Lead, Finance/Controller, Executive Sponsor, Cross‑functional signoff required, Other
• How will you validate partner readiness on Day 0 (list tests and acceptance checks)?

Money, Risk, and the Hidden Costs Nobody Mentions

• Beyond explicit chargebacks, what recurring financial or operational costs does your current EDI approach create (FTE time, duplicate processing, lost sales)?
• Do any trading partner contracts include liquidated damages, chargeback schedules, or financial penalties we must model? Options: Yes — strict penalty schedules, Yes — limited penalties, No formal penalties, Unsure
• What is your current internal monthly cost to operate EDI (people + hosting + tools) — ballpark? Options: < $5k, $5k–$20k, $20k–$75k, $75k–$250k, > $250k, Unsure
• How tolerant is Finance of migration‑related spend or temporary duplicate processing costs during cutover? Options: Very tolerant with clear ROI, Somewhat tolerant for critical partners, Not tolerant — low risk appetite, Unsure
• Are there compliance or audit requirements (SOX, PCI, retailer audits) that add complexity to data movement and logging? Options: Yes — strict compliance controls, Moderate controls, No specific compliance needs, Unsure

Ready to Move — Decision Path and Next Steps

• If we deliver a clear plan that reduces chargebacks and speeds onboarding, who will make the final decision and what is their timeframe?
• What remaining decision gates exist (procurement, security review, legal, budget) and their estimated dates? Options: Procurement, Security/SOC review, Legal/Contracting, Budget approval, Executive sign‑off, Other
• Would you prefer a pilot onboarding a small set of partners first or a phased wider rollout? Options: Pilot (recommended), Phased rollout, Big‑bang, Undecided
• What commercial model would you find most acceptable: fixed onboarding fee, subscription with a per‑partner charge, or fully managed services? Options: Fixed onboarding fee, Subscription + per partner, Managed services (flat), Performance‑based, Open to discussion
• What specific next step should we book now to maintain momentum (technical scoping call, exec alignment, procurement kickoff)? Options: Technical scoping call, Executive alignment meeting, Procurement kickoff, Security review pre‑work, Pilot partner selection, Other
• Is there anything else we haven’t asked that would change how we prioritize risk, timelines, or partner selection?

Quick Snapshot: Who's in the Room?

• Which roles will we collaborate with on EDI, integrations, and onboarding decisions? Options: IT Manager/Director, Supply Chain/Logistics Lead, E-commerce/Marketplace Lead, Operations/Warehouse Manager, Finance/Revenue Manager, Procurement/Purchasing, VP/Head of Business Unit, Other
• Which ERP(s), WMS, and e-commerce platforms are in scope for this initiative? Options: SAP ECC / S/4HANA, Oracle E-Business Suite / Cloud, Microsoft Dynamics 365, NetSuite, Manhattan/Blue Yonder WMS, Shopify/Magento/BigCommerce, Custom/Proprietary, Other
• What is the primary business reason you’re exploring a new EDI/connectivity approach right now? Options: Faster trading partner onboarding, Reduce chargebacks, Migrate off legacy EDI stack, Support drop-ship/marketplaces, Improve monitoring & uptime, Reduce IT burden, Cost savings, Other
• How quickly does your organization expect a measurable improvement (e.g., fewer chargebacks, faster onboarding)? Options: Within 30 days, 30–90 days, 3–6 months, 6–12 months, Longer / exploratory
• Tell us briefly about the last time you changed or upgraded a key integration (ERP, EDI, or WMS)—what went well and what surprised you?

If We Kept Doing What You're Doing, What Would Break Next?

• What recurring EDI or partner failures do you find yourselves accepting as 'normal'?
• How often do these failures interrupt operations or require manual intervention? Options: Multiple times per day, Daily, Weekly, Monthly, Rarely
• Which failure type hits you hardest—mapping errors, communication drops, missing acknowledgments, or compliance rejections? Options: Mapping/transformation errors, Communication/transport failures (AS2/SFTP/API), Missing 997/TA1 acknowledgments, Partner-specific compliance rejections, Late or missing ASNs/invoices, Other
• When these failures happen, who in your organization is forced to own the firefight and for how long? Options: IT team (internal), 3rd‑party integrator, Operations/Warehouse, Trading partner team, Finance/Revenue, Cross-functional war room, Other
• Can you share a concrete example of a recent failure that caused financial or operational pain—what happened, and what was the real cost?

Where Chargebacks Live (and Why They Hurt)

• How confident are you that you know the top causes of your chargebacks today? Options: Very confident, Somewhat confident, Not confident, We don't track causes well
• Which chargeback categories account for the majority of your penalties? Options: Incorrect/missing ASN, PO/Invoice mismatches, Late ship / late receipt, Invalid item/UPC, Labeling/packaging non‑compliance, Other
• Which trading partners are most likely to issue chargebacks, and how many partners typically generate the bulk of the cost? Options: Top 1–3 partners, Top 4–10 partners, More than 10 partners, Chargebacks are evenly distributed
• Describe your current process for resolving a chargeback—who owns the investigation, typical resolution time, and where it stalls.
• What tools or reports do you rely on today to detect compliance failures before they become chargebacks? Options: Internal alerts / scripts, Legacy EDI VAN portal, Spreadsheet/manual tracking, Dedicated compliance software, ERP reports, None

The Hidden Map: Your Current EDI Topology

• If I asked for a clean diagram of your current trading‑partner topology, how confident are you that it exists and is up to date? Options: We have an accurate diagram, We have an outdated diagram, No diagram exists, Unsure
• How many active trading partners do you currently exchange documents with (approx.)? Options: 1–25, 26–100, 101–500, 500+
• Which transport protocols and connectivity methods do you use across partners? Options: AS2, SFTP, FTP, Peppol/API, EDI VAN, Direct API/Web services, Email/Manual
• Do you run mappings and transformations centrally (integrator/platform) or spread across point‑to‑point systems and internal scripts? Options: Centralized platform, Combination/hybrid, Point‑to‑point per partner, Mostly manual scripts
• Who currently owns partner mappings, quality checks, and fixes—internal team, outsourced provider, or the partner? Options: Internal IT integration team, Supply chain/ops, External managed service, Partner-managed, Shared responsibility
• What are your current average transaction volumes (documents/day) and peak burst behavior—any predictable seasonality?

What Does 'Good' Look Like—If You Could Wave a Wand

• If you could eliminate one EDI-related worry overnight, what would it be and why does it matter?
• What target onboarding cadence would fundamentally change your business—how many partners per week or month would be a win? Options: 1–2/week, 3–5/week, 10+/month, Depends on partner complexity
• What uptime, message delivery, and compliance SLA numbers would satisfy IT, ops, and finance stakeholders? Options: 99.9%+, 99.5%+, 99%+, Other / custom
• Which KPIs would you point to in an executive review to prove the new approach is working? Options: Chargebacks $/month, Onboarding time per partner, Error rate %, Mean time to resolution (MTTR), Transactions per day without manual touch, Other
• How should ROI be measured for this project—direct chargeback reduction, IT FTE savings, faster time‑to‑revenue, or a mix? Options: Chargeback reduction, IT headcount/time savings, Faster partner onboarding (revenue), Operational efficiency (less manual work), All of the above

What's Stopping the Change (Even If Everyone Agrees)

• What internal beliefs or practices would need to change for a new platform to succeed here?
• What constraints feel most real right now—budget cycles, staff availability, upgrade windows, or risk tolerance? Options: Budget/timing, Availability of skilled staff, ERP upgrade/migration windows, Vendor lock‑in/contract terms, Executive alignment/risk aversion, Other
• Have you attempted a migration, pilot, or tool change before that stalled? If so, what blocked momentum?
• When you imagine migration risk, what specific scenarios worry you most (data loss, partner downtime, mapping regressions, billing issues)? Options: Data loss/corruption, Partner downtime during cutover, Incorrect mappings causing rejections, Billing/invoice reconciliation problems, Other
• How flexible are your trading partners about planned test windows, and who typically negotiates those windows? Options: Very flexible, Somewhat flexible, Inflexible; strict windows, Varies widely by partner

Let’s Test the Fit: Real Scenarios That Matter

• Pick three trading partners or document flows that would make the best pilot to prove value—who are they and why?
• For each priority partner, what are the top two failure modes we should reproduce and resolve during a pilot?
• Which specific document types and variations cause the most trouble (PO 850, PO 855/changes, ASN 856, Invoice 810, Inventory 846, Remittance 820, etc.)? Options: PO (850), PO Acknowledgement/Change (855/860), ASN (856), Invoice (810), Inventory (846), Remittance (820), Other
• What acceptance tests would signal a partner is production‑ready—automated 997s, matched invoice/PO, <X> days error‑free, or something else? Options: Automated acknowledgements (997/TA1), Zero critical rejections for X days, Successful end‑to‑end item/price/qty match, Throughput at expected peak volumes, Other
• Who will be our day‑to‑day contact for test execution and escalation for those pilot partners?

Measuring Success — Who Signs Off?

• Which stakeholder will have final sign‑off on onboarding and acceptance criteria—IT, Supply Chain, Ops, Finance, or a committee? Options: IT, Supply Chain / Ops, Finance, Cross‑functional committee, Executive sponsor
• Are there financial thresholds or governance gates (e.g., chargeback reduction target, cost per partner) that must be met for project approval? Options: Yes—specific thresholds exist, No specific thresholds, Not sure
• How often should we report progress and to whom (weekly ops, biweekly steering, monthly execs)? Options: Weekly ops, Biweekly project/steering, Monthly executive, Ad hoc as issues arise
• How will ongoing ownership look after onboarding—do you want a managed service, co-managed model, or fully in‑house? Options: Managed service (we outsource), Co‑managed (shared responsibilities), Fully in‑house (we operate), Undecided
• Who is the single person or team accountable for long‑term success metrics (reduce chargebacks, maintain uptime)?

First Small Bet: A Minimal Scope to De‑Risk

• If we agreed to a small, time‑boxed pilot, what is the minimum success outcome that would justify expanding the program? Options: X% reduction in errors, Onboarding 1–3 partners in <30 days, Zero critical rejections for 14 days, Clear operational runbook and SLA, Other
• Which partner(s) would be least risky yet most representative for that pilot (low complexity but high volume)?
• What timeline and rollback constraints must we honor for a pilot to be acceptable to your stakeholders? Options: 2–4 weeks, 4–8 weeks, 8–12 weeks, Depends on partner
• What internal resources can you commit to the pilot (FTE hours/week from IT, ops, mapping experts)?
• What would a safe, agreed escalation path look like if a pilot begins to cause partner disruptions? Options: Immediate pause and rollback, Rapid cross‑functional war room, Predefined fallback to legacy VAN, Escalate to executive sponsor