Start with Names, Roles & the Moment That Brought Us Here

• Who are you, what is your title, and what part of the supply chain do you directly own?
• Which function owns carrier performance and on-time-in-full (OTIF) accountability at your company? Options: Logistics/Transportation, Supply Chain Operations, Customer Fulfillment, Procurement, 3PL Network, Other
• Briefly describe the most recent shipment that caused a production line shutdown or a retail stockout — what happened and who first noticed?
• How quickly do you need a proven fix in place to avoid a repeat of that incident? Options: Immediately (weeks), 1–3 months, 3–6 months, Longer / exploratory
• Who should be our day-to-day contact for running a pilot and making operational tradeoffs?

Who's on the Bus — Name the People Who Actually Make the Call

• If the COO asked right now 'who prevents the next shutdown?', can you give names, titles, and decision authority for each relevant stakeholder?
• Which of these roles should be involved in the pilot decision and sign-off? Options: VP/Head of Supply Chain, Director of Logistics, Operations Manager, IT/TMS Lead, Procurement/Budget Owner, Warehouse Manager, Retail Ops/Category Manager, 3PL Account Manager, Other
• Which stakeholders will require executive-level ROI versus operational proof before they approve expansion? Options: Executive ROI (Finance/COO), Operational proof (Logistics/OPS), Both, Undecided
• Are there external stakeholders (major customers, retailers, 3PL partners) whose approval or notification is required for pilot activities? Options: Yes — retailers, Yes — 3PL partners, Yes — large customers, No, Not sure
• What is your typical internal procurement or legal approval timeline for pilots of this scope? Options: Under 2 weeks, 2–4 weeks, 1–2 months, Over 2 months, Variable / case-by-case

The Nightmare Scenario — Tell Us the One That Still Haunts You

• Tell us about the most damaging late-shipment event in the last 24 months — what broke, what was the cost (financial or otherwise), and why did it escalate?
• How often do you experience critical late shipments on your top lanes (those that would trigger shutdowns or lost promotions)? Options: Weekly, Monthly, Quarterly, Rarely / annually, Never
• Which lanes, SKUs, or suppliers would cause the largest immediate business impact if a shipment missed its window?
• How are exceptions typically discovered today (e.g., carrier email/portal, plant report, customer/retailer complaint, manual checks)? Options: Carrier portal/email, Plant/warehouse reports, Customer/retailer complaint, TMS alerts, Manual phone/email checks, Other
• Estimate how many hours your team spends per week chasing shipment status and carrier updates across all systems. Options: Under 5 hrs, 5–15 hrs, 15–40 hrs, 40–80 hrs, Over 80 hrs
• How does it feel in the control room when a surprise happens? (capture emotions, tensions, and common reactions)

If We Could Measure One Thing — Pick the Metric That Would Make You an Advocate

• If you had to pick a single KPI that would convince leadership to expand a pilot, which would it be? Options: On-time delivery % (OTIF), ETA prediction accuracy vs carrier, Hours saved chasing status, Mean time to detect exceptions, Number of prevented shutdowns, Alert relevance (false positive rate), Other
• For that KPI, what is your current baseline and the target threshold you'd require in a 90-day pilot? Please provide numbers or ranges.
• Which secondary metrics will influence your decision (choose all that apply)? Options: Carrier integration coverage, Data latency and freshness, Integration success rate (TMS/ERP), User adoption / time-to-first-action, Alert timeliness, Reduction in manual tickets/calls, Other
• How will you validate ETA prediction accuracy during the pilot — who will own the comparison to carrier ETA and actual arrival?
• How often do you want progress reports during the pilot, and in what format? Options: Weekly dashboard + call, Bi-weekly summary, Monthly business review, Real-time dashboard only, Ad-hoc on request

What Would 'Success' Actually Feel Like in 90 Days?

• If this pilot met your acceptance criteria, what specific day-to-day changes would you expect your team to see and do differently?
• Which operational behaviors are essential to change for value to stick (select all that apply)? Options: Relying on predictive ETAs vs carrier portals, Automating escalation workflows, Reducing manual status calls/emails, Proactive carrier management, Cross-functional playbooks (Ops/Procurement/IT), Other
• What percentage reduction in time spent chasing status would make the case to expand to more lanes? Options: 10–20%, 20–40%, 40–60%, 60–80%, 80–100%
• What specific evidence will you present to the VP/COO to unlock budget for rollout?
• If the pilot falls short, what remediation would you expect (e.g., tuning, extended pilot, scope change, off-ramp)? Options: Tuning and retest, Extend pilot with revised lanes, Narrow scope and retry, Terminate pilot, Other

Barriers We Must Beat — Data, Integration & People

• What’s the single biggest technical or organizational blocker that has derailed similar pilots in the past?
• Which systems will we need to integrate with for a meaningful pilot? Options: TMS, ERP, WMS, Carrier portals/feeds, IoT/telemetry providers, Data lake/BI, Other
• For each required integration, do you expect API access, SFTP/messaging files, or manual data extracts? Options: APIs available, SFTP/files only, Manual exports required, Mixture of the above, Unknown — need to check
• Do you have security or compliance requirements we must meet (SOC2, SSO/SAML, IP allowlist, data residency)? Select all that apply. Options: SOC2, SSO/SAML, IP allowlist, Data residency restrictions, NDAs/Master Services Agreement, None, Other
• Are there carriers or partners that historically refuse or fail to provide timely feeds or GPS telemetry? Options: Yes — specific carriers, Yes — last-mile partners, No, Not sure
• Who on your side will provide sample shipment data and can they deliver it within 7 business days? Options: Yes — ready now, Yes — within 7–14 days, Yes — but longer, No / need to arrange, Unknown

Commitments, Timelines & Escalation — Who Puts Their Name Down?

• If the pilot proves value, who will own the decision and budget to scale, and what formal approval will they require?
• What is the latest acceptable start date for a 90-day pilot to align with your business priorities (e.g., promotions, production cycles)? Options: Within 2 weeks, Within 1 month, Within 2 months, Timing is flexible
• Which internal commitments can you already confirm now (data access, IT support hours, SME availability), select all that apply? Options: Data access confirmed, IT integration support committed, Operational SME time committed, Executive sponsor committed, Budget pre-approved, None confirmed
• Who should be the escalation contact on your team for technical or timeline blockers, including name, role, and preferred contact method?
• How would you rate your organization's appetite for a vendor-led pilot with weekly checkpoints and a final business review? Options: Very high, Moderate, Cautious, Low
• Would you be open to a short executive briefing mid-pilot to maintain sponsorship and accelerate decisions? Options: Yes — required, Yes — optional, Maybe, No

Wrap: Confidence, Concerns, and the Next Best Step

• On a scale from 1–10, how confident are you that a 90-day pilot can demonstrate measurable improvement for your highest-risk lanes? Options: 1, 2, 3, 4, 5, 6, 7, 8, 9, 10
• What would move your confidence up two points? Be specific — resources, proof points, timelines, or risk guarantees.
• What remaining concerns or unknowns would you like us to address before we draft a pilot statement of work?
• Would you like us to draft a proposed pilot statement of work and success criteria for your review? Options: Yes — please draft, Maybe — want more discussion, No — not ready
• Who else should join the next meeting to accelerate decisions (name, role, and why their presence matters)?
• Preferred primary channel for pilot coordination and status updates? Options: Email, Slack, Microsoft Teams, Phone/Zoom, Vendor portal/dashboard

Quick Snapshot: The Basics We’ll Build On

• Roughly how many inbound shipments do you manage each month? Options: <50, 50–200, 201–1,000, 1,001–5,000, 5,001+
• Which transport modes make up your inbound mix today? Options: Truck, Rail, Ocean (container), Ocean (bulk), Air, Intermodal, Other
• List the top three origin→destination lanes by volume or criticality (format: origin - destination - why it matters).
• Which carriers or carrier types do you rely on most across those lanes?
• What TMS, ERP, or WMS systems will we need to integrate with (name and version if possible)?
• Who on your team owns day-to-day shipment monitoring and who signs off on pilot success?

If a Late Shipment Could Shut Down Production — Would You Have Seen It Coming?

• Tell us about the most recent late-inbound incident that caused meaningful disruption—what happened and when did you first learn about it?
• When that disruption occurred, how long was the window between the shipment actually falling behind and your team being alerted or aware? Options: Real-time/within 1 hour, 1–6 hours, 6–24 hours, 24–72 hours, We only knew after the missed delivery
• What was the business impact of that incident (select all that apply and estimate where you can)? Options: Production line downtime, Retail out-of-stock/promotion miss, Expedited freight cost, Customer SLA penalty, Rework or overtime, Other—please quantify in next field
• Approximately how much revenue or cost was affected by that event (or leave blank if unknown)?
• Who internally had to mobilize during that event and how did you coordinate response (phone, email, spreadsheets, TMS notes)? Options: Phone + text, Email threads, Shared spreadsheet, TMS/ERP manual updates, Ad-hoc chat apps (Slack/Teams), Other

Are You Still Letting Carrier ETAs Be the Final Word?

• How much of your current shipment visibility comes directly from carrier-provided ETAs versus your own tracking sources? Options: Mostly carrier ETAs (>80%), Majority carrier ETAs (50–80%), Balanced (30–50% carrier), Mostly our own sources (<30% carrier)
• Which carriers consistently provide GPS or near-real-time telemetry versus only milestone scans? List by carrier if possible.
• How often do carrier ETAs differ from actual arrivals by more than 12 / 24 / 48 hours on your critical lanes? Options: Almost never, Occasionally (monthly), Often (weekly), Very often (multiple times/week), Unknown
• Share an example where relying on carrier ETA changed a decision you made—what was the outcome?
• Do carriers provide automated status feeds (API, EDI, webhook) today? If yes, which carriers and what feed types? Options: APIs, EDIs, SFTP batch files, Email reports, No automated feeds, Other

Where Do Your People Burn the Most Time Chasing Status?

• When a shipment goes off-plan, what is your team’s typical escalation workflow from detection to resolution?
• On average, how much time does your team spend per incident chasing status until it’s resolved? Options: <30 minutes, 30–60 minutes, 1–3 hours, 3–8 hours, 8+ hours
• How many people are usually involved across teams (ops, customer service, procurement) when chasing a single exception? Options: 1, 2–3, 4–6, 7–10, 10+
• What tools or temporary workarounds do your teams use today to keep track of exceptions (shared docs, whiteboards, ticketing systems)? Options: Shared spreadsheet, Email chains, Chat channels, TMS manual notes, Helpdesk/ticketing, None/Ad-hoc
• How does this chasing behavior show up in employee feedback, turnover, or morale—what have people told you about it?

Which Lanes Keep You Up at Night?

• If you had to pick three lanes to fix first for the biggest immediate impact, which would they be and why?
• For each of those lanes, what are the typical shipment frequency and value (low/med/high)? Options: Low frequency / Low value, Low frequency / High value, High frequency / Low value, High frequency / High value, Unknown
• Which lane characteristics tend to cause the most problems (select all that apply)? Options: Cross-border customs, Port congestion, Last-mile handoffs, Intermodal transfers, Poor carrier performance, Limited telemetry from carrier
• Which lanes would you nominate for a 90-day pilot to prove ETA accuracy and exception effectiveness?
• How do you currently prioritize lanes for operational focus—by volume, value-at-risk, or historical lateness? Options: Volume, Value-at-risk, Historical Lateness, Customer importance, Other

What Would Earlier, Better ETAs Actually Change for You?

• Which KPIs matter most to you for on-time performance and acceptance of a pilot? Options: On-time delivery %, ETA prediction accuracy (hours), Alert-to-resolution time, False positive rate, Reduction in manual chase hours, Other
• What threshold would you consider a meaningful improvement for ETA accuracy on a pilot (e.g., reduce error to within X hours)?
• How would you quantify success for exception alerts—what false-positive rate or lead time would be acceptable?
• Who will be the primary consumer of ETA and alert improvements (operations supervisors, planners, execs)? Options: Operations/Dispatch, Logistics Planners, Customer Service/CSRs, Supply Chain Director, VP/Exec
• If we delivered the expected improvements, what downstream business processes or decisions would change immediately?

How Ready Is Your Tech Stack To Turn Data Into Action?

• Which systems will we need to connect for the pilot (select all that apply)? Options: TMS, ERP, WMS, Carrier portals/APIs, BI/Analytics, EDI, Other
• Are APIs or automated data extracts available today from your TMS/ERP for onboarding sample shipment history? Options: APIs available, SFTP/flat file extracts, EDI only, No automated extracts — manual export only, Unsure
• Can you provide 60–90 days of historical shipment data for pilot lane selection and model calibration? Options: Yes, full dataset, Partial data available, Only recent samples, No, we cannot
• Who will be our technical point of contact for integrations and how do they prefer to work (email, weekly calls, tickets)?
• What internal IT or security approvals are normally required before connecting to third-party visibility platforms?

What Would a Safe, Successful Pilot Look Like to You?

• If a pilot could only prove one thing in 90 days, what single outcome would make you feel confident to expand?
• What pilot duration and minimum lane count feel realistic for you? Options: 30 days / 1–2 lanes, 60 days / 3–5 lanes, 90 days / 3–10 lanes, Custom - please specify
• Which carriers must be included in the pilot to make results meaningful?
• What resources can your team commit to the pilot (data lead, integration engineer, ops owner)? Options: Data lead, Integration engineer, Operations owner, Executive sponsor, No dedicated resources yet
• What would be an acceptable escalation path if we identify urgent risks during the pilot? Options: Daily standup, Dedicated Slack/Teams channel, Email + SLA, Escalation to exec sponsor, Other

Who Needs to Believe This Will Work — And Why?

• Who are the decision-makers and economic evaluators for a visibility solution in your organization?
• Which stakeholders are most likely to resist change and what are their main concerns?
• What metrics or reports will the VP of Supply Chain want to see to justify roll-out beyond the pilot? Options: On-time % delta, Cost savings (expedited/freight), Reduction in manual hours, Carrier performance scorecards, Other
• Who will be the internal champion responsible for day-to-day progress and adoption during the pilot?
• How do you prefer we surface pilot progress—weekly dashboards, short executive summaries, or live review sessions? Options: Weekly dashboards, Bi-weekly exec summary, Weekly live review, Ad-hoc as needed

If We Could Start Today, What’s the Smallest Step That Proves Value?

• What’s the earliest date you could share sample data or grant feed access for an initial assessment? Options: Within a week, 1–2 weeks, 2–4 weeks, More than a month, Unsure
• Which single lane or shipment type would you designate as a ‘quick-win’ to validate ETA improvements?
• What are your top three concerns about running a pilot with an external visibility provider?
• What support would make your team comfortable moving forward (data mapping help, integration engineering, change management, training)? Options: Data mapping assistance, Integration engineering, Dedicated onboarding manager, End-user training, Change management playbook
• Finally, who should we loop in next from your side to remove blockers and set a pilot kickoff date?

Quick Intro — Who’s on Deck?

• Who will be our primary operational contact for the 90‑day pilot? Options: Logistics/Operations Manager, Director of Logistics, Transportation Planner, TMS/Integration Admin, IT Project Manager, Other
• Which teams will be actively involved day‑to‑day during the pilot? Options: Logistics/Operations, Carrier Relations, IT/Integration, Warehouse/Receiving, Procurement, Finance, Other
• What TMS and ERP systems are currently in production that we’ll need to integrate with? (List product and version if known)
• How do your teams currently consolidate carrier tracking today? Options: Manual portal checks / email / phone, Spreadsheet aggregation, A single TMS feed, Existing visibility platform, Other
• Roughly how many active lanes (origin→destination pairs) do you expect to include in the pilot? Options: 1–5, 6–15, 16–30, 31–75, 75+

If a Carrier Feed Fails Tomorrow, What Keeps You Awake?

• Have you experienced a carrier feed or tracking blackout that caused a missed delivery or production impact in the last 12 months? Tell us what happened.
• Which carriers in your lane mix provide GPS/real‑time telemetry vs milestone scans vs only ETA updates (select all that apply)? Options: Carrier provides GPS/real‑time, Carrier provides milestone scans only, Carrier provides ETA updates only, Carrier provides no electronic updates
• How often do you notice gaps or stale data from carriers that require manual follow‑up? Options: Daily, Several times a week, Weekly, Monthly, Rarely/Never
• When data gaps occur, what do you typically do to fill them? (Select all that apply) Options: Call the carrier, Email operations team, Escalate to account manager, Use backup carrier portal, Accept the risk and monitor, Other
• And how long has this pattern of carrier data inconsistency been a recurring issue for your team? Options: Under 3 months, 3–12 months, 1–3 years, 3+ years

Where the Data Gets Stuck — Integration Reality Check

• How confident are you that your TMS/ERP can accept automated inbound shipment updates (APIs or file drops) without major customization? Options: Fully ready with APIs, Ready with minor config, Requires moderate customization, Requires significant rework, Unknown / need assessment
• Do you currently use middleware or an integration platform (iPaaS) between carriers and your systems? Options: Yes — commercial iPaaS (e.g., Mulesoft, Boomi), Yes — homegrown middleware, No — direct integrations only, No — manual file exchanges
• What authentication and access patterns are available for your systems and our integrations (select all that apply)? Options: OAuth2 / modern API tokens, Basic auth / API keys, SFTP file drops, EDI, No remote access currently
• Who manages provisioning (API keys, SFTP accounts, VPNs) on your side and what SLA do they typically follow for requests?
• If provisioning requires security review or compliance sign‑off, how long does that approval typically take? Options: <3 business days, 3–10 business days, 2–4 weeks, More than 4 weeks, Not applicable / no review required

How We’ll Know the Feed Is Healthy

• What would feel unacceptable in a carrier feed during the pilot — missing location updates, incorrect ETAs, or delayed timestamps — which is the single biggest dealbreaker for you? Options: Missing location updates, Incorrect predicted ETAs, Delayed or batched timestamps, Incomplete event fields (missing carrier IDs, stop IDs), High false‑positive alerts
• Which acceptance criteria should we use to validate a carrier feed as 'production ready'? (Select up to three) Options: >90% hourly update coverage, ETA error within X hours, Event timeliness under Y minutes, No critical missing fields, Successful secure handoff of sample payloads
• What sample data artifacts can you provide quickly for testing (choose all that apply)? Options: Historical EDI/ASN files (90 days), Raw carrier event feeds, TMS shipment export (CSV/JSON), Carrier API credentials for sandbox, None available immediately
• What latency or freshness requirement must we meet for alerts to be actionable for your operations team? Options: Real‑time (<5 min), Near real‑time (5–30 min), Hourly, Same day
• Which specific lanes (or a short list of 3–5 worst performer lanes) do you want us to prioritize for sample validations? Please list lane codes or origin→destination descriptions.

Who Owns What — and What Happens If They’re in a Meeting

• Who will be assigned as the data owner for carrier feed activations and who will approve access?
• What is your formal escalation path when a carrier feed or integration breaks during the pilot? Options: Operations → Carrier Relations → IT, Operations → IT directly, TMS Vendor → IT → Operations, Other / custom escalation
• Do you have backup or secondary owners for integration tasks in case primary contacts are unavailable? Options: Yes — named backups, Yes — role backups (no named person), No backups assigned, Unsure
• What target response time (SLA) do you require for on‑call fixes during the pilot (from notification to first response)? Options: <30 minutes, <2 hours, <1 business day, 2–3 business days
• Are there internal change control windows or maintenance freeze periods during the pilot we should avoid? Options: Yes — list them below, No regular freezes, Unsure

Hidden Complexity: Legacy Systems and Off‑Network Partners

• Which systems or partners in your flow are known to be 'hard to integrate' (legacy TMS, regional carriers, last‑mile partners)? Please name them and describe the limitation.
• Are there carriers or 3PL partners you expect we cannot integrate with electronically during the pilot? Options: Yes — list them below, No — all expected carriers are electronically integrable, Unsure
• When shipments move through intermodal legs or third‑party handoffs, how often do you lose tracking granularity today? Options: Frequently (most intermodal legs), Occasionally (~25–50% of legs), Rarely (<25%), Not applicable / no intermodal legs
• Do you currently perform data normalization or mapping for carrier IDs, event codes, and location identifiers before ingesting into your systems? Options: Yes — automated normalization, Yes — manual mapping, No — raw data ingested, Partially
• What internal business rules or transformations must we respect when delivering events to your TMS/ERP (e.g., custom location codes, timezone handling)?

Pilot Test Plan — Let’s Make This Brutally Real

• If the pilot proves the platform, what’s the single metric you expect improved most (on‑time delivery, ETA accuracy, reduced manual chase hours, or something else)? Options: On‑time deliveries %, ETA prediction accuracy (hours), Reduction in manual status chase hours, Faster exception detection / resolution, Other
• Which of the following acceptance tests should be mandatory for lane validation? (Select all that apply) Options: Predicted ETA vs actual within X hours, Alert delivered within Y minutes of exception, No dropped events for >Z% of shipments, Successful TMS event ingestion without errors, User acceptance by operations team
• What is the minimum sample size or run time you consider meaningful for assessing feed quality on a lane (pick one)? Options: 30 shipments, 100 shipments, 2 weeks of live data, 30 days of live data, Other / discuss
• Who on your team will perform the acceptance validation and sign off on each lane?
• If a lane fails acceptance, what is your preferred next step—retry, root cause with carrier, expand sample, or abort? Options: Retry after remediation, Open carrier investigation, Expand sample and retest, Pause and remove lane from pilot, Other

Emotional Buy‑In — How This Pilot Must Make You Feel

• What’s your biggest fear entering this pilot — wasted time, false confidence in data, operational disruption, or something else? Options: Wasted time/resources, Overpromised accuracy, Disruption to operations, Alert fatigue, Other
• Who are the stakeholders that must feel confident about the results at the end of 90 days (select all that apply)? Options: VP/Head of Supply Chain, Director of Logistics, Operations Manager, IT/Infrastructure Lead, Finance/ROI owner, Other
• Beyond hard metrics, what qualitative change would make the pilot feel like a clear success to your team (e.g., less firefighting, fewer calls to carriers)?
• How realistic is your team’s capacity to support the pilot given current projects and priorities? Options: Ready to commit full support, Can allocate partial / limited support, Capacity constrained — need schedule alignment, Not sure yet
• If there was one small internal promise you could secure today to make the pilot succeed, what would it be (e.g., a standing 30‑minute weekly sync, named SLA for provisioning)?

Start With the Moment That Still Makes You Wince

• How often do unexpected late inbound shipments disrupt operations at your site(s)? Options: Weekly, Monthly, Quarterly, Less than quarterly, Rarely/never
• Think of the most recent incident that caused measurable disruption—briefly describe what happened, which lane(s) were involved, and the outcome.
• Which type(s) of site were impacted in that incident? Options: Manufacturing plant, Retail distribution center, 3PL/contract warehouse, Cross-dock, Regional DC, Other
• Approximately how many hours did your team spend chasing status and coordinating fixes during that event? Options: < 4 hours, 4–12 hours, 12–24 hours, 24–72 hours, > 72 hours
• Estimate the primary financial impacts you felt (choose all that apply) and, if possible, provide a rough magnitude. Options: Production downtime, Expedited freight costs, Lost sales/stockouts, Labor overtime, Customer penalties, Unable to quantify

If the Next Delay Could Shut Down a Line, Are You Ready to Admit Why?

• What single belief or assumption about your inbound visibility keeps you from feeling confident you can avoid another surprise shutdown?
• Which leaders would be most exposed if an inbound shipment shuts down a critical production line or misses a key retail window? Options: Logistics/Operations Manager, Director of Logistics, VP of Supply Chain, Plant/Factory Manager, Head of Customer Fulfillment, Other
• How do you currently define 'on-time' for inbound shipments (what milestone and tolerance)? Options: Dock appointment adherence, Arrival at facility, Availability at production line, Delivery within SLA window, Other
• When an ETA slips, what information do you lack before you escalate to senior leadership?
• How quickly does leadership expect an explanation and remediation plan after a missed ETA? Options: Within 1 hour, Within 4 hours, Same business day, Within 24 hours, No firm expectation

Where Visibility Falls Off the Map

• Which leg, handoff, or carrier type consistently blinds you—and why does that keep coming up?
• Which modes and handoff points show the biggest visibility gaps for your operations? Options: Ocean port-to-yard, Port terminal scans only, Rail interchange, Drayage/first-mile, Long-haul trucking, Last-mile carriers/contractors, Cross-dock transfers, Air cargo milestone-only
• What percent of your carriers provide high-frequency GPS/telematics vs milestone scans only? Options: > 75% GPS, 50–75% GPS, 25–49% GPS, <25% GPS, Unknown
• How many distinct carriers do you rely on across the lanes you’d consider for a pilot? Options: 1–3, 4–7, 8–12, 13–20, 20+
• How long have these visibility gaps existed for your organization—weeks, months, years? Please add specifics if relevant.

If Predictive ETAs Were Always Right, What Would Change?

• Imagine our ETA predictions meet your acceptance criteria—what is the first operational change you would make to avoid shutdowns or stockouts?
• Which KPIs should the 90-day pilot prioritize to prove value to your team and the executive sponsor? Options: On-time delivery %, ETA prediction accuracy (hours), Alert timeliness, Reduction in manual status checks, Exceptions resolved pre-impact, Carrier performance identification
• For each mode you operate (ocean, air, rail, truck), what ETA accuracy window would you require to consider predictions actionable?
• How much lead time on exception alerts would be meaningful to prevent a shutdown (e.g., 24h, 12h, 6h, 2h)? Options: >24 hours, 12–24 hours, 6–12 hours, 2–6 hours, <2 hours
• What concrete pilot success signals would make you recommend enterprise rollout to the VP/COO?

What Would It Take to Trust a New Source of Truth?

• What is the fastest way a new ETA source could lose credibility with your operations team?
• Which integration, privacy, or contractual concerns could prevent us from running a pilot on your lanes? Options: TMS/ERP API restrictions, Carrier contract limitations, Data privacy / customer PII concerns, IT resource constraints, Regulatory/compliance issues, Other
• How comfortable are you sharing 90 days of historical shipment data and current lane-level data to train and validate models? Options: Very comfortable, Somewhat comfortable, Need legal review, Not comfortable
• Which data formats/connectors are available from your systems (select all that apply)? Options: REST API, SFTP CSV extracts, EDI 214/315, Flat-file exports, Native TMS integrations, No reliable connector / custom
• Who must approve carrier data access and integrations in your organization (name roles or departments)?

Let’s Play Devil’s Advocate: Where Will This Pilot Struggle?

• If the pilot didn’t deliver, what single failure mode would you cite first—data quality, false alerts, poor integration, or something else?
• Select the top risks you want us to prioritize during pilot planning. Options: Carrier feed inconsistency, High false-positive alert rate, TMS/ERP integration delays, Incomplete lane coverage, User adoption/resistance, Insufficient historical data
• What rate of false-positive alerts (per 100 alerts) would you find acceptable before confidence erodes? Options: < 5%, 5–10%, 11–20%, 21–40%, >40%
• How many data discrepancies per 100 shipments (mismatched ETA, missing events) would you accept while the model calibrates? Options: < 1%, 1–3%, 4–10%, 11–20%, >20%
• If an integration or carrier activation slips, what escalation path and SLA do you expect from us and your internal teams?

Who Signs Up, Who Shows Up, and What Do They Commit To?

• What would make you confident enough to commit your highest-volume or worst-performing lanes to a 90-day pilot?
• Which internal roles must be actively involved during the pilot? (select all who will participate or need updates) Options: Logistics/Operations Manager, Director of Logistics, TMS/ERP Admin, IT / Integration Engineer, Plant Manager, Procurement/Carrier Relations, VP Supply Chain, 3PL Account Manager
• Realistically, how much weekly time can each core stakeholder commit (per person)? Options: < 1 hour, 1–2 hours, 3–5 hours, 5–10 hours, >10 hours
• Please list the specific lanes (origin → destination) you propose for the pilot—prioritize the top 3–5 worst-performing.
• What does a successful handoff to production look like after the pilot? Name the milestones, metrics, or approvals you require.