Getting Oriented — a quick snapshot of your role and program

• Who are you and what role do you own for ocean freight decisions? Options: Supply Chain Director, Logistics Manager, Trade Compliance Officer, Procurement Manager, Operations Manager, Other
• How many trade lanes do you actively manage today (e.g., Asia→US West, North Europe→Mediterranean)? Options: 1, 2, 3, 4, 5, 6+
• Roughly how many ocean shipments do you move per month across your network? Options: 1–10, 11–50, 51–200, 201–500, 500+
• What's the primary reason you're exploring a new logistics relationship right now? Options: Capacity issues with current carrier(s), Spike in demurrage/detention charges, Documentation errors/customs delays, Cost reduction, Need for better end‑to‑end visibility, Other
• Who typically evaluates and signs off on a new forwarding partner in your organization? Options: Me, Procurement, Finance, Operations, Cross-functional committee, Other
• What's one recent shipment story that best captures what keeps you up at night (briefly describe)?

Who’s in the room — and who’ll stop the deal?

• If your current freight program could be summarized in one frustrating sentence, what would it be?
• Which stakeholders must align before a new provider is approved, and which of them has final veto power? Options: Procurement, Supply Chain/SC Director, Operations, Trade Compliance, Finance, Legal, IT
• How long does it typically take from initial evaluation to contract signature in your organization? Options: <2 weeks, 2–4 weeks, 1–3 months, 3–6 months, 6+ months
• What political or organizational tensions usually emerge during that decision process (e.g., carrier loyalty, incumbent discounts, internal risk aversion)?
• How much weight do the following factors carry when stakeholders score a provider: price, on‑time reliability, documentation accuracy, claims history, responsiveness? Options: Price, On‑time reliability, Documentation accuracy, Claims handling, Responsiveness/communications
• When decisions slow down, what's the common blocker and how long has that been the pattern?

Where value is leaking — the failures you tolerate

• How often do you experience these failure modes: demurrage, customs holds, missing docs, booking rollovers, detention, cargo damage, or misrouted shipments? Options: Daily, Weekly, Monthly, Quarterly, Rarely
• Which of these failure modes costs you the most in hard dollars or operational disruption? Options: Demurrage/detention, Customs delays/penalties, Reconsigning/misrouting, Documentation rework, Inland delivery delays, Cargo damage/loss
• Who currently tracks and owns resolution for those exceptions when they occur? Options: Shipper operations, 3PL/account manager, Carrier, Customs broker, Logistics coordinator, Other
• What systems hold your shipment and exception data today (TMS, ERP, spreadsheets, carrier portals)? Options: TMS, ERP, Carrier portals, Custom spreadsheet, Other
• On average, how long from exception detection to resolution for high‑impact issues (e.g., customs hold, demurrage)? Options: <24 hours, 1–3 days, 4–7 days, 1–2 weeks, 2+ weeks
• Tell us about a recent exception that still frustrates you: what broke, who owned it, and what was its downstream impact?

What would a successful trial actually prove?

• If one pilot shipment could prove your supplier/provider selection was right, what single outcome would convince you? Options: Transit time reliability, Zero documentation errors, No detention/demurrage, Clear exception handling, Total landed cost visibility
• Which trade lane would you pick for a trial and why (volume, pain, strategic importance)?
• What are the non‑negotiable success metrics for that trial (choose up to three)? Options: On‑time arrival %, Documentation accuracy %, Customs clearance time, Transit time variance (days), No demurrage/detention, Total cost vs baseline
• What’s an acceptable transit window and variability for that lane (e.g., 18±2 days)?
• What maximum incremental cost (if any) would you accept for a trial that demonstrably reduces exceptions? Options: No increase, Up to 3% premium, 3–7% premium, 7–15% premium, Depends on ROI/terms
• How will you operationally validate documentation accuracy and exception handling during the pilot (who inspects, what evidence do you need)?

Imagine 'no surprises' — what ownership looks like

• If exceptions stopped costing you time and money for 90 days, what would change in your day‑to‑day work?
• Which services must be included per lane for you to feel covered: forwarding, customs brokerage, port agency, inland transport, warehousing, or other? Options: Forwarding, Customs brokerage, Port agency, Inland transport, Warehousing, Insurance, Other
• For each included service, who should be the accountable owner on our side vs yours?
• What SLA targets would give you confidence (e.g., docs accuracy >99%, customs clearance <24–48 hours after arrival)?
• Describe the onboarding tasks that absolutely must be completed before first live load (e.g., customs registration, EDI/FTP feed, proof of insurance).
• Which contingency plans do you expect for major port disruptions (alternate ports, modal shifts, expedited customs lanes)? Options: Alternate port options, Air uplift contingency, Priority customs channel, Temporary warehousing, Expedited inland transport

Red lines — constraints, compliance, and deal breakers

• What regulatory or trade compliance constraints are non‑negotiable for you (e.g., ISF/ENS timings, embargoes, bonded procedures)?
• Are there specific documentation, data‑sharing, or security standards we must meet (e.g., EDI, encrypted SFTP, SOC2, ISO)? Options: EDI/EDIFACT, API/JSON feeds, Encrypted SFTP, SOC2 compliance, ISO standards, None
• What insurance, liability, or claims limits are required for new providers?
• Are there contractual constraints that would immediately stop a deal (length of lock‑in, exclusivity, audit rights, data residency)? Options: Contract length >1 year, Exclusivity clauses, No audit rights, Data residency mandates, Other
• How sensitive are you to sharing booking and cost data with a new partner during evaluation? Options: Comfortable sharing full data, Share anonymized/aggregated data, Share only on NDA, Uncomfortable sharing currently
• Has your organization failed a customs or compliance audit in the past 3 years? If yes, what was the issue and is it resolved? Options: No, Yes — resolved, Yes — ongoing

Mapping the first 90 days — realistic milestones and owners

• Given your priorities, which timeline feels realistic to run a pilot, finalize commercial terms, and go live? Options: Pilot in 2–4 weeks; go‑live 6–8 weeks, Pilot in 4–8 weeks; go‑live 2–3 months, Pilot in 2–3 months; go‑live 3–6 months, Longer (6+ months)
• Which internal resources will you commit to onboarding (names/titles): ops lead, IT integrator, customs contact, procurement sponsor?
• What integrations or data feeds are required for trial and go‑live (TMS, ERP, carrier EDI, customs portal)? Options: TMS, ERP, Carrier EDI/portal, Customs portal/API, SFTP/FTP, None
• Who will be our day‑to‑day operational contact during the pilot, and who escalates commercial issues?
• What are your hard go/no‑go criteria after the pilot (specific metrics, stakeholder approvals, or budget signoffs)?
• What training or documentation would your team need to operate smoothly after handover? Options: How‑to playbooks, Dedicated onboarding sessions, Recorded training modules, On call support for X days, Other

Are you ready — next steps, risks, and commitments

• If we can meet your top three success criteria in a pilot, how likely are you to move forward with us? Options: Very likely, Somewhat likely, Unsure, Unlikely
• What remains the single biggest obstacle to running a pilot within your desired timeline?
• How would you prefer we communicate progress during pilot and onboarding (weekly calls, async updates, dashboard access)? Options: Weekly calls, Bi‑weekly calls, Asynchronous updates (email/slack), Shared dashboard access, Other
• Which executive or stakeholder should we include in a one‑pager that summarizes pilot scope and success metrics?
• When would you like us to present a proposed pilot plan (date or time horizon)? Options: Within 1 week, 1–2 weeks, 2–4 weeks, 1–2 months, Flexible
• What would make you feel confident enough to say 'let’s run the pilot' today?

Opening: Show Us Your Shipping Picture

• Which trade lanes do you currently operate on (pick all that apply)? Options: Asia → North America, Asia → Europe, Europe → North America, Latin America → North America, Intra-Europe/Regional, Africa → Europe/North America, Other (please specify)
• Roughly how many ocean shipments (TEU equivalents or bills of lading) do you move across all lanes each month? Options: 0–50, 51–200, 201–500, 501–1,000, 1,001–2,500, 2,500+
• Who in your organization is primarily responsible for managing each lane day-to-day? (role names and approximate split)
• Who are the top 3 carriers/forwarders/agents you use today (by lane if it varies)?
• Which shipment types represent most of your volume? Options: 20ft/40ft containers, Bulk (dry/liquid), Breakbulk/project cargo, Reefer/temperature controlled, Mixed
• If you could pick one word to describe your current confidence in your end-to-end ocean shipments, what would it be? Options: Confident, Wary, Overwhelmed, Under-resourced, Optimistic

Are We Stuck Accepting What’s Normal?

• What recurring logistics problems have you learned to tolerate as 'just the way it is'?
• How often do those problems reoccur—weekly, monthly, quarterly, or seasonally? Options: Weekly, Monthly, Quarterly, Seasonal/Peak only, Rarely
• When these issues occur, which of the following impacts do you see most often? Options: Demurrage/detention charges, Production stoppage/downstream delays, Customer service escalations, Unexpected freight cost increases, Inventory shortages
• How long have you been accepting these issues before attempting a systemic fix? Options: Less than 6 months, 6–12 months, 1–3 years, 3+ years
• What emotional impact do these persistent issues create for your team or leadership (frustration, distrust, fatigue, other)?
• What attempts have you made to solve these problems previously, and why do you think they didn’t stick?

Where the Paperwork Trips You Up

• How frequently do documentation errors (B/L discrepancies, incorrect HS codes, missing certificates) cause clearance delays? Options: Almost always, Often, Sometimes, Rarely, Never
• Who prepares and validates your shipping documentation today? Options: Internal ops team, Internal trade compliance, Third-party customs broker, Carrier/forwarder, Hybrid — multiple parties
• Which documentation types cause the most friction in your lanes? Options: Commercial invoice, Packing list, Bill of lading, Certificates of origin, Phytosanitary/health certificates, Dangerous goods docs, Other
• Do you use structured data transfers (EDI/API) for bookings and docs or rely mostly on emailed PDFs? Options: Full EDI/API integrations, Partial EDI/API + emails, Mostly emailed PDFs/manual docs, Not sure
• Tell us about a recent documentation failure—what happened, how was it discovered, and how long to resolve?
• If documentation accuracy improved tomorrow, what operational or financial outcomes would change for you?

When Things Break: Failure Modes and Fallout

• If you had to name the single failure mode that causes the biggest recurring cost or disruption today, what would it be?
• Which of these failure modes have you experienced in the last 12 months? Options: Demurrage/detention, Customs holds/inspections, Misrouting/container on wrong vessel, Carrier schedule reliability, Container/container damage, Incomplete inland handoffs
• When a failure occurs, how quickly do you detect it on average? Options: Within hours, Within a day, 2–3 days, A week or more, Only when billable charges appear
• What’s your average time-to-resolution once a problem is detected? Options: <24 hours, 1–3 days, 4–7 days, 7–21 days, Longer than 21 days
• Who usually ends up owning the resolution—internal team, carrier, broker, port agent, or a combination? Options: Internal ops, Carrier, Customs broker, Port/terminal agent, Multi-party collaboration
• Approximate annual cost impact from these failures (demurrage, re-books, expedited fees, claims)? Options: <$10K, $10K–$50K, $50K–$200K, $200K–$1M, $1M+

Who Pulls Which Levers (and What Gets Dropped)

• Do you have a clear RACI (or equivalent) for booking, documentation, customs, and inland moves? Options: Yes — documented and followed, Yes — documented but inconsistently followed, Informal/implicit, No
• Which internal and external contacts should we know as primary escalation points for each lane?
• Are there contractual SLAs with carriers/forwarders today? If so, what are the consequences when SLAs are missed? Options: Yes — financial penalties, Yes — service credits, Yes — informal expectations, No SLAs
• How does your team typically escalate an exception that threatens a shipment’s timely release? Options: Standard ops escalation process, Ad-hoc emails/calls, Dedicated 24/7 desk, No clear escalation path
• What decisions do you wish were owned by a single accountable party rather than split across teams?

How You Measure Success — And Where Reality Misses the Mark

• Which KPIs are tracked today and are most visible to leadership (pick all that apply)? Options: On-time arrival, Transit time variance, Documentation accuracy rate, Dwell at port/terminal, Demurrage/detention spend, Claims rate, Customs clearance time
• For the KPIs you track, what are your typical current values versus target goals (give lane-level where possible)?
• How often do you receive performance reporting (daily, weekly, monthly, on-demand)? Options: Daily, Weekly, Monthly, Quarterly, On request
• Which KPI, if improved by 20%, would deliver the biggest business benefit in the next 12 months? Options: On-time arrival, Documentation accuracy, Dwell time reduction, Demurrage reduction, Faster customs clearance
• How confident are you in the data feeding your KPIs (accurate, partially accurate, poor, unknown)? Options: High confidence, Moderate confidence, Low confidence, Don't know

If You Could Snap Your Fingers — What Would Change?

• If you could eliminate one persistent headache overnight, what would it be and why would it matter?
• For a successful trial shipment on a priority lane, which of the following outcomes would prove value to you? Options: On-time arrival within agreed window, Zero documentation exceptions, No detention/demurrage events, Faster customs clearance than baseline, Total landed cost below threshold
• What transit time window and cost threshold would you accept on a trial to consider it successful?
• Which stakeholders must be signed off on trial success (roles and decision criteria)?
• How would you like lessons from a trial captured and turned into operational changes (playbooks, shared dashboards, weekly reviews)? Options: Playbooks/SOPs, Shared performance dashboard, Weekly review meetings, Onboarding checklist updates, All of the above

Quick Inventory: Systems, Data, and People We’ll Need

• Which core systems do you use today to manage shipments and data? Options: TMS (name), ERP (name), WMS (name), Customs portal, Manual spreadsheets, Other — please list
• Do you have existing EDI/API connections with carriers, brokers, or terminals that we can leverage? Options: Yes — multiple active integrations, Partial connections (some carriers), No — mostly manual, Unsure
• Can you provide sample shipping documents (BL, commercial invoice, packing list) and a sample customs filing we can review? Options: Yes — readily available, Yes — with lead time, No
• Who are the people we’ll need access to for a trial (names, roles, best contact method)?
• Are there regulatory or compliance constraints (special licenses, restricted goods, bonded warehouses) that would affect a trial? Options: Yes — significant constraints, Some constraints but manageable, No constraints, Unsure

Small Bets, Big Signals: How We Start

• What is the smallest, fastest experiment (lane + shipment count) that would convince you to proceed to onboarding?
• Which lane would you choose for a trial and why (commercial importance, trouble hotspot, or ease of control)?
• What timeline feels realistic to launch a trial from contract to first shipment? Options: <2 weeks, 2–4 weeks, 1–2 months, 2–3 months
• What blockers must be removed before a trial can start (data access, stakeholder sign-off, sample documents, customs registrations)?
• How will you judge whether the trial warrants scaling—what 2–3 metrics must we hit?
• Who needs to be in the kickoff meeting to make decisions quickly during the trial?

Start Here: A Quick Snapshot of Your Role and Scope

• Tell us your name, title, and the trade lanes you actively manage (e.g., Asia→North America, Europe→Africa).
• Roughly how many ocean shipments does your team move each month across all lanes? Options: Under 50, 50–200, 201–500, 501–1,000, Over 1,000
• Which best describes your current freight model? Options: Single primary forwarder/carrier, Multiple forwarders managed in-house, Mix of carriers and spot forwarders, In-house coordination with ad-hoc brokers, Other
• Which internal teams do you coordinate with regularly for ocean shipments? Options: Procurement, Operations/Warehouse, Trade Compliance/Customs, Finance/Accounts Payable, Sales/Customer Service, Other
• If there’s one quick thing we should know about your current situation, what is it?

Are We Just Paying Demurrage and Calling It 'Normal'?

• How often do late arrivals, customs holds, or documentation errors cause measurable cost impacts (detention, demurrage, fines)? Options: Weekly, Monthly, Quarterly, Rarely, Never
• Can you quantify the typical monthly cost impact when exceptions occur (select range)? Options: Under $1,000, $1k–$10k, $10k–$50k, $50k–$200k, Over $200k
• Tell us about a recent shipment that went wrong—what happened, and what were the downstream consequences?
• When these problems happen, whose day gets disrupted the most inside your organization? Options: Operations, Procurement, Trade Compliance, Warehouse/Receiving, Customer Success, Finance
• How long have you been tolerating these kinds of issues before actively looking for a change? Options: Less than 3 months, 3–6 months, 6–12 months, Over a year, Ongoing for years

Who Really Owns the Decision When Things Go Sideways?

• When a carrier delay or customs hold threatens a critical shipment, who is the final decision-maker for rerouting, paying charges, or escalating claims? Options: Supply Chain Director, Logistics Manager, Trade Compliance Officer, Procurement Lead, C-Level (VP/Director), No single owner
• List the people or roles we should include in escalation and onboarding conversations (names or titles).
• How long does your internal approval cycle typically take for urgent logistics decisions (e.g., reroute, pay demurrage)? Options: Same day, 1–3 days, 4–7 days, Over a week, Varies widely
• What keeps decision-makers from acting faster when exceptions arise—process, budget, visibility, or something else? Options: Lack of data/visibility, Budget/authorization friction, Unclear roles, Fear of liability, Other
• How would you feel if we proposed a named escalation owner and SLA-backed response times for exceptions? Options: Relieved, Cautious but optimistic, Skeptical, Not interested

Where Paperwork Becomes the Bottleneck (and Why It Feels Personal)

• Which documents most frequently cause holds or delays for your shipments? Options: Commercial Invoice, Packing List, Bill of Lading, Certificates of Origin, Import/Export Licenses, Other
• How often do documentation errors lead to a customs hold or rejected entry? Options: Always, Often, Sometimes, Rarely, Never
• Describe the current process for preparing and validating shipping documentation—who does what and what tools do they use?
• What technical systems do you rely on for documentation and filing (ERP, TMS, customs portal, spreadsheets)? Options: ERP (e.g., SAP/Oracle), TMS, Customs broker portal, EDI integrations, Manual spreadsheets, Other
• If we could eliminate one recurring documentation failure for good, which would deliver the biggest relief and why?

If a Trial Shipment Delivered Perfectly, What Would Actually Change?

• What measurable signals would convince you the trial was successful (choose up to three)? Options: On-time arrival, No customs holds, Zero documentation errors, Lower total landed cost, No detention/demurrage, Fast customs clearance
• What specific KPI thresholds would you need to see for us to consider the trial a win (e.g., on-time ≥ 95%)?
• Beyond KPI numbers, what operational or organizational change would make you feel confident to roll this service out more broadly?
• Who needs to sign off on trial success internally, and what decision criteria do they use?
• How would you prefer we demonstrate reliability during the trial—real-time dashboards, daily standups, or an after-action report? Options: Real-time dashboard access, Daily check-in calls, Detailed after-action report, Weekly summary emails, Combination

What Would Make Onboarding Feel Safe — Not Like a Leap Off a Cliff?

• What are your biggest fears about onboarding a new maritime logistics partner? Options: Disruption to existing flows, Hidden costs, Loss of control/visibility, Extended downtime, Customs compliance mistakes, Other
• Which of these pre-deployment items are already in place for the lanes you want to trial? Options: Company customs registration complete, EORI/Importer numbers ready, EDI/API data feeds active, Assigned contacts at carriers/terminals, No pre-registration done
• Who will own the internal onboarding tasks on your side (systems, user access, approvals)? Options: Logistics Manager, IT/Integration Lead, Trade Compliance, Procurement, Other
• How much IT integration are you willing to commit to for a pilot—full EDI, batch file exchange, or manual upload? Options: Full EDI/API, Batch file transfers, Secure manual uploads, Minimal/no integration
• What timeline feels realistic for onboarding the trial lane end-to-end (from paperwork to first shipment)? Options: Less than 2 weeks, 2–4 weeks, 1–2 months, Over 2 months

When the Port Chokes, Who’s Got the Playbook?

• Do you currently have contingency plans for major port disruptions (strikes, closures, weather, canal delays)? Options: Yes, detailed playbook, Yes, informal plans, No formal plans, We rely on carriers
• If a port disruption affected a priority lane, what is the maximum time your operation can tolerate before critical impact occurs? Options: 24 hours, 48–72 hours, 4–7 days, Over a week
• Which mitigation strategies would you prefer we prioritize during disruptions? Options: Alternate routings/carriers, Expedited customs clearance, Temporary warehousing, Port-to-door intermodal solutions, Cost-sharing/claims management
• Describe a past disruption where the response worked well—or failed spectacularly—and what you learned.
• How important is contractual clarity around disruption responsibilities when you evaluate a partner? Options: Critical, Important, Nice to have, Not important

How Will You Decide — Metrics, Money, or Momentum?

• What is the single most important criterion you use to choose a freight forwarder or port services partner? Options: Transit-time reliability, Documentation accuracy, Total landed cost, Claims history, Customer support/response time, Other
• Which procurement or contracting hurdles typically slow down final mutual commitment? Options: Insurance and liability terms, SLA clarity, Payment terms, Service scope ambiguity, Integration requirements
• What is your expected timeline to move from a successful trial to a signed contract and scaled rollout? Options: Immediately after trial, Within 1–3 months, 3–6 months, Longer/uncertain
• Who in procurement/finance needs additional assurances before approving ongoing spend for a new logistics partner?
• If we offered an SLA-backed pilot with a clear claims process, would that materially change your willingness to sign? Options: Yes, definitely, Possibly, Unlikely, No

Signals You'll Hold Us To — Reporting, Claims, and the Little Things

• Which KPIs do you need visible in a dashboard to trust us day-to-day? Options: On-time arrival, Customs clearance time, Documentation error rate, Detention/demurrage events, Claims open/closed, Cost variance vs. baseline
• How often do you want performance updates during the trial and after go-live? Options: Real-time, Daily, Weekly, Monthly, On-demand
• Describe your ideal claims resolution timeline and the level of visibility you expect during a claim.
• What format of evidence or reporting helps your finance team close the books faster after a claim or exception? Options: Standardized PDF reports, CSV export for ERP, API data feed, Detailed incident reports
• What ongoing governance cadence would make you feel confident—monthly business reviews, quarterly performance reviews, or something else? Options: Monthly business review, Quarterly review, Ad-hoc reviews for issues, Combination

Next Steps — What Would Help You Say Yes?

• After this conversation, what immediate information would you like from us to move forward (pricing, SLA draft, trial plan, references)? Options: Pricing, SLA draft, Trial execution plan, Customer references, Integration checklist
• Who else should be invited to the next meeting to keep momentum?
• What would make you feel most reassured about running a pilot with us—to the point you’d commit calendar time now?
• How soon would you be willing to schedule a kickoff call to plan the trial lane? Options: This week, Next 2 weeks, Within a month, Later—need more prep
• Any final concerns or boundary conditions we should know before proposing a trial plan?

Quick Intro: Where This Conversation Starts

• Tell us briefly: what products or SKUs do you ship by sea and which 1–3 trade lanes are highest priority right now?
• Which of these cargo types best describes most of your ocean shipments? Options: Standard containerized (FCL/LCL), Breakbulk/project cargo, Dry bulk, Liquid bulk/chemical, Refrigerated (reefer)
• How many ocean shipments (containers or vessel loads) do you average per month today? Options: 0–10, 11–50, 51–200, 201–500, 500+
• Who should we include from your side in follow-ups (roles/titles)? Options: Supply Chain Director, Logistics Manager, Trade Compliance Officer, Procurement Manager, Operations/Plant Lead, Other

Who Holds the Keys? (Decision Roles & Timelines)

• If your current procurement process cost you an extra two weeks of lead time, who would notice first and who would have to approve changes?
• Which internal stakeholders must sign off on a new freight-forwarding partner? Options: Procurement, Supply Chain/Logistics, Finance, Operations/Plant, Trade Compliance/Customs, C-Suite
• What is the typical decision timeline for selecting a new logistics provider? Options: Immediate (weeks), 1–2 months, 3–6 months, 6+ months
• What non-negotiable controls or certifications must a partner have (e.g., ISO, AEO, C-TPAT)? Options: Customs broker license, AEO/Trusted Trader status, ISO 9001/14001, Cargo insurance limits, Security clearances, Other
• Who in your organization owns demurrage/detention costs when they occur? Options: Logistics, Finance, Operations, Shared/Depends case-by-case

Where Your Cargo Lives Today (Real Operational Mapping)

• Which single trade lane creates the most operational friction for you right now?
• For that lane, describe the typical routing and partners involved (carrier, port, terminal, customs broker, inland hauler).
• Which parts of the end‑to‑end flow are currently measured and reported to your team? Options: Gate-in time, Vessel ETAs/ETDs, Customs clearance time, On-time delivery to door, Demurrage/detention days, Claims frequency
• What systems hold your shipment data today? Options: TMS, ERP, Spreadsheets, Carrier portals, Custom broker systems, Other
• How confident are you that the documentation being submitted for customs is complete and accurate across lanes? Options: Very confident, Somewhat confident, Occasionally issues, Often inaccurate

What’s Really Breaking the Chain (Acute Pains & Repeats)

• When shipments are delayed, who ultimately bears the cost and how visible is that impact?
• Which failure modes crop up most often (select all that apply)? Options: Documentation errors, Customs holds/audits, Port congestion, Carrier rollovers/cancellations, Inland pickup delays, Cargo damage/loss
• How frequently do you record demurrage or detention charges in a typical quarter? Options: Never, Rarely (1–2), Several times (3–6), Monthly or more
• Tell us about a recent incident that caused excess cost or supply disruption—what happened and what was the real business impact?
• When exceptions happen, how satisfied are you with the visibility and response time from your current providers? Options: Very satisfied, Somewhat satisfied, Not satisfied, We lack measurable visibility

The Assumptions We Keep Making (Hidden Beliefs)

• What if your 'trusted' forwarder is the reason delays persist—how would that change internal priorities?
• Which commonly accepted trade-offs are you most tired of (cheaper rates vs. reliable documentation, speed vs. cost, single carrier dependency)? Options: Cheaper rates over reliability, Single carrier dependency, Limited EDI/integration, Ad-hoc exception handling, Manual paperwork tolerance
• How often do you accept manual workarounds (spreadsheets, ad‑hoc phone calls) instead of automating flows? Options: Almost always, Often, Sometimes, Rarely
• What internal processes do you assume are 'good enough' but worry might be masking larger risk?

What Would ‘No Surprises’ Actually Feel Like?

• Imagine your next 30 shipments arrived on time with complete paperwork—what immediate business outcomes would that unlock?
• Which KPIs would prove the partnership is meeting expectations? (pick top three) Options: On-time arrival %, Documentation accuracy %, Customs clearance time, Demurrage/detention days, Claims rate, Total landed cost variance
• What is your target on‑time arrival rate that would feel like an upgrade? Options: 95%+, 90–95%, 85–90%, <85%
• Beyond metrics, how would you describe the cultural or emotional difference in working with an ideal provider?
• If we could guarantee documentation accuracy for trial shipments, what internal approvals would that unlock for a wider rollout?

Testing the Promise: What a Meaningful Trial Looks Like

• If we ran a trial on one lane, what single outcome would make you call it a success instead of 'interesting'?
• Which lane should we prioritize for a trial based on strategic impact and feasibility? Options: Inbound from Asia, Outbound to Europe, Latin America lane, Intra‑regional short haul, Other
• What are the minimum acceptance criteria for a trial shipment (select all that apply)? Options: On-time gate-in/arrival, Correct customs docs submission, No demurrage/detention, Accurate delivery to inland site, Full EDI timestamps
• How long of a trial period would give you confidence (number of shipments or weeks)? Options: 1–3 shipments, 4–10 shipments, 30 days, 60–90 days
• Who on your team will be the day‑to‑day point of contact during a trial?

Operational Reality Check: Systems, Data & Handoffs

• Where do your handoffs most often fail: data exchange, physical transfer, or commercial clarity? Options: Data exchange (EDI/API), Physical handoff (terminals/inland), Commercial responsibilities, Customs documentation, Other
• Which systems must integrate for effective operations (pick all that apply)? Options: TMS, ERP, WMS, Customs/broker platform, Carrier portals, E‑commerce/OMS
• How would you rate your team's ability to produce timely, accurate shipment documentation today? Options: Excellent, Good, Inconsistent, Poor
• Do you have standard SLAs or playbooks for exception handling? If yes, how often are they followed? Options: Yes — always followed, Yes — sometimes followed, No formal SLAs, We have them but they’re outdated
• What data points would you want visible in real time for every high‑priority shipment? Options: Gate-in/ETA/ETD, Customs submission/clearance status, Container status & photos, Exception alerts, Carrier/terminal contact details

Barriers to Change: Political, Financial & Cultural

• What's the single internal force most likely to stop a successful go‑live even if the trial succeeds?
• Which commercial concerns would block approval (contract length, liability terms, billing cadence)? Options: Contract length, Liability/claims terms, Pricing transparency, Billing frequency, Currency/payment terms
• How does your finance team prefer to see demurrage and detention accounted for (absorbed by carrier, billed monthly, disputed case-by-case)? Options: Absorbed by carrier/3rd party, Billed and disputed later, Allocated to business unit, Other
• What organizational changes would be required to scale a new provider across multiple lanes?
• Who would champion the change internally and who is likely to resist?

Commitments That Matter: Timing, Visibility & Risk Controls

• If we walked away today, what's the one operational risk you'd most regret not addressing?
• What onboarding timeline is realistic for you to be ready for a limited go‑live? Options: 2–4 weeks, 1–2 months, 2–3 months, 3+ months
• Which onboarding items are non‑negotiable before go‑live (select all that apply)? Options: Customs registrations complete, EDI/API connections active, SLA and claims process agreed, Staff trained, Contingency plans in place
• What level of reporting cadence would you expect during trial and first 90 days (daily, weekly, KPI dashboard)? Options: Daily exceptions, Weekly summaries, Real-time dashboard, Monthly review
• What risk mitigations would make leadership comfortable to proceed (caps on exposure, pilot-only liability, escrowed funds)?

Final Question: What Would Make This Partnership Irresistible?

• If we could guarantee one thing for the first three months, what should it be to make you feel this was the right decision?
• Are there quick wins we could deliver in the first 30 days that would prove value? Options: Faster customs clearance, Reduced documentation errors, One‑lane transit reliability, Lower demurrage exposure, Improved visibility
• Realistically, when would you be prepared to start a trial if terms and resources align? Options: Immediately, Within 30 days, 1–2 months, Later than 2 months
• Who else should we loop in now to accelerate decisions and execution?