Who’s in the Room?

• Who is our primary sponsor for this travel program conversation? Options: CFO, Head of Travel / Travel Manager, Procurement Director, Head of HR, COO, Other (please name), Unsure / Multiple
• Which functions should we expect to consult with during evaluation and why? Options: Finance, HR / People Ops, Procurement, Legal, IT, Travel Operations, Safety / Security, Business Unit Leaders, Other (please name)
• Who will be our day-to-day contact and who is the final decision authority (names and titles please)?
• How would you describe the level of executive sponsorship right now? Options: Executive champion actively involved, Sponsor identified but lightly involved, No executive sponsor yet, Multiple competing sponsors, Unsure
• If you had to pick one person who will block the decision, who is it and what’s their main concern?

Are Decision Makers Truly Aligned — or Just Cordoned Off?

• Which function currently holds final budget sign-off for travel programs, and has that ever changed recently? Options: Finance, Procurement, Business Unit CFOs, Corporate Travel / Ops, HR, Shared across functions, Changed recently, Unsure
• Where have you seen misalignment between stakeholders derail travel or vendor decisions in the past 18 months?
• When competing priorities arise (cost vs. employee experience vs. duty-of-care), how are trade-offs typically decided? Options: Finance-led tradeoff, Procurement negotiates, Executive steering committee, Ad-hoc by sponsor, No formal process
• Describe an example where a decision was delayed because teams couldn’t agree—what was the cost (time, dollars, risk)?
• What signals would you need to see from other stakeholders to feel comfortable moving forward? Options: Signed memo of support, Budget approval, Legal terms approved, Pilot sign-off from Travel Ops, HR safety plan confirmed, Other (please specify)

What Would ‘Success’ Make You Feel Like?

• If this program hit its goal, which outcome would you celebrate first — lower cost, compliance, faster response to incidents, or something else? Options: Net savings / reduced spend, Higher policy compliance, Improved traveler safety/location accuracy, Faster expense reconciliation, Improved employee satisfaction, Other (please specify)
• Choose the measurable success metrics you’d expect us to track during a pilot or rollout. Options: % policy compliance, Average cost per trip, Savings captured vs baseline, Time to locate traveler, Expense reconciliation time, Traveler NPS, Duty-of-care incident resolution rate, Other (specify)
• Which single metric must improve for this program to be considered a success by Finance? Options: % savings vs baseline, Reduced travel variance month-to-month, Lower cost per trip, Improved cashflow timing, Other (please specify)
• What are the quantitative targets you’d set for your top 2 metrics (numbers or ranges please)?
• Beyond metrics, how would you describe the emotional or cultural shift that success would create in your organization?

What Keeps Finance Up at Night?

• How visible is travel spend today in your financial systems? Options: Line-level visibility in ERP, Aggregated but delayed, Fragmented across cards/expense tools, Mostly unknown / estimates, Unsure
• Estimate the annual travel spend under management today and any material leakage percentage you suspect.
• Which spend categories drive most of your travel cost (air, hotels, ground, per diems, other)? Options: Airfare, Hotels, Ground transportation, Taxis / rideshare, Meals / per diem, Other (specify)
• What internal controls or approvals are required now before travel is booked or expensed? Options: Manager approval, Budget owner approval, Pre-trip approvals for certain roles, No consistent approvals, Other (describe)
• What minimum ROI or payback period would Finance expect for a program like this? Options: <3 months, 3–6 months, 6–12 months, 1–2 years, Other / Unsure
• How do unexpected travel costs (cancellations, last-minute bookings) typically get handled financially?

HR & Duty-of-Care: How Scared Are You?

• How confident are you that you can locate and contact employees within two hours during a travel disruption? Options: Very confident, Somewhat confident, Not confident, We have never tested this
• Have you experienced a duty-of-care incident (medical, natural disaster, security) where locating employees was a challenge? Tell us what happened.
• Which traveler data sources do you currently rely on for safety (corporate booking system, expense reports, HR database, mobile app check-ins, none)? Options: Corporate booking system, Expense system, HR system (work location), Traveler-provided itineraries, Mobile location app, None
• What is your acceptable failure rate for locating a traveler during an incident (percentage)? Options: 0%, <1%, 1–5%, 5–10%, >10%
• How does HR want to balance traveler privacy vs. ability to locate people in emergencies? Options: Pro-privacy, limited location, Balanced with clear consent, Prioritize locating in emergencies, Undecided / needs policy

Procurement’s Line: Process, Policies, and Red Lines

• What procurement steps must a supplier complete before contracting (RFP, security review, vendor risk assessment, reference checks)? Options: RFP / RFQ, Security assessment, Legal review, Vendor risk / compliance check, Reference checks, Sole-source allowed, Other (specify)
• Are there mandatory supplier terms you cannot accept (data residency, indemnity caps, audit rights, SLAs)? Options: Data residency, Indemnity limits, Audit rights, SLA penalties, Publicity / references, Other (specify)
• Which contracting model does procurement prefer for this category? Options: Annual subscription, Transaction-based (per booking), Volume-tiered, Master services + statement of work, Hybrid
• Typical procurement cycle time from SOW to signed contract? Options: <2 weeks, 2–4 weeks, 1–2 months, 2–3 months, >3 months
• What would immediately be a non-starter for Procurement on a travel program?

Travel Ops’ Truths: The Day-to-Day That Nobody Sees

• What operational tasks consume the most Travel Ops time today (booking support, emergency response, reconciliation, supplier issues)? Options: Booking support, Emergency / traveler assistance, Expense reconciliation, Supplier management, Reporting / analytics, Other (specify)
• What tools or manual processes cause the most frustration for your ops team?
• How many full-time equivalents (FTEs) support travel operations today and is that count sustainable if travel volume grows? Options: Fewer than 1, 1–3, 4–7, 8–15, 16+
• How quickly must ops resolve a traveler assistance ticket on average to meet expectations? Options: <30 minutes, 30–60 minutes, 1–4 hours, Same day, Longer
• If we automate policy enforcement, what operational handoffs or upskilling will you need?

What’s Been Tried — and Why It Didn’t Stick

• Have you run pilots, used aggregators, or worked with travel management companies before? Which ones?
• What were the top three reasons prior efforts did not deliver expected results?
• Which stakeholder objections were hardest to overcome during those attempts? Options: Employee resistance, Procurement terms, Insufficient savings, Poor technology fit, Lack of executive support, Other (specify)
• What concrete changes would have made past initiatives successful in your view?
• What internal champions or processes existed that helped adoption at scale in the past?

Timeline, Trade-offs, and the Politics Map

• If you had to commit to a go/no-go decision date, when would that be and why? Options: Immediately, Within 30 days, 30–60 days, 60–90 days, >90 days
• What are the non-negotiable capabilities you must have at launch versus things we can phase in? Options: Managed booking with policy enforcement, Rate negotiation (supplier discounts), Expense integration, Traveler location & alerts, Reporting / savings tracking, Other (specify)
• How politically sensitive is the decision inside the company (low / moderate / high), and who are the informal influencers? Options: Low, Moderate, High
• If the decision slips, what internal or external events might cause it to be deprioritized? Options: Budget reprioritization, Leadership change, Competing projects, Economic downturn, Other (specify)
• Who needs to be visibly aligned for this to feel safe to sign? Options: CFO, Procurement, Head of HR, Travel Ops, Legal, CEO / COO

Pilot & Acceptance: Where Will We Prove the Promise?

• What business unit, region, or traveler segment would make the most persuasive pilot for your stakeholders? Options: Sales team (high travel), Field engineers, Leadership travel, Regional office (APAC/EMEA/AMER), Customer success teams, Other (specify)
• What minimum duration and sample size do you expect for a credible pilot? Options: 30 days / 50 travelers, 60 days / 100 travelers, 90 days / 200+ travelers, Other (specify)
• Which pilot success criteria will be used for acceptance (please rank top 3)? Options: % policy compliance, Net savings realized, Traveler satisfaction (NPS), Time to locate travelers, Operational workload reduction, Data / integration completeness
• Who will sign off on pilot acceptance from each function (Finance, Procurement, HR, Travel Ops)?
• What data or reports would convince Procurement and Finance that the pilot delivered on promises? Options: Detailed savings vs baseline, Booking channel mix, Compliance dashboard, Incident response logs, Expense reconciliation delta, Other (specify)

Commitment & Change: Can the Organization Actually Reset Behavior?

• How willing is leadership to require employees to use managed booking channels? Options: Mandate for all employees, Mandate for select groups only, Strongly encourage but not mandate, Not willing to require usage, Undecided
• What forms of employee resistance do you expect and why (habits, tool frustration, perceived loss of flexibility)?
• Who will own change management and communications, and do they have capacity and budget? Options: HR / People Ops, Travel Ops, Corporate Communications, Procurement, Joint team, No owner yet
• Are you open to pilot incentives or policy levers to encourage adoption (preferred rates, booking credits, enforcement rules)? Options: Yes — incentives, Yes — enforcement, Prefer education only, No incentives planned, Undecided
• Describe one internal story or belief that could undermine adoption if left unaddressed.

Final Check — Red Flags, Deal Breakers, and the Small Print

• What are absolute deal breakers that would stop you from moving forward?
• How long does your legal or compliance review typically take for a vendor contract of this size? Options: <2 weeks, 2–4 weeks, 1–2 months, 2–3 months, >3 months
• Which SLAs or penalties are non-negotiable (response time, uptime, data accuracy, traveler support hours)? Options: Response time SLA, Uptime / system availability, Data accuracy guarantees, 24/7 support, Incident resolution time, Other (specify)
• Would you consider a phased commercial commitment (pilot-first with conversion criteria) or require full contract at signing? Options: Pilot-first, convertible, Full contract required upfront, Partial commitment with options, Undecided

Start Here: A Quick Snapshot of Today

• Roughly how much does your organization spend on employee travel per year? Options: Under $1M, $1M–$5M, $5M–$20M, $20M–$50M, Over $50M, Unsure / need help estimating
• How many employees travel for work in a typical year (headcount, rough)? Options: Under 100, 100–499, 500–1,999, 2,000–9,999, 10,000+, Unsure
• Who currently owns day-to-day travel operations in your company? Options: Corporate Travel Team / TMC, Procurement, Finance, HR, Individual departments/self-booking, Mixed responsibilities
• Which single outcome feels most urgent to your leadership right now? Options: Reduce cost, Increase policy compliance, Improve duty-of-care, Streamline expense reporting, Improve traveler experience, Unsure / multiple
• If you could summarize the single biggest travel pain in one sentence, what would you say?

How Travel Really Gets Booked (Not How You Hope It Does)

• Who in your organization treats the managed travel program like an optional suggestion—and why do they get away with it?
• Estimate the percentage split of bookings across these channels today. Options: Managed corporate booking tool / TMC, Consumer OTAs (e.g., Expedia/Booking), Direct vendor sites (airlines/hotels), Expense-led bookings (receipt-only), Personal cards + reimbursement, Other
• What are the top three reasons employees bypass the managed channel? Options: Price appears lower on consumer site, Ease / habit, Mobile booking preference, Lack of awareness of policy, Approval delays, No corporate inventory for route, Preferred supplier loyalty
• How do approvers and managers typically react when presented with an out-of-policy booking? Options: Approve to avoid delay, Send back for rebooking, Escalate to procurement, Require justification, No consistent process, Other
• Tell us about a recent specific booking that skirted the program—what happened and what was the outcome?

Where Money Quietly Walks Out the Door

• What’s the single most common mechanism of negotiated-rate leakage in your program today?
• Which of these leakage types show up most in your data? Options: Out-of-policy bookings, Unused negotiated rate codes, Upgrades purchased outside contract, Split bookings avoiding corporate fares, Expense reclassifications, Duplicate bookings / cancellations
• Roughly what percent of theoretical negotiated savings do you think is being captured today? Options: Under 10%, 10%–30%, 30%–50%, 50%–70%, Over 70%, Don't know
• Which supplier categories are most often outside the negotiated program? Options: Domestic airlines, International airlines, Chain hotels, Independent hotels, Ground transportation / rideshare, Short-term rentals (Airbnb), Other
• Share an example of a recent negotiation gap or supplier behavior that cost you money.

Expenses: Trails, Gaps, and Mystery Charges

• How often do expense reports contain charges that have no matching booking record? Options: Almost always, Often, Sometimes, Rarely, Never, We don't track this
• What are the most common mismatches between booking and expense data? Options: Different traveler names, Different dates/times, No booking reference, Personal vs business mix, Incorrect merchant categorization, Multiple receipts for same trip
• Who is responsible for reconciling travel spend vs. bookings today? Options: Finance (accounts payable), Travel operations / TMC, Procurement, Department managers, No one / ad hoc
• On average, how long does it take to close a travel expense reconciliation (days)? Options: Under 7 days, 7–14 days, 15–30 days, 30–60 days, Over 60 days, We don't have an SLA
• Describe a time an expense issue revealed a larger control or policy failure—what did you learn?

When Duty-of-Care Becomes a Risk, Not a Checkbox

• If a regional emergency occurred right now, how confident are you in locating every traveler within 24 hours? Options: Very confident, Somewhat confident, Not confident, No visibility at all, Unsure
• Which traveler data points are reliably available to you in real time? Options: Current location / last known lat-long, Upcoming itinerary, Emergency contact, Medical / special needs flags, Mobile device contact, None of the above
• Have you experienced a situation where you couldn't contact or locate a traveler? What happened and what was the impact?
• What systems and processes trigger traveler outreach during disruptions? Options: Automated alerts from booking tool, Manual outreach by travel team, HR-led check-ins, Security partner notifications, No formal process
• What would make you feel decisively safer about your duty-of-care capability? Options: Real-time location feeds, Centralized traveler roster, Automated mass notifications, 24/7 traveler support desk, Stricter managed-booking mandates

Data Flows: Is Your Information Plumbing or a Paper Trail?

• How many times does booking data change hands (systems or teams) before finance recognizes the spend? Options: 1–2 handoffs, 3–4 handoffs, 5+ handoffs, Unknown / ad hoc
• Which systems are involved in the travel-to-pay flow today? Options: TMC / booking tool, Expense management system, ERP / AP, HRIS, Security platform, BI / reporting tool, Manual spreadsheets
• Do you have automated feeds from booking systems into expense or finance systems? Options: Yes — real-time, Yes — batched nightly, Partially / some routes only, No, Unsure
• What key data fields fail most often during integrations (examples: PNR, corporate card ID, cost center)?
• If you could fix one data flow today, which would it be and why?

Policy Compliance: Why Rules Slip and How That Feels

• Which part of your travel policy do employees treat as guidance rather than a rule? Options: Airfare routing/fare class, Hotel class or brand, Ground transport choices, Advance booking windows, Class of service (e.g., business vs economy), Other
• How do employees learn about policy updates today? Options: Email, Intranet / portal, Manager communication, Training sessions, Never / ad hoc
• What consequences, if any, exist for repeated out-of-policy bookings? Options: None, Manager coaching, Cost recovery / denial of reimbursement, Disciplinary action, Case-by-case
• How do you currently measure policy compliance and how often is that reported to leadership? Options: Automated weekly dashboard, Monthly manual reports, Quarterly reviews, Ad hoc analysis, We do not measure
• Share a story where a policy change improved compliance — what made it stick?

The Friction Points That Stop Adoption

• What single user experience problem causes employees to abandon the managed booking channel most often?
• Which of these UX issues come up most in feedback? Options: Slow mobile experience, Limited inventory or rates, Complex approval flows, Lack of preferred suppliers, Poor integration with calendar/expense, Confusing corporate discount application
• How important is mobile-first booking for your traveler population? Options: Critical, Very important, Somewhat important, Not important, Unsure
• Who inside the organization is currently championing travel program adoption? Options: CFO, Head of Travel, Procurement Director, HR Leader, Regional Managers, No clear champion
• Describe one recent piece of traveler feedback that made you rethink an operational assumption.

Success Signals & Quick Wins That Prove Momentum

• What single KPI would convince your leadership this program is working within 90 days? Options: % bookings via managed channel, Realized negotiated savings ($), Policy compliance rate, Average time to reconcile travel spend, Traveler satisfaction score, Ability to locate travelers in crisis
• Which of these short-term wins would you prioritize for a pilot? Options: Capture leakages on a single supplier, Enforce managed booking for one business unit, Integrate booking feed into expense system, Implement traveler location feed, Run targeted training for high-frequency travelers
• What targets would you set for that pilot (e.g., % compliance lift, $ savings, SLA improvement)?
• How quickly would you expect to see measurable change after pilot launch? Options: 30 days, 60 days, 90 days, 6 months, Unsure
• Who needs to see pilot results to greenlight broader rollout? Options: CFO, Head of Travel, Procurement, HR/Legal, Business Unit Heads, All of the above

Deciding What to Fix First (Practical Roadmap)

• Which of these constraints would most limit your ability to move quickly? Options: IT integration capacity, Supplier negotiations lead time, Budget approval, Change management / adoption risk, Data quality and availability
• Who would be the hardest stakeholder to convince to change travel behavior—and what would sway them?
• If we delivered one clear deliverable in the first 60 days, which would you prefer? Options: Managed-channel routing for a priority group, Real-time booking-to-expense feed, Duty-of-care traveler roster with live locations, Savings validation report for last 12 months, Policy refresh and communication bundle
• Are there legal or compliance constraints (e.g., data residency, GDPR) that we must account for during discovery and integrations? Options: Yes — GDPR/data residency, Yes — industry-specific regs (finance/healthcare), No significant constraints, Unsure / need to confirm
• What would success look like at 6 months—give us three specific, measurable outcomes.

Quick Snapshot: Where Are We Right Now?

• How ready would you say the program is for deployment today? Options: Fully ready, Mostly ready (minor gaps), Partially ready (several gaps), Not ready
• Who on your team is the single owner for launch readiness and final sign-off?
• What's your target go-live date and how fixed is that timeline? Options: Fixed — must meet date, Preferable — some flexibility, Soft target — flexible, No target yet
• If I asked for the top three items we must complete before launch, what would you list?

If Launch Fails, Who’s Looking Bad?

• Imagine the pilot slips or fails — who inside your organization will feel the immediate pressure (titles/roles)?
• How would a missed launch affect the CFO’s or travel manager’s priorities for the next quarter? Options: Reallocated budget, Program de-prioritized, Leadership review, No major change, Other
• What reputational or operational consequences worry you most if bookings or duty-of-care visibility are unreliable after launch?
• Who are your internal escalation contacts for vendor or traveler safety incidents during the first 90 days?

Why Are We Still Relying on Patchwork Data Feeds?

• Why do current travel and expense feeds fall short of what you need for reliable reporting?
• Which of these data feeds are required for launch and what’s their current status? Options: PNR/ticket data, Hotel booking feed, Expense feed (T&E), HR roster, Directory/SSO, None of the above
• How frequently do you need each feed to refresh for your operational needs? Options: Real-time, Hourly, Daily, Weekly, Ad-hoc
• Can you provide a sample of each feed or a data dictionary — and if not, what’s blocking that? Options: Samples available, Partial samples, No samples — internal approvals, No samples — vendor/API issues, Other
• Which data fields have historically been missing or unreliable (e.g., traveler email, mobile, cost center, PNR status)?

What Could Break When We Activate Suppliers?

• If supplier activation doesn’t go smoothly, where will the first operational gaps show up (bookings, rates, invoicing, support)? Options: Bookings/routing, Negotiated rates, Invoicing/payment, Supplier support, Traveler support
• Which supplier agreements are fully signed and which still require legal or procurement approvals? Options: All signed, Most signed, Some signed, None signed
• Do any of your suppliers require onboarding steps on their side (portal setup, credentials, testing) that could delay activation? Options: Yes — several, Yes — a few, No, Unsure
• How do you prefer to handle supplier rate shortfalls discovered during activation: renegotiate, tiered roll-out, or absorb in pilot? Options: Renegotiate, Tiered roll-out, Absorb in pilot, Other

Who Really Controls Access — and Are They Ready?

• Which identity and access method will you use for admins and travelers (SSO/SAML, OIDC, local accounts, SCIM provisioning)? Options: SSO/SAML, OIDC, SCIM provisioning, Local accounts, Other
• How mature is your team’s user lifecycle process (onboarding, role changes, offboarding) and who enforces it? Options: Mature — automated, Mature — manual, Inconsistent, Nonexistent
• Are there any compliance, security, or privacy approvals required before we can provision admin or integration accounts? Options: Yes — security review, Yes — legal/privacy, Both, No
• Would you like us to run an admin-access test window to validate permissions before pilot launch? Options: Yes — recommended, Maybe — depends on timeline, No
• Who should receive admin training first, and how many dedicated admin seats will you provision for the pilot?

Do Your People Actually Want This Change?

• What makes your frequent and infrequent travelers resist booking through managed channels today?
• How would you rate employee sentiment toward centralized booking and enforced policy? Options: Generally positive, Mixed — depends on role, Skeptical, Hostile
• Who are the natural champions and who are likely blockers — by department or role?
• What change-management tactics have worked in past rollouts (pilot incentives, manager mandates, targeted training)? Options: Incentives, Manager mandate, Hands-on training, Automated nudges, Other
• How will you measure adoption within the first 30, 60, and 90 days (metrics, thresholds, reporting cadence)?

How Will We Know Deployment Is Actually Working?

• If you woke up 30 days after launch and everything was working perfectly, what three measurable things would you expect to see?
• What are the non-negotiable acceptance criteria for the pilot to be considered successful?
• Which KPIs must be tracked automatically versus manually during the pilot (savings, compliance, location accuracy, ticketing SLA)? Options: Savings tracking, Policy compliance, Traveler location accuracy, Booking routing rate, Support response SLA
• Who will approve the acceptance checklist and how will disagreements be adjudicated?
• What roll-back or mitigation triggers should pause expansion if key metrics fall below thresholds?

What Are the Hidden Integration and Policy Dependencies?

• Which internal systems must integrate before launch but are often overlooked (payroll, ERP, duty-of-care system, TMC APIs)? Options: Payroll, ERP/Finance, HRIS, Duty-of-care platform, Expense system, Other
• Are there travel policy documents or limits that still need executive sign-off? Options: All signed, Some need executive sign-off, Significant policy work remains, No policies exist yet
• What legal, regulatory, or insurance requirements could create deployment constraints (data residency, cross-border rules, GDPR, CCPA)?
• When employees book outside managed channels, how will we capture that data for duty-of-care and savings measurement? Options: Expense feed capture, HR reporting, Traveler self-reporting, We cannot capture currently
• Which third-party vendors must confirm connectivity (expense provider, corporate card processor, supplier portals) and who is responsible for each?

Let's Agree Next Steps — Who's Doing What and When

• If we don't commit to the top three actions today, when do you think this project will realistically slip to? Options: Within 2 weeks, Within 1 month, 2–3 months, No idea
• Please select the priority actions you will commit to completing in the next 14 days. Options: Provide sample data feeds, Sign supplier agreements, Provision admin SSO/test accounts, Confirm pilot traveler list, Approve policy documents
• Who will be the named internal point of contact for each committed action (name and role)?
• When would you like a readiness review checkpoint with our team (choose a time window)? Options: Within 1 week, Within 2 weeks, Within 1 month, After initial setup
• Is there anything we haven’t asked that keeps you up at night about deployment?

Getting Comfortable — Who's in the Room?

• Give a brief snapshot of your travel program: annual travel spend, regions covered, and approximate number of travelers.
• Which teams will be actively involved in evaluating and implementing a travel program? Options: Finance / CFO, Travel program manager, Procurement, HR / People Ops, IT, Legal, Operations / Travel Ops, External consultant
• Who holds final commercial authority to sign a travel management contract in your organization? Options: CFO, Head of Procurement, Head of Travel/Program Manager, CEO/Founder, General Counsel, Other
• What immediate event or metric prompted you to explore a managed travel program now? Options: Audit showing <70% compliance, Recent travel disruption / safety incident, New CFO cost mandate, M&A or rapid growth, Inefficient expense processing, Other
• What is your target decision timeline for selecting a travel partner? Options: <30 days, 30–60 days, 60–90 days, 3–6 months, Undecided/longer
• Who will be the primary day-to-day contact for a pilot and post-launch operations?

Why Keep Letting People Book Outside the Program?

• We often see teams quietly tolerate out-of-policy booking — what do you think you’re gaining by tolerating it?
• Estimate how much of your business travel is currently booked outside managed channels (approx %). Options: <10%, 10–25%, 26–50%, 51–75%, >75%, Not sure
• What are the top reasons employees bypass the managed channels in your company? Options: Price perception on consumer sites, Speed / convenience, Preference for loyalty programs, Lack of awareness of policy, Policy is too restrictive, Technology usability issues, Other
• Tell us about a recent example where an out-of-policy booking caused a real problem (cost, compliance, or safety). What happened?
• How long has this pattern of unmanaged bookings been tolerated in your organization? Options: Less than 6 months, 6–12 months, 1–3 years, 3+ years, Not sure
• How do the people who must enforce policy feel about poking at this—frustrated, resigned, powerless, or energized to change? Options: Frustrated, Resigned, Powerless, Energized to change, Mixed feelings

When Money Disappears: Where Are Savings Slipping Away?

• If you had to guess today, what percentage of potential negotiated savings do you think is currently captured? Options: <20%, 20–40%, 41–60%, 61–80%, >80%, Don't know
• Which spend categories create the most leakage for you? Options: Airfare, Hotels, Ground transportation, Car rentals, Per diem / incidental expenses, Corporate card misuse, Other
• How do you currently measure travel savings and where do those numbers come from? Options: Finance reports, Expense system, TMC invoices, Manual sampling/audits, We do not measure consistently, Other
• Do you have negotiated supplier rates or corporate discounts in place today? If yes, how consistently are they applied? Options: Yes — consistently applied, Yes — inconsistently applied, No discounts in place, Unsure
• Share an example of a recent pricing or booking surprise that increased travel cost unexpectedly.
• Who in finance or procurement reviews travel cost anomalies and how often? Options: Monthly, Quarterly, Ad hoc, Never, Multiple stakeholders share this

When Travelers Go Missing: How Real Is Your Duty-of-Care Risk?

• Imagine a regional disruption — how confident are you that you could locate and contact all employees in the affected area within 2 hours? Options: Very confident, Somewhat confident, Not confident, No capability / not sure
• Have you experienced an incident where locating a traveler failed or was slow? What were the human or business consequences?
• What traveler location data sources do you currently have (select all that apply)? Options: Corporate booking records, Expense reports, Mobile check-ins / apps, HR records, None, Other
• Who owns emergency response and traveler welfare today (HR, Security, Travel Ops, or other)? Options: HR / People Ops, Security / Risk, Travel Ops / Program Manager, Facilities / Operations, No clear owner
• How would failure to locate an employee affect your organization emotionally and operationally (brief example)?
• What SLA or accuracy threshold for traveler location would make leadership feel safe? Options: >95% accurate within 2 hours, 80–95% within 2 hours, Within 24 hours is acceptable, Not sure

If We Made the CFO Sleep Better Tonight, What Would Change?

• If the CFO asked you to name the single most important measurable outcome for this program, what would it be?
• What is your target for out-of-policy booking reduction or policy compliance (choose a target range)? Options: Raise compliance to >90%, Raise compliance to 75–90%, Improve modestly by 10–25%, We have no formal target
• What financial target would make this project a success (absolute $ savings or % of travel budget)? Options: <$50k, $50k–$250k, $250k–$1M, >$1M, Prefer not to quantify yet
• Which KPIs beyond savings and compliance matter most to you? (select up to 3) Options: Time to locate travelers, Time to process expense reports, Traveler NPS / satisfaction, Booking lead time, Percentage of bookings via managed channels, Supplier rate adoption
• How quickly does leadership expect to see measurable results after launch? Options: Within 30 days, 30–90 days, 3–6 months, 6–12 months
• What would success look and feel like to HR, Finance, and frequent travelers respectively?

Prove It to Me — What Would a Pilot Have to Deliver?

• What single pilot failure would cause you to stop the program or not proceed to full launch?
• Which modules must be included in a pilot for you to evaluate value properly? Options: Managed booking / agency, Policy enforcement, Expense integration, Traveler tracking / duty-of-care, Supplier negotiated rates, Reporting & dashboards
• What integrations are non-negotiable for a pilot (HRIS, ERP, expense tool, SSO, supplier APIs)? Options: Expense platform (Concur/Certify/Expensify), HRIS (Workday/ADP/Oracle), Single sign-on (Okta/Azure), ERP / Finance system, Supplier NDC or content feeds, None are mandatory
• What sample scenarios or traveler segments must be included in the pilot to prove viability? Options: Frequent road-warriors, Infrequent travelers, Sales / client-facing teams, Global travelers crossing regions, Executive travel
• Define three clear acceptance criteria that would let you sign off on pilot success (metrics, thresholds, and evidence).
• Who will provide final pilot sign-off and what format of evidence will they require (dashboard, audit sample, formal report)? Options: CFO, Head of Travel, Procurement, Joint approval, Other

Who Will Push Back — And What Will They Say?

• Which stakeholder is most likely to block this program and why? Options: Finance (cost/ROI concerns), Procurement (supplier terms), HR (employee sentiment), IT (integration/security), Business unit leaders (change resistance)
• For each key approver, what is their top fear or objection we should anticipate?
• What governance or procurement steps will be required before contracting (RFP, security review, legal redlines)? Options: RFP, Security review / SOC2, Legal negotiation, Vendor due diligence, None / informal
• How does your internal decision process typically run—fast and centralized or slow and federated? Options: Fast and centralized, Moderate with a few stakeholders, Slow and federated across regions, Varies by category
• Is there a precedent procurement or legal clause that has killed similar vendor relationships in the past? If so, describe briefly.
• Who will be responsible for change management and traveler communication during rollout? Options: Travel Ops / Program Manager, HR / People Ops, Internal Communications, Procurement, No one assigned yet

If We Rolled This Out Tomorrow, What Would Break?

• What is the single operational gap most likely to derail launch within the first 90 days?
• Rate the quality of your core data feeds (traveler roster, corporate card feeds, HR data). Options: High quality / up to date, Moderate quality / some gaps, Poor / significant gaps, No reliable feeds available
• Which supplier agreements would need to change or be renegotiated to deliver expected savings? Options: Airline contracts, Hotel programs, Ground transportation, Car rental, No supplier changes needed / unsure
• What admin bandwidth do you have for onboarding, policy setup, and ongoing management? Options: Dedicated full-time resource, Part-time resource, Shared responsibilities across teams, No internal capacity right now
• How do you anticipate travelers will react to mandatory managed booking and enforced policy? Options: Welcome it, Neutral / adapt, Resistant, Strongly resistant
• What quick mitigations could we use to reduce the biggest launch risk you named earlier?

How Will We Know We're Winning — The Exact Validation Checklist

• Which exact metrics and thresholds will constitute an acceptable pilot outcome (please be specific — e.g., 75% managed bookings, $X saved, 95% traveler location accuracy)?
• What reporting cadence and artifact types do you expect for validation (daily dashboard, weekly snapshot, formal final report)? Options: Daily dashboard, Weekly summary, Bi-weekly review, Final formal report at pilot end, Ad hoc on request
• Who must sign the acceptance certificate and who will operate the post-pilot governance board? Options: CFO, Head of Travel, Procurement, Joint sign-off
• For compliance and savings tracking, which data sources will you accept as evidence? Options: TMC invoices, Expense system export, Booking platform logs, HR trip roster, Third-party audit
• How will you validate traveler location accuracy during the pilot (sample checks, simulated disruptions, real incident verification)? Options: Sample audits, Simulated disruption exercise, Real incident retrospective, Automated location reports
• If acceptance criteria are not met, what remediation or escalation path do you want to follow? Options: Extend pilot with remediation plan, Apply financial remedies, Re-scope and retest, Terminate the trial
• Is there anything else you want captured in the validation checklist that would make internal stakeholders comfortable signing off?