Start: Tell Us About Today

• Who will we be working with on this effort and what are their formal roles? Options: Facilities Director, Director of Operations, Business Manager/Finance, Maintenance Supervisor, Energy Manager, IT Lead, HR/Payroll, Other (please name)
• How many sites and buildings does your district/university actively manage? Options: 1–9, 10–24, 25–49, 50–99, 100–249, 250+
• Briefly describe the current system(s) you use for work orders, PMs, and capital planning (spreadsheets, paper, software name, or 'none').
• What’s one recent maintenance story that best captures how work gets done today (a single event or typical day)?
• How comfortable are you with the accuracy of your equipment inventory and asset ages right now? Options: Very confident, Somewhat confident, Limited confidence, Not confident at all

Are You Just Managing or Leading the Buildings?

• If your reactive backlog doubled next year, what would that reveal about the way you prioritize maintenance today?
• Estimate the split between reactive (emergency) work and planned preventive work across your portfolio. Options: Mostly reactive (80%+ reactive), Reactive-heavy (60–80% reactive), Balanced (40–60% reactive), Planned-heavy (20–40% reactive), Mostly planned (<20% reactive)
• Which recurring failures cause the most disruption to schools or campus operations (select all that apply)? Options: HVAC failures, Plumbing issues, Electrical outages, Roofing/water intrusion, Security/locks, Custodial staffing gaps, Other
• When a critical system fails, how long does it typically take from report to resolution and who drives that process?
• How does this day-to-day reality make you feel about your ability to meet board or administrative expectations? Options: Confident we’ll meet expectations, Uneasy but coping, Frequently frustrated and strained, Overwhelmed and under-resourced

Where the Hidden Costs Live

• How much do you believe deferred maintenance and emergency repairs are costing the district/university each year (dollars, percentage of budget, or a qualitative estimate)?
• Which types of costs keep coming back on your budget forecasts (select all that apply)? Options: Unplanned emergency repairs, Overtime labor, Expedited parts/shipping, Energy waste, Contractor markups, Shortened asset life, Other
• Tell us about your energy visibility: do you have building-level utility meters, submeters, or only district-level invoices? Options: Building-level meters, Submeters on some buildings/systems, Only district-level bills, We are not sure
• How accurate is your spare parts and inventory knowledge across sites? Options: Real-time accurate inventory, Mostly accurate with gaps, Spotty, relies on memory, No reliable inventory
• Give an example of a hidden cost we could help you expose — what would it look like numerically or operationally?

Who Holds the Keys — Decision Roles & Momentum

• If we brought a proposal that clearly showed cost avoidance and faster time-to-serve, who in your organization would actually approve budget and rollout? Options: Facilities Director, Superintendent/Provost, Business Manager/CFO, Board or Board Committee, IT/Procurement, Other
• What is your typical procurement timeline from evaluation to signed contract (weeks/months) and what are the predictable calendar constraints (e.g., fiscal year, board cycles)? Options: <1 month, 1–2 months, 3–4 months, 5–6 months, 6+ months
• Describe any approval gates or stakeholders who have blocked similar projects in the past and why.
• What concrete evidence or deliverable would accelerate approval for you (example: one-year ROI model, pilot success metrics, reference site visit)? Options: ROI model, Pilot with data, Reference district call, Detailed scope & SOW, Other
• How do politics, unions, or site principals influence rollout decisions in your environment?

What Would Success Actually Feel Like?

• Imagine it’s 12 months after launch and your team is proud—what three changes would make you say the project was a success?
• Which measurable signals would prove success for operations, capital planning, and energy respectively? Options: Reduced emergency work orders, Shorter average resolution time, More accurate capital backlog, Energy cost per sq. ft. down, Improved PM compliance, Other
• Who needs to see which dashboards or reports for the project to be considered successful (select all that apply)? Options: Site Principals, Maintenance Technicians, Facilities Director, Business Manager/CFO, Board/Trustees, Energy Manager, Other
• What acceptance criteria would you require before signing off on pilot and full rollout (examples: data imports complete, mobile app live, PMs automated)?
• How would these success outcomes change the way you justify capital requests or operations budgets to leadership?

What Would Need to Change for This to Work?

• If we asked you to stop one current process to make room for a new system, what would you be willing to stop and why?
• Which integrations and data sources are must-haves for the platform to be effective (select all that apply)? Options: Financial/ERP, HR/payroll, Student information system, Metering/energy data, BMS/SCADA, Identity/SSO, Inventory/parts, Other
• How ready is your data for import (floorplans, asset lists, historical work orders) — can you estimate percent complete? Options: >90%, 60–90%, 30–59%, <30%, None
• Who would own day-to-day platform administration, training, and governance after launch? Options: Facilities Director, Maintenance Supervisor, IT, Shared team, External vendor/consultant, Other
• What training or change-management approaches have succeeded with your teams in the past?

Red Flags & Deal Breakers — Tell Us the Truth

• What specific warning signs in a vendor relationship have caused you to stop a project before completion?
• Which of the following would be a non-starter for you when evaluating a solution? Options: Poor mobile experience, No offline technician access, Lack of integrations, No single sign-on, No proof of K–12/higher-ed references, Unclear data ownership
• Describe a past implementation that failed — what went wrong and how long did it take you to recover?
• What minimum SLAs, support hours, or response expectations must a partner commit to for you to proceed? Options: Business hours support, Extended business hours, 24/7 critical support, Dedicated account manager, Structured weekly check-ins
• What budgetary or fiscal constraints could force you to pause or reduce scope after contracting?

Quick Wins & First Deliverables

• What is one deliverable in the first 60–90 days that would make you feel the project is on track? Options: Pilot PM automation, Mobile app live for 1–2 sites, Asset inventory import, Energy baseline dashboard, Capital backlog report
• Which short-term KPIs should we target to demonstrate value quickly (pick up to three)? Options: PM compliance rate, Average time-to-restore, Emergency work orders reduced, Energy spend per month, Inventory accuracy, Technician utilization
• Who on your team will be the champions to validate those early wins and commit to measuring them?
• How would you prefer pilots to be structured — single site, cluster of similar sites, or cross-section of building types? Options: Single site, Cluster of similar sites, Cross-section (elementary, middle, high, admin), Phased by region
• What communications would you want to share internally once an early win is achieved (format and audience)?

Final Check — Timeline, Commitments & Next Steps

• If we lined up a pilot start date today, what realistic earliest start date could you commit to given procurement and staffing? Options: Immediately (within 2 weeks), 1–2 months, 3–4 months, 5–6 months, 6+ months
• What are the three non-negotiable milestones you need to see on a project plan before giving a go/no-go?
• Who will be the single point of accountability for the success of the implementation from your side? Options: Facilities Director, Project Manager (internal), Maintenance Supervisor, Business Manager, Shared responsibility
• What would make you say 'this is the wrong time' to move forward (internal or external factors)?
• Would you be open to a short pilot agreement to validate outcomes before full procurement? Options: Yes — pilot preferred, Maybe — need more info, No — must commit to full rollout

Start with a Quick Snapshot (so we don't waste your time)

• How many buildings/sites does your team actively manage today? Options: 1–5, 6–20, 21–50, 51–150, 151+
• Who's the person on your team we should think of as the operational owner for facilities decisions? Options: Facilities Director, Director of Operations, Business Manager/Finance, Buildings Supervisor/Maintenance Lead, Third-party vendor, Other
• Roughly how many full-time equivalent maintenance staff support your portfolio? Options: 0–2, 3–5, 6–10, 11–20, 21+
• Which channels do you currently use to receive work requests (select all that apply)? Options: Email, Phone, Paper forms, Online portal, Text/SMS, Site principals submit, Students/teachers submit via form, Other
• If you had to name one thing that wastes the most time in your day, what would it be?

When 'Normal' Breaks: How Surprises Become Emergencies

• How frequently do equipment failures or site issues occur that you did not reasonably anticipate? Options: Daily, Several times a week, Weekly, Monthly, Rarely
• When those surprises happen, which of the following describes the most common cause? Options: Aging equipment, Deferred maintenance backlog, Improper preventive maintenance, Poor installation/repairs, Unknown equipment condition, Data gaps (no history), Other
• Tell us about one recent unplanned failure that had outsized impact (what failed, where, and what happened)?
• How long does it typically take from the first report of a problem to meaningful action (dispatch, part ordered, or repair started)? Options: <2 hours, 2–8 hours, 8–24 hours, 1–3 days, More than 3 days
• How do these surprises usually feel for you and your team—manageable, crushing, or somewhere in between? Options: Mostly manageable, Occasionally overwhelming, Often crushing, Unsure

The Work That Never Gets Done (and Why You Pretend That’s OK)

• What percentage of scheduled preventive maintenance tasks are completed on time? Options: >90%, 70–90%, 40–70%, <40%, We don't track
• What are the top three reasons PMs are missed or deferred in your district? Options: Staffing shortages, Parts or materials unavailable, Competing reactive work, Unclear schedules, No centralized PM system, Weather/school closures, Other
• How big is your backlog of deferred maintenance or outstanding work orders right now? Options: Minimal (monthly manageable), Moderate (months of backlog), Large (year+), Unknown/no reliable number
• Which type of deferred work causes the most risk to operations or budgets (pick up to two)? Options: HVAC, Roofing, Plumbing, Electrical, Structural/Building envelope, Accessibility/Code issues, Energy-related upgrades
• Describe a specific example where deferred maintenance led to a larger capital request or emergency expense.

Who Actually Owns What (Even When It Feels Unclear)

• If a critical HVAC failure happens at a school at 2am, who is ultimately responsible for decisions and communication? Options: Facilities Director, Site Principal, Maintenance Supervisor, District Operations, Outsourced vendor/contractor, Other
• Which roles on your team currently approve work, order parts, and sign off on completed jobs (select all that apply)? Options: Technician/Lead tech, Maintenance Supervisor, Facilities Director, Business Manager, Site Principal, Third-party vendor, Other
• Where do responsibilities blur between site leadership (principals) and central facilities—for custodial work, minor repairs, and capital requests?
• How do role handoffs typically occur when a job crosses sites (e.g., technician assigned from another school or a contractor brought in)? Options: Clear written process, Informal calls/texts, Email threads, No consistent process, Other
• What would make ownership and approvals less political or reactive in your district?

Blind Spots and Missing Data That Pickpocket Your Budget

• Which of these data points are you missing or unsure about across your portfolio? Options: Accurate equipment inventory, Equipment age and install date, Last service history, Spare parts inventory, Energy consumption by building, Maintenance costs by asset, Condition assessments
• How confident are you that your equipment lists and serial numbers match what's actually in the field? Options: Very confident, Somewhat confident, Not confident, No reliable inventory
• Tell us about a time missing data led to a failed budget ask, audit finding, or project delay.
• Which reporting or dataset would change how you prioritize capital requests if you had it tomorrow? Options: Asset condition score, Lifecycle cost model, Energy ROI per site, Work order trend analysis, Inventory & spares visibility, Technician labor utilization
• What current integrations or systems feed your facilities information (select all that apply)? Options: ERP/Finance, HR/Payroll, Building automation systems (BAS), Energy management, Spreadsheets only, No integrations, Other

Workflow Reality Check: From Request to Resolution

• When a work request is submitted, what is the single biggest choke point that slows resolution? Options: Triage/prioritization, Dispatch scheduling, Parts availability, Approval processes, Technician travel time, Lack of diagnostic info
• How do you currently prioritize work orders (select all that apply)? Options: Safety/Code, Instructional impact, Energy/cost impact, First-come first-served, Principal priority, Automated SLA rules, Other
• Describe the most common information missing from a work request that forces a site visit or repeat trips.
• Which mobile or in-field tools do your technicians use today (if any)? Options: Paper forms, Generic mobile app (not facilities), Dedicated CMMS/mobile app, Email/phone only, No mobile tools
• What measurable turnaround time (request→resolved) would feel acceptable to your stakeholders? Options: <4 hours, 4–24 hours, 1–3 days, 3–7 days, >7 days
• How would faster or clearer workflows change the school day, budgeting, or community perception?

If You Could Snap Your Fingers: The Outcomes That Actually Matter

• If your maintenance operation delivered exactly what the district needed in one year, what would be different at review time?
• Which of these outcome areas would be most persuasive to your board or administration? Options: Reduced reactive spend, Demonstrated deferred maintenance reduction, Lower energy bills, Improved occupant comfort, Faster work order resolution, Better compliance/documentation
• What specific metrics would you want to see in order to approve continued investment (pick up to three)? Options: % PM completion, Average repair cost per asset, Backlog age, Energy $/sqft, Capital needs by priority, Technician utilization, SLA adherence
• How would you describe success to a skeptical superintendent in one short sentence?
• What time horizon feels realistic for the district to realize meaningful results (and why)? Options: 3 months, 6 months, 12 months, 2+ years, Unsure

What Would Getting Help Look Like—And Who Needs to Say Yes

• When vendors promise rapid transformation, what specific doubts make you push back or delay? Options: Too expensive, Hidden complexity, Requires more staff, Data migration risk, Political buy-in, Past failed projects, Other
• Who must be aligned internally for a pilot or rollout to proceed (select all required approvers)? Options: Facilities Director, CFO/Business Office, Superintendent/Chancellor, IT Director, Site Principals, Union/HR, School Board
• What concerns would your IT team raise about a new platform (security, integrations, data residency, other)?
• If we proposed a pilot at one or two sites, what would be a non-negotiable success signal for you to expand? Options: Reduced reactive hours, PM completion improvement, Energy savings realized, Positive technician feedback, Cleaner asset inventory, Other
• What internal resources could you commit to a pilot (hours/week, named owners, data export support)?

Next Small Steps: Low-Risk Experiments That Prove Value

• What's one small, low-risk experiment you'd be willing to try in the next 60–90 days to test a new approach? Options: Pilot PM scheduling at 1 site, Inventory reconciliation project, Energy dashboard for 3 buildings, Mobile work order trial for techs, Automate recurring PMs, Other
• Which site(s) would make the best pilot—where impact is visible and failure is contained? Options: Elementary school, Middle school, High school, District office/central facility, Mixed-use campus, Other
• What data access would we need to run that pilot (select all that apply)? Options: Basic asset list, Work order history, Energy usage by meter, Parts inventory, Technician schedules, None (we can collect)
• Who would be the internal owner accountable for the pilot's day-to-day progress? Options: Facilities Director, Maintenance Supervisor, Assigned Technician, Business Manager, IT liaison, Other
• What would make you say 'this pilot was worth it'—one clear, measurable decision point we can use?

Quick Snapshot: Who's In The Room?

• Please confirm the district/university name, your role, and the best phone/email to reach you for day-of coordination.
• How many sites and individual buildings should we plan to include in the first deployment wave? Options: 1 site / 1-5 buildings, 1 site / 6-20 buildings, Multi-site district (2–10 sites), Large portfolio (10+ sites)
• What is your target go-live window for the initial deployment (month/quarter)? Options: Within 2 weeks, 2–6 weeks, 6–12 weeks, Next quarter, Unspecified / flexible
• Who are the three people we should consider ‘must attend’ for deployment decisions (name, title, area of responsibility)?
• Which existing systems are actively used today for work orders, PMs, energy, or capital planning? Options: Spreadsheets only, Legacy CMMS, Energy management system (EMS/BMS), ERP/Finance system, Helpdesk ticketing, Other

If We Ship This Tomorrow, What Would Feel Like Failure?

• What would count as an unacceptable outcome in the first 30 days after go-live?
• Which recurring problem today do you worry will still be happening after deployment unless we address it up front? Options: Technician mobile access issues, Lost or incorrect equipment records, Work orders not routed correctly, Data sync failures with finance/HR, User adoption / resistance
• How much downtime or disruption is tolerable during cutover at a typical site (hours per day)? Options: No downtime, Under 2 hours, 2–4 hours, Full day acceptable, Several days acceptable
• Describe a past rollout or IT change that went poorly—what happened and who bore the impact?
• On an emotional level, what keeps you awake when you think about this deployment?

Do You Really Know Your Inventory—or Are We Guessing?

• Roughly what percentage of your critical assets (HVAC, boilers, pumps, major electrical) have reliable age and condition data today? Options: <20%, 20–50%, 50–75%, 75–90%, 90–100%
• Which asset classes do you have some confidence in tracking right now? Options: HVAC/R, Boilers/Chillers, Electrical panels, Roofing & building envelope, Plumbing, Custodial inventory, Other
• Do you have an existing asset register or FMS export we can map to (CSV, Excel, SIF, CAFM export)? Options: Yes—CSV/Excel available, Yes—system export but needs cleanup, Partial lists only, No centralized register
• How are assets currently identified on site (asset tags, serial numbers, free-text names, none)? Options: Barcode/QR tags, Serial numbers in spreadsheets, Location-based naming, No consistent ID
• If we needed to run a rapid inventory blitz, what onsite resources could we assign to help (techs, custodians, site admins)? Options: Dedicated techs available, Site admin support, Custodial teams, No spare capacity right now

Can We Get to Your Data Without Roadblocks?

• What's the single most likely technical blocker to getting clean, timely data into our platform?
• Which systems do we need to integrate with for this deployment (select all that apply)? Options: Energy meters / EMS / BMS, Finance/ERP (purchase orders, GL), HR/SSO (user provisioning), Student information or scheduling systems, Third-party vendor portals, None
• Do you have APIs, scheduled exports, or third-party integrators in place for those systems? Options: APIs available and accessible, Scheduled exports available, Requires manual exports, No integration capability
• Who owns credentials and network access for integrations (IT director, vendor, external integrator)? Provide name/title.
• Do you enforce single sign-on (SSO) or have specific authentication methods we must use? Options: SSO required (SAML/OAuth), LDAP/Active Directory, Local accounts acceptable, Unsure / need to check
• Are there windows (days/hours) when systems are available for bulk data migration or API testing? Options: Business hours, After hours weeknights, Weekends, Only during scheduled maintenance windows

Who Decides — And Who Will Own It When Things Get Messy?

• If a priority decision is needed mid-deployment, who has final sign‑off authority (name/title)?
• Which roles will be first-line owners for these areas after go-live? Options: District-level facilities director, Site-level lead custodian, Maintenance supervisor, IT systems admin, Business office/finance
• Who will be the primary trainer(s) for technicians and site staff, and do they have prior experience with CMMS training? Options: In-house trainer(s) with experience, In-house but no prior experience, External trainer/vendor, TBD
• How many people should we provision as system admins and what level of permissions will they need? Options: 1–2 admins, 3–5 admins, 5+ admins, Unsure
• What internal escalation path should we follow for outage, data, or user adoption issues (names, channels)?

Which Risks Are Non-Negotiable For Your Board or Insurer?

• Which compliance, privacy, or audit obligations constrain how we deploy (FERPA, HIPAA, state procurement, insurance clauses)? Options: FERPA, HIPAA, State procurement rules, Insurance loss-prevention, None, Other
• Do you require network segmentation, on-prem components, or vendor security attestations before we connect devices or systems? Options: Network segmentation required, On-prem connector preferred, Vendor security docs needed, No special requirements
• How should we handle access for third-party contractors and temporary staff during rollout (guest accounts, supervised access)? Options: Guest accounts with expiry, Supervised site access, Contractor-specific roles, Open access (not recommended)
• What backup or rollback plan do you expect if initial data import or cutover causes issues? Options: Full rollback to legacy system, Partial rollback by site, Staged rollback plan, No rollback planned
• Are there insurance or liability thresholds (e.g., limits on downtime, critical system availability) that we must meet?

What Will ‘Ready’ Actually Look Like on Day 60?

• Imagine we pass acceptance testing—what three measurable signals tell you we’ve succeeded?
• Which routine workflows must be working end-to-end before closeout (select all that apply)? Options: Work order creation & assignment, Preventive maintenance scheduling, Technician mobile workflows, Purchase order integration, Reporting to leadership
• How many technicians and site users must be trained and independently able to use the mobile app before you consider the wave complete? Options: All technicians at wave sites, Majority (>70%), Core users only, Undecided
• What reporting or dashboard views are essential for your board or admin to sign off on acceptance? Options: Deferred maintenance summary, PM compliance, Work order turnaround, Energy trend dashboards, Capital spend forecasts
• If acceptance criteria aren’t met, what remediation window would you want (days/weeks) and who signs off on re-testing? Options: 7 days, 14 days, 30 days, Custom plan

A Small Step Today That De-Risks Tomorrow

• What is one low-effort data export, attachment set, or asset list you can share in the next 7 days to accelerate mapping?
• Which stakeholder can commit to a 60-minute technical call this week to unblock integrations?
• Which quick win would demonstrate progress to your leadership within 14 days (sample report, cleaned asset list, pilot site go-live)? Options: Pilot site go-live, Sample executive report, Cleaned asset CSV, Technician mobile demo
• What internal communications or change management support would make your team more receptive to the rollout? Options: Leadership memo, Site-level briefings, Hands-on shadowing for techs, Short how-to videos, Other
• Finally, what is the best way for our team to follow up in the next 48 hours (email, call, shared folder link, scheduled meeting)? Options: Email summary, 15–30 minute call, Share secure folder link, Schedule planning meeting

Getting to Know Your World

• Tell us briefly about your role and the team you rely on day-to-day (titles, headcount, and who covers what)
• How many sites and buildings are you responsible for today? Options: 1–5, 6–20, 21–50, 51–100, 100+
• What systems are currently used to track work orders, preventive maintenance, and inventory? Options: Spreadsheets (Excel/Sheets), Email / Phone requests, Paper system, Homegrown database, Another FM platform, None
• On a typical week, how many active work orders does your team manage (open + in-progress)? Options: <25, 25–50, 51–100, 101–250, 250+
• What feels like the single biggest frustration you carry about how facilities work gets done?
• If you could change one thing about how your team communicates about work and priorities, what would it be?

Are You Holding Back Hidden Costs?

• How often do you suspect deferred maintenance is creating unexpected emergency spend? Options: Weekly, Monthly, Quarterly, Annually, Unsure
• Give a recent example of a failure that caused outsized cost or disruption—what happened and what was the real cost (labor, temporary fixes, lost instruction time)?
• Which of these areas are you most worried about hiding true costs in your portfolio? Options: Aging HVAC & boilers, Roofing and envelope, Plumbing failures, Electrical reliability, Custodial/cleaning gaps, Energy inefficiency
• How do you currently calculate or justify capital requests tied to deferred maintenance? Options: Detailed condition assessments, Anecdotal requests, Spreadsheet estimates, Vendor quotes only, We don’t currently
• What would it mean to your budget conversations if you could show a dollar value and timeline for avoided failures?

Where Does Your Time Really Go?

• If a week could be magically replayed, what portion of your team's time would you say is genuinely reactive versus preventive? Options: Mostly reactive (75%+), More reactive than preventative (50–75%), Balanced (40–60/40–60), More preventive than reactive, Almost all preventive
• Describe a typical reactive work order that draws your crew away from planned tasks—what triggers it and how long does it take to resolve?
• Which workflows repeatedly cause delays or confusion for technicians and site staff? Options: Work order intake/triage, Parts/inventory access, Scheduling conflicts, Permit/lockout processes, Sign-offs & acceptance
• How do technicians access instructions, manuals, or history when they’re in the field? Options: Paper binders, Shared network drives, Mobile app, Call supervisor, They don’t have reliable access
• What emotions come up for you when you look at the backlog right now (overwhelmed, resigned, hopeful, motivated, other)? Options: Overwhelmed, Resigned, Hopeful, Motivated, Frustrated, Other

Who’s Winning—and Losing—When Things Break?

• When a major issue happens, who ultimately makes the go/no-go decision and who feels the consequences most intensely? Options: Facilities Director, School Principal/Site Leader, Business Manager/Finance, Superintendent, Board/Trustees, Other
• Tell us about a time a facilities issue landed on the superintendent’s or board’s desk—what made it escalate and what was missing from the report?
• How do parents, teachers, and school leaders typically report problems—what channels and what frustrations exist for them? Options: Email, Phone, Paper note, Online portal, Direct to principal, Other
• Which stakeholder’s buy-in do you think is most critical to unlock bigger investments in facilities? Options: Board/Trustees, Superintendent, Business Manager, Town/City Officials, Community/Parent Groups, Other
• How confident are you that every stakeholder would agree on what ‘good’ looks like for a successful implementation? Options: Completely aligned, Mostly aligned, Some disagreement, Major disagreement, Unsure

If Data Could Speak, What Would It Say?

• What would be most surprising about your asset inventory if you could instantly get an accurate export of equipment age, last service, and condition?
• How often do you find discrepancies between what's on paper and what's actually on site? Options: Always, Often, Sometimes, Rarely, Never
• Which data gaps cause the biggest blind spots when planning capital projects or scheduling PMs? Options: Equipment age/location, Service history, Spare parts and inventory, Energy consumption per building, Maintenance labor hours
• If you had a dashboard that showed three metrics your board would care about, which three would you pick?
• How comfortable are you sharing raw maintenance data with finance for budget requests? Options: Very comfortable, Somewhat comfortable, Hesitant, Not comfortable, Unsure

What Would A Stress-Free Week Look Like?

• Imagine a week where every scheduled preventive task is completed and nothing critical breaks—what would that allow you to accomplish?
• Which outcomes would signal success to you after a first rollout (pick up to three)? Options: Reduced emergency calls, Higher PM completion rate, Faster technician response time, Clear inventory visibility, Better capital forecasting, Improved energy metrics
• What would success look like to school leaders and the board (in plain language they would understand)?
• How would you quantify an improvement so finance would approve ongoing funding (example: X% reduction in emergency repairs, $Y avoided spend)?
• Which timeline feels realistic for meaningful change in operations and reporting? Options: 30 days, 60–90 days, 6 months, 12 months, Longer

What Would Make This Change Stick?

• What has caused past tools or processes to fail at adoption—what stopped your team from using them?
• Which of these would most increase your team’s chance of adopting a new platform? Options: Hands-on technician training, Trainer-on-demand, Simplified mobile UX, Clear owner assignments, Automated PMs, Integration with payroll/finance
• How do technicians and site staff prefer to learn new systems (in-person, recorded sessions, step-by-step job aids, peer champions)? Options: In-person training, Live virtual sessions, Short recorded modules, Written guides/job aids, Peer mentoring/champions
• Who would be your internal champions and who might actively resist? Describe motivations for both.
• What governance or reporting cadence would keep this momentum after go-live (weekly stand-ups, monthly dashboard reviews, quarterly board updates)? Options: Weekly, Bi-weekly, Monthly, Quarterly, Ad hoc

Mapping The First 90 Days Together

• If we had to show tangible value in 90 days, what are the three most important things you’d want completed?
• Which of these baseline items must be true before we begin configuration? Options: Complete site inventory, Access to historical work orders, Integration with payroll/finance, Designated project owner, Techs issued mobile devices
• What acceptance criteria would you use to sign off on a phased rollout (examples: PMs running at X%, techs using mobile Y times/day, inventory accuracy Z%)?
• What internal approvals and procurement steps typically slow a project down in your district? Options: Budget committee, Board approval, IT security review, Vendor contracting, Other
• How would you like us to package early wins so leaders can see progress quickly (example: executive one-pager, site-by-site scorecards, before/after case studies)? Options: Executive one-pager, Site scorecards, Monthly dashboard, Short demo sessions, Other

Commitments & Red Flags Before We Move Forward

• What are the non-negotiable commitments you need from a vendor for a successful partnership? Options: Dedicated PM, Training guarantee, SLA for issues, Data ownership clarity, Integration support
• Which contractual or procurement terms have tripped you up in past vendor relationships? Options: Renewal terms, Hidden fees, Data access limits, Long lock-in periods, Lack of support
• What internal signals would tell you this partnership is at risk (drop in usage, unresolved tickets, budget cuts, stakeholder complaints)? Options: Drop in usage, Unresolved tickets, Budget cuts, Stakeholder complaints, Missed milestones
• How do you prefer to measure vendor performance (uptime/SLAs, adoption metrics, reduction in emergency spend, PM completion rate)? Options: SLAs/response time, Adoption metrics, Cost savings, PM completion, Energy/utility improvements
• Is there an upcoming budget cycle or board meeting that defines your decision window? Options: This month, Next 1–3 months, Next 3–6 months, Next 6–12 months, No set window

Quick Snapshot: Numbers That Tell The Story

• Total annual facilities operating budget (ballpark) Options: <$250k, $250k–$1M, $1M–$5M, $5M–$20M, $20M+
• Estimated % of maintenance spend that is reactive vs planned Options: >90% reactive, 70–90% reactive, 50–70% reactive, 30–50% reactive, <30% reactive
• Percentage of preventive maintenance tasks completed on schedule Options: <25%, 25–50%, 51–75%, 76–90%, 91–100%
• Do you have a current capital plan or five-year CIP? Options: Yes, detailed and prioritized, Yes, but needs work, No formal plan, In progress
• What’s a realistic next step you’d like from us after this discovery? Options: Detailed proposal and timeline, Proof-of-concept at one site, Executive briefing for board, Estimate for inventory capture, Not sure — need help prioritizing