Starting Point: Tell Us About Your District

• In one sentence, what is the single biggest reason you’re exploring a new SIS right now?
• Which best describes your district size and composition? Options: Under 1,000 students, 1,000–5,000 students, 5,000–15,000 students, 15,000–50,000 students, 50,000+ students
• How many schools and school types (elementary, middle, high, alternative) are in scope for this project? Options: 1–3, 4–10, 11–25, 26–50, 51+
• Describe any unique grade configurations, multi-district collaboration, or charter/network relationships we should know about.
• Which of these outcomes is most urgent for your district right now? Options: Accurate state reporting / funding, Reducing teacher workload, Migrating historic records, Modern parent/student portals, Integrations reliability, Other

Who Holds the Keys—and What Do They Really Care About?

• If the project goes sideways, who will be blamed first? Options: CIO/CTO, Assistant Superintendent, Registrar, Business Office, Project Steering Committee, Other
• List all decision-makers and influencers who must sign off (title + role in decision).
• How confident are you that each stakeholder understands what 'success' looks like for them? Options: Very confident, Somewhat confident, Not confident, We’ve never articulated success per stakeholder
• For each stakeholder group, what is the single non-negotiable requirement (e.g., transcript format, Gradebook features, data latency)?
• Which timeline best matches your decision window for awarding a contract? Options: Immediate (30 days), This quarter (60–90 days), This school year (3–6 months), Next school year (6–12 months), Flexible/Undecided
• Who will be the day-to-day project owner we should plan to work with?

Where Your Data Breaks Down (and How It Feels)

• How often do you find state reporting or compliance issues that require manual spreadsheet fixes? Options: Every reporting cycle, Often, Occasionally, Rarely, Never
• Describe the most recent data quality incident that caused extra work or risk (what happened, who noticed, how long to resolve).
• Which data domains are most fragile today? Options: Enrollment/demographics, Attendance, Grades/transcripts, Special education/IEPs, Schedules, State reporting fields, Other
• How are you currently tracking and prioritizing data quality issues (tooling, owners, cadence)? Options: Dedicated data quality tool, Manual spreadsheets, Ad-hoc tickets, No formal tracking
• What percentage of state reporting submissions are reviewed or corrected manually before submission? Options: 0–10%, 11–25%, 26–50%, 51–75%, 76–100%
• How does data inaccuracy make you or your team feel—stressed, resigned, defensive, motivated to fix it? Tell us with an example.

Integration Web: Who Depends on Your SIS?

• If one integration fails during peak season, which downstream service would cause the biggest operational crisis? Options: State reporting, LMS/Assessments, Special Education system, Food services, Transportation, Parent/Student portal
• Inventory the systems that consume SIS data and their owners (LMS, HR, Food service, Bus routing, Assessment vendors, State upload tools).
• Which integrations are currently live via API vs. batch exports vs. manual uploads? Options: APIs (real-time), Scheduled batch exports, Manual CSV uploads, Point-to-point middleware, We are not sure
• Do you have documented API credentials, test environments, and integration owners ready to engage? Options: All documented and ready, Partially documented, Not documented, No test environment
• What are your SLAs or expectations for data freshness across consumers (minutes, hourly, daily)? Options: Near real-time (minutes), Hourly, Daily, End-of-day, Other
• Who will own cutover coordination with your third-party vendors during migration?

Scheduling & Grading: The Everyday Pain

• If a teacher could change one thing about the current grading and schedule experience, what would they do first?
• Which scheduling models are in use across your district? Options: Traditional periods, Block scheduling, A/B rotations, Rolling schedules, Mixed across schools
• Describe the most time-consuming workflow teachers complain about (grade entry, seating charts, gradebook standards, transfer grades).
• How do you currently handle standards-based grading alongside traditional percent-based grading? Options: Fully supported, Workarounds required, Separate systems, Not used
• What training cadence has historically worked (or failed) for teachers when new systems are rolled out? Options: Multi-day in-person, Short online modules, Embedded coaches, Ad-hoc webinars, No formal training
• Share a concrete example where a scheduling or gradebook limitation impacted instruction or student placement.

State Reporting: The Funding Stakes

• Imagine a state audit flagged funding errors tied to SIS data—how plausible does that feel today? Options: Very plausible, Somewhat plausible, Unlikely, Impossible
• Which states and specific reports (e.g., membership, special ed, discipline, transcript extracts) must we configure for your district?
• Do you have historical rejections or corrective submissions—how often and for which reports? Options: Multiple times a year, Once a year, Rarely, Never, Not sure
• What absolute constraints must the new system meet for state reporting (file formats, deadlines, audit trails)?
• Who at the district owns state reporting day-to-day and who signs off on final submissions?
• If we could eliminate one recurring reporting headache overnight, which would deliver the biggest operational or financial relief?

Migration & Timeline Reality Check

• If you had to bet: will the migration take more or less time than your current timeline assumes? Options: More time, About the same, Less time, Unsure
• How many years of student records, transcripts, and historical data need to be migrated? Options: Current year only, 3–5 years, 6–10 years, 10+ years, All historical records
• Which data sets are high-risk during migration (transcripts, demography, schedules, historical grades)? Options: Transcripts, Historical grades, Schedules, IEPs/Special Ed, Attendance, State reporting fields
• What rollback or parallel-run strategy would make your leadership comfortable during cutover? Options: Full parallel run, Phased cutover by school, Quick rollback plan, Pilot then full deploy, No preference
• Who are the technical and business owners we should plan for migration testing and sign-off?
• Describe any previous migrations you’ve done—what went unexpectedly well or poorly and why?

Success Signals, Governance & Long-Term Adoption

• If we launched tomorrow, what three metrics would prove this project is a success in year one?
• How will ongoing governance be structured after go-live (steering committee, monthly ops, vendor SLA)? Options: Steering committee + monthly ops, Quarterly reviews only, Ad-hoc vendor meetings, No plan yet
• What adoption barriers keep you up at night—teacher change fatigue, data ownership disputes, budget constraints, or something else? Options: Teacher change fatigue, Data ownership issues, Budget/staffing, Parent/community friction, Other
• Which success-monitoring tools or dashboards would you want in place immediately after launch? Options: Adoption dashboard (logins/usage), State reporting health, Data quality exceptions, Integration error feed, Custom executive summary
• What ongoing support model makes you most comfortable: dedicated district success manager, quarterly health checks, or on-demand ticketing? Options: Dedicated success manager, Quarterly health checks, On-demand ticketing, Hybrid (manager + ticketing)
• What would make your leadership publicly celebrate this project—specific outcomes, cost savings, or a smooth school-year start?

Tell Us About Your District's Day-to-Day

• Roughly how many schools and students are we talking about? Options: <500 students, 500–2,499 students, 2,500–9,999 students, 10,000+ students
• Which grade ranges and campus types do you manage (select all that apply)? Options: K-5 / Elementary, 6-8 / Middle, 9-12 / High, Alternative programs, Charter sites / Partners
• What SIS are you currently using and how long has it been in place? Options: Vendor A (0–3 yrs), Vendor A (4–9 yrs), Vendor A (10+ yrs), Vendor B / Other (specify below)
• Who is the day-to-day owner of the SIS inside the district? Options: CIO/CTO, Director of Operations, Registrar, Business Office, Shared/No clear owner
• Which core SIS modules do you actively use today? (check all that apply) Options: Enrollment/Registration, Attendance, Scheduling/Master Schedule, Gradebook/Grades, State Reporting, Transcripts, Special Education, Other
• How would you describe the district’s overall appetite for change right now? Options: Actively pursuing replacement/upgrade, Evaluating but not committed, Only if forced by compliance, Undecided

If Your SIS Were a Moment of Truth — Where Would It Break?

• When the system breaks at a critical moment (reporting, grading, or scheduling), what usually fails first? Options: State export accuracy, Scheduling constraints, Gradebook syncing, Integrations to other apps, User interface causing errors
• How often do you run manual fixes or scripts to make state reporting accurate? Options: Daily, Weekly, Monthly, Only at reporting time, Rarely / Never
• Tell us about the last two incidents where data issues led to meaningful impact (funding, student placement, audit response). What happened?
• Which data domains do you feel least confident about today? Options: Demographics, Enrollment history, Attendance, Course/section mappings, Grades/transcripts, IEP / Special education data
• How long have these reliability problems been tolerated inside the district? Options: <6 months, 6–18 months, 1–3 years, 3+ years
• What is the typical internal emotional reaction when teachers or registrars discover a data error (frustration, panic, resignation)? Give an example.

Who Actually Makes the Call — And Who Lives With the Consequences?

• Do the people who decide on SIS selection experience the day-to-day pain the staff do? Options: Yes, closely connected, Partially aware, Mostly not aware, I don’t know
• List the stakeholder groups that must sign off on a replacement (pick all that apply). Options: Superintendent, CIO/IT, Business/Fiscal, Curriculum/Instruction, Principals, Teachers/Unions, Board of Education
• Who currently prepares and signs state reporting submissions? Options: Registrar, Data Analyst, IT, Business Office, Hybrid team
• What are the top three non-negotiable priorities that each stakeholder group has expressed?
• How aligned are stakeholders on timeline and risk tolerance for a migration? Options: Fully aligned, Mostly aligned with a few concerns, Misaligned across key groups, No alignment yet

Where Integrations Quietly Fail

• If an external app lost access to your SIS data tomorrow, how many downstream services would be impacted? Options: 1–3, 4–9, 10–19, 20+
• Which systems currently integrate with your SIS (select all that apply)? Options: LMS (Canvas/Schoology), Assessment platforms, Food service, Transportation, Special education vendor, State reporting portal, Identity/SSO providers, Other
• How are most integrations implemented today? Options: Real-time API, Scheduled API calls, Flat file extracts (SFTP), Manual CSV uploads, Third-party middleware
• When integrations fail, who is alerted and what steps are taken?
• Have you experienced silent data drift between systems (e.g., rostering or grades not matching) and for how long before it was discovered? Options: Almost immediately, Days, Weeks, Months, Not sure
• What SLAs or uptime expectations do your critical integrations need to meet? Options: Real-time / near-real-time, Daily sync, Weekly, Ad hoc

Scheduling: The Rubik's Cube No One Solved

• Does every campus follow the same scheduling model, or do models vary across the district? Options: Uniform model district-wide, Multiple models across schools, Each school unique, Hybrid within schools
• Which scheduling constraints create the most headaches? (pick up to three) Options: Teacher FTE / load, Room capacity / lab access, Program pathways / prerequisites, Special education push-in/pull-out, Athletics/extracurricular balancing, Staffing shortages
• How long does building a master schedule typically take from start to finish? Options: <2 weeks, 2–6 weeks, 6–12 weeks, 3+ months
• Describe a scheduling failure that directly impacted students (overcrowded sections, missing course offerings, graduation plan errors). What was the root cause?
• What tools or workarounds do schedulers and counselors use today to solve constraints? Options: Spreadsheet-based, Third-party scheduling tool, Manual adjustments in SIS, Outsourced scheduling, Other
• How do schedule changes during the year (mid-year transfers, staffing changes) get handled?

Grading, Transcripts, and the Teacher Experience — Is It Human-Friendly?

• If teachers could change one thing about the gradebook tomorrow, what would it be?
• Which grading paradigms do you support today? Options: Traditional points/percent, Standards-based, Combined/hybrid, Not sure
• How often do teachers report usability issues that lead to late grade submissions? Options: Daily, Weekly, Monthly, Rarely
• Have teachers adopted any shadow systems (spreadsheets, paper gradebooks) to work around the SIS? If so, describe.
• What known problems exist with transcript generation or formats for college/state acceptance?
• How important is mobile access for teachers grading on the go? Options: Critical, Important but not critical, Nice to have, Not important

Show Me the Data: Migration, Cleanup, and Trust

• How many years of historical student records need to migrate into a new system? Options: Current year only, Previous 1–3 years, 4–6 years, All historical records
• Which data elements are most likely to require cleanup before migration? (select up to four) Options: Course/section codes, Graduation plans/credits, Demographic fields, Special education records, Attendance history, Grade histories/transcripts
• What tools or processes have you used for data reconciliation historically? Options: Custom scripts, ETL tools, Manual verification, Vendor-assisted migration, No formal process
• Describe any recent migration, upgrade, or major data cleanup effort and the lessons learned.
• Who in your organization will be responsible for final data validation and sign-off? Options: Registrar, Data Analyst/Coordinator, IT Lead, Hybrid team
• Would you require the ability to rollback to the legacy system during initial cutover? Options: Yes, mandatory, Preferable but not required, No, we accept one-way cutover

Compliance and State Reporting — Where Are You Most Nervous?

• If a state audit found multiple reporting errors tomorrow, how exposed would the district be? Options: Severe exposure (funding/audit risk), Moderate exposure (manual fixes needed), Low exposure, Unsure
• Which state reporting packages or formats do you submit today (select all that apply)? Options: State portal upload, Flat file spec (CSV/XML), Third-party reporting tool, Direct API to state, Not standardized
• Have you missed or had to resubmit a state submission in the past 3 years? If yes, what caused it? Options: Yes — data mismatch, Yes — timing/late submission, Yes — format/schema error, No
• What manual workarounds are in place to meet state reporting requirements?
• Which compliance areas give you the least confidence (attendance, special ed reporting, graduation/completion, teacher assignments)? Options: Attendance, Special education, Graduation/completion, Teacher credentials/assignments, Other
• What would it take for you to feel completely confident in year-end state submissions?

If We Could Fix One Thing First, What Would Change Overnight?

• If you could remove the single biggest daily frustration, what would it be and why would that matter?
• Which three outcomes would you prioritize in the first 90 days of a new system? (select up to three) Options: Accurate state reporting, Reliable master schedule, Teacher gradebook adoption, Seamless integrations, Clean historical data
• What political or organizational obstacles might slow down delivering those quick wins?
• How willing are you to run the new system in parallel with the legacy system during validation? Options: Very willing, Somewhat willing, Prefer not to, Not possible
• What success metrics would make the first phase a win (time saved, error reduction, user satisfaction)? Please be specific.

Next Steps: Who, How, and What's Non-Negotiable

• What is your ideal decision timeline for selecting a new SIS? Options: Immediate (30 days), Near-term (2–3 months), This school year (4–9 months), Longer-term (9–18 months)
• Who must be present from your side for a technical discovery and a commercial review?
• Are there immovable constraints we need to accommodate (contractual, union rules, state deadlines)? Please list.
• What level of vendor involvement do you expect for migration, integrations, and training? Options: Full vendor-managed, Co-managed with district, District-led with vendor support, Unsure
• How do you prefer to evaluate references and proofs-of-concept (site visits, sandbox access, pilot schools)? Options: Site visits, Sandbox access, Pilot with subset of schools, Reference calls only, Combination
• Who should we contact to schedule the next technical session, and what’s the best way/time to reach them?

Tell Us About Your District’s Story

• Who will be the primary contacts for this project from your district (roles and names if available)?
• How many schools and students does your district manage today? Options: 1–5 schools / <1,000 students, 6–20 schools / 1,000–5,000 students, 21–50 schools / 5,000–20,000 students, 50+ schools / 20,000+ students, Prefer not to say
• Which grade configurations and school types do you operate (select all that apply)? Options: Elementary (K–5), Middle (6–8), High (9–12), K–8, K–12 combined campus, Alternative/Charter, Virtual/EDTech school
• What scheduling models are currently in use across your district (tell us where each applies if mixed)? Options: Traditional period/block, A/B rotating, Hybrid/alternate day, Year-round/trimester, Individual school choice (mixed)
• How long has your current SIS been in place, and what made you start looking for a replacement now?

What’s Actually Breaking — Even If You’ve Learned to Ignore It

• When you step back, where do you see the single biggest source of daily friction that costs time, certainty, or funding? Options: State reporting preparation, Gradebook/teacher workflow, Schedule-building, Data integrations, Transcript/credits issues, Parent portal complaints, Other
• Can you share a recent example where that friction led to a measurable problem (missed deadline, funding risk, compliance notice, or prolonged teacher overtime)? Please describe the incident and outcome.
• How often do manual workarounds occur to meet compliance or reporting deadlines? Options: Every reporting cycle, Monthly, Quarterly, Rarely, Never
• Which teams or roles are carrying the heaviest burden from these workarounds (select all that apply)? Options: District IT/CIO, Data/Assessment team, Registrars, Counselors/Transcript staff, Principals/APs, Teachers, Business office/Finance
• How does this ongoing friction feel to your team—annoying and manageable, a career-long frustration, or an urgent crisis that needs immediate resolution? Options: Annoying and manageable, A frequent drain on morale, Risking legal/compliance exposure, Urgent — must fix this year

Who Holds the Keys — and Who Gets Left Out?

• If we assume the decision moves forward, who has final sign-off for purchasing and acceptance of the new SIS? Options: Superintendent, Board of Education, CIO/Director of IT, Assistant Superintendent, Finance/Business Manager, Other
• Who are the essential stakeholders that must be engaged and convinced for successful adoption (list roles and any political dynamics we should know)?
• How would you describe the district’s appetite for change right now—conservative (minimize disruption), balanced (improve outcomes while managing risk), or aggressive (prioritize rapid modernization)? Options: Conservative, Balanced, Aggressive
• Who owns data quality, and how are ownership and stewardship currently enforced across student records, attendance, and grading? Options: District data team, School registrars, IT with data stewards, No clear owner/varies by school
• Which stakeholder groups have the most influence over timeline and go/no-go decisions (select up to three)? Options: District leadership (Supt/AS), Board, IT/CIO, Registrars/Student Services, Principals, Business office, Teacher leadership/unions

If State Reporting Were Effortless — What Would Change?

• Imagine your state reporting required zero manual fixes—what immediate benefits would the district realize (funding certainty, staff time, fewer audits, etc.)?
• What specific compliance or certification requirements are non-negotiable for your district (state-specific formats, export windows, audit trails)?
• Which success signals would convince you the system meets state reporting needs (select up to three)? Options: Zero manual edits before submission, Pass first-state validation, Automated audit logs, Faster submission turnaround, Reduction in staff overtime, Positive auditor feedback
• Do you have state-specific custom fields, transcript formats, or legacy reporting hacks we must replicate or retire? Please list them or describe where we can review examples.
• How tolerant is your district of a phased approach to state reporting (pilot one region/year vs. all-at-once)? Options: Prefer all-at-once, Prefer phased by school/grade, Open to pilot first then expand, Undecided

The Migration That Won’t Disrupt the School Year

• What single migration failure would be intolerable for your district (lost transcripts, broken schedules on Day 1, payroll issues, etc.)? Options: Lost transcripts/credits, Schedules incorrect Day 1, State reports failed, Parent/staff access down, Integration outages impacting meal/transport
• Which data sets must be migrated with absolute fidelity (select all that apply)? Options: Student demographics, Historical grades & transcripts, Course and section history, Attendance history, Special education records (IEPs), Scheduling rules and master schedule, State IDs/assessment links
• What are your cutover constraints—dates/times when a cutover is impossible, or must occur (e.g., grading windows, report card cycles)?
• What rollback measures or contingency plans must be in place to feel comfortable with a migration (how many days of parallel operation, who approves rollback)? Options: Full rollback available, Partial rollback by module, Parallel operation for defined window, No rollback — strict cutover
• Which external systems must remain uninterrupted during migration (select all that apply)? Options: LMS (Canvas/Schoology), Food service, Transportation routing, Assessment platforms, HR/payroll, State submission portals, Parent/student portals

Teachers, Parents, and The Day-to-Day: Will They Adopt It?

• If teachers found the new gradebook unintuitive, how would that show up in your metrics or operations? Options: Drop in grade submissions, Increased helpdesk tickets, Parent complaints, Delayed report cards, No clear metric
• Describe the biggest teacher or office-staff complaint about your current system—what do they say and how long has it been that way?
• Which training model do you believe will achieve the best adoption in your district? Options: Hands-on in-person training, Hybrid: in-person + online, Train-the-trainer, Asynchronous video & guides, Embedded in-app help
• How do you prefer to measure adoption success post-implementation (select up to three)? Options: % of teachers actively using gradebook, Timeliness of attendance submissions, Parent portal logins, Number of support tickets, Pass rate of state exports, Teacher satisfaction surveys
• Are there union agreements, district policies, or procurement obligations that could shape training windows or rollout approaches? Options: Yes — requires negotiated windows, Some policies to consider, No significant constraints, Unsure — need to check

What Would Make This Implementation a Certified Win?

• If you could pick one metric that would prove to your board and staff this implementation was a success, what would it be and why?
• What is the realistic timeline you’re targeting for contract approval and implementation (select closest)? Options: Next 30 days, 1–3 months, 3–6 months, 6–12 months, Undecided/No firm timeline
• What budget signals or procurement milestones should we be aware of (funding approvals, grants, end-of-year budgets)?
• Which responsibilities do you expect the vendor to fully own versus district-owned during implementation (integrations, data cleansing, scheduling support, training)? Options: Vendor owns, District owns, Shared — specify in notes
• What would you like the next step to be after this discovery conversation (pilot, reference call, technical deep-dive, budget workshop)? Options: Technical deep-dive, Pilot program, Implementation plan estimate, Share references, Budget/Procurement workshop

Tell Us About Your District — a quick snapshot

• How many students are in your district (total enrollment)? Options: <500, 500–2,499, 2,500–9,999, 10,000–49,999, 50,000+
• Which grade bands do you operate (select all that apply)? Options: Elementary (K–5), Middle (6–8), High (9–12), PreK, Alternative/Adult
• What SIS are you currently using (or most recently used)? Options: PowerSchool, Skyward, Infinite Campus, Tyler, Custom/Locally built, Other
• How long has your current SIS been in production for the majority of your district? Options: <1 year, 1–3 years, 4–7 years, 8–12 years, 12+ years
• Which scheduling models exist across your schools (choose all that apply)? Options: Traditional period schedule, Block schedule, A/B rotating, Hybrid/flexible, Individual school-specific models
• In one sentence, what is the single biggest reason your district is exploring a new SIS now?

If We’re Honest, What’s Really Driving This Change?

• What would you say is the primary pressure forcing a change today—compliance, teacher frustration, integrations, data migration risk, or something else? Options: State reporting / compliance, Teacher gradebook UX, Complex scheduling needs, Data quality / migration risk, Integrations with other apps, Contract/cost pressure, Other
• How long have you been tolerating the issues you just described? Options: Weeks, Months, 1–2 years, 3–5 years, 5+ years
• When these problems surface, how often do you rely on manual workarounds (exports, spreadsheets, phone calls)? Options: Daily, Weekly, Monthly, Quarterly, Rarely
• Give a brief real example of a workaround that created risk or extra cost for your team recently.
• What emotions do these recurring problems tend to create among your staff (pick up to three)? Options: Frustration, Fear (of audit/funding loss), Resignation, Embarrassment, Urgency to change, Determination
• If nothing changes in the next 12 months, what’s the most likely negative outcome you expect?

Where the Data Breaks Down — mapping your fragile spots

• Which downstream systems rely on your SIS data today (select all that apply)? Options: LMS (Canvas/Moodle/Google Classroom), Special Education / IEP tools, Food service, Transportation, Assessment platforms, State reporting portal, Other
• Which data domains experience the most frequent errors—enrollment, attendance, schedules, grades, or transcripts? Options: Enrollment, Attendance, Master schedule, Grades/gradebook, Transcripts, State reporting exports
• Approximately what percent of student records will need cleanup before migration (provide your best estimate)? Options: <5%, 5–15%, 16–30%, 31–60%, 60%+
• Describe a single high-risk data scenario (e.g., incomplete transcripts for graduating seniors) and its consequences.
• Do you currently have automated nightly exports or do most downstream apps pull live via API? Options: Automated nightly exports, Live API integrations, Mix of both, Manual pushes (CSV/email)
• Who owns data quality day-to-day in your district (role/title)?

Who Holds the Keys — people, priorities, and timelines

• Who are the critical decision roles we should plan to engage (select all that apply)? Options: CIO/Director of Technology, Assistant Superintendent/Curriculum, District Registrar, Business/Finance, Principals/School Leaders, Teachers/Instructional Coaches, Board Member/Procurement
• What does success look like to each stakeholder group (brief bullets or success criteria per role)?
• Where are you in the procurement process today? Options: Exploring options / early research, Comparing demos / short-listing, Budget approved / procurement started, Final decision stage, Implementation planning
• What timeline do you have in mind for vendor selection and go-live? Options: Next 30 days, 1–3 months, 3–6 months, 6–12 months, 12+ months
• How flexible is that timeline—what would need to change to move it sooner or push it later?
• Which outcomes are absolute deal-breakers (non-negotiables) for your approval? Options: State reporting fidelity, No data loss for transcripts, Teacher gradebook acceptance, Integration coverage, Budget cap, Other

Teachers, Schedules, and Real-Classroom Workflows — the daily reality

• If you could fix one teacher-facing problem today, what would it be (grading speed, mobile access, gradebook accuracy, etc.)?
• Which teacher workflows cause the most tickets or helpdesk time (select up to three)? Options: Entering grades, Taking attendance, Creating assignments, Accessing student history, Parent communication, Schedule changes
• How are schedules currently built—centrally by district, by school, or mixed? Options: Built centrally by district, Built at school level, Hybrid (district templates + school edits)
• Share a short story of a schedule or gradebook issue that disrupted instruction recently.
• What level of teacher/staff training do you expect during implementation? Options: Comprehensive in-person, Live remote training, Self-paced online modules, Train-the-trainer, Minimal / on-demand
• How do you measure teacher adoption and satisfaction today? Options: Helpdesk metrics, Surveys, Usage analytics, Anecdotal feedback, We don't currently measure

State Reporting & Transcripts — the compliance heartbeat

• Which state(s) or reporting bodies must we be configured for? Options: Single state (please specify in next question), Multiple states, Federal reporting only, Other
• List the state(s) or specific reporting portals and any known quirks we should know about.
• Have you experienced audit findings or funding impacts due to reporting errors in the last 5 years? Options: Yes — material, Yes — minor, No
• What transcript formats (state or district-specific) are required for graduating students and transfers? Options: State template, Custom district template, Common core transcript, College-prep package, Other
• What acceptance criteria would make you confident the system meets compliance (examples: sample state export validated, zero critical errors in test runs)?
• How often do you run pre-submission checks today and who signs off before official state submissions? Options: Weekly, Monthly, Per-submission, Only at submission time

What Would Success Actually Look Like — metrics, signals, and sign-off

• Which of these would be your top three success signals for a successful implementation? Options: State reports pass with zero critical errors, Teacher adoption >75% in first semester, Migration fidelity >98%, Reduction in manual workhours, On-time cutover, Positive parent feedback
• Please specify numerical targets for any KPIs that matter most (adoption %, error rates, time savings, etc.).
• Who will be the formal acceptance signatories for project milestones and final go-live?
• What governance cadence would you prefer post-deployment for issues and enhancements? Options: Weekly during deployment, Bi-weekly for 3 months, Monthly ongoing, Quarterly reviews
• What are acceptable tolerances for migration discrepancies (e.g., how many transcript issues are allowable before rejecting migration)? Options: Zero tolerance, <1% records, 1–3% records, Depends on severity

Risks, Constraints, and the Things That Don’t Make the RFP

• What technical constraints must we work around (on-prem data stores, legacy integrations, limited API access, firewall restrictions)? Options: On-premise database, Limited API capability, Strict firewall/VPN, Custom legacy exports, None of the above
• Are there legal, union, or contractual constraints that could block staging, training, or cutover windows? Options: Yes — contractual timing, Yes — union/staffing constraints, No known constraints, Unsure
• List any blackout dates or seasonal constraints we must avoid (e.g., state testing, registration windows, graduation).
• Which third-party vendors are the highest risk for blocking integrations (name them and why)?
• Do you have an internal contingency/contingent budget to handle unexpected migration work? Options: Yes — allocated, Yes — possible but not allocated, No

Quick Wins and Pilot Ideas — where to prove value fast

• If we wanted a pilot to build confidence quickly, which scope makes sense—gradebook for one school, transcript validation for graduating class, or full enrollment migration for a pilot school? Options: Gradebook pilot (one school), Transcript validation (graduating cohort), Enrollment & scheduling pilot, Integration-only pilot, Other
• Which school(s) or cohorts would be the best candidates for a pilot and why?
• What would count as a successful pilot after 4–8 weeks (specific measures)? Options: Teacher adoption metric, Zero critical export errors, Data migration fidelity, Positive stakeholder feedback
• What internal support do you need from us during a pilot (data mapping, onsite coaching, custom exports)? Options: Data mapping support, Onsite or live training, Custom report/export build, Dedicated migration engineer, Other
• How long of a pilot would you consider meaningful but not disruptive? Options: 2 weeks, 4 weeks, 6–8 weeks, One semester

Commitments & Next Conversations — planning our path forward

• Based on this conversation, how ready are you to move to a technical discovery or demo (choose one)? Options: Ready now — schedule discovery, Need internal alignment first, Waiting on budget/procurement, Not ready
• Do you have a preferred date or window for a technical workshop that includes your data team and registrar?
• Who else should be in the next meeting (list names and roles)?
• Which documents would be most helpful for us to review in advance (sample exports, state specs, current schema, helpdesk logs)? Options: Sample data exports, State reporting specs, Current data schema/ERD, Helpdesk/ticket logs, Master schedule examples, Other
• What would you consider the single most important outcome from our next conversation?