Start Here: Tell Us About Your World

• Which best describes your role in special education at the district? Options: Special Education Director, Compliance Coordinator, Assistant Superintendent, Director of Student Services, Case Manager/Lead, IT Director, Finance Director, Other
• Roughly how many students with active IEPs does your district serve? Options: Under 250, 250–499, 500–999, 1,000–2,499, 2,500–4,999, 5,000+
• How is your special education team organized day-to-day (who owns case management, who owns compliance, where does IT sit)? Describe briefly.
• Which tools or systems are currently involved in your IEP and compliance workflow? Options: Spreadsheets (Excel/Google Sheets), Paper files, Legacy special education system, Student Information System (SIS), Medicaid/EHR billing system, Custom/in-house database, Parent portal (separate), Other
• When you think about special education compliance right now, what is the single worry that affects you most at night?

Who Really Decides—and What Sways Them?

• If one person or group could veto a district-wide change to your IEP platform today, who is it—and why would they say no? Options: Superintendent, School Board, Business Office/Finance, IT Department, Teacher/Union leadership, Parents/Advocates, Special Ed Leadership, Other
• What are the top three decision constraints they cite most often (pick up to three)? Options: Budget/timing of budgets, Data security/privacy, Integration complexity, Staff workload/time for training, Loss of historical data, Vendor stability/track record, Change fatigue, Other
• How does procurement typically work for major ed tech purchases in your district? Options: Formal RFP process, Cooperative purchasing (e.g., state bid), Direct purchase/PO, Pilot then procurement, Unsure/varies
• Which stakeholder group’s approval matters most to you personally when evaluating a platform—special education leadership, IT, or finance—and what one metric will convince them? Options: Special Education leadership – compliance outcomes, IT – security & integrations, Finance – total cost of ownership, Other
• Tell us about a recent internal decision that went well or poorly—what persuaded people, and what surprised you?

Where the Clock Breaks: Timeline Blind Spots

• Think back to the last time timelines failed—what single breakdown triggered the most fallout (audit, complaint, parent escalation)? Options: Scheduling delays (meeting not held), Missing consent or notices, Service implementation lag, Data/reporting mismatch, Lost documentation, Other
• How often do you experience missed or late IEP milestones (eg meeting dates, reevaluations, service start dates)? Options: Multiple times per month, Monthly, Quarterly, A few times a year, Rarely
• When a timeline slips, where does the root cause usually live (people/process/technology)? Options: People (scheduling, staff shortages), Process (unclear ownership/workflow), Technology (no alerts or bad data), Policy/state rules confusion, Multiple of the above
• What monitoring or alerting do you currently have (if any) for upcoming deadlines—and how reliable is it? Options: None, Manual calendar reminders, Spreadsheet-based flags, Legacy system alerts, SIS alerts, Other
• Describe a specific instance when an alert or lack of one changed the outcome—what happened and how long has this been a pattern?

Paper Trails and Puzzle Pieces: Mapping Your Data

• If you had to produce a reconciled state/federal report tomorrow, which systems would you have to combine—and do you trust the output? Options: One system (single source), Two systems, Three or more systems, Impossible without manual reconciliation, Unsure
• Which data sources do you currently rely on for IEP content and reporting? Options: SIS (enrollment/ demographics), Legacy special ed system, Spreadsheets, Medicaid/claiming system, Paper records, Third-party assessment tools, Other
• How many years of historical IEP and service data must be preserved and accessible for compliance purposes? Options: Less than 1 year, 1–3 years, 4–6 years, 7–10 years, 10+ years
• Who owns data quality and extracts today (role/team), and how often do they run reconciliation checks? Options: Special Ed Data Lead/Coordinator, IT/Data Team, Finance/Business Office, Absence of a clear owner, Other
• Tell us about a time you found conflicting data during reporting—what was the conflict, how was it resolved, and how much staff time did it consume?

When Compliance Feels Scary: Real Risks and Stories

• What is the most serious compliance finding, complaint, or legal exposure your district has faced in the last five years—and what was the proximate cause? Options: State monitoring finding, Due process hearing, Parent complaint leading to settlement, Significant corrective action plan, Medicaid billing disallowance, Other
• What were the operational and emotional impacts—staff time, reputation, costs—of that event?
• Since that event, what short-term fixes were put in place and which ones stuck? Options: Additional training, New checklists/processes, Temporary staffing, System changes, No durable changes, Other
• How much transparency do parents and advocates have into IEP timelines and service delivery today? Options: Full transparency (parent portal/access), Partial (paper notices only), Minimal/no transparency, Varies by school
• If you could wave a wand and eliminate one compliance risk instantly, which would it be and why?

What Would Success Actually Look Like?

• If a state monitoring team left with zero findings, what three operational changes would have had to happen? Options: Perfect timeline adherence, Consistent IEP documentation quality, Accurate, reconciled state reporting, Parent engagement/consent tracking, Robust training for case managers, Other
• Which of the following success signals matters most to you right now (pick one)? Options: No missed timelines, Consistent IEP templates and quality, Automated reconciled reporting, Parent portal adoption, Reduced litigation/complaints
• What specific metric would you use to prove success at 6 months and at 12 months?
• Who on your team would celebrate the success first—and who would be quietly skeptical? Tell us their perspectives.
• How soon would you expect to see meaningful change if a modern platform were implemented well? Options: Within 30 days, 1–3 months, 4–6 months, 7–12 months, Longer than a year

Barriers to Change: What Would Stop You?

• If someone suggested moving away from spreadsheets or your current system, what’s the most convincing argument your district would make to stay put? Options: Cost concerns, Disruption to staff, Historic data loss risk, Integration difficulty, Unproven ROI, Other
• Which of these change risks worries you most about a new platform? Options: Poor data migration, Insufficient training/time, Parent backlash, Downtime during go-live, Ongoing vendor support failures, Other
• Have you attempted a similar platform change before? If yes, what failed and what was learned? Options: Yes – implementation failed, Yes – partial success, No – first attempt, No, but pilot attempted
• What internal resources (people/time) could you realistically dedicate to an implementation in the first 90 days? Options: 1–2 staff part-time, 3–5 staff part-time, Dedicated project manager + team, Minimal internal capacity (vendor-led), Unsure
• What would make you confident that a vendor could de-risk the transition for your district? Options: Clear data migration plan, State-form experience, Dedicated trainer/on-site support, References from similar districts, Fixed milestones & penalties, Other

Next Steps Together: Timing, Budget, and Commitment

• If you had to set a go/no-go decision date today, when would you choose—and what three items must be resolved before then? Options: Within 30 days, 1–3 months, 3–6 months, 6–12 months, 12+ months
• What budget source would fund this initiative if approved (pick all that apply)? Options: General fund, Special education grant, ESSER/one-time funds, Capital/technology budget, Cooperative purchase saving, Other
• Who are the core people who must sign off for procurement and implementation (names/roles)?
• Would you prefer a pilot (limited schools/IEP types) or a full-district rollout to start? Options: Pilot first, Full rollout, Hybrid (phase by function), Unsure
• What would be an acceptable acceptance criteria checklist for go-live (examples: timeline alerts tested, sample state export validated, parent portal active)? List your top 5.

Start Here: Tell Me About Your World

• How many students with active IEPs are you responsible for? Options: < 250, 250–499, 500–999, 1,000–4,999, 5,000+
• Walk me through your current IEP workflow from referral to annual review — who touches the record and when?
• Which people or roles interact with your special education platform most often? Options: Case managers, Related service providers, Building administrators, Special education director, IT, Finance/Medicaid team, Parents/guardians
• Which systems do you use today to track IEPs, service delivery, and state reporting? Options: Spreadsheets, Legacy special ed SIS, Student Information System (SIS), Home-grown database, Third-party special education platform, Paper-based
• How confident are you that your current tools reliably produce reconciled student-level data for state submissions? Options: Very confident, Somewhat confident, Uncertain, Not confident at all
• Who currently owns compliance escalations in your district and how do they typically surface? Options: Special education director, Compliance coordinator, Assistant superintendent, Building principal, State monitoring alerts, Other

Is a Missed Timeline a Quiet Crisis in Your District?

• Roughly how many IDEA timeline misses or corrective action items has your district experienced in the past 12 months? Options: None, 1–3, 4–7, 8–15, 16+
• Describe the most recent missed timeline — what went wrong and where did the breakdown start?
• When a timeline slips, which immediate outcomes occur most often? Options: Parent complaint, State finding, Compensatory services required, Attorney involvement, Internal remediation, No immediate consequence
• How long have timeline misses been a recurring issue in your district? Options: New problem (this year), 1–2 years, 3–5 years, Longstanding (>5 years)
• How does the burden of chasing timelines affect your team emotionally and operationally?
• What worst-case consequence do you fear most if timeline issues continue? Options: State corrective action, Costly due process outcomes, Loss of public trust, Increased audit scrutiny, Staff burnout

Where the Data Hides (and Why It Betrays You)

• If you asked for a reconciled student-level report for state submission right now, how long would it take and how confident would you be in its accuracy? Options: Under an hour — highly confident, A day — somewhat confident, Several days — unsure, Weeks — not confident
• List every data source you rely on for special education records, reporting, or billing (SIS, time sheets, Medicaid, paper files, etc.).
• Which of those sources are integrated automatically vs. requiring manual exports or entry? Options: Fully integrated (API/ETL), Partial integrations, Manual CSV/Excel uploads, Paper-to-digital processes, No integrations
• Where do you see the most frequent data mismatches — student demographics, services delivered, hours, or enrollment/status? Options: Demographics, Services delivered, Session hours/frequency, Enrollment/status, Eligibility dates, Other
• How often do you perform reconciliations or cross-system audits before submitting state data? Options: After every submission, Quarterly, Annually, Ad hoc, Never
• If a primary data source becomes unavailable during a reporting window, what contingency plans do you have?

When Documentation Becomes a Liability

• Have you faced legal exposure, parent attorney involvement, or state findings explicitly tied to documentation quality in the last three years? Options: Yes — multiple times, Yes — once, Close call but no formal action, No
• Tell me about a time documentation quality undermined a decision or left the district vulnerable — what was missing or inconsistent?
• Which parts of the IEP packet are most often incomplete or inconsistent? Options: Present levels/goals, Service logs, Progress monitoring, Parent consents/notifications, Transition plans, State-specific form fields
• What checks do you have in place before an IEP is finalized, and why do those checks sometimes fail?
• Roughly how much time would you estimate case managers spend daily fixing paperwork versus delivering services? Options: < 1 hour, 1–2 hours, 3–4 hours, 5+ hours
• When you think about potential due process hearings, what parts of your documentation cause the most anxiety and why?

Imagine a Defensible Compliance Posture — What's Different?

• If your district could guarantee passing any state monitoring visit without corrective action, what would need to be true about your processes and records?
• Which measurable success signals would prove to you that risk is under control? Options: Zero timeline misses, IEP completion rate >95%, Reconciled state submission accuracy, Reduced due process claims, Lower case manager admin time
• What specific acceptance criteria would you require to sign off on an implementation as 'compliant and ready'?
• How would you want state and federal report outputs validated during acceptance testing? Options: Sample student reconciliation, Full-dataset test submission, Side-by-side export comparison, Third-party audit, Other
• Who in your organization would need to sign off on compliance readiness (name roles and their top concern)?

What Would 'Effortless' Case Management Look Like?

• If case managers could reclaim 50% of their administrative time, which work would you want them to prioritize instead? Options: Direct student services, Parent outreach and engagement, Coaching teachers, Quality improvement projects, Professional development
• Which repetitive tasks are highest priority for automation (scheduling, notifications, service logging, progress updates, billing)? Options: Meeting scheduling & invites, Timeline alerts & escalation, Service delivery logging, Automatic state report prep, Medicaid claim batching, Parent notifications/consents
• How do you currently onboard and train new case managers on workflows, and what has been most and least effective?
• What common objections or resistance do staff raise when a new tool is introduced? Options: Learning curve, Time to migrate data, Fear of job change, Lack of trust in accuracy, Insufficient training/support
• What metrics would convince you that automation is delivering value for staff and for compliance? Options: Time saved per case manager, Reduction in timeline misses, Improved audit pass rate, Decrease in documentation errors, Faster state submissions

Who Needs to Be in the Room Before We Change Anything?

• If a single stakeholder could veto this project today, who would it be and what is their primary concern?
• Identify the decision-makers and influencers we should engage (role and one-line concern): special education director, IT, finance/Medicaid, HR, school leaders, parents, board.
• Which stakeholders must approve data sharing, integrations, or student-level exports before implementation can proceed? Options: IT/security, Legal, Superintendent, Data privacy officer, Board, Other
• How do you prefer to receive project updates and escalate blockers (email, weekly calls, shared channel, executive summaries)? Options: Weekly update emails, Weekly status calls, Shared Slack/Teams channel, Monthly executive summary, Ad hoc as issues arise
• What procurement or budget timing constraints (fiscal year, grant cycles, state deadlines) will limit our schedule?

Trade-Offs You’re Willing to Make (and Those You’re Not)

• What compliance or data-security requirement is absolutely non-negotiable for your district?
• Would you prefer a phased implementation (start with core timelines and reporting) or an all-in launch? Why? Options: Phased implementation, All-in launch, Depends on guarantees
• How much customization of state IEP forms do you consider essential versus optional? Options: Full state-form parity required, Core fields mandatory, others optional, Flexible: we can adapt workflows
• What level of parallel-running or downtime is acceptable during migration to ensure no interruption to services? Options: Full parallel run for X weeks, Nightly data syncs only, Short planned downtime, No downtime acceptable
• If budget forces choices, which modules should we prioritize first (IEP workflows, reporting, Medicaid, parent portal, training)? Options: IEP workflows, State/federal reporting, Medicaid billing, Parent portal, Training & change management

If We Partner, What Does 'Success' Look Like in 6–12 Months?

• Six months after go-live, what concrete evidence would make you say this partnership succeeded?
• Which KPIs should we track together to prove value (select up to five)? Options: Timeline miss rate, IEP completion rate, Case manager admin hours, State report reconciliation errors, Number of corrective actions, Parent engagement metrics
• How frequently do you want executive-level reviews vs. operational check-ins during the first year? Options: Weekly operational, monthly executive, Biweekly operational, quarterly executive, Monthly operational only, Quarterly reviews
• Who should participate in user-acceptance testing and sign-off (roles and minimum headcount)?
• If KPI targets are missed, what remediation steps would you expect (training, configuration changes, phased rollback, additional support)? Options: Targeted retraining, Configuration adjustments, Increased support hours, Escalation to leadership, Other

Start Here: Who’s at the Wheel?

• Tell us your role and the size of the student population you oversee (brief) Options: Special Education Director, Assistant Superintendent, Compliance Coordinator, Case Manager/Teacher, Other
• How many students with IEPs does your district serve? Options: <100, 100–499, 500–1,499, 1,500–4,999, 5,000+
• Which systems or tools are you currently using to manage IEPs, service logs, and reporting (select all that apply)? Options: Spreadsheets (Excel/Sheets), Legacy special ed system (name in next answer), SIS seating as primary source, Paper/manual forms, Homegrown database, Other
• If you selected 'Legacy' or 'Other' above, name the product(s) or method and the one thing you wish worked differently
• On a scale from 'barely keeping up' to 'confident and proactive', where would you place your current compliance posture? Options: Confident and proactive, Mostly compliant but reactive, Barely keeping up, At risk of formal findings
• Who else on your team should we include in this conversation so we aren’t missing operational realities? (roles or names)

What Would It Cost to Keep Doing Nothing?

• If a missed timeline resulted in a formal finding tomorrow, what are the tangible consequences your district would face? Options: Financial penalties, Corrective action plan, Compensatory services, Legal costs/attorney involvement, Reputational damage, Other
• How often do you experience missed IEP timelines that require corrective follow-up? Options: Weekly, Monthly, Quarterly, Annually, Rarely/never
• Tell us about a recent case or audit that exposed a compliance gap—what happened and what was most painful about it?
• When compliance problems surface, who typically hears about them first and how does it affect staff morale? Options: Special ed director, Building principal, Case manager, Parents/attorney, Other
• Which of these do you feel has been under-investigated as a root cause in your district? Options: Process ambiguity, Training gaps, Data fragmentation across systems, Insufficient staffing, Policy misalignment, Other

Which Manual Step Would Break Under Pressure?

• Which specific manual or manual-adjacent step in your IEP workflow gives you the least confidence when volume or complexity increases? Options: Timeline tracking/alerts, Parent notifications/consents, Service logging and attendance, State report reconciliation, Data migration from legacy systems, Other
• Walk us through your current IEP workflow from referral to annual review—where do handoffs happen and who owns each handoff?
• Which data sources must reconcile for state and federal reporting in your district (select all that apply)? Options: SIS (student demographics/attendance), Special ed system/service logs, Medicaid claiming system, HR/staffing data, Assessment/achievement systems, Other
• Do you have state-specific IEP forms or fields required by your state? If so, which ones are non-negotiable? Options: Yes — state IEP form(s), Yes — state-specific addenda, No — standard form suffices, Unsure
• Which integrations feel mission-critical to you (pick top 3)? Options: SIS integration (e.g., PowerSchool, Infinite Campus), SSO/identity provider (e.g., Azure AD, Google), Medicaid billing, Assessment platforms, Staff rostering/HR, Parent portal/E-signature
• How would you describe the quality of the data you currently receive from those sources—give a specific example if possible

If Compliance Felt Defensible Tomorrow, What Would You See?

• Describe the top three measurable signals that would convince you the district is reliably meeting special ed compliance (pick up to three) Options: Zero missed timelines, Consistent IEP completion quality, Automated reconciliation with state reports, All service delivery logged and auditable, Parent access and consent tracked, Timely Medicaid claims
• Which KPIs do you currently track and which are missing that you'd want automated? Options: Timelines met, IEP completion rate, Service delivery percent, Parent consent turnaround, State report reconciliation rate, Other
• What would it feel like to your team and to parents if timelines and documentation were consistently reliable?
• What parent portal capabilities would matter most to your families? Options: View IEPs and meeting notes, Consent and e-signature, Service logs and progress updates, Scheduling/notifications, Bilingual support, Other
• If we had to prove your compliance posture to a monitoring team in one dashboard, what three pieces of evidence must be front-and-center?

What Would Cause You to Say 'No' to a Solution?

• What are your non-negotiable deal-breakers for adopting a new special education platform? Options: Lack of state form support, No SIS/Medicaid integration, Poor data migration plan, Insufficient training, No parent portal, Unclear security/PII controls
• How do you prefer training to be delivered for case managers with mixed tech skills? Options: Role-based live sessions, On-demand video + knowledge base, Train-the-trainer model, Blended: live + on-demand, Other
• What does a successful data migration look like to you—what must be preserved and what can be rebuilt?
• Who needs to sign off on acceptance criteria before you consider go-live successful? Options: Special Ed Director, IT / Security, Finance, Building Principals, Parent/Advocate representative, State liaison, Other
• What level of vendor support during the first 90 days would make you feel comfortable? Options: Daily onsite/remote check-ins, Weekly structured reviews + SLAs, On-demand support with guaranteed response time, Minimal support—self-service focused

Who Owns Risk, Data, and Decisions?

• If you were suddenly unavailable, who would be accountable for special education compliance and why?
• Which permission model best fits your district’s needs (who should be able to edit, who should view only)? Options: Case manager edit / admin review, Teacher edit / principal approve, Role-based least privilege, Open access for speed, Custom per-district model
• Which SSO/identity providers are in use or preferred for staff and parent access? Options: Azure AD, Google Workspace, Okta, Clever, District LDAP, No SSO / local accounts, Other
• Describe any state or district data governance policies or privacy restrictions we need to honor
• What risk controls would you insist on before approving a build (examples: sandbox testing, role-based test sign-offs, data masking)? Options: Sandbox with anonymized data, Stepwise rollout by building, Pre-go-live acceptance testing, Formal sign-off checklist, Automated audit logs

Decision Rhythm: If We Started Today, What’s the Timeline?

• What is the earliest realistic go-live window you would consider for a full roll-out (given procurement and internal approvals)? Options: <3 months, 3–6 months, 6–9 months, 9–12 months, 12+ months
• What procurement or budget cycles do we need to align with? Options: Current fiscal year, Next fiscal year, Grant cycle, Emergency funds/one-off, Unsure
• Who are the final decision-makers and what is their typical decision timeline?
• What does a smooth pilot look like to you (duration, scope, metrics we must hit)? Options: 4–6 weeks small cohort, 8–12 weeks district pilot, Semester-long pilot, Phased building-by-building
• What communication cadence and channels work best for progress updates and escalation? Options: Weekly email summary, Biweekly steering committee, Slack/MS Teams channel, Monthly executive summary, As-needed escalations
• What would be a small, meaningful next step you’d like to take after this discovery? Options: Technical deep dive call, Executive briefing, Pilot proposal, Data sample review, Security questionnaire

Quick Snapshot: Who's Leading This Work?

• Who is the primary district lead we should design this plan around (name + role)?
• Which of these best describes your district’s scale? Options: <500 students, 500–2,499 students, 2,500–9,999 students, 10,000+ students, Charter/Multiple LEAs
• Which system currently houses your student and special education data? Options: In-house SIS (e.g., PowerSchool, Infinite Campus), Third-party special ed system, Spreadsheets / paper, Combination (SIS + spreadsheets), We’re not sure
• Who else will need to be engaged for discovery and decision-making (select all that apply)? Options: Special Education Director, Compliance Coordinator, Assistant Superintendent, IT Director, Finance/Business Manager, Medicaid Billing Coordinator, School Principals, Parent Representative, Other
• Briefly describe one recent moment that made you think “we need a better system” (what happened and who noticed)?

Are You Quietly at Risk?

• When was the last time your district received a compliance finding, corrective action, or formal parent complaint related to IEP timelines or documentation? Options: Within last 6 months, 6–12 months ago, 1–3 years ago, Never / Not sure
• How often do you miss an IEP milestone (evaluation completion, meeting within timeline, annual review) across the district? Options: Weekly, Monthly, Quarterly, Rarely, Unsure
• When compliance issues surface, what tends to be the outcome for the district (select all that apply)? Options: State corrective action, Compensatory services awarded, Increased monitoring, Attorney involvement / due process, Internal remediation only, No consistent pattern
• Which recurring compliance gap worries you most right now and why?
• How does it feel when you think about your district’s readiness for the next state monitoring visit? Options: Confident, Cautiously prepared, Worried, Overwhelmed

Where Does Paperwork Break Down?

• Which part of the IEP lifecycle causes you the most operational friction (scheduling meetings, documentation, service logging, progress monitoring, reporting)? Options: Scheduling meetings, IEP documentation quality, Service delivery logging, Progress monitoring, State/federal reporting, Parent communications
• Describe a typical handoff between case managers and related service providers — where do these handoffs interrupt compliance or data quality?
• Which data sources must reconcile for state reporting (select all that apply)? Options: SIS, Special Ed system, Related services logs, Medicaid billing, Attendance, Assessment platforms, Other
• How do parents currently access their child's IEP and service logs? Options: Parent portal with full access, Email / PDF copies, Paper only, No consistent method, Other
• Tell us about a recent instance where documentation gaps created extra work or risk — what was the root cause and impact?

If a State Monitor Walked In Tomorrow…

• If a state monitor inspected your files tomorrow, what single weakness would you be most afraid they'd find?
• Which of these outcomes would feel most meaningful after a successful monitoring visit? Options: No findings, Minor corrective actions only, Validation of improved workflows, Clear reconciliation of state data, Other
• What would a defensible compliance posture look like to you in concrete terms (examples: every IEP within timeline, reconciled extracts, auditable service logs)?
• How would achieving that posture change the day-to-day experience of case managers and administrators?
• Which stakeholder’s buy-in matters most to reach that posture and why? Options: Special Ed Director, Superintendent/Asst. Supt., IT Director, Business/Finance, Parent Advisory Group, Union/Staff Leadership, Other

What’s Really Getting in the Way of Change?

• Why haven’t past attempts to improve special ed workflows fully stuck?
• Which of the following barriers are most relevant for your district (select up to three)? Options: Budget constraints, Limited IT capacity, Staff turnover / shortages, Resistance to new tools, Complex state form requirements, Data quality issues, Training bandwidth
• How confident are your case managers with using digital tools for IEPs and service logs today? Options: Highly confident, Somewhat confident, Limited confidence, Prefer paper / not confident
• Describe one staffing or workflow change that would most increase the chance of a successful rollout.
• If you had to prioritize constraints to address in the next 90 days, which two would you choose and why?

How Will You Know This Worked?

• What are the top 3 measurable signals you want to see improve after implementation (pick up to 3)? Options: % of IEPs completed on time, Reduction in state findings, Service delivery log completeness, Parent portal adoption, Time spent per IEP, Accuracy of state export data, Medicaid claim reconciliation
• What target level for those signals would feel like a clear success (give numbers or percentages)?
• Who will own tracking those success metrics on an ongoing basis? Options: Special Ed Director, Compliance Coordinator, IT/Analytics, Business Office, Other
• How frequently do you want progress reports during implementation (select one)? Options: Weekly, Bi-weekly, Monthly, At milestones only
• If progress stalls against these metrics, what governance or escalation path currently exists?

The Tech Fit: Can Your Systems Talk?

• Which systems MUST integrate with the special ed platform for you to consider a full rollout? Options: SIS (e.g., PowerSchool), Medicaid billing, SSO / Directory (Active Directory, Azure), State reporting submission interface, Assessment systems, Payroll/Finance
• Do you have a preferred method for data exchange for state reports and exports? Options: SFTP extracts, API / real-time, Flat-file upload (CSV), Vendor-managed submission, Unsure / need guidance
• What is the current state of student ID and demographic matching across systems? Options: Consistent and clean, Some discrepancies, Major mismatches, We don’t track this
• Who in your IT team will be our primary technical contact for integrations and SSO?
• List any state-specific IEP forms or reporting quirks we should know about up front.

People & Process: Who Will Own It?

• If we fast-forward 90 days post-go-live, who do you expect to be the daily owner of system configuration and compliance dashboards? Options: Special Ed Director, Compliance Coordinator, Dedicated Data Analyst, IT Admin, Vendor-managed
• Who will be the primary champions and trainers for case managers and providers (name + role)?
• How many distinct user groups and permission sets will you need (e.g., case managers, providers, admins, parents)? Options: 1–3, 4–6, 7–10, 10+
• What training cadence works best for your team during rollout (select all that apply)? Options: Live cohort sessions, On-demand videos, Role-based workshops, Train-the-trainer, Office hours / drop-in clinics
• What acceptance criteria must be met before you’ll sign off on go-live (describe or list key tests)?

Risk, Legal, and Parent Relations: What Keeps You Up at Night?

• If a parent’s attorney reviewed your IEP documentation today, where would they likely find the strongest vulnerability?
• Do you have existing policies for data retention, audit logging, and electronic signatures that the new system must respect? Options: Yes – documented, Yes – informal, No, Unsure
• How should we handle parental consent, electronic signatures, and audit trails to satisfy your legal counsel?
• Have you had litigation, OCR complaints, or due process hearings related to special education in the last five years? Options: Yes – multiple, Yes – one, No, Prefer not to say
• What reporting or documentation would you want prepared in advance to reduce risk during a future complaint or hearing?

Realistic Next Steps That Respect Your Bandwidth

• Given your priorities and constraints, what is a realistic target window for a pilot or initial rollout? Options: 30–60 days, 61–120 days, 3–6 months, 6+ months, Unsure
• Which subset of schools or student populations would you prefer to pilot with and why?
• What level of vendor involvement feels right for your pilot (select one)? Options: Full hands-on support, Co-managed, Advisory only
• What concerns would prevent you from approving a pilot this quarter?
• If we left this conversation with three clear commitments, what would they be (who will do what by when)?