Who's in the Room — and Who's Quietly Deciding?

• Which district roles will be active participants in this LMS evaluation and decision process? Options: Technology Director, Chief Academic Officer, Curriculum Coordinator, Building Principals, Teacher Representatives, Instructional Coaches, Special Education Director, Board Member(s), Parent/Guardian Representative, Other
• Who will have final sign-off authority for the purchase and district-wide rollout? Options: Board approval required, Superintendent, Technology Director, Chief Academic Officer, Shared authority (committee), Other
• Which individuals or groups have historically blocked or slowed adoption of new instructional tools here? Tell us names/roles and a quick example of what held them back.
• How involved do teachers and building coaches typically get in pilot selection and feedback cycles? Options: Deeply involved — co-designers, Consulted regularly, Occasionally consulted, Rarely involved, Not involved
• What emotional outcome does each key stakeholder want from this change? (e.g., 'less firefighting' for tech, 'consistent instruction' for curriculum leads, 'simplicity' for elementary teachers)
• Which timeline best matches your ideal decision window? Options: Next 30 days, Next 2–3 months, This semester, Next school year, No firm timeline

Are We Just Managing Chaos or Actually Solving It?

• How many distinct instructional platforms are teachers actively using across the district today? Options: 1 (already consolidated), 2–3, 4–6, More than 6, Unsure
• Name the primary platforms currently in use (list by name and which grades/buildings use them).
• How reliable is your current SIS rostering and grade sync from vendor tools? What kinds of errors are most common? Options: Very reliable, Mostly reliable with occasional errors, Frequent sync errors, Manual rostering required, We don't sync grades
• Where do parents most often report confusion or frustration when trying to find assignments and grades? Options: Multiple logins, Inconsistent location of assignments, No mobile-friendly view, Delayed grade visibility, Unclear communication from teachers, Other
• Walk us through a typical teacher workflow for creating and grading an assignment in each grade band (elementary, middle, high, special education). What differs and why?
• What accessibility or IEP-related gaps have you observed in current tools (e.g., screen reader support, alternate formats, accommodations tracking)? Provide specific examples.
• How do you currently measure day-to-day usage across schools (active teachers, assignments posted, parent logins)? Options: SIS reports, Vendor analytics dashboard, Manual tracking, We don't measure consistently, Other

What’s Getting in the Way of Teachers Actually Using One Platform?

• What would have to be true for your teachers to finally stop patchworking multiple tools and use a single LMS every day?
• Which pain points push teachers to keep using a second tool (select all that apply)? Options: Simpler interface for young students, Advanced features for high school, Special ed accommodations not supported, Gradebook mismatch with district policy, Parent communication gaps, Assessment import/export issues, Other
• How much time do teachers typically spend per week troubleshooting platform issues or workarounds? Options: <1 hour, 1–3 hours, 3–6 hours, 6–10 hours, 10+ hours
• Tell us about a recent day or week when platform fragmentation caused a real problem—what happened, who felt the impact, and what was the outcome?
• Which grade bands feel most at risk of not adopting a common LMS and why? Options: Elementary, Middle, High School, Special Education, All equal risk, Unsure
• Who currently owns teacher support for these tools (district IT, building tech, vendor support, teacher leaders)? How well is that working emotionally and operationally? Options: District IT, Building-level tech/coach, Vendor support, Hybrid model, No clear owner

If We Were Measuring Success, What Would It Prove?

• Which of these district success signals matter most to you right now? (pick up to three) Options: Teacher daily active use, Assignment frequency by grade band, Standards tagging & coverage, SIS grade sync accuracy, Parent portal engagement, Accessibility/IEP compliance, Reduced tool count, TCO reduction
• Set a realistic target for teacher daily active use within 6 months of pilot (choose a range). Options: >80%, 60–80%, 40–60%, 20–40%, <20%
• What level of SIS grade sync accuracy would you consider acceptable at pilot completion? Options: 99–100%, 97–99%, 95–97%, 90–95%, <90%
• How will you quantify parent portal satisfaction in a way that matters to your board? Options: Parent NPS/CSAT survey, Login rate / adoption, Qualitative parent focus groups, Reduction in parent help tickets, Other
• What are your non-negotiable acceptance criteria for pilot success (list top 3–5 measurable items)?
• Which stakeholder-specific definitions of 'good' should we individually document (e.g., tech director uptime, curriculum lead standards mapping, teacher ease of use)? Options: Technology Director, Curriculum Coordinator, Building Principals, Instructional Coaches, Teachers by grade band, Special Education Team, Parents/Guardians, Board

Picture a Single LMS That Actually Works — What Do You See?

• For elementary teachers, what three features would make the LMS feel simple enough to use every day?
• For high school teachers, which advanced capabilities are must-haves (select all that apply)? Options: Rubric-based grading, Discussion boards, Advanced assessment item types, Weighted grading schemes, Integration with lab/subject tools, Other
• For special education staff, what workflows or integrations are essential to keep IEP accommodations connected to assignment workflows?
• How would a single LMS reduce instructional tool fragmentation in practice? Give an example scenario for a student with classes at multiple schools or grades.
• Which parent-facing features would make families stop asking 'Where is the assignment?' (pick up to three)? Options: Single sign-on for all kids, Daily digest emails/texts, Mobile-friendly assignment timeline, Clear grading visibility, Translations and accessibility options, Two-way messaging with teachers
• If you could snap your fingers and fix one persistent workflow problem across the district, what would it be and why?

What Would We Have To Agree To — Really — For This To Move Forward?

• Which modules must be included in the initial scope of a pilot for you to consider it meaningful? Options: Gradebook with SIS sync, Standards tagging and reporting, Parent portal, IEP/accommodations workflow, Assessment import/export (QTI), Resource library by grade/subject, Other
• What is the ideal pilot size and composition (number of schools, grade bands, teacher profiles)? Options: Single school — focused grade band, Multiple schools across bands, District-wide small sample, Pilot with special education focus, Unsure — need recommendation
• Who should own pilot coordination and communications on the district side? Options: Technology Director, Curriculum Coordinator, Instructional Coaches, Building Principals, Designated pilot coordinator (new role)
• What training formats are most effective for your teachers by grade band? Options: Live in-person, Live virtual (grade-band specific), On-demand microlearning, Coaching with instructional coaches, Train-the-trainer model, Blended approach
• What budget, contracting, or procurement constraints should we be aware of that could delay mutual commitment?
• What materials, timing, and narrative does the board expect to see before approving a district-wide rollout? Options: Pilot results and metrics, Total cost of ownership analysis, Training and support plan, Risk mitigation plan, Case studies from similar districts, Other

Ready for Launch — What Still Needs to Be Unblocked?

• Do you currently have the necessary SIS access and API credentials to support roster and grade sync for a pilot? Options: Yes — full access, Yes — partial access, No — we need to provision access, Unsure
• What are the biggest technical risks you foresee for data migration or live sync during pilot and how would you like them mitigated?
• Which accessibility checks must pass before you’ll accept pilot rollout (select all that apply)? Options: Screen reader compatibility, Keyboard navigation, Color contrast, Alt text and captions, IEP accommodations workflow tested, Translation/localization
• Who signs IT approvals for external platforms and what typical lead time should we plan for?
• What pilot support cadence will make teachers feel safe to try something new (select one)? Options: Daily on-call support, Weekly check-ins, Bi-weekly coaching sessions, Embedded coach in classrooms, Office hours + on-demand tickets
• What checklist items must be complete for you to consider the full district launch 'go' following pilot?

How Will We Measure, Celebrate, and Course-Correct Together?

• Which KPIs will you want in an ongoing dashboard after launch (pick top 4)? Options: Teacher daily active use, Assignments posted per week, Standards coverage rate, SIS grade sync success rate, Parent portal logins, IEP accommodation completion rate, Support ticket volume, Teacher satisfaction score
• Who on the district side will review these KPIs and at what cadence? Options: Weekly — Technology Director, Weekly — Curriculum Team, Monthly leadership review, Quarterly board report, Other
• What would trigger a joint post-launch review or remediation (give specific thresholds or qualitative signals)?
• How do you prefer to maintain a shared backlog for enhancements and issues post-launch? Options: Shared ticketing system with priorities, Quarterly roadmap workshops, Joint product council, Ad-hoc working groups, Other
• What early wins would you celebrate publicly to build momentum with teachers, parents, and the board?
• Realistically, when would you expect to evaluate pilot outcomes and decide on district rollout? Options: Within 30 days of pilot end, Within 60 days, Within 90 days, Longer than 90 days, Unsure

How Are You Really Running Instruction Today?

• Walk me through a typical school day — where do teachers actually go to post assignments, collect student work, and record grades?
• Which classroom platforms, assessment tools, and parent-facing systems are currently in use across the district? Options: District LMS (name), Google Classroom, Schoology, Canvas, Seesaw, ClassDojo, Assessment vendor(s), Custom district tools, None/Not standardized, Other
• Which platforms are tied to specific grade bands, departments, or buildings? Please map platform → grade/department.
• How consistently do teachers follow district guidance about where to post assignments and final grades? Options: Always, Most of the time, About half the time, Rarely, Never
• Tell me about a recent situation where a student, teacher, or parent couldn’t find assignment or grade information — what happened and how was it resolved?

What’s Secretly Eating Your Time?

• If you had to name the single administrative headache that costs your team the most time each week, what would it be?
• On average, how many distinct logins or tools do building techs and classroom teachers juggle to keep rosters, grades, and communications working? Options: 1–2, 3–4, 5–6, 7+
• Which workflows currently require manual workarounds or repeated human intervention? Options: Gradebook sync/entry, Roster corrections, Attendance reconciliation, CSV imports/exports, Parent notifications, Standards tagging, IEP accommodation application, Assessment imports, Other
• Describe a specific workaround someone on your team performs regularly — who does it, how often, and why it’s necessary.
• How does this operational burden show up in teacher feedback or in the time available for planning and instruction?

Are We Leaving Families Out?

• What’s the single most common complaint you still hear from parents about accessing their child’s assignments or grades?
• How do parents and guardians currently access assignment and grade information? Options: SIS parent portal, Teacher email or message, Multiple classroom apps (varies by teacher), Paper/handouts, No reliable channel, Other
• Estimate what percentage of families can reliably find daily assignments and current grades without asking a teacher. Options: 0–25%, 26–50%, 51–75%, 76–90%, 91–100%
• Share a recent example of a parental escalation or board question about visibility — what did it reveal about how parents experience your tools?
• What supports exist for multilingual families and how often are translations or bilingual resources actually provided? Options: Automated translation in tools, District-provided bilingual materials, Bilingual staff outreach, Third-party translation services, No dedicated support, Other
• How often do caregivers tell you they are confused about which platform to use? Options: Daily, Weekly, Monthly, Rarely, Never

Grade-Band Reality Check — From Kindergarten to Senior Year

• What parts of your current platform mix completely break down when you move from elementary to high school?
• For each grade band (K–2, 3–5, 6–8, 9–12), list the top two teacher workflows that must be supported for daily instruction.
• Which features are non-negotiable for high school teachers versus elementary teachers? Options: Rubric-based grading, Discussion boards, Simplified one-click assignment, Parent task lists, Student portfolios, Timed assessments, Multimedia submissions, IEP accommodations visibility, Other
• How do teachers currently differentiate assignments for students needing modified work or alternate standards?
• How are building coaches and instructional techs deployed by grade band—formal training cycles, on-call support, or peer mentoring? Options: Grade-band scheduled trainings, On-call technician support, One-on-one coaching, Peer-led communities, No formal coaching, Other
• Tell me about one time a grade-band mismatch (tool capability vs classroom need) led a teacher to avoid the platform — what was the impact?

Roster & SIS — Where the Truth Hides

• If your SIS integration were suddenly flawless, what manual tasks would your team stop doing tomorrow?
• Which SIS or student data systems do you use, and are there multiple systems across schools? Options: PowerSchool, Skyward, Infinite Campus, Aspen, Other, We don't have a unified SIS
• How frequent and accurate are roster and grade syncs today? Options: Real-time/near real-time, Daily batch, Weekly, Manual imports, Irregular/spotty
• How often do roster mismatches or sync failures occur, and what is your current process to detect and fix them?
• Who in your organization owns SIS credentials, API access, and the final signoff for integration testing? Options: District IT, Vendor/Integrator, Building admin, Curriculum office, Other
• Are there procurement, security, or vendor policies that typically slow or block integrations (e.g., contract terms, SSO requirements, data use agreements)? Options: Yes — strict constraints, Yes — moderate constraints, No, Unsure
• Describe the last time a grade sync problem affected family reporting or state reporting — what were the consequences?

Accessibility — When Compliance Isn't Enough

• Where do students with IEPs and 504 plans still fall through the cracks in your current digital workflows?
• Which accessibility standards, accommodations, and reporting requirements does your district need to meet? Options: IEP tracking/IDEA, Section 504, WCAG 2.1 AA, Assistive tech compatibility, State-specific accessibility rules, Other
• How do teachers currently assign and track required accommodations in their day-to-day workflows?
• How often do teachers unintentionally fail to apply accommodations to assignments, and what causes those misses? Options: Frequently, Occasionally, Rarely, Never, Unsure
• Which assistive technologies or content formats are mission-critical in your district (e.g., screen readers, captions, audio books)? Options: Screen reader compatibility, Closed captioning, Audio books / audiobooks, Text-to-speech, Alt text for images, Large print / zoom, Other
• Share an example where accessibility or accommodation failures impacted a student's learning or led to an audit/complaint.

If We Could Fix One Thing This Year

• If you had to pick one tangible improvement that would convince teachers, parents, and the board that progress is happening, what would it be?
• Select the top three near-term priorities that would deliver the most visible impact. Options: Reliable SIS sync/rostering, Unified parent portal, Simplified teacher assignment flow, IEP accommodations tracking, Standards tagging and reporting, District-level analytics and visibility, Reducing number of classroom tools
• Which internal stakeholders must be aligned for that change to move forward? Options: Technology Director, Curriculum Director, Building Principals, Teacher Representatives/Union, Board Members, Parents/Community, Other
• What constraints (budget, contract terms, staffing, procurement timelines) are most likely to block progress this year? Options: Budget, Existing vendor contracts, Staff capacity, Procurement/board calendar, SIS vendor limitations, Training availability, Other
• What would success look like in 90 days and at the end of the school year for this priority?
• Who should be the single point of contact for a pilot or initial rollout to minimize friction? Options: District Technology Director, Curriculum Coordinator, Building Coach/Lead Teacher, Vendor-led Project Manager, Other

Quick Wins & Next Steps

• What evidence or small wins would make your leadership comfortable expanding a pilot into a broader rollout?
• Which schools or grade bands would be the ideal candidates for a pilot and why? Options: Elementary cluster, Upper elementary, Middle school, High school, Special education program, Combination of above
• What pilot duration, acceptance criteria, and measurable success metrics would you require to consider it successful?
• What level of vendor involvement and training cadence would feel appropriate for a pilot? Options: High-touch onsite support, Hybrid onsite + virtual, Mostly virtual training, Train-the-trainer with district leads, Minimal vendor involvement
• List any procurement, compliance, or board approval milestones we should plan around in the next 6–12 months.
• How would you prefer progress updates and decision points during a pilot to be delivered? Options: Weekly written reports, Biweekly checkpoints, Live dashboard access, Monthly executive summary, In-person steering meetings

Quick Pulse: Where Are We Right Now?

• Which statement best describes your district’s immediate readiness for an LMS pilot or cutover? Options: We haven’t started planning, Planning but no technical work, SIS access and mapping started, Data migration in progress, Pilot rostered and scheduled, Ready for phased rollout
• Who on your team will be our primary operational contact for deployment activities (name, role, best contact method)?
• What is your target window for initiating the pilot roster (month/quarter)? Options: Next 30 days, 1–3 months, 3–6 months, Next school year, Undecided
• Thinking about past rollouts, what has felt most stressful for your staff during go-live windows?
• On a scale of 1–5, how would you rate stakeholder alignment today between IT, curriculum, school leaders, and teachers? Options: 1 - Highly misaligned, 2 - Somewhat misaligned, 3 - Neutral, 4 - Mostly aligned, 5 - Fully aligned

If Your Rosters Aren’t Perfect, Everything Breaks — How Confident Are You?

• If rostering errors caused missing students or incorrect sections during the pilot, how damaging would that be to your adoption goals? Options: Critical risk, High concern, Manageable, Minor impact
• Which SIS systems are in use across your district (select all that apply)? Options: PowerSchool, Infinite Campus, Skyward, Tyler, eSchoolPlus/ASPEN, Other / Custom
• Do we already have read-only or admin credentials we can use for mapping and test imports? If yes, please list access scope and expiration. Options: Yes — full API/admin, Yes — limited API/read-only, No — need to request access, Unsure
• How frequently does your SIS publish roster changes that need to sync (e.g., nightly, weekly, real-time)? Options: Real-time / API, Nightly, Weekly, Only at term boundaries, Varies by school
• Tell us about the last time rostering caused a teacher-facing issue — what happened and how long did it take to resolve?

Who’s Truly Responsible When Data Fails?

• When student data or grade syncs fail, who is expected to own incident resolution from your side? Options: District IT, School tech coach, District SIS vendor, Site admin, Other — please specify
• What internal SLAs or timelines does your team operate under for resolving critical SIS or sync issues? Options: Same day, 24–48 hours, 3–5 business days, No formal SLA
• Which teams need formal change notices before we deploy mapping changes (select all that apply)? Options: IT, Curriculum Office, Building Principals, Teachers, Special Education Office, Parent Communications
• If we identify a data ownership gap during pilot, who has authority to make the final call on a remediation path?
• How does your district prefer to receive incident updates during a pilot—email, ticketing portal, daily standup, or other? Options: Email, Ticketing portal (e.g., JIRA), Daily standup call, SMS/Slack, Other

What Would a Failed Migration Look Like Here?

• If a migration caused permanent data loss or corrupted grade history, how would that impact reporting and compliance for your district? Options: Severe impact, Significant, Manageable with workarounds, Minimal
• Which data domains are highest priority to preserve and validate during migration? (pick all that apply) Options: Student roster & demographics, Enrollment history, Grades & grade history, Assignment submissions, IEP/accommodation records, Parent/guardian contacts
• Do you have a canonical export we should mirror during migration testing (e.g., nightly CSV, API schema)? If so, please describe format and cadence.
• What rollback or recovery processes do you currently have for data migrations? Options: Full nightly backups available, Point-in-time restore, Manual re-import procedures, No formal rollback plan
• How much time can your team allocate to parallel validation (teacher/coach checks) during a test migration window? Options: <4 hours, 4–8 hours, 1–2 days, Multiple days per window, Depends on school schedule

How Accessible Will This Feel to Your Students and Families?

• If students with accommodations can’t access assignments day one, how quickly must we have a fix before you consider pausing the pilot? Options: Within hours, 24 hours, 72 hours, Longer
• Which accessibility standards or regulations are top of mind for your district (select all that apply)? Options: IDEA / IEP requirements, Section 504, WCAG 2.1 AA, State-specific accessibility rules, Other
• Describe any existing workflows where IEP accommodations must appear directly inside the assignment/grade workflow rather than in a separate tool.
• Have you conducted accessibility audits on your current tools? If yes, what were the primary findings and remediation priorities? Options: Yes — major issues, Yes — minor issues, No formal audit, Audit in progress
• Which assistive technologies (screen readers, switch devices, captioning tools) are commonly used across your schools? Options: JAWS, NVDA, VoiceOver, Switch device support, Closed captioning, Other / district-specific

Pilot Reality Check: Is the Pilot Designed to Prove or to Just Survive?

• If your pilot only proves the system can run without major outages but doesn’t move teacher behavior, would you still consider it successful? Options: Yes — stability is success, No — adoption must change, Partial — depends on metrics
• Which groups are you planning to include in the pilot (select all that apply)? Options: Elementary teachers, Secondary teachers, Special education staff, School tech coaches, Parents/guardians, Students (classroom use)
• What measurable success criteria will determine whether the pilot advances to district-wide deployment? Options: Teacher adoption %, Assignment frequency, SIS grade sync accuracy, Parent portal usage, Accessibility compliance
• How will you set up pilot rosters to reflect real district complexity (co-teaching, split classes, itinerant teachers)?
• Who will run teacher feedback sessions during the pilot, and how often will they occur? Options: District curriculum team, Building coaches, Vendor-led sessions, Weekly, Biweekly, At pilot milestones

How Tight Is Your Cutover and Support Plan?

• If we hit a major issue during cutover, what is the maximum time the district can tolerate degraded grading or assignment access? Options: Hours, 24 hours, 48–72 hours, Longer with compensations
• Which escalation paths exist today for after-hours critical incidents (select all that apply)? Options: On-call IT staff, Vendor on-call support, School admin escalation, No formal after-hours process
• What does your ‘Tier 1’ teacher support look like during rollout—who answers quick how-to questions on day one? Options: Site tech coach, Vendor support desk, Help center + knowledge base, District helpdesk
• Describe the communication plan you expect for parents when the pilot goes live (channels and message owners).
• Would you prefer a phased cutover by grade band, by school, or a simultaneous district window? Options: By grade band, By school/cluster, Simultaneous district, Hybrid phased

Who Signs Off — And What Keeps Them Up at Night?

• If the board or superintendent asks: 'Why should we trust this system with student grades?', what evidence will they expect to see?
• Which approval is the final gate for full launch (select one)? Options: Board approval, Superintendent sign-off, Chief Academic Officer, Technology Director, Other committee
• What materials and timelines do you need from us to support your board presentation or executive briefing? Options: Pilot results summary, Technical readiness checklist, Risk mitigation plan, Training plan by grade band, All of the above
• Which stakeholder worries do you hear most often about launching a new LMS (pick top three)? Options: Data loss, Teacher adoption, Parent confusion, IEP compliance, Costs and recurring fees, Integration complexity
• Who from your leadership should be included in our weekly deployment checkpoint calls?

Migration and Testing: How Will We Know the Data Is Right?

• If we surface mismatches between SIS and LMS data during testing, how many iterations of fix-and-validate do you expect to allow before freeze? Options: One, Two, Three, No predefined limit
• Which validation checks are non-negotiable before pilot start (select all that apply)? Options: Roster counts by section, Grade sync verification, Assignment submission integrity, IEP accommodation flags, Parent contact linkage
• Do you have a sandbox or staging SIS instance we can use for full end-to-end tests? If not, what is the feasible alternative? Options: Yes — sandbox available, No — can arrange read-only export, No — only production available with precautions, Unsure
• Who will sign off on validation artifacts (e.g., test run reports, sample teacher checks)? Options: IT lead, Curriculum lead, School principal, Vendor deployment manager, Other
• Please describe one real data quality issue you expect we’ll need to address during testing (examples: multiple email formats, duplicate student IDs, split sections).

Training & Support: Are We Setting Teachers Up to Succeed?

• If teachers feel the platform is just another obligation, how likely are they to adopt it beyond the pilot? Options: Very unlikely, Somewhat unlikely, Neutral, Somewhat likely, Very likely
• Which grade-band training formats resonate most with your staff (select all that apply)? Options: Short micro-learning videos, Live hands-on workshops, Role-based coaching (grade band), Self-paced modules, Office hours/support drop-in
• Who currently does coaching for teachers at the building level and how many hours per week can they dedicate to pilot support?
• What teacher success metrics should we report weekly during pilot (select up to three)? Options: Active teacher logins, Assignments posted per week, Grade sync accuracy, Parent portal logins, IEP accommodation usage
• Would you like vendor-led co-teaching sessions during initial weeks or a train-the-trainer model with your coaches leading after? Options: Vendor-led co-teaching, Train-the-trainer, Combination, Unsure

Risk Register & Contingencies: What Keeps Us Prepared?

• If a critical risk materializes during pilot, what authority level can pause the rollout immediately? Options: Technology Director, Superintendent, Pilot Steering Committee, Vendor + District mutual agreement, Other
• Which of these do you already maintain and can share to accelerate risk planning? Options: SIS integration docs, Network firewall rules, Data governance policy, IEP data flow diagrams, None of the above
• What contingency would you prefer for grading continuity if grade sync is interrupted (select one)? Options: Temporary manual grade entry, Hold final grade posting, Use a parallel grade export, Other — describe
• Are there seasonal constraints (state testing windows, grading periods, holidays) we must avoid for cutover? Options: State testing windows, Final grading periods, State reporting deadlines, Summer break, No major constraints
• Please list any district-specific compliance or legal requirements that must be validated before launch (FERPA nuances, data residency, etc.).

Commitments & Next Steps: Who Does What and When?

• Based on today’s answers, which three actions would most reduce your deployment risk in the next 30 days?
• Who will be responsible on your side for each of these actions (name and role)?
• When should we schedule our first joint readiness checkpoint to review mapping, test results, and pilot roster confirmation? Options: Within 1 week, 1–2 weeks, 3–4 weeks, After initial test migration
• What would you like to receive from us before that checkpoint (select all that apply)? Options: Technical readiness checklist, Sample migration run report, Pilot roster template, Training plan by grade band, Communication templates for parents
• Are you ready to designate a single point of contact to approve final readiness artifacts, or do you prefer consensus sign-off across a small committee? Options: Single point of contact, Small sign-off committee, Depends on artifact

Start Here: In One Line, What Success Looks Like

• In one sentence, what single outcome would make this pilot an undeniable success for your district?
• Which stakeholders must feel that outcome was met for you to call the pilot successful? (select all that apply) Options: District Technology Director, Chief Academic Officer, Curriculum Coordinator, Building Principals, Teacher Pilot Group Leads, Special Education Director, Parent/Guardian Representatives, School Board Member
• What timeline are you using to evaluate pilot success (when do you expect to have enough evidence to decide)? Options: 2–4 weeks, 1–2 months, 3 months, A semester, Other
• Which types of evidence will you accept as proof (pick the ones that matter most)? Options: SIS grade sync accuracy, Teacher adoption rate by grade band, Parent portal login & engagement, IEP accommodation success rate, Teacher satisfaction/NPS, Standards coverage reports, Accessibility compliance checks
• Is there any non-negotiable criterion (a must-have that if unmet ends the pilot)? If so, describe it.

If This Pilot Was Going to Fail, How Would It Start?

• What single early warning would make you immediately question whether this pilot will meet expectations? Options: SIS grade discrepancies appear, High teacher drop-off after initial week, Parents unable to access student assignment info, IEP accommodations not applied correctly, Critical integration fails (LMS ↔ SIS)
• How quickly would you want to be alerted if that warning appears? Options: Immediately (automated alert), Within 24 hours, Within 3 business days, At weekly review
• Has your district experienced a similar pilot or rollout failure before? Tell us what happened and what you learned.
• When a pilot problem has occurred historically, who has typically been responsible for triage and communication? Options: District IT, Vendor Support, Building Tech Coach, Curriculum Office, Special Ed Team, Other
• What emotional impact do you worry such a failure would have on teachers, parents, or the board?

Who Holds the Power to Stop or Sprint This Project?

• Whose 'no' could block full adoption even if the pilot looks good? Be specific. Options: School Board, Superintendent, Chief Academic Officer, District Tech Director, Special Education Director, Teacher Union/Association
• Which group tends to need the most demonstration or evidence before changing systems—teachers, IT, parents, or leadership? Options: Teachers, IT/Operations, Parents/Guardians, School Leadership, Board
• How do building-level tech coaches and teacher leaders typically influence district-level decisions in your district?
• Which stakeholder can be your most effective advocate inside the district, and why?
• Who will compile the evidence package for the board presentation at pilot closeout? Options: Curriculum Office, District IT, Vendor Customer Success, Pilot Teacher Leads, Other

Trusting the Grades: SIS Sync & Data Integrity

• If grades in the SIS showed a 5% discrepancy from the LMS tomorrow, who would notice first and what would the immediate consequence be?
• How frequently do you need grade syncs to occur for the district to consider them 'accurate enough'? Options: Real-time, Every 15 minutes, Hourly, Daily, End-of-day
• Which gradebook rules or district-specific grading policies are most likely to cause mapping complications? Options: Weighted categories, Custom grading scales, Late submission policies, Extra credit rules, Grade import overrides, Other
• Describe a past data-mapping or rostering issue and how long it took to resolve. What would you change to get faster resolution?
• What acceptance test will you run to verify grade accuracy before full launch? (pick the tests you intend to use) Options: Sample-grade roundtrip check, Full roster reconciliation, Spot-check by teacher leaders, Automated data integrity reports, Parent-side grade confirmation

Teachers Across Grade Bands: The Usability Reality

• Imagine a 2nd-grade teacher and a high-school AP teacher each open the LMS for the first time—what would each likely complain about within 15 minutes?
• Which grade bands do you predict will need the most hands-on training and coaching during pilot, and why? Options: Elementary (K–5), Middle (6–8), High School (9–12), Special Education Staff
• How comfortable are your teachers with switching assignment workflows (creating, tagging to standards, differentiated assignments)? Options: Very comfortable, Somewhat comfortable, Neutral, Somewhat uncomfortable, Very uncomfortable
• What teacher-facing acceptance criteria will prove usability across grade bands? (select all that apply) Options: X% of teachers complete a guided assignment flow unaided, Average time to post homework below target, Positive usability score from teacher surveys, Reduced tool-surfing across multiple platforms, Classroom observation validates workflow
• How will you surface and act on qualitative teacher feedback during the pilot (e.g., tech coach notes, weekly focus groups)? Options: Weekly focus groups, Teacher surveys, Coaches' field notes, In-app feedback, Vendor-facilitated interviews

Parents and Guardians: Real Visibility or Illusion?

• How confident are you that a typical parent can find their child's daily assignments and grades within 90 seconds on your current parent portal? Options: Very confident, Somewhat confident, Not confident, We don't measure this
• Which parent-portal features matter most to your community (choose top 3)? Options: Assignment details & due dates, Real-time grades, Notifications & alerts, Two-way messaging with teachers, Multi-language support, Mobile app access
• What are the top barriers parents currently report when trying to use digital tools for their child? Options: Multiple logins across tools, Unclear where assignments are posted, Language barriers, Lack of device or connectivity, Low digital literacy, Privacy/confusion about data
• What parent engagement thresholds would you set as acceptance criteria for the pilot (e.g., % logging in weekly)? Options: >50% weekly, >70% weekly, >30% weekly, Active in-app exchanges with teachers, Other
• How will you validate parent understanding and satisfaction qualitatively (select methods you plan to use)? Options: Focus groups, Short in-app surveys, Parent-teacher meeting feedback, Helpdesk ticket analysis, Community town hall

IEP & Accessibility: The Non-Negotiable Experience

• If an IEP accommodation failed on a graded assignment, what are the practical and legal consequences for the student and the district?
• Which accommodations must be automated in the workflow for you to consider the system compliant? Options: Extended time on assessments, Alternate assignment versions, Assistive technology compatibility, Audio/visual supports, Auto-application of accommodations to new assignments
• How do you currently document and verify that accommodations are applied correctly? Describe the audit trail or checks you rely on.
• What acceptance tests will you run for IEP workflows (pick all that apply)? Options: Simulated student accounts with accommodations, Case manager checklist sign-off, Log review showing accommodations applied, Parent confirmation of accommodations, Random spot audits
• Who will be responsible for triaging accommodation failures during pilot (role and escalation path)? Options: Special Ed Coordinator, Building Case Manager, District IT, Vendor Support, Other

Signals That Matter: Choosing the Right Metrics

• Which single metric would you rather obsess over than a dozen vanity metrics? Options: Teacher active-use rate, SIS-grade parity, Parent weekly engagement, IEP accommodation success rate, Standards coverage completeness
• For the metrics you care about, what are realistic baseline numbers today (provide figures if known)?
• What magnitude of change over baseline would you need to see to call the pilot a measurable improvement? Options: 5%–10%, 10%–20%, 20%–50%, Greater than 50%, Other
• How often do you want these metrics reported during pilot (choose reporting cadence)? Options: Daily dashboard, Weekly summary, Bi-weekly deep-dive, Monthly review
• Who will own metric accuracy and resolve any discrepancies between LMS and district reports? Options: District Data Analyst, District IT, Vendor Analytics Team, Curriculum Office, Other

If We Open the Floodgates Tomorrow, What Breaks First?

• What single operational failure do you expect to surface first when the pilot scales to all participating classrooms? Options: Roster mismatches, Gradebook syncing errors, Teacher workload spikes, Support request surge, Parent confusion/overload
• What immediate mitigation would you want in place if that failure occurs (select all that apply)? Options: Rollback to previous system, Temporary reduced feature set, Dedicated vendor/IT hotline, Rapid communications to parents/teachers, On-site coaching support
• What is your acceptable maximum time-to-fix for a high-impact issue during pilot? Options: Under 1 hour, Under 4 hours, Same day, Within 48 hours, Depends on issue
• Who will lead communications to teachers, parents, and leadership when a high-impact issue arises? Options: District Communications Office, District IT, Vendor Customer Success, Building Principals, Other
• What contingency steps should be pre-approved so we can act immediately if the predicted failure occurs?

Decision Rhythm: Who Decides and When

• Who holds the final go/no-go authority for full launch, and what evidence will they require?
• What regular meeting cadence would you like during pilot to surface issues and make decisions? Options: Weekly operational sync, Bi-weekly steering committee, Monthly executive review, Ad-hoc as issues arise
• What does the 'evidence package' look like for your board presentation (pick all items you expect to include)? Options: Metric dashboard, Teacher testimonials & videos, Parent survey results, IEP compliance audit, Cost/benefit summary, Pilot scope & next-phase plan
• What deadline do you have for the final decision (date or milestone)?
• Who will be the single point of contact for vendor coordination and who will own internal change management? Options: District Tech Director, Curriculum Coordinator, Project Manager (district), Vendor Customer Success Manager, Other