Digital learning leadership

Annual Timeline for Digital Learning Support

A practical annual cycle for coordinating instructional technology, supporting educators, guiding application decisions, and preparing schools for each transition in the academic year.

The work follows the school year

Digital learning support connects classroom needs with district systems, professional learning, vendor support, and school leadership. Responsibility for this work may rest with one coordinator or be shared across several district and school-based roles. The work shifts throughout the year: summer emphasizes readiness, fall focuses on onboarding and adoption, winter turns toward evidence and planning, and spring centers on decisions, transitions, and preparation for the next school year.

This guide is a planning model rather than a fixed compliance calendar. Local staffing, contracts, instructional priorities, bargaining agreements, and school calendars will affect the timing and ownership of individual activities.

Four areas of focus

Instructional support

Coaching, professional learning, onboarding, and practical resources that help educators use digital tools with purpose.

School partnership

Regular planning with school leaders and school-based digital learning champions to identify needs, coordinate support, and share updates.

Application stewardship

Usage review, application evaluation, renewals, retirements, vendor coordination, accessibility, privacy, and implementation planning.

Continuous improvement

Teacher and leader feedback, adoption data, focus groups, and reflection that shape the next cycle of support.

Semester One

Readiness, onboarding, early support, and a first review of needs and adoption.

July Prepare

By July 1: Share vendor summer learning opportunities and important application updates.
Confirm school-based digital learning champions and current school-based points of contact for each app.
Review end-of-year digital learning teacher surveys and spring application-usage data to identify support priorities.
Update the district digital learning guide, app vendor contacts, onboarding resources, and access-support process.
Plan back-to-school professional learning and a new-teacher digital learning orientation.

August Launch

Facilitate back-to-school professional learning and new-teacher orientation.
Make sure new educators can complete essential first-day tasks, including attendance, rosters, seating charts, and access to core platforms.
Communicate the process for reporting and resolving beginning-of-year access issues.
Schedule brief welcome visits and introduce the available digital learning resources and support channels.

September Listen

Meet with school leadership teams to establish beginning-of-year priorities and digital learning support plans.
Promote one-to-one coaching and other job-embedded support opportunities.
Collect early feedback about application access, functionality, and implementation barriers.
Complete new-teacher welcome visits and connect follow-up requests to the appropriate support team.

October Support

Continue coaching and follow up on school planning commitments.
Review application usage and adoption patterns to identify underused licenses and support needs.
Prepare a first-semester teacher check-in survey and schedule conversations with school-based digital learning champions.

November Evaluate

Facilitate a school-based digital learning champion meeting and gather school-level updates.
Distribute the first-semester teacher check-in survey.
Review fall usage data and instructional feedback to plan spring support.
Begin evaluating applications for renewal, expansion, reduction, or retirement using cost, use, instructional value, accessibility, privacy, and support requirements.

December Synthesize

Request semester application-usage reports from districtwide and school-based vendors.
Analyze teacher feedback and identify professional learning priorities for spring.
Communicate known application changes and renewal timelines to stakeholders.
Begin transition planning for tools that may be discontinued at the end of the school year.

Semester Two

Evidence review, portfolio decisions, end-of-year transitions, and preparation for the next cycle.

January Analyze

Combine survey findings and application-usage data into a concise midyear summary.
Schedule midyear data-review meetings with school leadership teams for February.
Identify applications, schools, or educator groups that need additional professional learning or coaching.
Renew outreach for one-to-one digital learning coaching.

February Review

Facilitate midyear data-review meetings with school leadership teams.
Conduct a structured review of the digital learning application portfolio.
Develop preliminary recommendations for application renewal, retirement, expansion, or additional support.
Schedule spring contract-renewal conversations for March. School leaders, office managers, and designated contacts should attend.

March Decide

Facilitate spring contract-renewal conversations with schools. School leaders, office managers, and designated contacts should attend.
Confirm which applications are expected to continue into the next school year.
Document outstanding questions, dependencies, funding decisions, and transition needs.

April Commit

Update the end-of-year digital learning leadership and teacher surveys and schedule May end-of-year meetings with school leadership teams.
Finalize app renewal recommendations and support renewal activities with the responsible stakeholders.
Notify schools about applications expected to retire and begin planning for content export or migration.
Prepare end-of-year communications and plan teacher focus groups.

May Transition

Facilitate end-of-year recap and renewal discussions with school leadership teams.
Distribute the digital learning leadership and teacher surveys and communicate deadlines for saving or exporting content from the LMS and other applicable apps.
Create practical end-of-year tips for archiving courses, preserving materials, and preparing applications for rollover.

June Reflect and reset

Share final app renewal and retirement updates before staff leave for summer.
Promote vendor summer learning opportunities and provide resources for newly adopted applications.
Facilitate an end-of-year digital learning recap and teacher focus groups.
Use feedback and usage evidence to recommend next steps.
Draft the next year’s professional learning scope and sequence and begin summer readiness planning.

Responsibilities that continue throughout the year

Provide ongoing support and regular updates to school leadership teams and school-based digital learning champions.
When the district is considering the purchase of a new districtwide app, support an application pilot and monitor implementation.
Maintain current app resource guides, vendor contacts, and technical support resources.
Offer digital learning coaching and respond to emerging instructional needs.
Collaborate with IT, data, curriculum, purchasing, privacy, and school-based teams.
Track decisions, follow-up actions, and evidence needed for future digital learning support.

How to use this guide

Adapt the sequence to the local calendar, assign an owner to each activity, and move recurring work into a shared planning system. Use the monthly sections as conversation starters with school leaders and school-based digital learning champions—not as a one-size-fits-all checklist.