Advancing Digital Equity — Crew Insight Report · sideby
Crew Insight Report  ·  Advancing Digital Equity
Mid-March – June 29, 2026

Advancing
Digital
Equity

A portrait of learning from a national crew of educators who spent 12 weeks examining digital barriers — and building the moves to address them.

10Crew members
33Unique peer pairings
sideby.io · All data de-identified · For facilitator use AWSP + National · Spring 2026
51
sideby Sessions
Peer and solo sessions
102
Ideas Captured
From sideby sessions
22
Small Wins Created
Successes or lessons learned
2
Small Wins Launched
Shared with the full crew
Session Activity

How the crew engaged

All 51 Sessions — Paired vs. Solo
Paired (31)
Solo reflection (20)

Each dot is one substantive session. Paired = synchronous 20–30 min peer conversation. Solo = individual 10–15 min guided reflection.

Success Signs by Competency Strand

Success Signs are observable evidence indicators from the AI for Deeper Learning (AI for DL) framework — mapped from this crew's Small Wins and session transcripts.

PH · Professional Habits
8
MA · Supporting Students
6
LM · Learning Mindsets
4
AL · Authentic Learning
2
CT · Critical Thinking
1
Representative signs documented
Peer-to-peer exchange initiated Staff reflecting independently Teachers reaching out to share Consistent digital access Supporting digital skill differences Student vulnerability named as learning Meaning making observed Parents requesting to learn
Platform Activity — Ideas & Small Wins
Total captured (Ideas + Small Wins)
124
Launched — visible to full crew
2
Draft — private to learner
122

High draft volume reflects active private reflection — not low engagement. Drafted Ideas and Small Wins are only visible to the individual learner who received or created them.

98% of captured learning stayed private — the richest reflections rarely surfaced to the full crew
18 Unique Peer Pairings

Each node is one crew member. Lines show paired sessions; line weight reflects number of sessions together. 18 cross-organizational connections formed over 12 weeks.

18unique pairings
10crew members
31paired sessions

What this crew revealed

The shape of the learning

This crew came in asking how to use digital tools more equitably. They left asking a harder question: who decides what counts as access, and what do we owe the people the system keeps missing?

Across 51 sessions and more than 91 documented Ideas and Small Wins, crew members moved from awareness of digital barriers toward concrete, context-specific leadership moves. The most significant learning happened when educators stopped diagnosing a systemic problem from a distance and started working it from inside their own sphere of influence — one conversation, one walkthrough, one audit at a time.

What made this crew distinctive: they named fear directly. Fear of AI tools, fear of FERPA violations, fear of looking incompetent in front of staff. That directness produced more specific — and more useful — leadership moves.

For facilitators, the question this data raises: what comes next for people who identified clear barriers and made initial moves, but haven't had structure to go deeper?

The barrier wasn't teachers' ability. It was fear, and a missing mental model. Understanding AI conceptually isn't enough. Teachers need physical, usable tools like prompt banks to sustain independent use.
Coaching synthesis · ADE + AI-Powered Differentiation Small Win
Teachers need physical, usable tools like prompt banks and purpose-built GPT setups to sustain independent use. Understanding AI conceptually isn't enough.
Coaching synthesis · ADE + AI-Powered Differentiation Small Win
Most of what looks like a student problem is actually a design problem. I stopped being fooled by the difference.
Educator reflection · ADE badge

Patterns across the crew

Five themes that surfaced

What came up repeatedly and with specificity across transcripts, Ideas, and Small Wins — not just once, and not in passing.

01
The Barrier Is Almost Never the Technology

What looked like a tool problem was a trust, confidence, or design problem. Tools exist; support doesn't. Access is issued; belief is withheld.

"The barrier is almost never the technology. It's the audiobooks nobody knew could save a place, the speech-to-text nobody trained anyone to use."
02
Teacher Proficiency Shapes Student Access

A teacher's comfort with a tool determines what students can access. Supporting teacher digital fluency is an equity intervention — not a professional development nicety.

"How well you know a tool directly shapes what your students can access."
03
Fear Is Specific and Nameable

Fear of AI, FERPA, incompetence — this crew named fear with precision. Most sharply: fear is causing some schools to exclude students with IEPs from AI tools entirely, framing restriction as protection. That is not protection. That is inequity.

"The fear of AI is going to limit students' access to knowledge, and particularly within the lens of special education, that really concerns me."
04
Student Voice Is Missing From Decisions

Decision-makers aren't using the same tools as students. Student experience — slow logins, navigation barriers, undifferentiated exam prep — rarely anchors adult decision-making. This crew named the mindset shift explicitly.

"I used to think that teachers knew what tools were needed for the classroom. But now I think that students are the ones that know what they need digitally for their classroom."
05
Sphere of Influence Is a Source of Power

The most effective moves were targeted, built on relationships, and designed to outlast the person who made them.

"The design principle underneath it is: how do I make this work not need me?"

AI for Deeper Learning Framework

Competency Strand Activity

This map shows where crew learning clustered across the five competency strands of the AI for Deeper Learning framework. Bold items reflect areas with documented evidence. Lighter items represent areas not yet surfaced in this crew's data.

Professional Habits of Learning & Innovation
PH1 · Why — Personal AI vision; ethical stance
PH2 · Goals — Set & pursue AI learning goals
PH3 · Exchange — Peer reflection & insight-sharing
PH4 · Experiment — Try new things with AI tools
PH5 · Iterate — Adapt practice based on evidence
PH6 · Knowledge — Foundational AI knowledge
PH7 · Lead Teams — Build professional capacity
Supporting All Students to Meet Academic Standards w/ AI
MA1 · Differentiate — Personalized learning via AI
MA2 · Curriculum — AI-aligned curriculum dev
MA3 · Feedback — AI-assisted formative feedback
MA4 · Data Tracking — Progress via AI analysis
MA5 · Assessment — AI-supported assessment design
MA6 · Equity — Minimize AI impact on equity gaps
MA7 · Data Privacy — Student data & AI policy
Fostering Critical Thinking & Problem Solving w/ AI
CT1 · Inspect — Critically examine AI outputs
CT2 · Revise — Model revising AI outputs
CT3 · Scenarios — AI-generated problem scenarios
CT4 · Task Design — Higher-order AI task design
CT5 · Breakdown — Break complex tasks with AI
Designing Authentic, Real-World Learning w/ AI
AL1 · Project Design — AI-assisted project design
AL2 · Connect — Real-world contexts via AI
AL3 · Research — AI-supported research & data
AL4 · Creativity — AI-assisted creative projects
Fostering Students' Learning Skills & Mindsets w/ AI
LM1 · Student Goals — Goal-setting with AI
LM2 · Metacognition — AI metacognition with students
LM3 · Responsibility — Student accountability
LM4 · Ethics — AI systems & human values
LM5 · Guidelines — Responsible AI usage norms
LM6 · Human Advantage — Center human skill
LM7 · Productive Struggle — Design for persistence

Bar indicators reflect depth of evidence in crew data — not performance quality or evaluative grade. Bold items = documented evidence present. Lighter items = not yet surfaced in this crew's data.

sideby's AI for Deeper Learning Framework is informed by the UNESCO AI Competency Framework for Teachers, the colleague.ai AICE Framework, Teach AI with EC + OECD & code.org frameworks for AI learning, and the Hewlett Foundation Deeper Learning Competencies — evolving as AI evolves and shifts what this technology can mean for deeper learning and education.


Course Learning Targets

Where evidence is strongest

Five Learning Targets (LTs) aligned to PSEL and CCDEI standards. Evidence depth reflects richness of crew data — not a performance grade or evaluation.

LT 1
Examine how identity, privilege & access shape understanding of digital equity
Crew members reflected on personal bias, generational technology assumptions, and how their own access shapes perspective. One member explicitly named this as intellectual honesty still in progress.
Evidence depth
PSEL 1, 2, 3 · CCDEI 1
LT 2
Identify evidence-based digital barriers in their school community
Strongest cluster across the crew. Every crew member named at least one specific, grounded barrier — from FERPA fear in special ed to navigation gaps for neurodiverse students to the device gap between administrators and students.
Evidence depth
PSEL 3, 4, 9 · CCDEI 4
LT 3
Enact leadership moves that repurpose existing resources
Strong evidence. Six documented Launched moves; many more in Draft. All used existing relationships as the design lever — from one-on-one coaching conversations to statewide advocacy.
Evidence depth
PSEL 1, 9 · CCDEI 3, 4
LT 4
Articulate a stance on the role of AI in advancing digital equity
Now stronger. The AI, Bias & Equitable Learning solo sessions produced clear, specific stances: without instruction AI becomes more inequitable for vulnerable students; fear-based responses to AI restrict access rather than protect it; students with IEPs being excluded from AI tools is an equity violation. The evidence here is both more numerous and more precise.
Evidence depth
PSEL 2, 3 · CCDEI 1, 4
LT 5
Evaluate the impact of leadership moves and plan next steps
Emerging. Most crew members identified initial success signs; fewer completed full iteration cycles. Developmentally appropriate for a 12-week experience — and points to a structural opportunity for what follows the badge.
Evidence depth
PSEL 1, 9 · CCDEI 3, 4

PSEL = Professional Standards for Educational Leaders (national). CCDEI = standards for cultural competency and equity in educational leadership. Both frame ADE badge learning targets and 6 equity clock hours.


What crew members did

Leadership Moves in action

Concrete actions taken inside each crew member's sphere of influence, using existing resources as design levers. These are documented steps — not aspirations.

🏫
Special Ed Lead
Targeted the least-confident educators first

Used existing collegial relationships — not hierarchy — as the lever. Surveyed comfort levels, built FERPA understanding, created purpose-built GPT setups. A one-way support effort became peer-to-peer exchange.

LT 2, 3Equity focus
💻
Online Science
Audited every lab for navigation accessibility

After student support specialists flagged virtual labs as the top barrier for neurodiverse students, audited all 9 class sections and built a walkthrough video bank. Students asked for more.

LT 2, 3Equity focus
🤝
Principal Coach
Added "back to basics" to every coaching session

Discovered the program assumed basic tech fluency nobody had provided. Added a structured check-in: "Where might you need support to get back to the work that matters?" Removing the assumption accelerated learning.

LT 1, 3AI-adjacent
🏛️
State Leader
Advocated for protected learning time at superintendent level

Identified no protected time for leaders to build digital fluency as the core structural barrier. Used an upcoming statewide platform rollout as leverage for superintendent-level advocacy.

LT 3, 5Systems
📋
Policy, State
Named equity omission in a draft statewide AI framework

Equity had been left out — not removed, just never included. Named it directly in the meeting: "We think we are, but we don't know."

LT 4Equity focus
🌀
School Leader
Built a committee designed to outlast its founder

After a learning walk surfaced equity gaps, built a committee and — before leaving the site — wrote a postmortem for the incoming coach flagging who was ready to keep going and what needed to happen next.

LT 3, 5Systems
📡
School Leader
Held the line on equal-access devices — equity over convenience

Faced with pressure to allow personal computers, chose to maintain school-issued Chromebooks for all students — accepting a lower performance ceiling to ensure no student is visibly disadvantaged by what they bring from home. "There's a known known baseline tech access in every kid's life."

LT 2, 3Equity focus
🎯
Prof. Learning Lead
Live AI demonstration in School Leader Collaborative

Collected real challenges from the room, ran a live prompt, and surfaced the output in real time — no slides, no theory. "In two minutes, Claude spit this out and they could see the finish line." Exposure as the entry point for skeptics.

LT 3, 4PH7 · Lead Teams

Small Wins & Ideas

What got documented

Small Wins are things crew members tried and learned from. Ideas are helpful thoughts, concepts, or goals. Both are generated through the sideby platform — some reflected back automatically from session transcripts, some written directly by learners. Drafted = private to learner; Launched = shared with the full crew.

Launched · Small Win
ADE Synthesis: Back to Basics

A coach discovered their program assumed a level of basic tech fluency nobody had actually provided. They added a "back to basics" moment to every coaching session. One participant mentioned they'd never understood time zones on their calendar — they figured it out together. That person started asking about everything. "When someone believes they can learn it, they're more likely to ask about it — and that's when their learning accelerates."

#Skill applied independently#Showing a colleague the same skill#Staff expressing positivity
Launched · Small Win
When Volunteers Became Learners

A leader's partnership with a classroom teacher rippled outward — parent volunteers started asking to be taught. Three family learning nights followed. Families said: "this school is for us too."

#Parents actively engaged#Families requesting to learn
Launched · Small Win
A Committee Designed Not to Need You

After a learning walk surfaced equity gaps, a leader built a committee and wrote a postmortem for the incoming coach before leaving the site. The design principle: how do I make this work not need me?

#Purpose articulated#Continuity designed in
Draft · Idea
Good Form Looks Different for Everyone

Recognize that good form looks different for every teacher and learner. Coach toward each person's best form — not toward a single standard. Applies to coaching for digital equity as much as differentiation.

Draft · Idea
Package Your Own Expertise

Move beyond using AI like a search engine. Package specialized knowledge into a custom GPT with a knowledge base and instructions — making your expertise accessible without requiring you to be in the room.

Draft · Idea
Story vs. Idea: Making Learning Portable

Stories make a moment vivid. Ideas make it reusable. If we can help people move from "here's what happened" to "here's the point," we make learning portable across contexts and cohorts.


In their own words

Crew voice across the experience

Direct quotes from sessions, Small Wins, and Ideas — de-identified by role and context.

I LEARNED THAT AI IS ABOUT CONNECTING HUMANS AND BRINGING THEM OUT OF THE TECHNOLOGY NOT SUCKING THEM INTO IT FOR ETERNITY.
Educator · AI-Powered Differentiation session
AI doesn't know what good differentiation looks like. The human has to hold that vision. That doesn't feel like a new idea, it feels like something I've believed for a while that finally has the right words around it.
Educator · AI-Powered Differentiation
I could absorb a thousand peer-reviewed studies about the value of technology for kids and still see a teenager hunched over a phone and not be convinced. I'm naming that as bias, as identity, as something I'm not through yet.
Educator · ADE Reflection
The richest learning conversations happened in the TLC because the stakes were contained and people chose what to surface. The design question isn't about making growth visible. It's about who holds the key to what gets seen and when.
Solo Reflection session
The data that AI is trained on is historically trained on data that is already biased in what's been collected and how it's been collected, and it kind of re-emphasizes those loops.
Educator · AI, Bias & Equitable Learning session
Students seemed comfortable with these tools at a surface level. Many teachers created templates for students to make copies of. I wonder what it could look like to task students with using these tools to create their own templates and learning materials instead.
Educator · Design Levers session
Equity isn't just about access. It's about whether students have enough agency over the tools to actually benefit from them.
Educator · ADE Reflection
Digital equity needs to become a more intentional piece of how I facilitate leadership learning, not just something I'm adjacent to. The question I'm sitting with is less about what it is and more about how to actually bring it in.
Educator · State-Level Leadership
If we don't instruct and support kids on how to do that, I think the tool can be even more inequitable for certain students. They can't critically assess things if they don't have the foundational skills to do that.
Educator · AI, Bias & Equitable Learning session
This idea that students with IEPs need to be protected more against their own cheating. We can't have students with disabilities using these tools because they're just going to cheat.
Educator · Design Levers session
It just gives you vocabulary to look at administrative choices through another lens. Where and when during the day we teach English 11, how would digital equity view that choice? Digital equity is just like another little filter.
Educator · ADE Presentation of Learning

Key Terms

Platform & course terminology

Small Win
Something a crew member tried and learned from. Written by the learner or automatically reflected back by the platform after a session. Drafted (private) or Launched (shared with full crew).
Idea
A helpful thought, concept, or goal — often a coaching insight generated from a session transcript. Also Drafted or Launched.
Paired Session
A 20–30 min synchronous guided conversation between two crew members in the sideby platform. Transcript captured automatically.
Solo Reflection
A 10–15 min individual guided session in the sideby platform, used for Design Levers and AI, Bias & Equitable Learning content.
Leadership Move
A concrete action planned and implemented to address a Digital Equity Barrier, using existing resources as design levers. Part of Experiential Learning Challenge 2 in the course.
PSEL / CCDEI
PSEL = Professional Standards for Educational Leaders (national). CCDEI = standards for cultural competency and equity in educational leadership. Both frame ADE badge learning targets and 6 equity clock hours.

For the facilitator

What comes next for this crew

Three time horizons based on what's in the data — for thinking about follow-up, iteration, or a future cohort.

Right now
Consolidate & connect
  • Surface Launched Small Wins in a crew-wide discussion — most of the richest learning stayed in Draft
  • Document leadership moves with the design principle underneath, not just the action taken
  • Name the 18 unique cross-org pairings — that network is a resource beyond the badge
  • Prompt each crew member to identify one concrete next step before the crew disperses
Next cohort
Strengthen what's emerging
  • LT 5 (evaluating impact) needs more structure — consider a mid-badge iteration checkpoint
  • LT 4 (AI stance) was uneven — a dedicated reflection prompt earlier in the sequence could help
  • The "back to basics" protocol is a transferable facilitation move — document it explicitly for the next cohort
  • Paraprofessional access came up organically — consider making it an explicit Empathy Exercise option
Bigger questions
Worth holding
  • Most of the richest thinking stayed in Draft. What would make Launching feel safer or more useful?
  • This crew identified barriers with real specificity in 12 weeks. What supports continued iteration after the badge?
  • State-level members raised equity omission in policy work. Can those stories connect across cohorts?
  • When protected learning time is structurally unavailable, what does equitable digital onboarding look like?

The work doesn't stop when the badge does.

Every leadership move documented here was designed to outlast the person who made it. That's what equity work looks like when it takes root.

sideby · Advancing Digital Equity Badge Crew · Mid-March – June 29, 2026 · All data de-identified · For facilitator use