Next cohort starts July 2026

A Monthly Diagnostic for Engineering Leaders

The AI Leadership Audit

Twelve engineering leaders from different companies. Six patterns your dashboard can’t see. The most honest conversation about AI adoption you’ll have all year.

Join the Waitlist

You Already Know Something Is Off

You can feel the gaps forming. Your team adopted AI and something shifted. Engineers losing skills they spent years building. Metrics that look healthy while the codebase quietly fragments. A rollout that created compliance instead of buy-in. Recovery time that vanished from the engineering day without anyone naming it.

You’ve been thinking about this alone. Maybe you’ve mentioned it to a peer in a 1:1 or over drinks after a conference. But inside your own company, raising these concerns means navigating politics. Your skip-level is in the room. Your peers are watching. The conversation stays safe because the career risk of honesty is too high.

You need a room where you can say “I don’t know if our AI adoption is actually working” and have twelve other leaders say “same.”

That’s this cohort.

Twelve Leaders. Six Patterns. Zero Politics.

The AI Leadership Audit is a diagnostic framework built around six patterns that show up in every engineering org navigating AI adoption. They don’t appear in your sprint metrics or your adoption reports. They show up in the conversations your team is having without you.

In this monthly cohort, you work through all six patterns alongside twelve to fifteen engineering leaders from different companies. You apply the framework to your own org. You hear how other leaders are navigating the same challenges. You leave with clarity on what’s actually happening on your team and a plan for what to change.

Nobody is managing their reputation. Nobody is packaging the problem for a skip-level audience. Everyone is there because they felt something was off and wanted to figure out what it was.

What We Diagnose

Six patterns that show up in every engineering org navigating AI adoption. Each one is invisible on a dashboard. Each one is obvious to the engineers living with it.

01

The Mandate Problem

Did your team adopt AI because someone showed them where it helps, or because they were told to?

02

The Judgment Decay Problem

When was the last time you touched the system you’re making decisions about?

03

The Measurement Problem

Are you measuring what AI actually changed, or performing productivity for a dashboard?

04

The Atrophy Problem

If AI stopped working tomorrow, could your team still do the jobs they were hired for?

05

The Recovery Problem

Where in your team’s day is nobody asking them to evaluate anything?

06

The Culture Problem

Does your team have a shared framework for when and how to use AI, or did everyone just figure it out on their own?

The Cohort Experience

Before the Session

You receive The AI Leadership Audit , a diagnostic document that walks through all six patterns with real stories, diagnostic questions, and weekly action items. Read it before the session. Come in having already sat with the uncomfortable parts.

During the Session (3 Hours, Virtual)

Hour 1

The Diagnosis

Facilitated self-assessment. You identify which patterns are most present in your own org. The room gets honest fast because nobody shares an org chart.

Hour 2

The Peer Diagnostic

Small group work. You hear how other leaders are experiencing the same patterns at their companies. What they’ve tried. What failed. What actually moved the needle. This is the part you can’t get anywhere else.

Hour 3

The Action Plan

You build a concrete action plan for one pattern you’re going to address in the next 30 days. Not a roadmap. Not quarterly milestones. One specific change. The room pressure-tests it before you leave.

After the Session

30-day follow-up check-in with Jono. Did the thing you committed to actually happen? What changed? What didn’t? The audit doesn’t end in the session. It ends when your team notices something is different.

What You Get Here That You Can’t Get Anywhere Else

Honesty without career risk.

Inside your company, admitting “I don’t know if our AI adoption is working” has consequences. In this room, everyone is there because they’re asking the same question. The vulnerability is the entry fee.

Twelve perspectives instead of one.

You’ve been diagnosing your org through your own lens. Hearing how twelve other leaders see the same patterns at their companies changes what you notice at yours.

Benchmarking against reality.

Not against a McKinsey report or a conference talk from a company with completely different constraints. Against peers who are navigating the same challenges in real time with real teams.

A network that lasts.

The leaders in your cohort are facing the same problems you’ll face next quarter. That relationship is a phone call away instead of a conference away.

What You Walk Away With

You walk back into your org on Monday with something you didn’t have on Friday.

  • Clarity on what’s actually broken. You’ve been carrying a vague sense that something is off with your AI adoption. After three hours with the diagnostic and twelve peers, you’ll know exactly which patterns are hurting your team and which ones aren’t. That clarity alone changes how you lead the following week.

  • A plan you’ve already pressure-tested. You won’t leave with a generic framework. You’ll leave with one specific change you’re making in the next 30 days, built from your own context, challenged by twelve people who have no reason to be polite about it.

  • Perspective you can’t get inside your own company. You’ll know how other leaders at other companies handled the same rollout challenges, the same measurement traps, the same engineer frustrations. That perspective changes the questions you ask in your next planning meeting.

  • Confidence to name the problem. Half the battle is having the language for what you’re seeing. After working through the six patterns, you’ll be able to walk into your next leadership meeting and articulate exactly what’s happening with your AI adoption in terms that your VP, your CTO, or your board will understand.

  • A network of peers who get it. Twelve leaders who sat in the same room, worked through the same patterns, and are navigating the same challenges. Those relationships don’t end when the session does.

Who This Is For

  • VPs of Engineering, Directors, and Senior Engineering Managers who want to invest in their own development

  • Principal and Staff Engineers who are leading AI adoption or moving into leadership roles

  • Tech Leads responsible for how AI tools land on their teams

  • Any engineering leader who feels something is off with their AI adoption and wants to figure out what it is alongside peers who feel the same way

Who Facilitates This

Jono Herrington

Jono built and led Converse’s global digital engineering org at Nike, scaling the team across the US, Serbia, and India. He’s spent 15+ years building platforms and the teams behind them.

He still writes code. He still reads pull requests. He still prototypes before he promises a timeline. He led AI adoption across a distributed engineering team without a single mandate ... and watched 500+ engineers in an online thread describe what happens when their leaders chose mandates instead.

Every diagnostic pattern in this cohort comes from a failure he experienced first or documented from the front lines of engineering leadership during the AI transition.

Investment

The cost of one conference ticket. The value of twelve leaders telling you what nobody inside your company will.

The ROI math writes itself.

Inaugural Cohort (July 2026)

$1,500

Limited to 15 participants

  • Pre-session AI Leadership Audit document
  • 3-hour facilitated virtual session with Jono Herrington
  • 30-day follow-up check-in
  • Access to the cohort peer network

Monthly Cohorts (August 2026 onward)

$2,000

Limited to 15 participants per cohort

  • Pre-session AI Leadership Audit document
  • 3-hour facilitated virtual session with Jono Herrington
  • 30-day follow-up check-in
  • Access to the cohort peer network
  • New cohort every month
  • The next cohort is always less than 30 days away

No procurement process. No manager approval needed. This is a personal leadership development investment at a price point you can decide on yourself.

Next Step

Join the Waitlist

The inaugural cohort runs in July 2026. Fifteen seats. Once they’re filled, the next cohort opens in August. Drop your email and you’ll be the first to know when registration opens.

Want to Bring This to Your Whole Leadership Team?

The AI Leadership Audit also runs as a private workshop for your engineering leadership team. Same diagnostic framework. Deeply specific to your company’s org, codebase, and AI rollout.

Learn about the corporate workshop