This is the last note you’ll hear from us in 2025.
As the year closes, it’s natural to take stock of visible progress—tools approved, policies finalized, training completed.
But the most important progress with AI rarely shows up on a rollout plan.
As the year closes, this is the one honest, high-value reflection moment I believe leaders should carve time out for when it comes to AI, leadership, and strategy for 2026:
Has AI actually changed how I lead?
Not how my team works. Not what tools we’ve approved. But how I personally think, decide, and challenge assumptions.
Read on for my Deeper Dive on this topic, and the end-of-year CRIT™ prompt we designed to assess whether AI is truly transforming your leadership—or merely existing around it.
The 20% Executive Summary
Most leaders believe they’ve “started” with AI because the organization has approved tools or completed training.
That belief creates false confidence.
It begins when leadership changes how it works.
When senior leaders don’t personally use AI to rethink decisions, priorities, and assumptions, momentum stalls—regardless of access, policy, or training.
The Deeper Dive
We see this pattern across boardrooms and executive teams.
Leaders ask their organizations to transform while continuing to lead the same way they always have.
The message is subtle but unmistakable: do as I say, not as I do.
That doesn’t scale change. It caps it.
AI creates real leverage when leaders use it first—not to automate tasks, but to challenge strategy, surface blind spots, and pressure-test their own thinking.
Once leaders experience that shift personally, everything downstream changes. People follow behavior, not policy.
As 2025 closes, the question that matters isn’t whether AI exists in your organization—it’s whether it has changed how you lead.
Take Action with CRIT™
Use this CRIT™ prompt in your LLM of choice to assess whether AI is truly transforming your leadership—or merely existing around it.
CONTEXT
I am a senior leader reflecting on our organization’s AI progress at the end of 2025. We have approved AI tools, established governance, and offered training, yet results feel incremental rather than transformative. Here’s what I’m noticing (tailor the below with your personal observations, but here are some common themes): AI activity is scattered across functions, with no consistent definition of “what success looks like.” Some leaders use AI tactically (drafting, summarizing), but it hasn’t changed how we make hard decisions, set priorities, or pressure-test strategy. Our operating rhythm (meetings, planning, goal-setting, reviews) looks mostly the same as it did before AI. I suspect we have progress theater: visible adoption without leadership behavior change. In 2026, I need AI to improve decision quality, focus, speed-to-clarity, and execution—not just productivity. My goal is to identify the specific leadership behaviors that must change first, and define what “AI-driven leadership” looks like in practice week-to-week.
ROLE
You are an executive coach and AI thought partner specializing in leadership behavior change, strategic decision-making, and organizational leverage. You are direct, practical, and focused on what actually moves results.
INTERVIEW
Interview me one question at a time. Pause after each question and wait for my response. Your questions must surface specifics, not abstractions. Cover these areas: My role and top 3 business outcomes for 2026 (what must be true by Dec 31, 2026). How I currently make strategic decisions (inputs, cadence, who’s involved, how trade-offs get made). Exactly how I personally use AI today (when, for what, and what I don’t use it for). The leadership routines that have not changed at all (planning, meetings, reviews, 1:1s, strategy work). Where I’m asking the org to transform without me modeling it (and why). The one “hard truth” I suspect is true about our AI efforts but haven’t named clearly. Where AI should create leverage in my role specifically (judgment, prioritization, alignment, speed-to-clarity).
TASK
Based on my answers, produce: Leadership Constraint Diagnosis: Identify the 1–2 leadership behaviors most likely capping AI impact right now. “Modeling AI-Driven Leadership” Definition: Define what modeling looks like as weekly leadership behavior (not tools). Include specific examples tied to my operating rhythm (e.g., pre-meeting, planning, reviews, decision memos, exec alignment). 30-Day Leadership Shift Plan: Give me 3 concrete changes I will implement in the next 30 days. For each: the trigger, the new behavior, and how I’ll know it’s working. Executive Team Ripple Effects: Explain what my team will do differently once I change first, and what I should ask of my direct reports. One Line I Can Say Out Loud: Draft one clear sentence I can use with my exec team to set expectation: leadership behavior changes first.