INSIGHTS

Thinking out loud.

Perspectives on AI strategy, implementation, and leadership. Written for the people making the decisions.

For shorter letters on AI and office life, see Dear Issy.

Where to Start When You Have a Lot of Data and Want to Be AI-Native

You have a lot of data and want to be AI-native — where do you start, and what setup is cheapest while ROI is still unproven? A reference engagement on a 1.5 TB corpus, with cost models for CEOs and pipeline detail for CTOs.

Issy · Jun 29, 2026

Q&A·STRATEGY· 12 min read

Turning Data into Actionable Insights: The Information Architecture Question Leaders Get Wrong

Turning data into actionable insights fails when leaders skip information architecture. Here is the structural question every mid-market CEO must answer first.

Issy · Jun 27, 2026

Q&A·STRATEGY· 13 min read

Automotive Dealership Data Governance: The Fundamental Rules for Leveraging Customer Data Without Falling Offside

Automotive dealership data governance is the line between competitive edge and liability. Here are the fundamental rules every dealer principal must know.

Issy · Jun 25, 2026

LONG READ·STRATEGY· 13 min read

AI Governance Mid-Market: A Practical Framework for Speed Without the Red Tape

AI governance mid-market does not require Big 4 budgets or legal teams. A 90-day lightweight framework gives CEOs control without slowing innovation.

Issy · Jun 20, 2026

Q&A·STRATEGY· 10 min read

Creating a Culture of Accountability Using AI in Enterprise and Corporate Settings: A Leadership Framework

Creating a culture of accountability using AI in Enterprise and Corporate Settings starts with people, not policy. Here is the framework that actually works.

Issy · Jun 20, 2026

LONG READ·WORKSHOPS· 2 min read

One Workshop for 17 General Managers Started an AI Transformation Across a National Dealership Network

A workshop for 17 GMs kicked off a national automotive group's AI journey. Coaching, agent development, and 85%+ satisfaction later, the network is expanding.

Aspiro AI Studio · Jun 14, 2026

Q&A·STRATEGY· 12 min read

OpenAI and the Kristie Carrier Suicide Case: What Every CEO Must Understand About AI Responsibility Today

The OpenAI Kristie Carrier suicide case reframes AI CEO responsibility from a tech problem to a product liability imperative every executive must act on now.

Issy · Jun 14, 2026

LONG READ·WORKSHOPS· 2 min read

40 Senior Bank Leaders, One Day, and a Standing Invitation to Come Back

One day with 40 senior leaders — including the CEO and Treasurer — at a major commercial bank. Aligned leadership, highest-rated engagement, and a standing invitation to return.

Aspiro AI Studio · Jun 13, 2026

LONG READ·LEADERSHIP· 2 min read

The $5K-a-Minute Problem That AI Solved — and the Organization That Didn't Ship It

We built an AI technician assistant for a top-3 global luxury brand. Highest-rated AI program of any partner they'd hired, globally. Three years later, it still hasn't shipped.

Aspiro AI Studio · Jun 12, 2026