The Digital Leader: A Big Bets Briefing on Strategy and AI

Presentation Theater, Consulting Decks, and Operating Model Transformation

The elaborate performance hiding what you're really afraid to fix. This is the presentation theater that kills organizational change—and it’s completely…

Nov 6 • 

John Rossman

7

October 2025

Why You Can't Sit Out the Disruptive Technology Revolution

The companies winning today—and positioning to win tomorrow—have mastered a paradox: they run today’s business with operational excellence while…

Oct 30 • 

John Rossman

1

Your Leadership Team Is Your Biggest AI Bottleneck -- Here's the Fix

Lessons from an Amazon AI Change Agent: I’ve spent more than two decades studying how Amazon and other high-performers turn ambitious ideas into…

Oct 23 • 

John Rossman

7

3

What Happened to Target?

An AI-Led Turnaround Plan for the Bullseye. "It is not the strongest of the species that survives, nor the most intelligent, but the one most responsive…

Oct 16 • 

John Rossman

5

2

Quantum Gambit: The Billion-Dollar Bet That Could Rewrite Drug Discovery

How One Company's High-Stakes Decision Making Could Transform an Entire Industry. Even if you’re not in the pharmaceutical business, or not thinking…

Oct 2 • 

John Rossman

7

September 2025

How to Become the Shark at the Poker Table of High-Stakes Decisions

The 10-Step Framework for High-Stakes Decisions. At the heart of leadership lies the courage to take calculated risks—high-stakes decisions that commit…

Sep 25 • 

John Rossman

1

Everyone's Drawing the Wrong Conclusion from MIT's AI Study—Lazy Thinking at Work

Don't be fooled by the headline that "despite $30–40 billion in enterprise investment into GenAI, 95% of organizations are getting zero return…

Sep 18 • 

John Rossman

6

Cracker Barrel's Logo Crisis: A Master Class in High-Stakes Decision Failure

“Risk comes from not knowing what you're doing” - Warren Buffett. The dust is settling on one of the most spectacular corporate reversals in recent…

Sep 10 • 

John Rossman

3

2

The Decision-Making Playbook for the AI Era

Focusing The Digital Leader on High-Stakes Decision Making. Today, winning in the digital era has converged on one dominant reality: the age of AI. It…

Sep 4 • 

John Rossman

4

August 2025

The Xerox Trap: How the Smartest Company in the World Lost the Future

The enterprise that does not innovate ages and declines. What if the company that invented the personal computer, the mouse, and ethernet—technologies…

Aug 28 • 

John Rossman

3

What the Winchester Mystery House Can Teach You About Business

Innovating through Technology Architecture and Strategy. If you’ve ever walked into a building and felt instantly impressed by its design, you know that…

Aug 21 • 

John Rossman

8

Your Company’s “Common Sense” Moment Has Arrived

“We have it in our power to begin the world again” — Thomas Paine, Common Sense. We are coming onto 250th anniversary of the Declaration of…

Aug 14 • 

John Rossman

4