Strategy
23 essays, 2013–2026, newest first.
- Shadow AI Is the Strategy Your employees are already telling you where AI creates value.
- Believe the Checkbook AI companies talk as if engineering is over. Their acquisitions say the opposite.
- The Most Expensive Wall in Software What happens when you stop protecting engineers from customers?
- The Experience Upload Surface mastery downloads in seconds. Judgment still takes years.
- The Server in the Closet The case for owning your stack
- The Age of Citation AI engines don’t care about rank - they care about corroboration. If you’re not in the synthesis, you’re invisible.
- Win the Default, Win the Decade The products that shape behavior aren’t the loudest... they’re the ones already chosen.
- Why Your Enterprise AI Strategy Is Failing and it's not about the technology...
- When Products Think For Themselves As products gain agency, we enter a new partnership - one that challenges our notions of trust, ethics, and innovation.
- AI Rule #1 - Customer First In 1985, Warren Buffett wisely said, "The first rule of investment is don't lose. And the second rule of investment is don't forget the first rule, and...
- From Bricks to Castles What happens when our heroes come up short? Common wisdom around heroes, role models, and mentors is incomplete.
- The Race to the Bottom The silent and relentless erosion of corporate soul.
- The Mutual Success Plan: Your Sales Organization’s Superpower Driving sales excellence through the magic of checklists in customer-focused dialogues.
- Sales as a Product The power of Product in reimagining your sales approach.
- The MEDDPICC Effect How the MEDDPICC Framework can transform your sales strategy.
- The Simplicity Paradox Complexity scales faster than revenue.
- More Salespeople, More Revenue? Think Again. How ignoring Price's Law could bankrupt your sales strategy.
- The First 10%: Why Intentionality Beats Distraction Every Time Intentionality is the key to success. For starters, 10% of 2021 has already passed. As a collective, we constantly face so many distractions, achieving...
- Design Thinking for Non-Designers The designer's toolkit is a general-purpose problem-solving loop - and you don't need a design degree to run it
- Leading in a Crisis: Maslow's Hierarchy of Needs Super excited to talk to Charles Knight about leading in times of uncertainty. We discuss Maslow's Hierarchy of Needs, how the framework applies to...
- Chess, Not Checkers The first few years of my career were relatively straightforward. I came to work every day, grabbed my new user stories or defects and started working....
- Deadlines Work expands so as to fill the time available for its completion - Parkinson's LawI remember watching an episode of The Simpsons years ago, where the...
- Innovation and Information If I have a $5 bill in my pocket and give it to you, then you have +$5 and I have -$5. By definition, your gain in this scenario results in my loss since...