Direction Over Acceleration

When Execution Becomes Cheap, Strategic Choice Is the Ultimate Competitive Advantage

AI conversations have a natural starting point: What can this technology do?

It is an understandable question. Every few weeks, the answer gets larger. Models can write, analyze, code, search, reason, generate images, operate software, and increasingly take autonomous action rather…


The August issue of my Personal Strategy Compass newsletter is now available: “The Night Watchman: Converting Solitary Anxiety into Strategic Leverage.”

This issue grew out of something I started noticing in my own solitary planning blocks. Once I removed the usual operational noise and created some real white space, my analytical mind did…

I launched Personal Strategy Compass as a premium newsletter a year ago. The decision made sense on paper: quality content, established expertise, proven frameworks. But something never quite felt settled.

Not wrong, exactly. Just… misaligned.

Then I drew an Oblique Strategies card during my own quarterly planning: “Honor thy error as a hidden intention.”

If…

It’s mid-June, and for many legal professionals, there’s a subtle but powerful shift in the air. We’re at the halfway point of the year. The initial burst of January motivation has long since faded, and we’re deep enough into the year to see whether our original plans are holding up against reality. Too often, we…

You’ve blocked out your Personal Quarterly Offsite (PQO). Great start. But let’s be honest: carving out those few hours for strategic thinking is only half the battle, especially for busy legal professionals.

The real challenge? First, protecting that sacred PQO time from the inevitable barrage of external and internal distractions. Second, ensuring the brilliant insights…

Issue 5 of my Personal Strategy Compass Substack email newsletter (premium) has been published and sent. It has some new insights and some practical materials to help you move forward with my favorite personal productivity tool – Personal Quarterly Offsites. And I’ve made part of it available for free.

Over the years I’ve borrowed good…

Photo of Dennis with post-it notes behind him

Is your leadership team asking for more innovation from your law department? Is delivering innovation results on your department or personal annual objective list?

C-suites are demanding that their general counsels and law departments accelerate their efforts to keep pace with innovation goals across the organization. They want their law departments to be as creative…