Photo of Dennis Kennedy

Dennis Kennedy is a well-known lawyer, author, blogger, speaker and podcaster who is considered among the most influential authority on the application of technology in the practice of law. He is widely-praised for his ability to communicate complex technological and legal issues into language that non-experts can easily understand.

The Starting Gun for Legal AI Has Fired. Who in Our Profession is on the Starting Line?

Feet of sprinter standing by starting blocks

The legal profession’s “wait and see” approach to artificial intelligence is now officially obsolete.

This isn’t hyperbole. This is a direct consequence of the White House’s new “Winning the Race: America’s AI Action Plan.” After spending the last

If you are a high-achieving professional, you live with a fundamental tension. You know that deep, strategic thinking is the engine of your success, yet your calendar is a fortress that rarely permits the quiet time required for it. Important decisions loom, but the sheer complexity of your options leads to the all-too-familiar state of

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

I’ve been working on organizing and optimizing my AI prompts and prompting methodologies. I noticed that I have two major categories of approaches.

The first I call “complex, structured prompting.”

Google Gemini describes that, and I think accurately, as “a systematic, engineered way to interact with AI. It’s about building a personalized ‘cognitive operating system’

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

For years, I’ve explored productivity techniques, technology tools, and strategies. I now have found and developed one practice that has had the most profound impact – the Personal Quarterly Offsite (PQO).

Frankly, I believe the PQO is the most important work I do. It’s not just about setting goals; it’s about intentionally designing a life

Well, here we are again. Another February 15th and another blawgiversary for DennisKennedy.Blog. It’s hard to believe it’s been twenty-two years. since I wrote that first bold and triumphant announcement, echoing Babylon 5: “And so it begins . . .” I genuinely thought I was late to the blogging party back in 2003. Turns out

The latest issue of the Personal Strategy Compass newsletter (premium subscription only) is out, and it’s all about getting back on track with your quarterly goals – even if you’re feeling a little behind. We’re diving into the “grace period” PQO, a shorter, more forgiving approach to getting back on track after your Personal Quarterly

I’ve long advocated for Personal Quarterly Offsites (PQOs) as a powerful personal tool for legal professionals. Taking a half-day each quarter to step back, reflect, and plan can drastically improve focus, productivity, and long-term strategic alignment.

Let’s be honest: most “personal productivity” advice is, well, let’s just say overhyped. PQOs actually work because they are