AI-Assisted Leadership
The Future Belongs to the Leaders Who Know How to Ask the Right Questions
Decisions Determine Your Future
The decisions you make today determine your future.
That’s always been true. But in the age of AI, the cost of poor decisions is rising, and the opportunity for high-leverage decisions is skyrocketing.
That’s why AI-Assisted Leadership isn’t a gimmick or a trend.
It’s a necessary evolution.
Some argue that leadership will one day be handed over to artificial intelligence.
I don’t buy it. Nope. Not going to happen.
Leadership is human. It’s relational.
It requires empathy, vision, and values.
But what I do believe, and what I’ve experienced firsthand, is that the leaders who learn how to partner with AI will have a clear and compounding advantage.
This isn’t about replacing human intuition or experience.
It’s about supercharging it. Amplifying it.
Strategic Thinking Is the #1 Leadership Behavior
According to the Harvard Business Review, strategic thinking is the most important behavior for future-ready leaders.
Not charisma. Not hustle. Not intelligence. Strategy.
But what does it take to develop a great strategy?
Data. Information. Insights. Context. And the ability to think beyond the moment.
Too often, leaders rely solely on past experience to guide their decisions. While experience can be invaluable, it can also be limiting. Experience alone can lock you into outdated models.
But ask better questions, and you open the door to new possibilities.
This is where AI-Assisted Leadership begins.
What General Colin Powell Taught Us About Decision Making
General Colin Powell, one of my personal heroes, once said he made decisions when he had between 40% and 70% of the information.
Anything less was too risky. Anything more was too slow.
His 80% rule of thumb became legendary in leadership circles.
But here’s the challenge in today’s world: what happens when the speed of change accelerates and you need that 70–80% faster than ever before?
You turn to your new team of assistants.
My Secret Weapon in the Boardroom
I carry my iPad Pro into nearly every high-stakes meeting.
Not because I want to look tech-savvy. Not because I want to scroll emails.
I bring it because, with the right tools, it becomes the most powerful leadership companion I’ve ever had.
I’ve used ChatGPT to instantly summarize complex documents.
I’ve asked Claude to help me reframe a strategic issue.
I’ve leaned on Perplexity to pull market data in the middle of a call.
This isn’t theory. It’s the new reality of AI-Assisted Leadership.
You don’t need to pretend to know everything anymore.
You just need to know how to ask smart questions and have the courage to ask them out loud, even in real time.
Imagine This…
You walk into a boardroom. You’re expected to provide insight on a fast-moving issue that touches cybersecurity, business strategy, and ethics.
In the past, you’d either wing it, postpone the decision, or call in a specialist (if you had one).
Now imagine instead you’ve got three trusted advisors sitting right beside you:
Chad: Your fast-talking AI analyst who can answer anything technical or quantitative.
Claude: The wise, philosophical one who helps you see things from multiple angles.
Poindexter: The research nerd who digs up data and reports in seconds.
You’re not alone. You’re not scrambling. You’re calm. Focused. Supported.
That’s the power of AI-Assisted Leadership.
Connecting the Right Dots—Faster
Great decisions don’t come from having all the answers. They come from connecting the right dots.
But most leaders are swimming in noise. Emails, data, dashboards, distractions.
They don’t need more information. They need faster pathways to clarity.
Personal AI assistants are becoming the ultimate dot-connectors.
They help you reframe decisions. They surface unseen insights. They let you run multiple mental models at once.
They make strategy more dynamic and responsive.
With the right approach, AI becomes less about automation and more about amplification.
The Dawn of Personal Computing 2.0
We’re entering a new era.
Just like the PC revolution changed the way work was done in the 80s and 90s, we’re now seeing the rise of Personal AI as the next great inflection point.
This isn’t about simply “using tools.”
It’s about augmenting leadership itself.
The leaders of tomorrow will be those who implement tomorrow’s tools today.
Those who lean into AI not just as a back-office assistant, but as a front-line thought partner.
That’s the edge. And it’s not coming. It’s already here.
So, Are You Ready?
AI isn’t going to take your leadership role. But another leader who knows how to use AI just might. I know you’re tired of hearing similar-sounding statements. But that’s the reality.
The real question isn’t if you should embrace AI-Assisted Leadership.
It’s how quickly you’ll do it.
Because the leaders who move first will set the pace.
So, ask yourself:
Are you still leading from instinct alone, or are you training your instincts with insights?
Are you still making decisions in isolation, or are you bringing your AI partners into the room?
Are you prepared for the next wave of change, or are you still playing by last decade’s rules?
It’s time to make a choice.
Become the kind of leader who sees what’s possible before the rest of the world catches up.
This is AI-Assisted Leadership.
And this is your invitation to lead differently.