Let's get this out of the way: ChatGPT and Claude are not your assistants.
Sure, they can write emails, draft proposals, and summarize meetings. But if that's all you're using them for, you're missing the point entirely.
These tools are mirrors. They reflect how you actually work—the gaps in your thinking, the decisions you're avoiding, and the discipline you lack. And that's precisely why most people bounce off AI after a few weeks. They don't want leverage. They want relief.
We want fewer emails, not more. Fewer meetings. Fewer decisions. But leadership doesn't work that way. It's the opposite.
That's the through line. Everything I'm about to say reinforces it.
I use LLMs to expose where I'm undisciplined. Where am I avoiding decisions? Where am I confusing motion with progress? If you're looking for prompts to do your job for you, this won't help. But if you want a thinking partner that forces clarity, shortens cycles, and makes you more decisive—keep reading.
Your inbox is full of decisions you're avoiding—not messages you need to sort. We create routing rules, prioritization systems, and follow-up reminders. But at the end of the day, what are we pushing off?
As leaders, we spend our time answering questions, solving problems, and putting out fires because it feels productive. But when you use AI as a mirror, it forces you to declare: respond, defer, delegate, or ignore.
The real win isn't faster replies. It's fewer replies—or not replying at all. The edit you make is where your authority shows up.
Writing exposes thinking gaps. That's why people hate it—you have to connect thoughts together and put them on the page.
AI should not be inventing your messages. It should be removing the fog so your originality and humanity come through. Sure, in the short term, AI can help you crank out more content. But if that's all you're doing, you're losing yourself in the process.
The answer isn't getting more done in the same amount of time. It's getting less done—but the right things. AI isn't just your assistant; it's your coach, your antagonist. Someone to get in your face and say: Don't write that. It's not worth your time. Give it to someone else—or don't do it at all.
"I'll just wing it" is usually code for "I didn't prioritize this."
We go back-to-back-to-back. No time to prepare. Playing catch-up at day's end. For routine meetings where you know the subject cold, fine. But for strategy sessions, new clients, business initiatives—do you really want to wing it?
A few minutes of prep changes the entire dynamic. AI can research the topic, the players, the history, the context, and give you the sound bites. More importantly, AI can help you anticipate what people won't say out loud—the blind spots, the avoided conflicts, the consensus-seeking that waters down decisions.
If you're prepared, you control the conversation. Not the calendar.
Transcription is a godsend. But taking notes just to take notes? Recording meetings just to have them recorded? That's fake progress.
Notes feel safe because they postpone accountability. If we're not making decisions in meetings, if there are no owners for action items, no commitments, no RACI—then we're just meeting to meet. We feel productive. We're not.
AI can force that structure. It won't let you hide behind bullets.
A lot of leadership tension is choosing between two bad options. AI can help you understand the second, third, and fourth-order effects we often ignore under pressure. It can clarify the cost of delay.
That clarity doesn't eliminate risk. It makes risk explicit—so you go in with your eyes wide open.
"Brilliant decision! Good job!" Validation feels good. But the value comes from friction, heat, and debate.
A lot of teams lack a real challenger in the room—or silence the challengers they have. Consensus thinking leads to unanimous thinking leads to groupthink. Nobody decides until everyone agrees. You end up with vanilla, middle-of-the-road outcomes.
You want tension. You want debate. Train your LLM to challenge you every single day: Are you sure you want to go to that meeting? This doesn't align with your Q1 priorities. Someone else can handle this.
Strong leaders invite resistance from day one—not after the launch.
I ask leaders this question constantly: How much of your week do you actually spend doing your job? The answer, more often than not, is about 20 percent.
Whatever your title, whatever your salary—you're spending a fifth of your time on your actual role. The other 80% goes to waste: meetings, note-taking, lost initiatives, distractions, fires you didn't need to fight.
AI's role isn't to help you do more of those things faster. It's to tell you to stop doing them entirely—so you have time to actually spend with your people.
Volume is often a substitute for courage. More campaigns, more content, more messaging—but that's not the answer. When your messaging tries to please everyone, it pleases no one.
AI can hold up the mirror: You don't need this piece. You already have two that say exactly the same thing. Just be more consistent. Stop constantly reinventing the wheel.
Repetition is not boring. Inconsistency is expensive.
As Mike Tyson put it: Everyone has a plan until they get hit.
Your beautiful strategy deck doesn't execute anything. Your people do. When we talk about "alignment," it usually means no one actually owns the outcome. We spend all our time getting aligned on what the strategy is—but who's responsible? Who's doing what, when, and how do we measure it?
AI can take your strategy and turn it into tasks, owners, timelines, and RACIs. Then it becomes your monitoring agent, ensuring execution actually happens.
If execution isn't clear, strategy wasn't either.
If you have to re-explain yourself constantly, it drains more energy than execution. Every person on your team has their own context. Your communication needs to be a message of one—connecting specifically to the intern, the 20-year veteran, and everyone in between.
AI can hold your project memory so you don't constantly reset. It compounds context. Chaos resets it to zero.
Most AI failures come from overengineering—massive software, six-month rollouts, too much complexity. That's not how change works. That's not how people work.
One task, daily, for a month beats ten prompts all at once. Build the muscle. Let AI disappear into how you already work—like your phone, your email, your computer. It should just make you better. More human. More communicative. More productive.
Consistency creates leverage. Not novelty.
LLMs don't make hard work go away. They make avoidable work visible. They show you where you're unclear, where you're over-communicating, where you're deferring decisions.
If that feels uncomfortable—good. That's the point.
The leaders who get real value from AI aren't chasing prompts. They're willing to confront how they actually work.
Stop trying to boil the ocean. Pick one repetitive task. Write one good prompt. Use it every day this week.
The goal is not to work less. It's to lead with more clarity.
AI is not your assistant. It's your mirror.
Think about that. And we'll see you next week.