Hey, it’s Aaron. It’s a crisp, cool Idaho afternoon, and I’m sitting at my desk in the bullpen at Contio HQ in Eagle, Idaho.

I’ll let you in on a little secret. We are down to double-digit days before we launch MeetingOS out into the world. The team is heads-down, working long, hard hours trying to be ready for the big launch.

I’m so excited for this product — the AI operating system for meetings is going to be a BRILLIANT meeting strategist, a SUPERHUMAN memory, and a HYPER-INTELLIGENT Chief of Staff who has you prepped, organized, and following up better than the President.

All while snapping right into your existing calendar, working with every video call platform, and working for your in-person meetings too.

We are having a BLAST getting amazing feedback from our beta test group. I’m about to expand the beta group, and I want to prioritize YOU — the amazing people who were kind enough to subscribe to this monthly email.

If you want in, just hit reply and tell me — I’ll pull some strings, and get you to the top of the list right away.

Welcome again to all the new folks! I love hearing from you, so send back questions, thoughts, ideas, or just a hello any time by hitting reply.

Remember, great leadership is contagious. Thanks for being a subscriber.

The Leadership Sin Equally Bad as Micromanagement

I remember early in my career thinking the worst management sin was micromanagement. I promised myself I’d never be that boss — the one who hovered over people’s shoulders, second-guessed decisions, and slowed everything down.

I worked really hard to be the opposite. I prided myself on total delegation and trust. I gave people ownership, space, and freedom to run.

What’s strange is how well it worked with some people. And what a disaster it was with others.

It turns out, there’s a leadership sin that is equally as bad as micromanagement, and you can easily fall into it by treating two different people exactly the same way.

Allow me to explain.

Most leaders have a natural bias in their management style. Some are “hands on and supportive” by their nature. Others default to “total delegation and trust.”

The eye-opening truth is that your natural bias should not be the determining factor for your management. Instead, you need to err to one side or the other based on each individual employee’s task-relevant maturity.

The concept is deceptively simple: task-relevant maturity measures someone’s capability and confidence to perform a specific task. It’s not about title or tenure. A Senior Vice President that you hire from outside your organization might arrive with high maturity for strategic planning, and low maturity for how to give feedback to their employees.

Instead of trying to mold the person you are leading to your management style bias, the better approach is to adapt your management style to their task-relevant maturity.

When you give total delegation and trust to someone with high task-relevant maturity, it’s incredibly supportive. They feel empowered, respected, and motivated. You’re saying, “I trust you to own this,” and they rise to the challenge.

On the flip side, when you give hands-on support to someone with low task-relevant maturity, you’re doing them a huge favor. You’re coaching them through the turns, helping them learn, and building their confidence.

But flip it, and you’re in trouble.

Give hands-on support to someone with high task-relevant maturity, and that’s textbook micromanagement — you’re slowing them down and suffocating their initiative.

Give total delegation and trust to someone with low task-relevant maturity, and that’s the equally bad leadership sin of abdication. They feel abandoned. You’ve given them the keys to the car, but they don’t yet know how to drive.

The bottom line: there’s no universally right management style for you. You have to adapt to your people, and the work you’re asking them to do. The only “right” style is the one that fits the person and the moment.

So next time you’re not sure whether to dive in or step back, don’t overthink it. Just ask yourself: “What is this person’s task-relevant maturity?”

Your answer will tell you whether to coach, collaborate, or simply get out of the way.

Best Reads + Listens of the Month

• How to Get Better at Spending Money. My friend Morgan Housel is a brilliant writer and even better author of books, and has penned a new one called The Art of Spending Money. This Financial Times profile was a blast of a read. Go check it out, and then buy his book!

• When Donna White’s Candidate Flipped the Script. I got the chance to interview my brilliant friend and one of the best talent recruiters on earth, Donna White, for our “Worst Meeting Ever” podcast. You will learn a ton about recruiting, talent, and planning for great meetings in this short 18-minute listen!

• OpenAI’s Windows Play. Ben Thompson of Stratechery lays out the news from the Developer Day held by the makers of ChatGPT, and says they are making an audacious play to be the “Windows” of the next computing generation. This is a fascinating read.

If I can help, let me know.

That’s it for this month! As a reminder, I am coaching five CEOs or leadership teams. That’s all I have time for, but I’m having fun doing it, and it’s allowing me not to pay myself a lot from the new company while we are in the build phase. 😉 

I don’t think I could have been nearly as effective for my team without the help of a CEO coach. There’s just something about having someone who has walked that journey before as a “safe” sounding board who you can speak freely to.

At the moment, my coaching slots are full, but I am building a wait list as I have two slots that have been taken temporarily. If you want to discuss, click here to learn more about my approach, and hit reply if you’d like to talk about it.