Hey, it’s Aaron. I spent the week with my mastermind group, being poured into by 25 other remarkable CEOs and leaders. I hope I was 10% as helpful to them as they were to me. Then I flew home, got in at 1am, and now I’m sitting in my study with a cup of coffee, looking out at the beauty of a winter morning in Idaho. Nothing helps focus the mind on gratitude like that.

At the mastermind, we had five different content sessions and I used MeetingOS to capture all of them. The group was RAVING about the quality of the notes it generated.

To be honest, that kind of surprised me. We’ve focused most of our efforts on becoming the brilliant meeting strategist who helps you prepare meetings more effectively, and the superhuman memory who makes you 10x better in meetings.

But I have to agree — the level of personality, crispness, and concise clarity I’ve been getting out of MeetingOS has been powerful. And that powers an incredible level of shared understanding for teams. Despite the fact that I was traveling in different time zones, I used Contio AI to keep my finger on the pulse of our daily engineering standups.

Suffice it to say: I’m excited. And if any of this resonates with you as a leader who spends lots of time in meetings, and you want to try out and give us feedback on a security-first AI product that easily snaps into your existing world, give me a shout.

A few weeks ago, I decided to write December’s essay on the power of having a great board. I didn’t realize that my quarterly board meeting for Contio was scheduled for December 10, the day this monthly email comes out. It’s a fun coincidence that makes my point all the more powerful. If you don’t have a board yet or are underutilizing one, this month’s essay is for you.

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 here.

Why Great Boards Make Great Companies

I’ve worked for a Board of Directors since 2011, and that remains true at Contio. Sure, I own a majority of the company (for the moment), but one of the first things I did was go recruit two of my former board members from the Riskalyze days to join my new board.

A lot of people have asked — “why would you do that? You’re technically not required to have a board this early. Isn’t it a huge time suck to have to prepare slides and the whole drill?”

Believe it or not, before every board meeting, the most important time I block out isn’t actually building the slides, or updating the forecast.

It’s the time I block out to do something way more important: thinking.

Thinking about where we are strong, and where we need to step it up. Thinking about the toughest questions I’d ask about our strategy, our game plan, or our execution if I was a board member. Thinking about the ways I might be wrong, or even worse, blind.

That’s what great boards do. They make you better.

And yet, when I talk to founders or CEOs about their boards, I often get a shrug. “They’re fine.” “Mostly governance.” “Kind of a chore.”

If that’s your answer, you’re missing one of the biggest cheat codes in business leadership: a truly great board.

And I’ve had the good fortune to work with a few of them.

The Legal Role Is the Least Interesting One

Sure, every board has legal and fiduciary responsibilities. They’re the stewards of the company on behalf of its shareholders. They sign off on major decisions. They ensure you’re spending OPM — other people’s money — with care and intent.

That stuff matters. But it’s table stakes.

The best boards I’ve worked with or served on go far beyond governance. They’re intellectual sparring partners. Strategic accelerants. Emotional ballast. They’re not trying to run your company — they’re trying to make sure you run it at your absolute best.

They aren’t trying to take the reins from the CEO. In fact, they practically set up the CEO as a benevolent dictator of sorts, but one who once a quarter, has to walk into a room full of smart people and justify the decisions that he or she has been making over the last three months.

That structure — the built-in rhythm of accountability and discussion — is one of the greatest gifts a CEO can receive.

Why You Should Want a Great Board

Let’s make this concrete. Here’s why great boards are worth their weight in gold.

#1 — They force you to stop and think deeply. If you’re like most founders, you live in the now. You’re firefighting, selling, hiring, solving — for 60, 65, 70 hours a week. Board meetings force you to step back, connect the dots, and ask the hard questions: What’s really working? What isn’t? What have we learned that should change our assumptions? Tell me — when else in your calendar can you really do that?

#2 — They sharpen your thinking. Ever tried explaining a complex strategy to someone 10 IQ points higher than you? It’s humbling — and clarifying. Good board members don’t just nod along. They press. They probe. They ask “why” three times. And when you leave, you either believe your story more deeply, or you realize it had holes you hadn’t seen. Both outcomes are wins.

#3 — They bring elite perspectives. A great board at scale isn’t monolithic. It’s a mix of operators, investors, technologists, and domain experts. Each one sees your business from a different angle. When you’re in a fog — and every company hits fog — that diversity of perspective can be the map that gets you out.

#4 — They’re vested in your success. This part is underappreciated. Great board members aren’t just advisors. They’re stakeholders. That means they can — and often will — move mountains for you. Make the call. Open the door. Twist the arm. When things get hard (and they always do), you want people around the table who won’t just applaud if you win — they really, really want you to win.

#5 — They hold you accountable. Let’s be honest: self-accountability only gets you so far. Most founders are great at spinning up new ideas. Less great at killing old ones. A strong board doesn’t let you waffle. If you said X was a priority last quarter, and it’s still not done, they’ll ask why. That kind of pressure may not be fun, but it is productive.

Okay, But How Do You Build a Great Board?

You don’t need a board that agrees with you. You need a board that respects you — and challenges you.

That starts with selection. Don’t stack the board with investors who are just looking to protect downside. Look for people who ask great questions, think long-term, and care deeply about outcomes. Bonus points for those who’ve sat in your chair before.

Then give them something to chew on. A great board deck isn’t 85 slides of metrics. It’s 12 slides with the three hardest questions you’re facing right now — and your current thinking on each. Invite critique. Welcome pushback. Don’t pretend to have it all figured out.

Finally, treat board meetings like a privilege, not a burden. If you walk in expecting to get an A on your report card, you’ll walk away with very little. If you walk in seeking that powerful sounding board, you might walk out with a better company.

The Bottom Line

A great board won’t run your company for you…but they will make you a better CEO.

They’ll make you think harder. Lead better. Execute smarter. And when the storms hit — because they always do — they’ll help you see the path through.

Don’t settle for “fine.” Build a board that makes you raise your game.

Talent on the Prowl

I know of an incredible person who is newly available — her background is in HR, people operations, and program management — she’s someone who is incredibly great at supporting teams, building process, and helping people feel seen and supported. She’s worked in both in-person and remote roles.

I also know of an awesome guy with years of experience in sales and revenue operations who recently became available.

If you’re looking to add some great talent to your organization, hit reply and I’d be happy to make introductions.

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, I have a coaching slot empty, and am talking to a few candidates, but haven’t found the perfect fit yet. If you want to discuss, click here to learn more about my approach, and hit reply if you’d like to talk about it.