Now that I’m immersed in the space of executive communities, I’ve started noticing that most of them optimize for what’s easy to measure: growth, activity, visibility. Over time, those choices shape the room, often not for the better. When you design with scale in mind, discretion and alignment are usually the first things to erode.
The communities that endure optimize for different things: judgment, trust, and shared standards. These qualities take time to build and don’t show up cleanly in metrics, but they determine whether a community actually works.
The default community playbook
Most professional communities start with good intentions. But many default to familiar signals of success like member count, sales revenue, churn, content output, and social visibility.
Those metrics are legible and easy to track. They look good in a deck. But when builders focus primarily on numbers, they often overlook something critical: talking to their members.
If you stop talking to your community, you stop understanding what they actually need. And when numbers start driving decisions, design tends to simplify. One of the easiest ways to scale is to narrow the room.
Many communities are focused on a single vertical, whether women-only, GTM leaders, or founders above a certain revenue threshold. Building more expansively is harder. It’s easier to define a niche and scale within it.
But we know the real world isn’t organized that way.
Executives and CEOs aren’t responsible for one function. They’re responsible for understanding the entire business. If you only sit beside people who think exactly like you, your growth narrows.
When I think about how 5 to 9 is doing, I look at engagement, referrals, and how members support one another. Are they making introductions? Offering advisory calls? Showing up? Referring other leaders because they genuinely believe in the room?
These “metrics” matter. You wouldn’t refer someone to a community you thought was low value.
I’ve asked members why they left previous societies. The answers are consistent:
- It became too commercialized
- I wanted a more diverse group
- I didn’t feel like I belonged
- I wasn’t among peers
You can build a large membership. But at some point, you may lose the essence of what you were trying to create.
Why these metrics are alluring
Growth and visibility are expected. If you take funding, you have to grow. Boards want ROI. Debt financing requires repayment. If your goal is rapid expansion, scaling aggressively makes sense.
Revenue certainly matters. But what matters more to me is whether members are getting what they paid for.
Are they making the connections they hoped to make? Do they feel supported in ways they can’t at work? Are they learning from one another? Are relationships deepening?
That’s what I measure.
If I’m being honest, I don’t see many strong communities today. Maybe some founders don’t think it’s important to build them. I do, especially now. You can’t technologize human relationships. We need one another.
What gets lost when scale leads design
When scale becomes the primary objective, behavior changes.
A dinner can feel like a room, or it can feel like a stage. When people enter for the first time, there’s a natural caution. You’re reading the room. Deciding what to share. Gauging whether this is a place where you can speak honestly.
That decision is a choice.
One of our core values is excellence without ego. If we’re gathering with limited time, are we there to share wins and accolades? Or are we there to talk about failures and ask the hard questions we can’t always ask inside our companies?
Leaders often have to act like they have the answers when they represent their organizations. In this room, they shouldn’t have to.
Once trust is established, members go out of their way to make introductions, share referrals, and offer support. That kind of generosity doesn’t happen automatically online.
When members no longer need me to facilitate conversations, that’s when I know we’re building something real.
The qualities that actually make a room valuable
Judgment starts before anyone walks into the room.
We do reference checks seriously. What you’ve built matters, but how you built your character matters more. Our Code lives in our values. If those values aren’t taken seriously, the community loses integrity.
Discretion is critical. What’s shared in our rooms is handled with care. Leaders speak openly because they trust it won’t travel loosely outside the space.
Alignment shows up in behavior. I see it when new members join and others welcome them, articulate what we stand for, and carry the culture without me prompting them. If I’m the only one explaining what we’re about, I’ve failed. The essence should expand outward while the core remains intact.
These qualities don’t appear on a dashboard. But they determine everything.
Why the most important things resist measurement
I once met a founder who built a community organically from her university network. It was nearly impossible to get into because it was based on real connection. You couldn’t pay your way in. There was no marketing budget or public promotion.
It grew through trust and word of mouth. It became a profitable seven-figure business.
Incredible.
There are dashboards for everything today. But if we could quantify taste or engineer trust at scale, someone would have already done it. Human behavior doesn’t work that way. Technology can analyze behavior, but it can’t manufacture alignment.
I’m okay with that.
Designing for endurance, not applause
Yes, I’ve made choices that limit scale.
I was asked why I didn’t create a community just for women. It would have been successful. But I believe diverse tables create stronger leaders. I want women to win, and that often means learning how to win in rooms that aren’t exclusively female.
I’ve also chosen to ensure members are among true peers. That means declining applications. If the Society were for everyone, it would be for no one.
There are many ways to grow revenue faster. Growing too quickly risks higher churn and diluted trust. Making money is easy. Building something meaningful is harder.
You have to choose your hard.
A different definition of success
We’ve all been part of communities. Some feel like home and others feel like you’re wearing a mask.
In the right community, even when you’re exhausted, you still show up. When the weather is awful, you still make it to the event. You’re drawn to being around people who understand you. You can speak honestly and ask for help without feeling judged.
If a community is doing its job well, its members should feel less alone in the weight they carry.
Leadership is demanding. Coaching can help, but it’s still one-on-one. A trusted community creates shared strength.
That’s what endures.
