A year ago, I started a small experiment.

Could a group of experienced advisors who serve founder-led companies meet once a month — not to network — but to challenge each other, think better, and share what they are seeing in the field?

So, we formed a Vistage Trusted Advisor table in Chicago.

Ten professionals around a table.

Different disciplines.

No competition with each other.

Recruiting.

Banking.

Legal.

Wealth.

Consulting.

What has surprised me most over the past year: the depth of conversation that happens when the incentives are right.

Instead of “Who can I sell to?” the question becomes:

“What are you seeing with clients right now?”

We talk about deals that almost happened.

Leadership challenges inside family businesses.

Technology risks.

Growth opportunities.

Hard client situations.

The conversations are candid and often uncomfortable — which is exactly what makes them valuable.

After a year together, the group has decided we are ready to add two more members to complete the table.

At the same time, I will be launching a second afternoon cohort over the next two quarters as part of what we’ve been calling our Journey to 20.

These are not networking groups.

They are peer advisory tables for professionals who want to think better and serve their clients better.

If you work closely with privately held companies in the Chicago market and believe this kind of environment would sharpen your thinking, I’m always open to a conversation.

And if someone comes to mind who would thrive at a table like this, feel free to introduce us.