Insights

Executive Team Coaching in Chicago

Scaling Minds provides executive team coaching for privately held companies in the Chicago area, generally 50 to 200 people, where the leadership team needs to start carrying weight the CEO has been carrying alone. I'm based in Chicagoland, and most of this work happens in person, in your conference room, because that's where your team's actual patterns live.

This page is the short, direct version. The rest of this site goes deep on the patterns themselves; this is for Chicago-area CEOs deciding whether to pick up the phone.

Who is executive team coaching in Chicago for?

The companies I work with look like the Chicago midmarket actually looks: manufacturing and distribution businesses in the suburbs, professional services firms in the Loop, family-held companies on their second or third generation, the privately held operators that make up most of this region's economy and almost none of its press coverage.

The CEOs come in three flavors. Founders whose company outgrew the wiring. Successors who inherited a team that still operates like the previous owner is down the hall, and in Chicago family businesses, the previous owner often literally is. And hired CEOs, increasingly PE-backed, who walked into a leadership team they didn't pick and a clock that's already running.

Different doors, same room: an executive team that's smart, expensive, and somehow still routes everything through one chair.

What does working together look like?

In person, mostly, and on your real work. I sit in your actual leadership meetings, run sessions with your team in your building or somewhere quiet nearby, and work the patterns where they actually fire instead of in a hotel ballroom. Being local is the point: the work happens in your operating rhythm, monthly and sometimes weekly, not in quarterly fly-in events.

The shape of an engagement: a diagnostic up front, where I interview every executive and put one honest picture of the team on the table. Then sequenced work, because teams change in an order and skipping ahead is how the last consultant failed. One Chicago-area client, a third-generation distribution company, watched that order pay off the day their VP of Operations told the family CEO, in the meeting, that the expansion timeline was a fantasy, and instead of the conversation everyone feared, they got the first honest planning cycle in a decade. The system I run that work through is the Six Shifts, and I built it for exactly these teams.

If you're still sorting out what kind of help you need, coach, EOS implementer, peer group, consultant, I wrote an honest map of who does what. Read it first if the categories blur together. They blur for everyone.

How do you start?

A conversation, thirty minutes, no deck. You tell me what's actually happening with your team, I'll tell you whether it's the pattern I work on, and if it isn't, I'll point you at whoever fits better. Chicago's business community is small enough that referring you well matters more to me than closing you.

If it goes further, the next step is the diagnostic, and you'll know within a month whether this is working, because your team will already be having meetings that sound different.

Common Questions

Do you only work with companies in Chicago?

Chicagoland is home base, the city, the suburbs, the collar counties, and it's where the in-person rhythm is easiest to keep. I work with teams beyond the area when the fit is right, with travel built around the session cadence. For local teams, proximity is a genuine advantage: I can be in your Tuesday meeting on a Tuesday.

What size company is the right fit?

Roughly 50 to 200 employees, privately held, with a real executive team of four to eight leaders. Below that range, the team usually is the founder plus helpers, and the work is premature. Above it, the patterns are the same but the engagement looks different. The revenue range varies by industry; the constant is a leadership team that matters enough for its dysfunction to be expensive.

How is this different from a Vistage group or an executive coach?

Those develop the CEO. This develops the team, together, in the room where it operates. Plenty of my clients are in Vistage or YPO and stay there, because the products complement each other: the peer group is where the CEO thinks, and the team coaching is where the team changes. If only one leader needs development, hire an individual coach and save the difference.

What does it cost?

Engagements run from the tens of thousands for focused six-month work into low six figures for a full year with the whole system. The honest comparison number is what the team's current patterns cost annually, slow decisions, redone decisions, the executive you're about to lose, and for most companies that hire me, that number turned out to be larger. I'll help you estimate yours in the first conversation, before either of us decides anything.


Andy Hite is the founder of Scaling Minds and creator of the Six Shifts, a leadership operating system for executive teams at growing privately held companies. © Scaling Minds

Is your leadership team performing below its potential?

The Six Shifts Diagnostic shows you exactly where your executive team is stuck — and how to close the gap.

Start the Conversation