Leadership Labs · Fall 2026 Cohort · Enrolling Now

Stop being the place where everything lands.

Six working sessions to catch the leadership work that keeps skating away from you — and build the systems that hold it without you holding everything.

Join the Fall Cohort $2,500 through August 14 · $3,000 after · 12 seats · Starts September 1

Sound Familiar?

Things leaders say the month before they join

“I’m the bottleneck.”
“We’re doing too much and not enough is getting done.”
“This team is full of great people, but we’re not working together well.”
“I want to lead differently, but I don’t know how.”

If you’ve said one of these this quarter, you’re the leader this Lab was built for. The model that got you here — overfunctioning, holding the clarity, being the glue — has a ceiling, and you’ve found it.

Who It’s For

Leaders at the threshold

Labs is for seasoned leaders with real authority and autonomy — founders, executive directors, department heads, and senior team leads, often 15+ years into work that matters. You know what good leadership looks like, and you want the structure, accountability, and direct access to actually execute it. If you’re after a self-paced course or a big anonymous cohort, this isn’t that.

The Shift

What changes in a season

heroic soloingTeam-powered leadership
holding everythingSystems that hold
urgency-fueled executionSustainable rhythm
foggy expectations, dropped ballsClarity, cadence, and trust

The Six Sessions

A season of leadership work, one piece at a time

Leadership Orientation

Where you actually are as a leader, so everything after has a starting point.

Your Weekly Schedule

The structure that determines what’s possible for everything else.

Vision

Getting it out of your head and into a form your team can follow.

Readiness

What your team can actually do, and how to close the gap between that and what you’re asking of them.

OKRs

Objectives and key results that don’t collapse into project management.

Empowerment, Delegation & Accountability

How to hand off real work and make sure it doesn’t boomerang back to you.

How It Works

A lab, not a lecture

Work on your real team, not case studies

Every session applies directly to the team you lead right now.

Two hours, split in half

One hour of working conversation, one hour of lab time to build the actual thing.

A small cohort of twelve peers

Leaders at the same threshold, led live by Charlie on Zoom.

Leave with systems that outlast the Lab

An expectation clarified, a meeting rebuilt, a decision unstuck — every session builds a concrete asset for your team.

The Schedule

Six biweekly Tuesdays, live on Zoom

Every other Tuesday at 10am PT, two hours each. The biweekly pace gives you a real implementation window between sessions and keeps the rest of your calendar intact. Every session is recorded and shared with the cohort.

Sep 1 Sep 15 Sep 29 Oct 13 Oct 27 Nov 10

Why Charlie

Rigorous about work, honest about people

Charlie Gilkey

Charlie Gilkey is the author of Start Finishing (Sounds True, 2019) and Team Habits (Hachette Go, 2023), and the founder of Productive Flourishing. His work is cited in Inc., Time, Forbes, the Guardian, and Lifehacker. Before all that, he was an Army logistics officer in Operation Iraqi Freedom — and he’s a near-PhD in philosophy. Both show up in the Lab.

Organizations hire Charlie for private engagements that start in the five figures. Labs is the cohort door into the same body of work.

Want the approach in miniature first? Read the Team Habits Primer — free. If it maps to your team’s reality, the Lab will too.

What Leaders Say

Leaders who’ve worked with Charlie

“Charlie has been a game changer for my leadership and organization.”

Andrea Palacios · Girl Scouts San Diego

“Charlie has coached me on long-term strategy, board relations, and my own leadership patterns.”

Jeremie Miller · Executive Director, RAFT

“Charlie helped us become more direct, more confident leaders of our team.”

Eric Grey & Amanda Barp · Co-Owners, Watershed Wellness

Fall 2026 Cohort · 12 Seats

Leadership Labs

By November, the leadership work that used to land on you has somewhere else to live.

$2,500 thru Aug 14

$3,000 after August 14 — same Lab

Charlie GilkeyLed live by Charlie Gilkey
  • Six live sessions with Charlie, every other Tuesday
  • Two hours each — working conversation plus lab time
  • Applied to your real team, between sessions
  • Built on the Team Habits framework
  • Recorded and shared with the cohort
Enroll Now Twelve seats — when they’re gone, they’re gone. A fraction of a private engagement, which starts in the five figures. Not sure it’s a fit? Email Charlie before you enroll — he’d rather you be sure.

Questions

The practical stuff

How much time does this take?

Six two-hour sessions, every other Tuesday at 10am PT. The biweekly pace gives you a real implementation window between sessions and keeps the rest of your calendar intact.

What if I miss a session?

Every session is recorded and shared with the cohort, so you can catch up. The biweekly rhythm is built so you don’t fall behind.

Do I have to build the assets?

Each session builds a concrete asset for your team, but building it is optional — the working conversation stands on its own.

Is this coaching?

It’s a lab: structured, applied, cohort-based, and coaching-adjacent. You get direct input from Charlie, and the small-group format keeps the price a fraction of private work.

Can my organization pay?

Most members expense it. If you need an invoice or a letter for approval, ask.

When does the price change?

August 14. $2,500 before, $3,000 after — same Lab either way.

P.S.

The leadership work that keeps skating away doesn’t catch itself, and next quarter looks a lot like this one unless something changes the model. Twelve seats, starting September 1; the early price holds through August 14. Join the Fall cohort.