Advising Leaders, Teams & Orgs
Work better, together.
Charlie partners with conscious leaders to make their teams work better — the Team Habits approach, applied to the organization you’re actually running.
Tell me about your teamWhen Leaders Bring Charlie In
The moment usually looks like one of these
Rapid growth without integration
The team doubled, and the ways of working didn’t keep up.
After a merger or acquisition
Two cultures, one org chart, and no shared way of working yet.
A retreat that has to land
An offsite you can’t afford to spend on trust falls.
Strategy that has to execute
A leadership team that can set direction but struggles to make it happen.
New in the seat
A capable leader facing a role bigger than the last one.
A team running on empty
Good people, real fatigue, and a pace that isn’t sustainable.
The Engagements
Five ways Charlie works
One-on-one advising for leaders, with particular care for BIPOC, women, and accidental executives growing into the role.
Aligning the team around priorities and building the cadence that turns a plan into results. Works alongside 4DX, OKRs, EOS/Traction, or a Balanced Scorecard.
Designing and leading offsites, strategy retreats, and team-building sessions that produce something you keep. The agenda gets built around what your team is walking in with.
Named sessions your team can take one at a time or run as a series — Team Habits, Team Meeting Makeover, Team Readiness, Strategic Goal-Setting, Roles and Responsibilities, Team Strengths. Two hours for a working read on where to start, or a half day to leave with a plan.
Redesigning how the org is put together — the structure, the roles, and how the team gets rebuilt around the new shape. Adaptive approach, with a 4P lens: purpose, people, profit, and planet.
Why Charlie
Led at every scale that matters here
Charlie commanded and coordinated for the Army, with responsibility for hundreds of soldiers, and he has spent two decades advising leaders and teams across the military, nonprofits, and fast-growing companies. He is the author of Team Habits and Start Finishing.
Private engagements start in the five figures. If you want the approach in cohort form first, the Leadership Labs is the same body of work at a fraction of the cost.
“Charlie has a knack for naming what’s really going on and guiding teams to engage with challenges and opportunities. His facilitation helped us uncover valuable insights into our organizational patterns and optimize them.”
Leslie Griffin Robertson · FinTech Executive“He brings clarity to complex issues, keeps conversations focused, and creates space for innovative solutions to emerge. His strategic planning sessions are the best I’ve experienced in decades of leadership.”
Andrea Zamora · CEO, Waterfall Community Health Center“Charlie Gilkey masterfully uncovers the pivotal role habits play in shaping exceptional teams.”
Dr. Marshall Goldsmith · Thinkers50 #1 Executive CoachStart a Conversation
Tell me about your team
Send a note on where things stand and what you’re navigating. If it’s a fit, we’ll set up a conversation.