Guiding Leaders to Foster Cohesion, Drive Results, and Advance Thriving

Drawing on decades of experience across military, academic, and business landscapes, I provide strategic solutions that transform challenges into opportunities for growth.

Is This You?

If you're considering reaching out, it might be because:

  • You've moved into a new position you don't feel prepared for, you've hit an uncomfortable leadership plateau, or you know your blind spots are dragging you down even though you can't see them

  • You and your team have deep fatigue or burnout from the last few years of COVID and resets and there doesn't seem to be any light at the end of the tunnel

  • You've rapidly expanded your team, things aren't coming together, and you don't have time to fumble through the darkness to get it right

  • Post-merger or acquisition, you're looking at a group of talented individuals who need help meshing into a cohesive unit

  • You're tired of strategic retreats that feel disconnected from the real dynamics and needs of your team or organization.

  • Your management or leadership team recognizes a gap in effectively managing strategy execution or change and you're committed to building this competence.

How We Can Work Together

The following are some of the most common ways people engage me:

  • Executive Coaching: My leadership coaching is infused with insights from diverse fields, empowering you to make decisions with confidence and inspire your team towards shared goals. (Click here to learn more about executive coaching.)

  • Team Habits Assessment: Leveraging proprietary tools, I offer a tailored analysis of your team's dynamics, drawing on my broad experience to identify pathways to cohesion and growth.

  • Facilitation: My facilitation ensures that every session harnesses the collective energy of your team, guiding workshops and meetings toward productive collaboration and deep understanding, all the while reflecting a unique mix of strategic foresight and practical execution.

  • Strategy Execution Engagements: I support your team in transforming strategic visions into actionable realities, applying a blend of disciplined military strategy and entrepreneurial agility to ensure alignment and progress.

  • Fractional Chief of Staff: Offering strategic leadership support, I bring to your organization a wealth of experience in navigating complex challenges, streamlining operations, and aligning team efforts, all tailored to meet you exactly where you are.

If you'd like to move past bullet points and have a conversation to see how we might work together, click the button below to get in touch.

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About Me (Charlie Gilkey)


I've advised or led hundreds of teams, from Fortune 100 companies to tiny nonprofits, and there's not much I haven't seen and navigated when it comes to team and organizational challenges.

My approach is deeply informed by nearly two decades of interdisciplinary experience in systems thinking, strategic execution, leadership development, and innovation. I integrate my academic studies in ethics and sociopolitical philosophy with practical strategies for improvement, focusing on how leadership and team dynamics can enhance both productivity and personal satisfaction. My military service, including leading over 200 soldiers in the US Army, infused me with the grit, adaptability, tenacity, and strategic foresight essential for enduring success.

The goal of my work is to help organizations create a culture where success and well-being are intertwined, reflecting my belief and the research that positive work experiences are fundamental to individual fulfillment and organizational excellence.

My award-winning work, including my latest book, Team Habits, distills these insights into actionable strategies for creating environments where results and belonging coexist. Bringing together the strategic acumen and leadership of a military officer, the insight of a philosopher, and the flexibility and outcome focus of an entrepreneur, I am dedicated to transforming organizations with thoughtful, sustained momentum.


The testimonials below are representative of the typical outcomes from working with me. I can provide more tailored testimonials upon request.

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