Advising Leaders, Teams, and Orgs on How to Work Better Together

I'm Charlie Gilkey, aka the Team Habits Guy. I partner with conscious leaders and organizations and help them build teams that work better together.

If you're thinking about working with me, it's probably because …

    • 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
    • You've acquired or merged with another team, and while you might have the right people, how they're going to work well together isn't clear
    • You don't want to have yet another strategic retreat that doesn't address the realities of your team or organization, but you're not sure what to do differently to make it impactful and engaging
    • Your management team is finally open to accepting that they're not good at managing strategy execution or change management and you're ready to make it a team competence
    • 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 'em
    • 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

I have different engagement styles to address those situations, but here are the most typical kinds of engagements:

    • Team Habits Assessment: This engagement delivers a deep dive into your team habits and workways, pinpointing strengths and opportunities for growth. I provide actionable insights to fortify team performance, belonging, and outcomes, catering to teams at any stage of their journey.
    • Executive coaching: I advise leaders, managers, and owners so they get out of the whirlwind and drive strategic progress. I'm especially adept at advising BIPOC, women, and accidental executives who haven't been on the "leadership" track but find themselves in an executive or senior leadership seat nonetheless.
    • Strategy execution: These focus on supporting teams to align, prioritize, collaborate on, and operationalize their strategic priorities and initiatives. These engagements often integrate strategy execution frameworks like 4DX, OKRs, EOS/Traction, and Balanced Scorecard. They're equally great for senior leadership teams who need to get on the same page or teams of high-potential leaders who need to learn by leading.
    • Change management: These engagements center adaptive strategy, DEIJ, self-organized work, and 4P (purpose, people, profit, and planet) lenses. If you've tried a change management project and struggled, let's talk - my approach to change management addresses why change management initiatives fail.
    • Facilitation: I facilitate company offsites, strategy retreats, or rapid team-building events. For these, I co-create the event architecture to deliver the outcomes the event is intended to accomplish.

Oh, and I love bullet points.

If you'd like to move past bullet points and have a conversation to see how we might work together, fill out the form below and we'll have a no-cost, no-obligation discovery session to see what we can co-create together.

About Me (Charlie Gilkey)


I am the lead consultant, coach, and strategist at Productive Flourishing. I have nearly 20 years of fieldwork that incorporates systems thinking, strategy execution, leadership and organizational development, practical innovation, and communication.

Besides the technical expertise, I possess a passionate drive to help leaders and owners achieve more than they could have ever imagined. My experience includes leading 200+ soldiers in the U.S. Army, 14 years consulting leaders in various industries in for-profit and nonprofit industries, writing award-winning books, and serving on various boards. My newest book, Team Habits, is a guide to creating practices in teams that create great results and belonging.


The testimonials below are representative of the typical outcomes from working with me. I can provide more tailored testimonials upon request and you can also see more in my LinkedIn recommendations.

Andrea Zamora

Founder, Brite Side Consulting (former CEO, Waterfall Community Health)

Charlie has been a game-changer for my leadership and organization.  As an executive coach, he's one of the few people who can really see what's going on, clearly put it on the table, and anchor to the conversation until it's resolved. I can't hide anything from him and I don't want to because I know, no matter what, I and my organization will be better off from our empowering conversation. I engaged Charlie to facilitate team and board meetings for the same reasons -- he's flexibly able to keep us focused on exactly what we need to without getting bogged down into details and distractions that aren't important for the meeting at hand. It always amazes me how he is able to create space for the unexpected nuggets that arise and turn into innovative solutions to problems we didn’t know we had. I've done a lot of strategic planning sessions over my decades of leadership and his have been the best ones.

In addition to working with Charlie as an executive coach and engaging with him to facilitate team and board meetings, I also attended the first Level Up Retreat hosted by Charlie and Angela. I went thinking I was going to take back a plan to be a better leader and really what I've brought back is a different, better version of me. I came home with possibilities I didn't know I had; the possibilities of a magnificently delicious life. The beauty of that particular experience is that I have gone from a leader on paper with expectations and rules, following all of the books and podcasts over the last 10 years and scripting everything, to now leading from the heart. I can't put a price tag on that. It's priceless.

justine clay

Justine Clay

Business Coach

The moment a friend shared the Level Up retreat with me, I knew I had to make it happen.  It was a full mind, body, and soul 'yes.' I expected high-level business support and I definitely got all that and a lot more. What I hadn’t anticipated was how deep the work would go on a full-human level. Charlie and Angela are master facilitators and space holders for ALL the things that come up in the life and business of an entrepreneur.

I left with the business insights and strategies I expected, but also a whole lot of clarity about and compassion for myself that I hadn’t bargained for, but absolutely needed. If you’re a purpose-driven entrepreneur who is looking to make huge changes in your business and life, this retreat will blow your mind. Trust the process and let the insights and a-ha’s flow in.

Tom Guthrie

Founder - Messen Convention

If I were to use one word to describe my experience at Level up it would be "Transformational." My friends have told me that they can see it too.

I walked away ready to shine, having gained a set of powerful friends, useful working models, ways of looking at my internal world, several languages to describe it, so many great ideas, and a clear path forward.

I've recommended the retreat to friends and wish my retreat could have continued forever. The Level Up Retreat was a transformational pivot.

Alexis Grant

Founder, They Got Acquired

When I went looking for a business coach, I was overworked and stressed. I'd managed to bring in a lot of clients, but I didn't have the systems or people in place to service them all without losing sleep. Charlie helped me create a framework to do great work by hiring a project manager, setting expectations for my team, and developing systems so much of the company can run without me. After completing his six-month intensive, I'm now far less stressed, able to spend time on projects I enjoy, and have a clear plan for the upcoming year that includes more revenue and profit than ever before. I'd highly recommend Charlie for any small business owner, no matter where you're looking to take your company.

Eric Zimmer

Founder, The One You Feed

Working with Charlie has positively changed our business and life in ways that I couldn't have imagined before working with him. Our revenue has grown substantially, and for the first time in our business we had a highly profitable year.

Even more than that, though, is that happened during a year where we took 2 months off for travel and vacations and started working less in the business.

Equally important is that working with Charlie has helped me to feel more relaxed about where we are and more optimistic about the future. The peace of mind we have gotten from working with him is truly invaluable.

We are also a couple in life and business and Charlie has helped us navigate that more effectively.  He helps us to have hard conversations and grow together.

Each time it comes time to renew with him, I'm surprised that it's obvious that we should - our business and life is better with Charlie helping us navigate it.