Productive Flourishing

Coaching and Consulting for

Individuals, Teams, and Organizations

Turning visions, missions, and values into action is hard.

I help people like you build high-performing, high-belonging teams who are proud of the great work they’re doing in the world.

I intentionally work across sectors – for-profit, non-profit, military, academic, and religious – because I address universal team challenges. The insights from one sector transfer to others, making the process more transformative for all my clients.

🆕 Looking for 1:1 productivity coaching? Momentum Skills Coaching may be right for you. Click here to learn more.

Would You Like to Know More?

I'd love to see how I can help you. Please fill out the form below and we'll take the next steps about what's right for you.

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Here are some ways we might work together:

Executive Coaching
My executive coaching and development style rapidly unlocks a leader’s unique potential to lead their team. I’m especially adept at working with women, BIPOC, and neuro-diverse leaders who’ve tried to play by the rules, seen that cookie-cutter approaches don't work for them, and are ready to create a better new game.

Business coaching for scaleup founders and CEOs
At a certain point, how fast a business can scale depends on how quickly the founder and leadership team can evolve. I work with founders or CEOs who are balancing implementing enough structure to keep the team growing but not so much that it crushes the team’s entrepreneurial spirit.

Team strategy execution coaching
Whether it’s figuring out how to implement OKRs, converting the year’s strategic priorities into an actual roadmap, or creating special-purpose teams to solve strategic issues, I help teams and leaders convert the big idea or challenge into the why, who, what, when, and how to make them happen.

Strategic retreat facilitation
A great strategy retreat starts months before the day it happens, but it doesn’t end there. I work with teams to design retreats that build alignment, belonging, and clarity on the day(s) of the retreat that then turn into strategic guide rails that keep the team driving forward together in the quarters that follow it.

Why Work With Charlie?

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 business owners and leaders 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.

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How to See If We're a Fit

I would love to learn more about your needs. Our team is (intentionally) small, but mighty, and we have worked with some of the biggest names in business. 

Would You Like to Know More?

I'd love to see how I can help you. Please fill out the form below and we'll take the next steps about what's right for you.

  • This field is for validation purposes and should be left unchanged.

"If you are looking for some awesome, knowledgeable people to work with, these are the guys I highly recommend. Their friendliness and result-driven approach is what I love about them."

Gabrielle Javier-Cerulli

“Charlie stands out for me among other productivity coaches because his approach is so thoughtful and holistic. He doesn’t just teach the ‘how’ of flourishing as a creative person, he works hard on getting us to think about the why. His interviews with other [creators] and his own story provide reassurance that it’s possible to follow my vision despite all the obstacles life throws at me. The Monthly Momentum Calls he offers as a free resource have given me a chance to ask questions and apply what I’m learning to my own situation. Thanks for all the help, Charlie!”

Jonathan Mead

“Charlie brings a combination of military calm, big-hearted compassion, and generous vulnerability to every audience he speaks to. After his workshop I was left with the rare feeling of both a deep self-acceptance for where I'm currently at, AND a fire in my belly to get in-action around my big life goals. And since Charlie also gave us incredibly practical advice and frameworks to go about getting those goals accomplished, I'm actually using the things I learned in his workshop to build out my business. Many of the business leaders I most look up to, call Charlie their coach, and there's a good reason for that. Charlie knows what it takes to get results, and to move people to WANT to take action, and he does that effortlessly whether he's working with one-on-one coaching clients or speaking to a room of thousands. Charlie is a caring, funny, and results-producing speaker and he would be an incredible addition to any event.”

Harmony Eichsteadt

“Charlie has been instrumental in the creation of every product IttyBiz sells. He made it possible for me to launch my first information product, and has been more and more helpful with every additional avenue we have pursued. I can honestly say I would still be trading time for money as a primary business model if it weren't for Charlie Gilkey.”

Naomi Dunford

“I love that Charlie Gilkey's company is called Productive Flourishing. It's the perfect encapsulation of who he is: a deep thinker who provides thoughtful, strategic counsel on the optimal dynamics of running a small business (productivity), while keeping in view the ultimate aim of human beings (to flourish). When thinking through a challenge, he offers lucid general frameworks for gaining clarity and prioritizing, and he's also unusually adept at adapting those frameworks to a particular business (and human) context – and at identifying what your *next* challenge might be. Learn from Charlie, and you'll sharpen your future vision.”

Mytili Jagannathan

“One should have high expectations for a business coach who is a former military logistics officer. Thankfully, Charlie exceeds my expectations every time I meet with him. His insight is sharp and focused, delivered in a caring manner. There's not a single part of business that Charlie doesn't have experience with, and I am thankful for his support in helping me streamline and optimize my business processes!”

Andy Haynes