Coaching for Goal-Driven Entrepreneurs, Leaders, & Business Owners

Start finishing what matters most to you, with Charlie Gilkey and Productive Flourishing.

"Charlie has a wicked genius at catching people exactly where they are – sometimes when they don’t want him to catch them there – and coaxing them into stepping into their fullest potential and then co-creating a doable, understandable roadmap for growth. If you get a chance to work with Charlie, whether in a group or one-on-one, jump at it while you can."

Charlie’s results-centered coaching will help you sharpen your focus, improve your leadership skills, and grow your revenue.

Which best describes you?

I’m an entrepreneur, small business owner, or startup founder looking for guidance, help putting out fires, and advice on “Catch-22” decisions
I’m an executive leader who wants to provide the strong, supportive guidance my team deserves — without letting work take over my life
I'm not sure whether I'm classified as an entrepreneur or executive, or I may be somewhere in between

Coaching for Small Businesses, Microbusinesses, & Startups

If you’re working as hard as you can, but you don’t feel like you’re making real progress…

If you’re at the point where you don’t know how to take your business forward, but it can’t stay where it is…

If you’ve got ambitions for growth but no down-and-dirty, daily plan to get there…

Working with me will give you both the clarity and the motivation you need to get out of that painful limbo.

We’ll solve problems before they arise, implement systems that take the burden off your back, and systematically grow your revenue.

Click Here to See How We Can Make Your Business Work Better

"I worked with Charlie when I was desperately in need of some coaching and direction with my business, and he provided that and more. Very few people have Charlie’s talent of assessing a business holistically, analyzing potential obstacles and paving the way for success with clear, step-by-step guidelines. I also appreciate how he asks for feedback along the way to make sure everyone’s on the same page. Highly recommended!"

Coaching for Executive Leaders & Organizations

Finally feel like you’re leading your team to greatness — without leading yourself into burnout.

My executive coaching will help you develop processes, systems, and cultures to harness the collective brilliance of your employees.

In service of your goals, I and my team offer leadership coaching, process consulting, organizational development, planning facilitation, workshops, and off-sites for business teams.

Along with developing your leadership skills, we’ll figure out how to keep You, The Person, healthy, happy, and independent from You, The Leader.

Click Here to Start Building a Happier, More Productive Team

"I really can’t recommend Charlie highly enough.He has the most ridiculously firm grasp on the principles behind why businesses work or fail, but what’s most amazing is the way he’s able to turn that theoretical stuff into actionable steps that will help just about anyone.If you’re stuck, Charlie’s the guy to get you up off your ass and moving in the right direction."

Psst… Feel Like You’re Somewhere in Between “Entrepreneur” and “Executive”?

Maybe you don’t feel 100% comfortable calling yourself an executive. But the truth is that you’re facing a mix of executive challenges AND entrepreneurial challenges.

Businesses in the $1M–$10M revenue range (or with more than 100k subscribers) live in the messy middle between founder-centric and systems-centric. And that’s OK.

If you want to double or triple your business revenue without doubling or tripling the amount of time you spend chained to your desk, then let’s work together to find a sustainable way forward.

Click Here to Get Through the Growing Pains

Why Work With Charlie? (That's me.)

Business coaches often get a bad rap because they push cookie-cutter strategies that don’t work for everyone. I like cookies, but I like tailoring our work to your unique needs much better.

When you coach with me, you’ll have an edge over your competition. We co-create individualized strategies, plans, and innovations that push you to the top of your industry.

Along with making custom blueprints to take you from where you are to where you should be, I partner with you to help you actually implement, adjust, and optimize our work into your business.

From there, it’s a matter of methodically tackling the next-highest-leverage opportunities or core strategic challenges, ratcheting up our level of success with each completed project.

A few of my bona fides, in case you need ‘em:

I’ve worked with hundreds of founders, leaders, and entrepreneurs to build businesses that work better — for them, their teammates, their customers, and their ecosystems.
I also wrote a best-selling book that shows how to navigate the different life cycles of business growth.
I’ve given dozens of presentations to business owners in a variety of settings, and shared strategies, methods, and techniques for making better businesses.
I’m the go-to strategic coach for thought leaders who want to amplify their business, grow their reach, and build thriving teams.
My no-bullshit coaching is backed up by my experience. I currently run Productive Flourishing, a multi-six-figure business with 5 full-time employees and 5 contractors.

If you know you want someone to help you figure out the way forward and achieve your goals faster, get in touch with me at one of the links above or at: charlie (at) productiveflourishing.com