Hire Charlie to Speak

“Charlie has the brains and the heart to help you map your business and take it to the next level with total integrity.” – Jennifer Louden

If your audience is ready to figure out what to do with all the information they’ve been hearing and start taking action, Charlie Gilkey is an ideal choice to speak at your event. Listeners will walk away from his presentations with at least one insight that opens up their next step, takes their business forward, and all in a way that respects where they are on their journey. Listeners don’t just feel better – they’re armed to do better.

Interested in having Charlie speak at your event? Interviewing him? Contact Angela (AT) ProductiveFlourishing (DOT) Com.


Charlie Gilkey is an in-demand trainer, speaker, and business growth advisor who helps small businesses start finishing the stuff that matters. Focusing on strategy, planning, execution, and leadership development, Charlie has worked with hundreds of business owner-executives. He has a keen understanding of what makes individuals, organizations, and the marketplace tick, and he is known for sharing those insights in accessible, actionable ways. His work is regularly featured in places like Inc.com, BNET, MSNBC, Project Domino, Under30CEO, Upmarket, Small Business MO, and Carol Roth’s Unsolicited Business Advice Blog. Charlie’s new book The Small Business Lifecycle helps small business owners grow their businesses strategically by taking the right steps at the right time and is an Amazon #1 bestseller.


Charlie prefers to tailor the content of his presentations to meet the goals and needs of the organizations hosting him. He is known for his approachable demeanor, engaging natural storytelling, and his use of interactivity with the audience. Every presentation includes original content, and he excels at synthesizing the insights previous speakers have shared into his talks. He’s particularly suited for being the last presenter since he can tie many threads into a coherent, grounding, and actionable tapestry.

Below, you’ll find a selection of keynotes adaptable to your audience and topic focus.

How to Boost the Performance of Your Team

Summary: Get great people together and give them something to do, and great work will begin to happen, right? If only it were that easy.

Better teams create better results more effectively and sustainably. Getting there is the trick.

In this talk, Charlie will present some time-proven strategies, principles, and tips for how to boost the performance of your team. Much of the work of getting people to perform happens well before the work begins, so he’ll begin there, discussing how to make plans that work, how to communicate about how the work is coming along, and how to reinforce good work habits that keep people both excited and productive.

Embracing No Man’s Land: Why Changemakers Have to Keep Going Where No One Else Is

Summary: Whether you’re an entrepreneur working at your creative edges, a CEO implementing innovative ideas, or an employee working to create positive change at work, you’re going to find inner and outer resistance. As an individual, it’s difficult to keep moving forward when you don’t see anyone else doing what you are. And that’s exactly why you have to.

Charlie proposes that place where we feel lonely and at our edges is where we have to keep pushing through so we can truly succeed. Motivating and compelling, this talk will leave your audience with a renewed sense of purpose and ready to jump the next hurdle towards reaching their finish line.

Go Big or Go Home… Or Go Deep

Summary: Is having a big personality the only way to survive in business? Opening with an engaging story his Native American grandfather passed on to him, Charlie argues that you don’t have to be an extroverted salesperson to have a great business. By choosing to take their tribe further than the average product or service, small business leaders can combine strategy and compassion to create a more holistic, engaging experience for their people.

Also known as the “Small Fire” talk, your introvert participants in particular will thank you for bringing in Charlie to reinvigorate their passion for their businesses. Because why should the charismatic talkers have all the fun?

How to Create a Productive Environment That Doesn’t Suck

Summary: Being more productive doesn’t mean more TPS reports and poorly managed information systems. In fact, you can probably create a more productive work environment just by focusing on empowering your people in the right ways.

As a logistics officer, productivity expert, and small business strategist, there isn’t much Charlie hasn’t seen and done when it comes to creating productive work environments. Charlie focuses on creating better “people machines” by focusing on the people in the machines.

In this interactive, fun, and frank talk, your audience will learn the how’s and why’s to determine what changes they can make in their organization to help their people thrive.

Upcoming Speaking Engagements

  • January 2016: “Start Finishing This Year” for Wayfinding Academy
  • April 2016: “Winning Strategies Aren’t About Ideas – They’re About Execution” for Quiet Power Strategy Summit

Past Speaking Engagements

2016 Speaking Engagements

  • January 2016: “Start Finishing: 3 Key Strategies to Simplify Your Plans, Enjoy the Process, and Do Your Best Work” for Think Better, Live Better

2015 Speaking Engagements

  • October 2015: “Start Finishing: 3 Key Strategies to Simplify Your Plans, Enjoy the Process, and Do Your Best Work” for SimpleRev
  • August 2015: “Work Smarter, Not Harder – Using Systems Thinking to Get Better Results in Your Business” for Portland Small Business Development Center
  • August 2015:  “Start Finishing: The 10 Keys to Doing Your Best Work” for CampGLP, hosted by Jonathan Fields
  • June 2015: “Strategic Customer Development” for Portland Small Business Development Center
  • May 2015: “Navigating the Stages of Business Growth” for Small Business Website Masterclass with Pia Larson
  • February 2015: “How to Prioritize and Sequence Your Strategic Goals” for Protect and Profit from Your Intellectual Property with Rachel Rodgers – CreativeLive

2014 Speaking Engagements

  • October 2014: “Implementation So You Can Make Money” for IPA Series
  • October 2014: “Work Smarter, Not Harder – Using Systems Thinking to Get Better Results in Your Business” for Portland Small Business Development Center
  • September 2014: “Strategic Customer Development” for Portland Small Business Development Center
  • June 2014: “The 8Ps for Moving from a Helping Hunch to a Sellable Service Offering” for The Good Life Project Academy
  • June 2014: “Work Smarter, Not Harder – Using Systems Thinking to Get Better Results in Your Business” for Portland Small Business Development Center
  • March 2014: “Strategic Customer Development” for Small Business Development Center

2013 Speaking Engagements

  • November 2013: “Rock the Halls: Holiday Time Management and Productivity Tips for Online Entrepreneurs” for CopyBlogger
  • October 2013: “Communication Matchmaking: Managing Communication Styles, Preferences and Technology” for Citrix
  • October 2013: “The World Is Your Marketplace” for Small Business Development Center
  • July 2103: “Marketing the Right Things At The Right Time: How You Market Depends on Where You Are” for DexOne
  • May 2013: “5 Overlooked Principles of Execution” – SOBCon
  • May 2013: “Good Communication Saves More Time Than It Takes” for Toastmasters International
  • April 2013: “Money Talks: The Real Business Benefits of Effective Communication” for Citrix
  • 2013: “Strategy Execution for Entrepreneurial Success” – GLP Immersion

2012 Speaking Engagements

  • July 2012: Panelist at the Portland DexOne Local Leadership Event
  • May 2012: “Effective Decision Making Made Easy” for SOBCon

2011 Speaking Engagements

  • October 2011: “It’s Not About What You Value, It’s About What They Value” for Molly Gordon Self-Employment Telesummit
  • September 2011: “How to Find – And Focus On – What Actually Matters In Your Business” for Casey Truffo’s Practice Building Conference
  • June 2011: “How to Embrace the No Man’s Land of Authorship” for Book Breakthrough NYC
  • June 2011: Navigating the Small Business Life Cycle – Profit Catalyst
  • May 2011: “How to Grow Your Business, One Stage and Season At A Time” for the Young Women Social Entrepreneur group in Portland, Oregon

2010 Speaking Engagements

  • October 2010: “Go Big or Go Home .. or Go Deep,” for Andrea Lee’s Wealthy Thought Leader Event
  • October 2010: “Content Creation and Management Strategies” for the Hillsboro Chamber of Commerce’s “Social Media for Sales Success” workshop

2009 Speaking Engagements

  • Jan 2009: “Project Management Within Academia,” for the University of Nebraska Draught Mitigation Team

Video Samples

Click here to view the full presentations


Liz Strauss“When Charlie Gilkey is at the microphone, you can count on information and interaction that engage, energize, and motivate while making the path forward look natural and easy. Whether it’s a private meeting, panel of experts, or a presentation, don’t miss a chance to hear Charlie sharing his expertise on business online and off.”

Liz Strauss, International Business Strategist and CEO of SOBCon

Molly GordonCharlie is one of the best people to work with I’ve ever met. He’s easy going, smart, and delivers more than he promises. As a presenter in the 2010 Self Employment Telesummit he simplified complex business choices without dumbing them down–quite a feat.

I highly recommend Charlie as a teacher, mentor, and guide.

Molly Gordon, ShaboomInc.com

Barry Moltz“Charlie Gilkey’s advice is always direct and succinct. In other words, he is always on target!”

Barry Moltz, award-winning author, speaker, and consultant, from BarryMoltz.com

Terry Starbucker St. Marie“Charlie is one of the “go-to” people in our SOBCon family, for a very good reason: he is a unique and powerful communicator, a wonderful skill which he has put to great use in front of our audience at our SOBCon event in Chicago, and will again at our upcoming event in Portland. He has an ability to cut to the core of a lesson or issue, and present it with absolute clarity and purpose, compelling people to take positive action. We are honored to have him on our SOBCon team”

Terry “Starbucker” St. Marie; writer, consultant, and co-founder of SOBCon, from TerryStarbucker.com

Charlie reached me. I can still remember his advice in a big way.

Renee Radcliffe-Wasserman
Founder of The Self-Healing Zone

Charlie’s talk at YWSE rocked. He came ready with solid advice and challenging thoughts, and really tuned in to the audience. I think everyone walked away with more clarity about where they were at in their entrepreneurial ventures and what their next steps needed to be.

Andrea Bailey, YWSE Portland Board Member

Gladys-Boutwell“Thank you Charlie Gilkey for being part of the Toastmasters District 7 Spring Conference! I appreciate you submitting all the needed information timely, provided the needed videos that streamlined our decision to have you present, and then delivered. Your ability to be our “closer” by engaging the audience, having them know that you care for them, and then providing tips in a positive and emotional way. The feedback that I have received has all be positive in your presentation. Thank you for your energy!”Gladys Monroy Boutwell, DTM ~ Toastmasters District 7 Education Coordinator 2012-2013

Want Charlie to Speak For Your Event?

If you’d like Charlie to speak or present for your event, use the form below and we’ll get in touch with you shortly. We can also send a speaking/media kit to you, upon request.

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