We caught up with the brilliant and insightful Josh Wymore a few weeks ago and have shared our conversation below.

Alright, Josh thanks for taking the time to share your stories and insights with us today. Before we get into specifics, let’s talk about success more generally. What do you think it takes to be successful?

A few years ago, I was working on my first book, Humbler Leadership, and I was stresses. I’d set a deadline for myself to finish the manuscript by the end of the year, and it was November already. As I barrelled toward the finish line, my wife and friends kept gently asking, “Why the rush? Why does it have to be done by then?”

Finally, I stopped to truly wrestle with those questions. As I did, I realized that my aspirations to write a great book quickly were making me me rush, cut corners, and stress out. I often wanted to read another article or edit another paragraph, but I didn’t feel I could because of my ambitious timeline.

Eventually, I realized that my goal wasn’t serving me well, so I decided to change it. Instead of “Finish the manuscript by December 31,” my goal became “Enjoy the process of writing a really good book.”

As soon as I did, I naturally relaxed, slowed down, and found more peace. As I committed to mastering the craft of book-writing rather than merely focusing on the end product, my focus shifted from the product I was creating to the process I was following. In a sense, the book was no longer the meaningful outcome; my joy and writing ability were. To my surprise, I also found that zeroing in on the process and simply trying to do good work every day made the book so much better.

I believe this same principle holds true for anyone who wants to be great in their field of work. You can set sales and productivity goals galore, and those short-term focal points can inspire you to focus and work hard. But if you want to build a legacy…if you want to change an industry…f you want to create a brand that will outlast you, you have to give yourself to the craft.

Serve the work, and the work will serve you.

Grow yourself, and your work will naturally improve.

When your customer has a need you can’t solve but wish you could, invest the time to go become the kind of person who can solve that problem an the next seven like it.

True winners aren’t focused on proving themselves, but improving themselves.

Great, appreciate you sharing that with us. Before we ask you to share more of your insights, can you take a moment to introduce yourself and how you got to where you are today to our readers.

I spent the first decade of my career leading (and teaching leadership) in colleges and universities. I always had a dream of writing books and giving keynotes, but that felt like something that would have to wait until my 50s.

Then one day, a former student asked me to come do some work for her company. That was the excuse I needed to form my LLC. Soon after, a few friends found out about my new venture and asked me to come train their executive team or speak at an annual event. Before I knew it, I had paying customers.

As I approached a career fork in the road, I had a choice to make. Would I keep climbing the ladder of higher education or gamble on myself? As I thought about what the best hour of my week was, it wasn’t the hour I spent in meetings or driving revenue. It was the hour I was coaching or training my team of 22 people. So then I had this crazy idea: why not do that for 40 hours a week instead of one? Worst-case scenario, I would burn through all our life savings and have to tuck my tail and get a big-boy job in two years. So I called the organizations where I was a finalist and told them I was venturing out on my own. That was six years ago.

Since then, I’ve coached or trained hundreds of high-performing, high-potential leaders across two dozen Fortune 500 and just as many countries. My passion is helping leaders Become More of who they were made to be: more focused, purposeful, peaceful, and effective. I love that leaders come to me frustrated and tired and leave inspired and holistically healthier. It’s such a privilege to partner with folks in this way.

Any fun sales or marketing stories?

For years, I was annoyed and insecure about a flaw in my sales process. When leaders was referred to me for coaching, I closed the deal almost every time. I had the same success rate for keynote requests. But whenever a CEO wanted me to train their team, I’d lose more proposals than I won. I couldn’t figure out why.

One morning, I talking to a friend of mine named Charles Carrel who is a sales consultant. As we were talking about my process, I realized my error.

Failed proposals always followed a common pattern. An executive would come to me and say, “We want some leadership development. What do you recommend?” I’d spend three or four hours writing a custom proposal for them based on the little I knew about their company, and then fire it off. The result would be crickets.

I realized I was behaving like a doctor that a guy sees for his annual physical. The guy comes in and says, “My wife said I should see a doc since I haven’t for a while,” and the doctor instantly starts issuing prescriptions. Of course that guy’s not going to fill them. He doesn’t even know why he’s there.

But if that doctor instead takes time to ask the man questions about his energy, focus, physical pain, etc., they both might realize that he has a problem that needs addressing. Then the doctor can give a tailored recommendation that the man is much more likely to follow.

I realized I needed to slow the sales process down a lot more and help the client (and me) understand the true root problem. Ironically, by ignoring the client’s request to “send them my recommendations” I would serve them better.

So over several weeks, I built an organizational health assessment that I could use with clients like this to pinpoint leadership issues and create a targeted treatment plan for them. A few days later, I pitched the tool to a prospective client, and they loved it. it worked exactly as I hoped it would and built instant credibility with their team.

After years of frustration, I had finally closed this hole in my sales process. That felt really satisfying.

What else should we know about how you took your side hustle and scaled it up into what it is today?

See the previous story.

After starting, other big milestones were obtaining my ACC and PCC coaching certifications from the International Coaching Federation (ICF), landing my first Fortune 500 and Chick-fil-A operator clients, surpassing my previous income with my new business, and publishing my first book in 2023.

Contact Info:

• Website: https://joshwymore.com
• Linkedin: https://www.linkedin.com/in/joshwymore/
• Youtube: https://www.youtube.com/channel/UCoyI1Fi1yTfNp7lnZ6pEwAw/
• Other: Buy Humbler Leadership on Amazon: https://amzn.to/41XM3G7

Image Credits

Blacklight Media