What It’s Like to Hire a Speaking Coach: Discovering the Power of Spontaneous Self-Expression

Around the time my first book Building a Second Brain came out in June 2022, I started looking for a speaking coach.

I had just delivered my first keynote to a large audience at World Domination Summit, followed soon thereafter by my Google Talk. These experiences had been not only fantastic promotional opportunities but fulfilling and meaningful for me personally as well.

There is nothing quite like standing on stage and delivering a message you deeply believe in to an enthusiastic, roaring crowd.

At the same time, I could see clearly that “winging it” wasn’t a sustainable strategy for future speaking gigs. I’d been lucky to be offered a couple of valuable opportunities, but I wanted to start pursuing speaking more purposefully, as a skill and a craft that could serve me for decades.

I always like to start new projects by listing my intentions, and this time was no different. I decided I had six of them:

1. To build a world-class speaking business based on my BASB message
2. To use speaking to promote sales of both my book and our course
3. To connect with people on a human level and inspire them to greatness
4. To generate a new source of revenue for the business
5. To connect with like-minded thought leaders and learn from them
6. To master all the major elements of speaking

In other words, I wanted to use my new book as a springboard to launch a full-fledged speaking career, both to grow the business and for personal enrichment.

After interviewing several candidates, I decided to work with Michael Gendler, co-founder of Ultraspeaking. I liked his attitude and philosophy toward speaking, admired the education business he’d built around that philosophy, and the fact that he lived nearby in Los Angeles was icing on the cake.

Here’s what I learned and how I changed as a result of that collaboration.

Speaking as self-expression

I came in hot and heavy myopically focused on learning how to book corporate keynotes, nail big speeches, and maximize my profitability per hour. Like any good coach usually does, Michael quickly pumped the brakes and started asking me some basic questions about what I truly wanted.

I’ve often said in the past that the main job of a consultant is to repeatedly ask “So what are you really trying to accomplish here?” since much of the time we tend to be deep in the weeds on one narrow pursuit.

This turned out to be a fruitful question because depending on what I was trying to accomplish, there were usually far better ways of accomplishing a given goal. Looking at my list of six intentions above:

• If my goal was to promote sales of my book and course, it would be far more efficient to create online content that serves that purpose day and night, rather than flying to far-flung locations and talking to small groups of people.
• If my goal was to connect with people and inspire them, I could do that much more easily via local meetups, doing my own coaching, or simply hosting workshops on Zoom.
• If my goal was to grow the business and increase revenue, there are many other ways of doing that that don’t require trading my time for money.
• If my goal was to connect with other thought leaders, grabbing coffee with them is probably more effective than speaking on stages.

This exercise revealed something I’ve often noticed about setting intentions: if you have too many of them, no single one is important enough, which means none of them end up being fulfilled.

The intention that couldn’t be fulfilled any other way, and that stood apart, was to master all the elements of speaking. But that isn’t an end in itself. Michael and I spent a good amount of time digging into the root of that desire. The answer we arrived at was obvious as much as it was surprising: self-expression.

Michael’s philosophy, as embodied in the Ultraspeaking courses, is that speaking in public isn’t just about delivering corporate keynotes. It’s about self-expression, a much deeper and broader need that everyone can benefit from, whether it involves speaking up in a meeting of three people, communicating confidently over a group dinner, or simply being able to spontaneously share what you’re feeling in a conversation with one other person.

Ironically, self-expression is also at the root of my work. The reason I believe that curating and organizing and synthesizing information is worth doing is because of what it allows you to express: a message, a story, a cause, an idea. We came full circle and realized that my desire to improve at speaking was rooted in the same core desire that drives all my work: to communicate and connect with people more deeply and authentically.

With this clarified, much simpler intention in mind, we created an action plan with six main elements:

1. How to make public speaking an opportunity for me to become an amplified version of myself
2. How to bring playfulness, silliness, and humor into my speaking
3. How to make my speaking more variable and dynamic
4. How to speak more spontaneously, with minimal notes or preparation
5. How to structure prepared speeches for larger, more formal audiences
6. How to identify the main points of my message, and illustrate them with personal stories

My default approach to speaking is to be overly prepared, which tends to make me too rigid, caught up in my head, and obsessed with hitting every single point. Our action plan was designed to make the whole experience much more spontaneous, and thereby both reduce the burden of preparing my talks while also allowing me to connect with my audience as a human being.

Identifying my main ideas

We met for each session in the studio at my house, and in our second meeting, we began to identify the main messages that I wanted to communicate.

You might think that I already knew exactly what my message was, but the problem with being immersed in a subject every day is that it’s almost impossible to avoid losing the forest for the trees. The idea of a “Second Brain” is so expansive and multi-faceted that I could potentially address any one of a dozen different aspects of it.

We did a live brainstorming session, with Michael repeatedly asking me questions and prompting me to expand on certain points while he took notes. The result was a fascinating brain dump of ideas that could serve as takeaways from any talk I gave. Here is a page from Michael’s notes, which he shared with me afterward: