On Building a Keynote Speaker Career, Finding Your Voice, and Unlocking Performance at the Highest Level
I’ve been working with keynote speakers for a while now, and one of the things that’s really impressed me is their drive to make an impact. Is it important to build the business side? Absolutely. But the thing driving my clients hasn’t been primarily the revenue. It’s the impact they can make by getting their message out to a room/auditorium/stadium full of people.
So, I wanted to dive deeper.
I recently had the opportunity to interview Henna Pryor, CSP about her journey into keynote speaking, the frameworks behind her work, and what it really takes to build a successful speaking career. She and I have been connected for a while, have a mutual connection (thanks Jess Brady!), and I’ve been super inspired by her work.
Here’s what she shared:
1. What originally pulled you into keynote speaking, and when did you realize it could become a real part of your career?
So I think like many people in my industry, I never intended to be a keynote speaker. I didn’t even know that was an option.
I had Pakistani parents for whom it was, you know, doctor, lawyer, engineer. Those were the choices on the menu or at least the preferred choices on the menu.
But after a Big Four accounting starting career for a couple of years, I pivoted into executive search and staffing. I was very successful at that for about a decade and a half, but I had outgrown it.
What was interesting is a lot of my clients would say to me, “Oh, Henna, you’re our staffing partner or our search partner, but we really should pay you for all the executive coaching you do for us.”
So when I left my staffing career, I actually went in pursuit of executive coaching. I got my certification and thought I would build out an executive coaching practice.
More and more, my executive coaching clients would say, “Henna, can you come do this with my team?” Then it became larger departmental meetings, company off-sites, and eventually main stage keynotes.
It was very organic. And the bigger the room became, I realized that was the part that lit me up. Time flew. I had some natural talent in it that, with training, could be a real forte.
I realized how much fun I was having, and I invested deeply in it to make it the primary part of my career.
2. Was there a specific turning point that accelerated your speaking career?
There were hundreds of tiny micro-moments that accelerated it, but the biggest one was my decision to claim that as my primary career.
I called myself a speaker before I felt ready. I changed my title on LinkedIn to “Keynote Speaker” as soon as I made the decision.
Once I decided that being a professional speaker was what I wanted to do, I called myself that everywhere publicly.
Then I backed it up with investments: expensive speaking training, coaches, and ongoing development.
Naming myself as that before I was ready, and putting my money where my mouth was; those two things accelerated my speaking career more than anything else.
3. What core problem are you most passionate about helping audiences solve?
I work with high achievers who have already read all the books and know what to do.
They don’t struggle with optimism or know-how. What they struggle with is identifying the hidden corners where their performance is being held back.
They don’t have someone who can name those blind spots and productively call them out so they can get to the next level.
My audience is already successful, but they’ve plateaued because of hidden obstacles or blind spots.
That’s what I’m known for: helping them identify and move past those blockers through mental and social fitness.
4. What’s the core framework behind your work?
I don’t have one core framework; and I refuse to have one.
I have core techniques that underpin everything I teach, centered around identifying hidden blockers.
Each topic has its own framework:
- For Good Awkward, it’s embracing discomfort and navigating the “cringe chasm”
- For Influence, I teach three specific frictions
- For The Signal Gap, I teach eight layers of congruence that affect believability
The unifying principle is illuminating and naming the hidden blockers that stand in the way of outcomes.
I develop these ideas by constantly learning. I’m obsessed with research. I read widely (not just business books) and I think some of my best ideas come from combining unexpected sources.
5. What transformation do you want audiences to walk away with?
An event planner said this best:
“Henna, you productively call people out and make them happy that you did.”
I want people to realize: “Oh shoot, I’m my own obstacle.”
But instead of feeling defeated, they feel energized; because now they have awareness and tools to do something about it.
That moment where people have that uncomfortable laugh and realize, “That’s me”… that’s where transformation happens.
6. How do speaking opportunities typically come your way?
All of the above. Referrals, agencies, and relationships.
But I’m primarily a direct business.
Most of my work comes from:
- Word-of-mouth
- Referrals
- Inbound from content
- Stage-side leads
Stage-side leads mean that after I speak, someone comes up and says, “I need you for this organization.”
I aim for every keynote to generate the next three.
At the end of the day, it’s a relationships business.
7. How has speaking influenced your other ventures?
Significantly.
Speaking drives:
- Book sales (especially bulk purchases)
- Awareness of my work
- Growth of courses and content
The stage is a trust accelerator. People feel like they know you after seeing you speak.
That trust feeds everything: coaching, books, courses, and more.
Speaking creates a multiplier effect across all parts of the business.
8. What are lessons you wish you learned earlier?
Run your own race.
It’s easy to compare yourself to other speakers, but everyone has different strengths and paths.
Over time, you develop self-trust and find your own lane.
Also, shiny object syndrome is real.
You can’t do everything. You have to be intentional about your time and energy, especially balancing work and life.
9. What advice would you give to emerging speakers?
You may have valuable ideas, but if they’re the same as everyone else’s, it’s hard to stand out.
You need to develop your own point of view and your own voice.
That’s hard to replicate.
Also, don’t rely too heavily on AI. Go live life. Learn. Expand your perspective.
And remember:
You see other speakers’ highlight reels, not the behind-the-scenes work.
It takes what it takes.
The speakers you admire are working incredibly hard behind the scenes.
10. What are you most excited about in the next chapter of your speaking journey?
My new book is going to be so good.
It’s called The Signal Gap: How to Boost Believability and Influence in the Age of Doubt.
The research and stories are fresh, and people are going to say, “I haven’t heard it like this before.”
I’m incredibly excited to bring it to the masses.
Bonus: What does it mean to you to influence people from a stage?
What a blessing. What a gift.
I can’t believe this is my job.
To pour into people at scale (even five people, let alone 5,000) is incredible.
Most speakers don’t do this to hear themselves talk. They want to serve and improve people’s outcomes.
I will never take that for granted.
Thank you SO much to Henna Pryor for taking the time to share her insights with us! If you’re not already, go follow her to learn from her amazing content or to book her for a speaking engagement! https://pryoritygroup.com/
Also, go buy a copy of her book! https://amzn.to/4cDC5Ro
And pre-order her NEW book, The Signal Gap! https://amzn.to/4ttkD9x
Daniel Wakefield is a photographer, entrepreneur, and author. He is the founder of Top-Tier Headshots and the Accelerate Coaching Group, initiatives through which he helps professionals and creatives elevate their brand and business.
