Keynote speaker

Keynotes for a room that’s anxious about AI.

Most AI talks add to the dread: more tools, more urgency, more ways to fall behind. Mine go the other way: why this feels so existential, and how to rebuild who you are at work on your ability to feel and create, not just your ability to think. Funny, personal, a little confronting, and built around your room.

  • Inc. Top 100 Leadership Speaker
  • Harvard Business Review
  • Author of Good Authority
  • 25 years advising leaders

“Jonathan delivered exactly what our conference needed — a speaker who could challenge assumptions while inspiring action.”

Meera Oliva, CMO at Candidly

Audiences include TikTok, Amazon, Southwest Airlines, Okta, Strava, Panasonic Energy, McKesson, Sherwin-Williams, and ZipRecruiter.

What I talk about

The four I give most.

The first is the one everyone’s asking for right now; the others are what it opens up. These are starting points. Every one of them gets rebuilt around what your people are actually dealing with, after we talk.

AI: The Final Boss of Human Transformation

Most of us built our identity on how well we think. Now a machine thinks too. A funny, personal and slightly unhinged trip from the crib to the org chart, about why AI feels so existential and why this moment might be the best thing that ever happened to you.

Best for: Conferences, culture and future-of-work events, technology leadership

The room leaves with

  • Why resistance to AI is usually about identity, not stubbornness, and what to do about it
  • A ten-minute reflection exercise to run with your own team the next morning
  • Why the human work gets more valuable as the machine takes on the rest

Becoming Who You Actually Are

The conversations you avoid become the shape of your life. This one is about the ones that don’t come with a job title — with your family, your closest friend, and the version of yourself you keep postponing.

Best for: Wellness and lifestyle gatherings, retreats, mixed-audience conferences

The room leaves with

  • Why the conversations you keep replaying are the ones telling you who you are
  • How to say the true thing without burning down the relationship
  • Boundaries as an act of leaning in — not a way of staying out

The Accountability Dial

The five-stage practice that changes how leaders handle the conversation they’ve been avoiding.

Best for: Leadership summits, manager cohorts, all-hands, workshop settings

The room leaves with

  • A shared language for feedback that outlasts the event
  • The five stages, in order, and when to move between them
  • A script for the hardest conversation on Monday’s calendar

Building Accountability Cultures

Why most culture initiatives fade, and what to build instead of another poster in the hallway.

Best for: People and HR leadership summits, culture teams

The room leaves with

  • Why values statements don’t change behavior
  • Accountability as infrastructure, not aspiration
  • The first three things to change when you get back

How it usually looks

Virtual, offsite, or keynote.

Every one starts with a call so I understand the room, and ends with something people can use on Monday. What it costs is a conversation, not a page; ask and I’ll tell you plainly.

  • Virtual

    Virtual session

    90 minutes

    An interactive session over Zoom or Teams for a leadership team or a full all-hands. No travel, same conversation.

  • In person

    Leadership offsite

    Half a day, up to about a hundred people

    A working session for an executive team. People don’t just hear the method — they practice it on the conversation they’ve been avoiding.

  • Conference

    Keynote

    45 to 60 minutes

    Built for the room after a design session with you. Copies of the book for the audience are usually part of it.

Afterwards

“I saw many heads bobbing in agreement as Jonathan spoke. Attendees were snapping photos of the slides and taking notes furiously. Lots of requests for copies of the recording.”

Bridget L. Portier · University of Houston

On The Accountability Dial

“The most valuable takeaway was learning how to approach and navigate uncomfortable conversations.”

Program participant · Voltage Park Leadership Program

Voltage Park put its CEO and front-line managers in one room for an afternoon and left with shared language for the conversations they had been avoiding.

What happened

What happens next

  1. 01

    Send the details

    Event, approximate date, audience. Takes about two minutes and there’s no obligation.

  2. 02

    Discovery call

    Thirty minutes to understand the room, the moment your organization is in, and whether this is the right fit.

  3. 03

    Built for your context

    The talk gets designed around what your leaders are actually dealing with. Never a template off the shelf.

Jonathan Raymond, headshot

About the speaker

Jonathan Raymond

Jonathan Raymond has spent 25 years helping leaders close the gap between knowing what great leadership looks like and actually doing it. He is the author of Good Authority: How to Become the Leader Your Team Is Waiting For, which Seth Godin called “a modern classic.”

Jonathan created The Accountability Dial, a five-stage framework used by thousands of managers worldwide to hold people accountable with compassion. His work has been featured in Harvard Business Review and he was named one of Inc. Magazine’s Top 100 Leadership Speakers.

As the former CEO of EMyth, Jonathan led a multi-year transformation of a global coaching brand, learning firsthand that the most expensive gap in business is the one between knowing what to say and actually saying it. He spent the next nine years at Refound, the coaching and consulting firm he founded, before spinning out Ren, where he is CEO — an AI coach that helps people find the words for the conversations they have been avoiding.

Bios and headshots

Before you ask

What organizers usually want to know

How far in advance should we book?
For a conference keynote, six months or more is typical — those calendars fill early, and the pre-conference design session works best with real runway. Leadership offsites usually come together faster. Virtual sessions are the most flexible and can sometimes happen within a few weeks. If your date is sooner than that, send it anyway. Sometimes it works, and I'd rather tell you than have you assume it's a no.
How much do you customize the talk?
Every engagement starts with a discovery call, and what I learn there changes the talk. The frameworks stay the same — that's the part that's been tested on a hundred thousand managers — but the examples, the language, and the specific problems I name come from your organization. I'm listening for what your leaders are actually dealing with on a Tuesday. It's never a template pulled off the shelf.
How many people can attend?
Conference keynotes have no practical ceiling — I've spoken to rooms of every size. Leadership offsites work well anywhere from a single executive team up to about a hundred people; the larger the room, the more the format shifts from practice to demonstration, which we'd talk through beforehand. Virtual sessions work for a leadership team or a full all-hands, whatever the headcount.
Are copies of Good Authority included?
With the conference keynote, yes — I like the room to leave with the book, so copies for the audience are usually part of it. For offsites and virtual sessions, say the word and I'll sort out a bundle for the team.
Do you travel internationally?
Sometimes. I'm selective about international travel, so it's worth a conversation rather than a yes or no — tell me the event and the date and I'll be straight with you about whether it works. Travel and lodging are billed at cost. When travel doesn't make sense, a virtual session covers a lot of the same ground.
Can we record the session?
Yes, for internal use — replaying it for people who couldn't attend, or keeping it in your leadership library. Public distribution is a separate conversation. Just flag that you'd like to record when we're setting things up so I can plan for it.
How do I know if you're the right fit for our room?
Ask me and I'll tell you honestly. My approach is practical and a little confronting — it treats leadership as personal growth work, which means the room does some looking in the mirror. If your audience is ready for that, it lands hard and lasts. If you're looking for a purely motivational hour that leaves everyone feeling good and changes nothing on Monday, I'm the wrong choice, and I'll say so rather than take the booking.

Check availability

Tell me about the room.

No obligation. I’ll tell you honestly if I’m not the right fit for it.

Putting me on a program? Bios and headshots are here.