01
Keynote
A 30–60 minute talk drawn from the book and the twenty years of story behind it. Not a pep talk. Your people leave with a question they're still carrying a month later.
Speaking & Workshops
Ideas that move audiences to think and act.
A clear voice with a practical message: better questions build better lives, and better organizations. Keynotes and conversations on reinvention, leadership, and the courage to choose your life on purpose.
For leadership teams, organizations navigating change, and people facing a meaningful next chapter.
Inquire about bookingWhere
In person, anywhere
Virtual
Available worldwide
Audience
Flexible to the room
Response
Within one to two days
What to expect
The format changes. The questions don't.
Whether it's a ballroom keynote or a twelve-person offsite, David brings the same thing: honest questions that move a room from what's easy to what's true.
02
Fireside & Q&A
A moderated conversation with nothing rehearsed. Candid and unscripted, built around whatever your people are brave enough to ask.
03
Workshop & Offsite
A working session on the question ladder. Teams put words to the questions they've been avoiding, and leave with a plan for answering them.
Speaker Overview
Bring the right question to your room.
Planning an event should be the easy part. Everything you need to book David with confidence (the story, the signature talks, the formats, and how to reach him) lives on one page.
Topics
Starting over at 40+ in the age of AI. AI accelerates execution, but it doesn't validate the premise. Anyone's agent can read every job board, so the question is no longer "Are you hiring?" It's "What problem keeps coming up that nobody owns?" Questions that uncover the opportunities that never get posted.
Inquire about booking →The keynote behind the book. Most people don't blow up their lives; they wake up in one they never chose. A story-driven case for trading default momentum for a life you pick on purpose.
Inquire about booking →For founders, leaders, and teams. Every team is sprinting. The risk is sprinting at the wrong problem. Using the question ladder, teams put words to what they're actually solving, kill the work that doesn't matter, and make the decisions that move everything.
Inquire about booking →
Start a conversation
Planning an event or an offsite?
Tell me a little about it and I'll be in touch within one to two days. Prefer email? Write directly to rollo@hellorollo.com.