How to Pitch Like an Executive Pro

Better pitches don’t win the best stages; trust does. Bobbie Carlton breaks down how speakers move from chasing gigs to getting invited back again and again.

February 3, 2026

Most people chase speaking gigs like they’re applying for jobs: write a pitch, hit send, follow up until someone says yes.

Bobbie Carlton’s take is sharper: the real upgrade isn’t a better pitch, it’s becoming invite-able. Invitations are a different economy. They signal trust, reduce perceived risk for organizers, and compound into more stages, better stages, and eventually paid stages.

In 2017, Bobbie applied cold to speak at the Women in Tech Summit in Philadelphia. She was placed in a small room. Then the room overflowed—extra chairs, people sitting on the floor, a line at the back. The organizer peeked in, and Carlton thought, Yep, I’m getting invited back. She did—15 times over seven years, across multiple cities, with a different talk each year. That’s not luck. That’s proof she solved a real problem, delivered reliably, and was easy to rebook.

The following is her advice to stop pitching, and start getting invited. 

Invitations aren’t transactions

Pitching is transactional: you apply, you negotiate, you hope. An invitation means you’re a trusted partner, often via referral. That leads to a question most speakers avoid: Who would confidently recommend you? Not “who likes you,” but who would put their name on you.

Event organizers are not shopping for brilliance. They’re shopping for outcomes and no drama. They want someone who solves a recognized problem, has a clear point of view, and gives the audience something usable. But they want something even more: low risk. No surprises. No last-minute cancellations. No neediness. A speaker who makes their life easier.

Don’t confuse “visibility” with value

Carlton is practical about compensation. Yes, everyone wants a check, and too many events have no speaker budget. She offers a decision framework:

  1. Your happy price (paid fairly for the value and work).
  2. An audition audience (people who can pay your happy price later).
  3. A valuable trade (prestige stage, pro video/photos, credibility, access, customers).

 

Speaking at the UN is her example: she didn’t get paid, but she earned permanent leverage “I spoke at the United Nations,” which reduces risk for future bookers. Still, she warns against pretending exposure pays bills. (Lesson learned when she once got paid in car wash coupons.)

The three tests of “invite-ability”

Carlton’s most useful contribution is a set of filters for your “big idea” because vague, buzzwordy talks don’t get referred.

1) The Budgeted Problem Test
Is the problem important enough that people assign money to it? If your talk helps save money, make money, or reduce a visible risk, it’s premium. If nobody is spending on it, it’s “nice,” not invite-worthy.

2) The Unlike Others Test
Could ten other competent speakers deliver basically the same talk? If yes, you’re a commodity. Commodities get swapped, not invited. She calls out recycled “Atomic Habits”-style talks and generic “power of storytelling” sessions—hard to remember, hard to refer.

3) The Fluffify Test
Can someone else explain what you do in one sentence without buzzwords? If they can’t, they can’t recommend you, and committees can’t sell you internally. Titles like “Inspiring Change Through Authentic Leadership” may sound important, but they say very little, and vague messaging doesn’t secure a budget.

Your tools speak when you aren’t in the room

Most speaker decisions happen without you present, so your materials have to do executive-level work on your behalf: bio, speaker one-sheet, and especially a sizzle reel. A good sizzle reel is 2.5–3.5 minutes and has a story arc, not random clips. Its job is simple: de-risk you.

Carlton ties this to gravitas: precision, consistency, authenticity. Not overacting. Not stuffing your bio with every credential. The executive signal is restraint and clarity.

The fastest way to lose: be annoying

When asked what “annoying” looks like, her examples aren’t dramatic, they’re irrelevant and sloppy: weird attention grabs (“Do you like whiskey?”), AI pitches that get basic facts wrong, burying organizers in unnecessary information. Persistence isn’t presence. Presence is following up with value, not “just checking in.”

How you get discovered

Discovery isn’t magic. It’s repetition plus point of view: write, podcast, publish, comment consistently on your topic so your name becomes associated with it. And here’s the real definition of a “big idea”: it often involves respectful disagreement with the herd, a perspective that reveals what everyone else is missing. That’s what sticks.

If you want to pitch like an executive, stop acting like speaking is a numbers game. It’s a trust game.

Be the lowest-risk, highest-upside name on the short list:

  • solve a budgeted problem,
  • be unmistakably you,
  • make your idea easy to repeat,
  • prove you can deliver,
  • and be easy to work with.

 

Do that, and pitching becomes optional because the right rooms start pulling you in.

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