Viable and Fun: An Interview with Speaking Agent Charles Yao

"The foundation of your talk is always going to be your work, your observations, your conclusions. But that real-time connection with other human in a room—that matters just as much."

It’s me, Seneca.

After I posted the Agenting 101 Discussion that Meredith and I did at McNally, a reader commented that they would love to see the master class version of agenting content. I’d categorize my interview with speakers’ agent Charles Yao, Executive Vice President and DIrector of Speakers, at the Lavin Agency as just that. Knowing about speakers’ agents isn’t like knowing about query letters; you likely wouldn’t encounter the world of professional speaking until you are a bit more professionalized as a writer. I only know about Charles because we share a bunch of clients (namely, Nikole Hannah-Jones, Clint Smith and Adam Harris), and I’ve seen up close the helpful role public speaking plays in expanding their reach as authors. I thought to interview him because my own clients ask me about paid speaking work all the time, in part because my job is to answer such questions and in part because such info is hard to find. The role of speaking agents is even more opaque than that of literary agents. I encounter many up and coming writers who think they need a speakers’ agent long before they actually do. Charles explains at which stage in your career you should think about calling in a professional speakers’ agent as well as what you can do to help your own nascent career as a speaker.

In our chat below, Charles reveals at which point in your career you should think about calling in a professional speakers’ agent as well as what you can to help your own nascent career as a speaker before you’re at that stage. Read on to learn:

• What a speaking agent does & whether or not you need one

• What kind of organizations book speaking agents

• And what kind of topics they’re typically interested in

• How to boost your own visibility as a potential author/speaker

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You have a very particular and not widely understood job. How did you come to do it?

After university, I had a freelance gig designing DVD covers for a small Canadian documentary company, which is the most esoteric, specific thing, I know. Someone who worked there left to take a job at Lavin. She told me it was this think-tank-like place where a lot of authors and interesting people passed through. She said it was “totally my jam.” Well, that's an anachronism—I don't know if people talked like that back then! A few months later, I interviewed and got in!

One of my first jobs at Lavin was dubbing VHS cassettes of speeches and sending them to clients who asked for video evidence that a speaker could do a good job. The “physical mailing” part no longer exists, and is sort of funny to think about now, but the underlying part—having a good speaking video—has only gotten more important. Which I’m sure we’ll get to!

So how did you go from one rung up from the mailroom to what you do now?

Alia, It was one rung down. I did all the stuff people needed done, the random stuff. But that’s an amazing way to learn. One day, still early on, I told David Lavin, the head of the agency, that we should sign this pop culture critic whose books I liked. I’d seen him speak and he was hilarious. An unsolicited suggestion! I give David a lot of credit. He said, “You’re clearly enthusiastic. Find his contact and we'll go from there.” So I cold called the writer at the magazine he worked for, and that was my first signing! I wasn’t yet Director of Speakers, my current role, and I went on to do marketing writing, and then ran the entire department, but that was the seed, the start of what I do now.

So what makes you think a speaker will have an audience?

Well, for this speaker, it was belief and fandom and knowing that, at least on campuses, there’d be a market since his books were popular with a lot of university aged people.

In general, we decide on speakers by asking two questions: First, do we personally find this person, and their ideas, interesting? Like, do we want to spend time collaborating with them for months and years on end? And second, and never independent from the first question, is there actually a market for this speaker—places we could consistently book them? The second thing, the latter thing, is what makes it a viable business. The first thing is what makes it a fun business.

That's the best articulation I've heard of what agenting is—or at least to how I agent, which is always trying to balance those two prerogatives. I’m constantly having to choose between any number of writers, so I always ask myself, “Do I want to be stuck working on this subject, with this person, for years and years?” I can’t think purely in terms of personal interest though, and neither can you. Could you explain why having a market is so important and how you determine if there is one?

Good question! The market is the basis of your relationship. Otherwise, you would just be friends or colleagues! For the most part, our speakers are relatively well known—not celebrity-famous but super respected —and there’s an easy-to-see connection between their work and a potential speaking market. Sometimes, though, we do take on someone interesting, or someone early in their career, even when we know there's a limited market—but, end of day, there does have to be some market.

There are a handful of evergreen speaking markets and topics. It’s like how, in novels and films, there are only seven basic plots: revenge, rags-to-riches, etc. The timeless speaking topics include creativity, resilience, purpose, organizational culture and leadership, community-building, societal change, understanding new technologies, and a few others. If a speaker can bring something genuinely new to these existing conversations—novel takes on age-old problems—that’s the first step in sussing out whether they fit into any kind of a market.

So what does a speaker's agent do? What does pitching look like for you and who are you pitching?

A speaking agent, in some ways, is like a multiplication machine. We contact as many people as possible who would theoretically want to book our speakers. We’re proselytizing on their behalf in a way that, frankly, they would not have the time or the inclination or the insider expertise to do themselves.

You learn as much as you can about each speaker, every facet of how their work might suit an organization, a school, a not-for-profit—all the counterintuitive ways they might fit, as well as all the obvious, low-hanging-fruit ways.

It’s not necessarily that we call clients and say, “You should book Clint Smith!” You don't have to start with a speaker’s name. It’s a holistic conversation. It isn't, “Hey, we signed Speaker A, you should book Speaker A.” That will end with a dial tone! It’s more like, “What are the themes of your event?” Or “What problem are you trying to solve at your organization? What are the concerns? What are the victories you want to celebrate?” From there, you can pitch. But the pitching comes after the listening.

That’s the client-facing side, the proactive sales side. There’s also the speaker relationship side: being a thoughtful manager, an advice-dispenser, a market-interpreter, a person to bounce ideas off of, someone who will watch a recent video and tell a speaker, candidly, to maybe use fewer slides next time, ha!

It’s a weird and potentially crazy-lucrative industry, opaque by design almost. It’s not something that many speakers knew was even a thing before they got a cold-call from us or before they started getting requests! We were talking before the interview officially started about films like American Fiction or Soderberg’s Let Them All Talk—films that have characters who work as literary agents. Well, there’s no equivalent depiction of speaking agents or the industry in popular culture. Probably for the best! But all to say, a lot of the agent’s job is explaining the ins and outs as we go, being a steady guide, since there’s not a lot of public knowledge.

What kind of organizations are you working with? What is the range of places that you have speakers speak to?

The glib answer is: a client is literally any group that needs a speaker at that moment. The less glib answer is that there are four or five distinct-ish markets. The corporate market. The not-for-profits and associations market. Universities and colleges. The education sector, which is principals and superintendents and teacher groups. And then there's the soft-seat theater events where they put the speaker’s name on the marquee out front: “An evening with...” There are other types of organizations – again, literally any group that wants a speaker is a client – but those are the Mount Rushmore of Speaking Groups.

Corporate speaking is the biggest market. There, the main questions are: What can the speaker tell us that will help us be better at what we do, be more engaged, spark creativity, organize teams, make room for opposing viewpoints, find purpose, grow. What’s new in leadership? In innovation? What are the important technological, economic, or societal trends and how do they impact us?”

With universities, one question is, What do the people who book speakers think it would be important for a young person to hear about? What might help them be a better student while here and a better citizen after they graduate? With university events, having a speaker with some sizzle, some zeitgeisty buzz, a hot book, some cultural capital, is important. The organizers need to entice busy students to show up. Otherwise, they could go see the Dave Matthews cover band at the campus pub. (With many corporate events, the butts-in-seats problem is less of a thing. The program might be part of the workday or a mandatory work event.)

What percentage of your clients, roughly speaking, are authors?

Probably a higher percentage than at most other speaking agencies. That might be a personal thing. I'm a big reader and David is, too. David didn’t even have a TV until he was 27, so he’s read thousands of books. I used to publish a literary magazine for a few years with my wife, called Little Brother. So we've always been in that world. I mean, we also represent scientists and artists and business people who don’t have books, and they do just fine, but, for sure, having a book never hurts.

In terms of speaking: it’s not like the person who writes the book on the topic is any smarter, necessarily, than the person who didn't write the book. What a book does is it synthesizes and puts into a nice package the ideas you want to talk about--so that those ideas can travel much farther than if they were contained in just about any other form. The book gives you an excuse to get out there, gives others an excuse to interview you, have you on their podcast, invite you to their speaking events. One question clients ask: “Why this speaker and why now?” A new book, especially if it’s a bestseller, is the ultimate “why now” answer! Just to be super clear, though, an author should never write a book for the sole or primary purpose of trying to land speaking gigs.

Let's say you're a nonfiction writer or an expert in a given subject, and you want to build a speaking career. At what point should they reach out to someone like you?

So, picture a physical target—like a Jasper Johns painting—and think of the circles as all the possible speaking markets. There's the little blue dot at the center, and there are the bigger concentric circles around it. When you release a book, you’re in the little blue dot area. Which is to say: with no explicit effort, there are people who are interested in the subject. You’ll likely get speaking requests by doing nothing. Sweet! But this is a finite group, a little dot’s worth of market share. A speaker’s agent comes in handy when your work has the potential to find new audiences and move outwards and permeate into the second and third concentric circles, which represent the bigger speaking opportunities. In those markets, the speaking clients aren’t your absolute deepest fans, but they are open to new and good ideas, if pitched right. For these clients, it’s important that the book is well-reviewed, maybe it's a bestseller, maybe has caught fire in the larger culture. At that point, there’s enough there. You just need a concerted push and some choice framing from an agency to make it click with clients.

A good tell, then, is when an author starts getting random calls from organizations that have no ostensible connection to their book’s central topic. The interest is beyond the day-one, deep-cut people. Another tell is the applicability of the core idea of the book as it might apply in various settings: education, corporations, the not-for-profit sector.

Let's say you're an author, and because you are never going to have Charles Yao be your speaker's agent, because you're just not that in demand. But you want to signal to the world that you could do speaking. What are some things you might do?

There are easy things to do! They won't make you a superstar, they won't manufacture demand, but they will at the very least show potential buyers that you are, indeed, a viable speaker.

On your website, make a menu tab that says “speaking.” That sounds self evident. But it's not. Many buyers are not deeply invested in the industry. Why would they be? They’re not spending a massive amount of time keeping up with who the good speakers are—the way that someone might keep up with what shows to stream, what movies to watch, who the new bands are. It's no one's full-time job to book speakers! It’s something a person does once a year. Often, once in a lifetime. You have to signal that you're a speaker because you need to clearly tell a buyer, “Yes, I do speaking as well.” You can’t leave it to the more or less reasonable assumption that an author who wrote a book can also speak on that book. You, the author, have to say it. And many authors who I talk to never think to say it!

On the actual speaking page under the tab, you’d float in a photo, if you have it, of you on a stage, giving a talk. Proof you’ve done this! Under that, some text along the lines of, “When I do keynotes, I draw on my work to talk about X,Y,Z. My onstage style is this, and I draw on these examples, and, finally, this is one thing I’d like to leave the audience thinking about differently, maybe doing differently.”

You'll want to have a video of you speaking in a nice place. Elevated stage, good lighting, uncluttered background, implied big audience, maybe one or two camera angles. You might not have that just yet, and that's fine. But I cannot overstate how important a quality keynote video is. It's the final and non-skippable piece of assurance for a client before they book you. The client might think, “I love the ideas in the book. I can see how they relate to my event. But I don't know if the author will just read off a piece of paper when they show up. Or maybe they have that dreadful ‘Poet Voice,’ or maybe …” –you get the point!

I can imagine someone hearing that and they think, Wait, if I put the whole video on my website, why would anybody book me if they could just watch me?

For sure. That's why you put up just a short clip! A continuous two- or five-minute clip of you making one point, looking confident, is perfect. And don’t do any fancy editing. It doesn’t have to be Pierrot Le Feu! If you chop it up too much, it makes it seem like you can’t finish a thought; it's like you're hiding something. The point of the video, again, is to assure the person that's about to book you that: Yes, you've done this before. Yes, you are very comfortable doing it in front of a real live audience. “Nothing to worry about here!”

Is there anything else you'd like to share that we haven’t covered?

It’s helpful to remember that it’s called speaking. It’s not called reading or ideas-ing. A speech is not purely about conveying information. You can get information anywhere. Like, the act of speaking to a live audience – the cadence of your delivery, the pauses, the eye contact, your word choices, your personal speaking style, the ability to talk as if extemporaneously, your onstage presence – all of that is important. That’s the stuff that’s intrinsic to keynote speaking, to talking in front of other humans. I feel like a lot of new or potential speakers skip over that part. I wouldn’t necessarily call it the “performance” part, because that makes it sound a bit contrived. Let’s call it the “attempting to genuinely connect with the audience” part. Obviously, the foundation of your talk is always going to be your original research, your stories, your work, your experiences, your observations, your conclusions. But that real-time connection with other humans in a room—that matters just as much. This word has been dragged through the CheezWhiz, but authenticity really counts. I’m agnostic as to the style of speaking. There’s no formula for that part. There’s no “How to Draw Comics the Marvel Way” guide to speaking, in my books. Be funny, or don’t be. Use slides, or don’t. Bound around the stage, or stand still. What you want is to be the truest expression of yourself up there.