I’m not sure how it happened, but out of the many conferences in which I’ve spoken, I’ve only submitted two talk proposals. Both were to O’Reilly’s OSCON. One was in 2003. It was not accepted. Too bad; It would have been really good. The next was in 2004. It was accepted. It wasn’t all that great.

Every other time, I’ve been asked to speak–usually to give a keynote.

So before my first keynote speech, I had only delivered one conference talk. And I didn’t think it wasn’t any good (sorry OSCON 2004!). When the organizers of this conference contacted me, I responded and said the following, “I’d love to do this and I’m thrilled to be asked. Just to avoid embarrassment, though, are you sure you didn’t mean to email Martin Fowler?” Apparently they had a nice laugh and then responded saying they really meant me.

My next feeling was not relief. It was terror. It was a great honor to be asked to keynote at anything. But, why me? What would I speak about? What the hell is a keynote anyway?

As I did with many new challenges back then, I turned to my friend Dave Thomas. “Dave, they asked me to keynote and they didn’t mean Martin. What do I do?!” Dave was kind enough to give me the single most useful piece of advice I’ve ever gotten as a keynote speaker.

He said something like “Keynotes are after-dinner entertainment. Don’t try to teach them. Just keep them entertained and leave them with something to think about.”

So I did that and I think it went well. In fact, at this particular conference, one of the other keynote speakers got snowed in at home in Chicago and couldn’t make it. So for my first keynote appearance, I actually gave two. One planned and one that I wrote while at the conference. Pretty good practice!

Since then I’ve done enough of them in enough different circumstances (conference types, countries, with and without live translation, remotely via video, etc.) that I’ve had the chance to fail and succeed in a number of different ways. Occasionally, a friend or colleague encountering their first keynote calls or writes and says “Chad, they asked me to keynote. What do I do?!”

Here are some answers:

  • Dave was absolutely right. Entertain and provoke thought.
  • Do not introduce yourself. If you’re a keynote speaker, they probably already know who you are anyway. If they don’t, they won’t care while you introduce yourself.
  • Tell a personal story. Among other reasons, it will loosen you up and allow you to communicate better with your audience. A personal story is easier to deliver unrobotically than the programmed content you might be crafting. So use it to connect with the audience and to motivate the message of your talk.
  • Be vulnerable. Subtly admitting that you’re imperfect and not completely certain about everything puts you in the right frame of mind to engage with the people listening to you and to avoid the trap of trying to appear to be right about everything.
  • Don’t try to prove yourself. You’ve already been asked to keynote. If you get insecure and spend time proving why you’re the right person to be speaking on your topic it will sound like you’re arrogant, which you probably aren’t.
  • Converse with the audience. I personally look into the eyes of the people listening to me in exactly the same way I would if I were having a conversation over coffee. I go on a tangent and I can see that they’re bored so I change my approach. They might not be directly speaking to you, but they communicate with their reactions, and letting the communication happen in two directions is extremely important for both you and the listener.
  • Say significantly less than you think you need to. Don’t fall into the trap of trying to cram in as much as you can. Kent says this better than I will:
  • Read and apply Kent Beck’s three focusing questions
  • Create a story arc and apply a little drama if you can. There are many devices you can use for this. Watch your favorite speakers, and see how they use foreshadowing, repetition, rhythm, etc. Dave Thomas is amazingly gifted at this. Find some of his keynotes and watch for how he does it.
  • Express your opinions unapologetically. You’re a human–not an information dispenser. People can look up facts on the internet. They’re at the conference to listen to your perspective on things.
  • Leave your audience with something to wonder about. Unanswered questions are OK in a keynote.

I’m not the greatest keynote speaker to have ever lived, but I try to do them well and constantly aspire to be better. As with everything I write or speak about, I hope these tips are meaningfully helpful to at least one person.