Nick Caldwell

@nickcaldwell

Breaking in to public speaking

2017 badge pile

Last year I committed to a seemingly simple /dev/color goal for myself: do more public speaking.

Now, I thought I was a pretty good presenter because I’d done hundreds of internal presentations at work. But what I really wanted to do was presentations that would be visible to the world. Why? Well the easy half-answer is to say that it’s part of my job. When you make the transition into an executive role, one responsibility you pick up is the need to represent your company and become more “outward facing.” But that isn’t the whole story.

To be honest, I just think it’s fun! Nothing beats the adrenaline rush of presenting a topic you’re passionate about, especially when you can connect with the audience and squarely land your messages. People who are really into public speaking will all tell you the same thing: we do it for the love of performing, sharing, and inspiring!

It took some time to figure out how to break into the public speaking circuit, but in 2017 I had the opportunity to speak at more than 20 conferences and events! That’s up from about 5 in 2016. If you want to know how, keep on reading.

Breaking in

When I worked at Microsoft, getting a speaking gig was pretty straightforward: wait around until the next regularly scheduled press event, executive briefing, sponsored conference, or what-have-you and expect to be given a time slot. Big companies have their perks. But when I moved to the Bay Area and switched jobs last year things got a little harder.

Generally, to get invited to a speaking event you must have had experience at a speaking event. Catch-22! And although I’d done plenty of talks at Microsoft-sponsored events, this didn’t seem to count as “real world” experience when I applied to speak at conferences in the Bay Area. So, when I first reached out to conference organizers, the general response I got was along the lines of, “who are you and why should I care?”

Doesn’t count as speaking experience in the Bay Area. Should have worn a hoodie.

I was undeterred. As an engineer with a knack for breaking large problems into subproblems, my approach was practical:

a) There are only so many events happening where I’d be an appropriate speaker. Find them. 
b) Event coordinators need catchy topics to sell tickets. Create them.
c) Whatever I did should be repeatable and ideally get easier over time.

Let’s solve for a, b, and c.

Where do you even apply?

Since opportunities weren't exactly landing in my lap, the first thing I decided to do was figure out how the application process works.

Techmeme calendar is a pretty good starting point

Unfortunately, there is no one place where you can get a list of all the upcoming speaking opportunities. A friend recommended I look at Techmeme.com which does a great job of listing many of the larger events. Check that out and you’ll see more than 100 upcoming conferences — a buffet of opportunity. The problem is that conference sites often make the speaker application pages difficult to find.

So, my approach was to meticulously examine this Techmeme list, select 2-3 few conferences where my content would be a worthwhile contribution, hunt down the organizer’s contact information, proactively reach out with a thoughtful and personalized note, and then wait patiently for a response to come several weeks or months later.

Just kidding! I figured I’d apply to them all.

It turns out, finding the application pages for hundreds of conferences is surprisingly easy and affordable using task completion services. My favorite is a service called Fancy Hands, where for as little as $5 per task you have an army of virtual assistants at your disposal. I created a google sheet with a list of conferences, then asked my virtual army to look up the speaker submission pages and requirements for every single one. If a conference looked like a match, they flagged it in the spreadsheet and sent me a notification.

I fed my army a list of more than 500 conference site links harvested from Techmeme and other sources. $50 and one day later: only about 35 conferences had easily accessible speaker submission pages. Of those, about 15 were related to topics that I might be able to speak expertly about. I applied to those and was accepted to 6.

(For the curious, here is the list of speaker links that Fancy Hands made for me. It’s outdated now, but if you take my idea please pay it forward and share your updated list with the world.)

What to talk about?

Now that I’d figured out where to apply I needed a topic that would catch the organizer’s interest. In my opinion, the best talks are comprised of three elements: personal experience, a challenge the audience can relate to, and good storytelling. Given that formula, figuring out what to talk about is easy. Each and every day you are probably faced with numerous challenges that other people in the world are also struggling with. Now tell a story about the challenge from your viewpoint.

Conjoined circles of presenter success

If you want to go for extra points, ask yourself: is any of my experience part of the zeitgeist? If you are a block-chain or artificial intelligence guru, now is really your time to shine. If you can say anything remotely intelligible and fresh about D&I you may want to put your name out there.

Before moving on, there are some topics that never go over well. Unless you are at a pitch meeting, NEVER EVER EVER get in front of an audience and just talk about your company, product, or service. That may work at internal presentations because the audience is literally being paid to listen (or, less cynically, the audience is simply biased in your favor). But tech conference attendees generally don’t want to be pitched to, they want to learn.

Similarly, there are “easy” topics that never fail with the right audience. Rather than call those out, I’ll simply say that one of the best measures of success as a speaker is whether you can change the mind of even a single person in your audience.

Finally, part of being a great speaker is capturing the attention of your audience. That means having the empathy to understand that even though you may be crazy passionate about a 25-minute Emacs command-line coding demo, your audience may not feel it so much.

Start creating early

Ultimately, the presentation topics I came up with were simply about what I was dealing with at the time: scaling engineering teams, learning about Reddit communities, and becoming a black Silicon Valley tech executive. For each of these I decided to do two things.

First, I came up with catchy titles for the conference application forms. “Triple your team size without losing control!”, “From Hello World to VP of Eng,” “It’s not about you! The power of online community.” Having a good title was really quite important because I didn’t actually have any content to present yet.

Second, I made a blog post and deck for each those topics and published them on Medium and LinkedIn. Publishing this content forced me to think clearly about what I wanted to say and gave me valuable feedback before I got in front of an audience.

As the content got shared across social networks, it helped generate even more speaking opportunities. The wonderful thing about these opportunities is that the conference organizers reached out to me directly, often with suggestions on how I could tailor my content to their audience.

Practice makes perfect

Early on I just said yes to everything that came my way. Small events let me practice my message and get ready for the bigger events later on. The very first event I did last year was at Cloudera, where the organizer said, “we’ll give you 90 minutes, a 20-person audience, and you can say whatever you’d like.”

I used up every minute to present and get feedback on the first draft of my “Hello World to VP Eng.” presentation. I ended up cutting 2/3 of the content (in retrospect I really should send that poor audience a thank-you note). What remained became the basis for well-received presentations at much bigger events with AfroTech and Black Enterprise.

Slip in some self-promotion

The last tip I’ll share about practicing: remember to promote yourself responsibly. A single slide at the end of the presentation with contact information and a “Yes, I’m happy to do this talk again at your event,” goes a long way toward getting more opportunities and won’t offend the audience or the organizers.

Paying it forward

That’s it! It took me about 6 months to get the engine running. Now that I’ve got a few successful events under my belt I no longer have to go searching as hard for opportunities. 2018 started with more than 5 conference organizers reaching out to me directly.

That’s way more opportunity than I can handle for myself. The very cool thing about having this problem is that I can redirect these opportunities to my team members here at Reddit and to the people in my professional network. Leaders make new leaders and I’m hoping to see them shine bright up on stage this year.

Hoodie. Jordans. Comfortable, stylish, and Bay Area approved!

Thanks for reading! My next goal is to publish a book with the esteemed Marty Weiner so expect a 2019 post on how we did that!

rock on
-nick

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