Outlining

Usually I’ll come up with a great idea, like I think it’s important to reveal to the entire world that 2Pac is still alive and working at a San Francisco startup.

So then I have this great talk idea, but then I’m stuck facing the music: how the hell do I flesh this into an entire talk? There’s all these subtleties to cover, like should I talk about how 2 of Amerikaz Most Wanted was actually an allegory for his desire to work at a quiet Silicon Valley startup job for the rest of his life? Or maybe I should bring up his deeply suspect tattoo:

In either case, I almost always tackle a new talk by outlining first. There are a million different ways to do this, so your mileage may vary, but this is what’s worked for me.

Inside Outlining

I do something I’d like to call inside outlining, because it’s kind of a fun play on words and by inventing new terminology you can eventually ask for royalties.

Basically, write the important things first. These should be your main sections that are meaty enough to dive into greater detail.

It depends on the talk, but I think generally most talks are best served if you can deliver them in three sections. It’s limiting, to be sure, but it creates a much more cohesive narrative if you can lay down your main argument with three distinct sections, each with supporting details. So, for this Pac talk, I’d start out with these five bullets:

• Intro
• Section one: 2Pac loves the Bay Area
• Section two: Possible connections to the tech industry
• Section three: He lives in my basement
• Outro

Really avoid trying to flesh out this outline past this point, even if you want to. It’s good to sit on this for a little bit before getting too deep down the rabbit hole. Let it sink in and get a feel for whether you’re happy with this main foundation of your talk. If you’re not, then change it. If you want to add or remove more main sections, go for it: there are no rules in the world.

Rule number two: start fleshing out the outline. This is where the “inside outlining” comes into play, for me. I never really finish each point one-by-one. I sort of add one or two supporting points to each main point. Something like this (ignoring the intro and outro):

• 2Pac loves the Bay Area
• Possible connections to the tech industry
  • Path tattoo
• He lives in my basement

…then a couple more:

• 2Pac loves the Bay Area
  • Lived in Marin City for years
• Possible connections to the tech industry
  • Path tattoo
• He lives in my basement
  • No really, I have photos

As you get a better handle for the overall flow, you can start diving into more:

• 2Pac loves the Bay Area
  • Lived in Marin City for years
  • “Oaktown, Oakland definitely in the house”
• Possible connections to the tech industry
  • Path tattoo
  • White Man’z World (1996)
    • Clearly a metaphor for today’s tech industry
• He lives in my basement
  • No really, I have photos

For me, I tend to keep these outlines very short and high-level. I usually don’t get much further than three tiers: top tier is the slide introduction to the section, the second bullet level is a slide and large point inside that section, and the third level of bullets tend to translate to multiple slides supporting the #2 level of points.

Interested in seeing this in practice? Here is my raw outline for my How GitHub (no longer) Works talk. Those twenty-some lines generated 141 slides. For me, I just use an outline as a point to channel my thoughts, not as the verbatim bible of my talk.

Most of the time I only use about half of my outline in my actual talk… sometimes it’s just a springboard. That’s what works for me. And that’s what’s important for you, too: getting your thoughts converted to slides is hard enough, so try a few things out and find out what works for you.