Searls of Wisdom for September 2023

Wow, September came and went in a hurry.

Several coincident strategic goals at Test Double just so happened to land all at once, which feels great and is keeping us busy. Our new Head of Sales really hit the ground running, cultivating more new leads than I can remember seeing in a long time. We've got a ton of stuff cooking on the marketing front, too, which I'm confident will broaden our reach to new audiences that could use our help. Most importantly to me, the business finally has the leadership it needs for its CEO (and my co-founder) Todd Kaufman to finally take a multi-week break after 12 years of barely eking a contiguous week off. Seeing others stepping up in his absence to make tough decisions and brave hard conversations is heartening evidence of the resilience of the company. Good times.

Ha ha, business!

On the home front, it's October 1st, which marks the third month of Halloween and first month of Thanksgiving in the five-month-long corporate Hallothanksmas slog down here in Theme Park Land. As somebody who doesn't see the appeal of "horror" as a theme, I've got no interest in the non-edible aspects of Halloween, but as a huge fan of Naughty Dog's Last of Us series, I'm finding myself getting dragged to Universal Studios' Halloween Horror Nights by my family this Wednesday. We'll see if I last long enough to meet any clickers.

Okay, onto this month's briefer-than-usual essay. Which is a thing I'm typing in advance of writing it in an attempt to spare myself (and you) from an overwrought 4000-word screed.

How to give a decent podcast interview

Over the years I've been featured on a couple dozen podcasts. (Always the guest, never the host.) As with most things I've undertaken, no one ever told me how to do this. It never occurred to me to seek out "media training." I never Googled "top ten podcasting interview tips." The best hosts do a great job giving advice around audio equipment and fail-safe recording techniques, but since they tend not to have much experience as interview subjects themselves, no one ever conveyed to me how to… like, be interviewed. Complicating things further, representing a consultancy doesn't lend itself to a single straightforward Thing To Talk About. (Like tofu, consultants tend to take on the flavor of the ingredients around them.)

(If you haven't heard me be interviewed, this discussion with the Changelog in August is a recent example. For something more in-the-weeds, this conversation on Matt Swanson's YAGNI podcast was a lot of fun last year.)

A colleague asked my advice before he was to be interviewed recently, and I suddenly realized I'd never really reflected on the useful habits I've picked up over the years as an occasional guest. Everything I have to share here should be caveated with the fact that my experience is limited to programming and tech podcasts, and that genre is surely distinct from most others. Also, I'm going to skip right over any A/V stuff, as anything about audio has surely been covered better elsewhere.

Whether you're fortunate enough to be invited onto a podcast or you're pitching a podcast to consider hosting you, the first question to answer is (as always) why would you want to do this with your time? Many of you reading this are surely already a step ahead of me and thinking, "Easy: I do not want to do this." And if that's you, you're smarter than me! I had to earn the hard way that not being on podcasts is far less work than being on podcasts.

In my case, the "why" was always easy enough: our consultancy would be better off if more people knew about us, and being on someone else's podcast is a good way to reach a new audience. As for, "why podcasts in particular," the fact that Test Double embraces the fact software is fundamentally hard lends itself much better to long-form conversation than short-form alternatives. Having an hour to put an important issue in context, kick the tires from every angle, and weigh both sides of any trade-offs offers a much better example of what it'd be like to work with Test Double than a 30-second reel ever could.

Next, I essentially ask the host the same thing in reverse: why do you want to interview me? What do you want your audience to get out of this conversation?

Hosts are usually surprised to be asked this, but if they have it in mind we're going to talk about one thing and I had in mind another thing entirely, the last thing I'd want to do is drag an audience through a subtextual game of tug-of-war as the host asks questions to lead the conversation in one direction and I keep wrenching the steering wheel in the direction I want to take things. Best to get that sorted in advance so both parties have the same destination in mind.

At this stage, if it's not already clear, ask "is this worth my time?" I basically write off an entire working day to any podcast I'm on. I take about an hour prep to "get in the zone", block out my calendar to avoid any meetings before or after, and find that the performance of recording a podcast (even if it's only an hour, all-told) utterly drains me of any energy. For that time expenditure to be worthwhile, the podcast needs to have enough of the right kind of people listening to it. The best way to figure this out is probably to see how they rank on Chartable (where our friends at Changelog are doing pretty well!) Of course, beggars can't be choosers, and I tend to err on the side of taking too many opportunities—worst case I have an engaging conversation with someone who gives a shit about something enough to put the time into publishing a podcast.

Okay, so you know why you're doing it, you've agreed on what to talk about, and you've verified that it'll be worth your time. After you get the event in your calendar and you make sure your recording setup has you set up for success, there's not much left to do until game day.

Scratch that, there's nothing left to do until the day before game day.

I'll never forget that the second conference talk I ever gave was the morning after a raucous speaker dinner where I got to meet a number of my heroes for the first time (and as an also-speaking peer!). I leaned in a little too hard into the alcohol-lubricated networking opportunity at a much-too-loud bar and passed out successfully in the correct hotel room. The next morning my voice was completely shot. I remember wandering around Boulder looking for a pharmacy or something before settling on a tea shop and spending 30 minutes gently gargling a honey-drenched cup of herbal tea before going on stage.

Never put yourself in the position to have to gargle overpriced tea. Whatever you do in the run-up to your interview, make sure you protect your voice—however you might need to do that.

Likewise, sitting down with a notebook a day (maybe two) in advance is a great way to organize your thoughts and give your brain time to asynchronously process things a bit. That said, definitely avoid building out an outline or writing too much detail: it's a conversation not a presentation. Instead, I write impressionistically. I might work up a list of "STUFF I'LL BE PISSED IF I FORGET TO MENTION", in red sharpie. Consider jotting down some anecdotes or citations you can tie back to the topic at hand. One thing I make a point of doing: next to each note I highlight any associated emotions—it's really important to remember that expressing feelings is every bit as important as conveying facts, so giving those memories a day to simmer can genuinely increase their resonance when you recall them on air.

Okay, now it's game day. You're standing at your desk because your voice will carry better than if you were sitting. You've got all your devices set to Do Not Disturb. You've handed all your cohabitants $5 Starbucks gift cards to buzz off for a few hours. You've reinstalled Chrome so you can use the host's goofy Podcasting webapp thing. You're ready to roll.

The rest of my advice is probably best communicated in unordered bullets, because everything from intro onward is necessarily spontaneous and reactive, so you may as well embrace it:

• Just because podcasting is an audio format, bring the same level of energy you would to being on stage in front of a thousand people. Each listener is giving you an hour-or-so of their time—they deserve you at your absolute peak performance. Of course I wouldn't want to make anyone feel ruinously nervous, but I'd rather listen to someone with too many butterflies in their stomach than too few. Remember: you're the subject, and (what luck!) you happen to be the world's foremost expert in you. Bring the heat and don't phone it in
• You know how you're normally not supposed to ignore whoever's speaking while waiting for your turn to speak? If you're being interviewed, forget about all that. When other people are speaking, I'm unashamedly and furiously scribbling notes to make damn certain I remember what I want to say next. Podcasters can, of course, edit out any dead air if you need to pause and think, but (1) who knows if they actually will, and (2) listeners can pick up on a lack of energy and tempo in a conversation. When the host throws to you, be ready to keep the energy up by pouncing with a spring-loaded response
• Treat the host's questions less like form fields to be filled out and more like creative writing prompts. As an involuntary blabbermouth, I'm generally terrified of hogging all the airtime in a conversation, but an interview format actually necessitates longer responses from each participant. If you have a point to make, take the time to set the table with a story that listeners might empathize with and, when you're ready to make your point, slow your speaking pace and adjust your inflection to give it the right amount of weight. Don't skimp on the oomph. Make sure the things that matter most to you will have a chance to sink in for listeners
• I know as well as anybody that instructing someone to "be authentic" is a counter-productive suggestion. What I think people really mean in the context of something like an interview is be less inhibited than you think you need to be. Don't worry that saying something a bit out-of-bounds will be transcribed out of context and get you cancelled. Odds are, none of your enemies have that kind of time. And stress about whether every memory you recall and fact you cite will be verifiable in real time; if you shift your focus from delivering what you want to say in a persuasive, entertaining way and instead start waffling about the veracity of every statement, you'll lose all momentum. On the other hand, if you talk to the host like it's an intimate, private conversation—like you're letting them in on a secret with whatever you're about to share—you'll draw the audience in! Take advantage of that
• Unless you're going on the Howard Stern Show, odds are that your host will play it straight, which means there's no need for you to take things too seriously. Be the listener's fun uncle of this podcast episode. Loosen up. Tell a joke now and then. Don't be afraid to give the host shit if they open themselves up to it. I try to find opportunities to be self-deprecating, irreverent, and vulgar whenever possible. One of these days I might even remember to ask the host if swearing is OK before I drop an F-💣 on air
• First things last: don't you dare touch your computer. No mice. No keyboards. No real-time fact-checking. As soon as you let yourself get distracted by the screen in front of you, you're no longer devoting 100% of your brain juice to the task at hand: showing up as the brilliant and fascinating human that you are

Anyway, those are some thoughts on being interviewed.

The TLDR on TLDR

Last month I teased that I'd be on a livestream with my buddy Aaron, and… it happened! It was a lot of fun, because Aaron and I are both goofballs who mostly spend our time together trying to make ourselves and/or each other laugh. (I got a few jokes into his upcoming set at Rails World that I'm pretty proud of.)

Anyway, the thing we wrote is a little test runner called tldr (as in, "too long; didn't run"). It's a framework for writing Ruby tests that is designed to guarantee that it's always fast. It delivers on that guarantee by quitting if your tests take more than 1.8 seconds.

As usual, I got obsessed with seeing this thing through after our livestream and now it's an actual gem that's actually pretty good!

With any luck, I'll have a blog post out this week where I announce this thing properly. If you're a Ruby programmer, I hope you'll check it out and offer some early feedback.

That's all I have to say

Speaking of enforcing a time limit, I'm going to prove the naysayers wrong and actually get this thing out on the first of the month for once. So, uh, bye!