So I was prepping to interview John Lessard last Tuesday night, right? Big name, AI stuff. Felt totally out of my depth. Grabbed my notebook, jotted down like twenty questions. Standard bio stuff, his company, future of tech… the usual suspects. Felt prepared. Boy, was I wrong.
The Calm Before the Storm
Morning comes. Coffee kicks in. Stare at my list. Suddenly all my questions seem… lame. Like asking a chef how he boils water. Needs more punch. Scratch out half of them. Brain freezes. Panic sets in. Googled “good interview questions”. Found pages of generic advice. Useless.
Had a lightbulb moment. Ditched the notebook cold turkey. Instead, pulled up my phone. Scrolled through John’s recent talks and articles – stuff from the past month. Not the ancient history crap. Focused hard on what he just said. Looked for the tension points. Where he sounded excited? Frustrated? Hinting at something unfinished?
Walking Into the Lion’s Den (Okay, Zoom Room)
Connection works, thankfully. John pops up, looking relaxed. Standard intro hellos. I skip the fluff.
Lead with this: “John, you mentioned in your MIT talk last week that current AI models are basically ‘brilliant parrots’. What’s one thing you’d change tomorrow if you had the power to make it stop parroting?” Saw his eyes light up. He leans forward. Boom! We’re off. Real talk, not soundbites.
Stopped reading questions from a list. Listened like crazy. When he dropped a vague term – like “meaningful alignment” – I pounced: “When you say ‘meaningful alignment’ right there, what’s the first specific problem that pops into your head? Walk me through it.” Made him show his work, not just the polished answer.
Felt a weird shift. He started asking me questions back, testing if I really got it. Best compliment ever. The clock ran out way too fast.
What Actually Worked (And What Didn’t)
Forget the script. Trying to rigidly stick to my pre-planned questions felt like trying to milk a bull. Pointless and messy.
- Focus on fresh meat: Digging into his very latest stuff, even if it’s just a tweet. Shows you care about his now.
- Spot the friction: Zoom in where he seems passionate or annoyed. That’s gold.
- Make him unpack the suitcase: Ask “How? What specifically? Show me the step.” Don’t let buzzwords slide.
- Shut up and listen: Seriously. Pause after he talks. Often, the best nugget comes after his first answer.
Screwed up early? Yeah. My first few questions were safe and predictable. Saw him mentally check out for a second. Facepalm moment. Learned fast to go for the juicy bit immediately. Like ripping off a bandaid.
Realized interviewing isn’t an interrogation. It’s more like… poking the hornet’s nest just right to see what fascinating chaos flies out.
