Practical Prompting

Practical Prompting 12 - Guest Series - John Mathias' GenAI Journey

🎙️ Episode 12: Guest Series - John Mathias' GenAI Journey — From feeling behind to expert In this episode of Practical Prompting, Alex is joined by longtime collaborator John Mathias—law degree from Regent University, a stint at a think tank in DC, and now years of startup building. Act I: Dives into John’s personal journey with GenAI: his first experiments, everyday wins, and the “aha” moments that made AI feel less like a toy and more like a tool. Act II: Zooms out to the professional side: how those same skills translated into legal research, policy analysis, and startup workflows, plus the challenges and opportunities he’s uncovered along the way. 🎯 Your Challenge: Email alex@lololai.com [alex@lololai.com] with how many questions you ask GenAI each day. Connect with John: email-jmathias@lololai.com, [jmathias@lololai.com] website-lololai.com, [https://www.lololai.com/] linkedin-johnmathias [https://www.linkedin.com/in/john-mathias-85aa1524/]. Disclaimer: Views expressed are Alex’s own and do not represent any employer; no confidential information is shared. Connect: alex@lololai.com [alex@lololai.com]

Practical Prompting 11 - Why GenAI Feels Scary

🎙️ Episode 11: Why GenAI Feels Scary — Driving clarity through the foggy fear GenAI feels like quicksand: kids are already using it for schoolwork, headlines scream that most enterprise pilots flop, and “strategy” sounds like a buzzword. In this episode, we name the fear—and shrink it. You’ll get a simple, repeatable way to turn ambiguity into choices you can prove in 30 days. Act I: We start at the kitchen table (why getting started is daunting, what kids are actually doing with GenAI, and why that matters. Act II: We'll then jump to the workplace where strategy often stalls due to fear. Along the way, you’ll hear practical, real-world examples leaders face every week—like creating a “Monday Ops Pack,” and a starter GenAI strategy to get you started. 🎯 Your Challenge: Email alex@lololai.com [alex@lololai.com] with your Top-3 fears you feel or see with your own GenAI adoption. Disclaimer: Views expressed are Alex’s own and do not represent any employer; no confidential information is shared. Connect: alex@lololai.com [alex@lololai.com]

Practical Prompting 10 - Executive: Objection Anticipated

🎙️ Executive Series — Episode 10: Objection Anticipated — Turning AI Into Your Toughest Opponent In this Executive Edition of Practical Prompting, Alex and his AI co-host, Practically Speaking, turn a tactic into a habit: use AI to surface objections before your stakeholders do—so decisions get faster, safer, and sharper. Act I: The Couch Dilemma → The Hidden Criteria Play Alex walks through replacing a couch in hours, not months, by converting “vibes” into ranked constraints (back height, seat depth, dog-proof leather) and reframing the use case (reading + tea, not home theater). The result: fewer, better options and a cleaner ask. Lesson: many “objections” are your own unspoken criteria. Name them, and the noise falls away. Act II: AI as Your Objection Simulator We zoom out to leadership. Before your deck leaves your desk, run an AI premortem: simulate CFO/COO/Legal—or whichever roles are actually in the room—merge duplicates, and return only the top three objections with evidence and a two-sentence counter. Package it in a one-slide “Likely Objections” box and a Decision Card (Goal, 90% plan, Top-3 risks + counters, Clear Ask). This reframes prep from defensive to proactive and trims approval latency. 🎯 Your Challenge: Run the meta-prompt on one live proposal today. Email alex@lololai.com [alex@lololai.com] with your Top-3 objections and the single riskiest assumption you’ll test this week. Disclaimer: Views expressed are Alex’s own and do not represent any employer; no confidential information is shared. Connect: alex@lololai.com [alex@lololai.com]

Practical Prompting 09 - Executive: Managing Up

🎙️ Executive Series — Managing Up with AI Episode 9: From Two Pages to 100 Words (and Why Timing Beats Brevity) In this Executive Edition of Practical Prompting, Alex and his AI co-host, Practically Speaking, dig into one of the most overlooked leadership skills: managing up. Act I: We put a two-page update on the chopping block—distilling it into a high-impact, 100-word brief for a senior leader. You’ll hear why “shorter” isn’t the goal—decision-ready is—and how to use meta-prompts and guardrails (“with high accuracy”) to get AI-generated summaries that hit 97% of the mark in seconds. Act II: We zoom out to the strategy: managing up as timing, not just content. From building a “priority heat map” to experimenting with digital twins of senior leaders, Alex and PS explore how to align updates with what’s actually on the radar. We close with three AI-powered tactics you can use today to make your boss’s decisions easier, faster, and safer—plus a challenge to rethink objection handling as a daily habit. Whether you’re reporting to a VP or briefing the C-suite, this episode will help you shift from proving your team’s worth to steering leadership’s focus—at the right moment, with the right message. 🎯 Your Challenge: Email alex@lololai.com [alex@lololai.com] or tag Alex on LinkedIn with the next executive pain point you want decoded. Disclaimer: Views expressed are Alex’s own and do not represent any employer; no confidential information is shared. Connect: alex@lololai.com [alex@lololai.com]

Practical Prompting 08 - Executive: Zero to 30 a Day

🎙️ From 0 to 30 Prompts a Day (Executive Edition) – feat. Promptly Speaking What happens when you go from never touching AI to using it 30 times a day? In this Executive Edition of Practical Prompting, we break it down step-by-step—without adding a single new chore to your calendar. Act I: We tackle a pain point every executive knows too well: being looped into a sprawling, weeks-old email chain with zero context. You’ll hear exactly how to turn that time-sink into a 3-minute AI-powered “email chain autopsy” that leaves you with clarity, an agenda (if needed), and the right people in the room. Act II: We unpack the Spark → Scaffold → Flywheel system for building AI habits that stick—starting with small, high-impact wins, adding structure to make them repeatable, and scaling until AI is a genuine business partner in strategy, decision-making, and execution. And this week, there’s a twist—meet Promptly Speaking, my new AI co-host. With an English accent, a dry wit, and a knack for asking the questions you didn’t know you needed answered, she’s here to challenge my thinking, keep us grounded, and sneak in a joke or two. Whether you’re an AI skeptic, a curious exec, or already halfway to 30 prompts a day, this episode will leave you with practical tactics—and maybe a laugh—to accelerate your own AI adoption. 🎯 Your Challenge: Email alex@lololai.com [alex@lololai.com] or tag Alex on LinkedIn with the next executive pain point you want decoded. Disclaimer: Views expressed are Alex’s own and do not represent any employer; no confidential information is shared. Connect: alex@lololai.com [alex@lololai.com]