Turning generative AI from buzzword to business value.
Join host Alex, an operations strategist and lifelong experimenter, as he pressure-tests real-world ways to use off-the-shelf GenAI tools (ChatGPT, Gemini, Perplexity, Grok, & friends) to shave hours off workflows, unlock hidden insights, and spark culture change.
Each bi-weekly episode delivers:
1) Short, story-first breakdowns of successful pilots (and a few glorious flops)
2) Operator-minded prompt frameworks you can copy-paste today
3) Executive-level metrics to prove the ROI of “imperfect” experiments
4) Guests who actually run GenAI in the trenches—not just on slides
Disclaimer: This podcast is created in my personal capacity. The views expressed are my own and do not reflect the views or positions of any current or past employer. No internal or confidential information is shared.
Hit follow, rate the show, and email a screenshot of your review to get free access to my Udemy course "Prompting Like A Pro".
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 (mailto:alex@lololai.com) with how many questions you ask GenAI each day.
Connect with John: email-jmathias@lololai.com, (mailto: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 (mailto:alex@lololai.com)
26 Aug 2025
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 (mailto: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 (mailto:alex@lololai.com)
🎙️ 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 (mailto: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 (mailto:alex@lololai.com)
12 Aug 2025
Practical Prompting 09 - Executive: Managing Up
🎯 Your Challenge: Email alex@lololai.com (mailto: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 (mailto:alex@lololai.com)
8 Aug 2025
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 (mailto: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 (mailto:alex@lololai.com)
Episode notes
🎙️ Guardrails & Governance – From Kitchen Table to Boardroom
Why does “governance” sound scary when it’s really just handing your kid scissors — plus the rule “only at the kitchen table, blade down”? In this Executive Edition of Practical Prompting, host Alex Kalish shows how the same guardrails that protect family photos can save your company millions in breach fines.
Act I: Tiny Guardrails, Big Impact
Kid-Friendly Content Policy – A 150-word, emoji-powered house rule that keeps kids (and their data) safe in AI chats.
Voice-Assistant Auto-Delete Drill – One prompt, three taps, and every Alexa recording purges itself after 90 days.
Skip the buzzwords—see how consent, clarity, coverage, and quick checks turn abstract “AI safety” into a fridge-magnet rule.
Act II: Risk & Compliance at Enterprise Scale
“Tea” App Meltdown – Viral women-only dating app shipped Firebase keys in its code; 72 k selfies and 1.1 M DMs splashed across the internet.
What to do Today – Changing thought processes from "we need a plan" to "we carved out an enterprise license."
Good intentions aren’t a defense; if an intern can git push an API key at 2 a.m., you need guardrails yesterday.
You’ll learn how to 🔍
Translate “governance” into simple, repeatable household habits.
Recognize potential issues before they hit the headlines.
Establish governance without sacrificing speed.
🎯 Your Challenge: Email alex@lololai.com (mailto: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 (mailto:alex@lololai.com)
29 Jul 2025
Practical Prompting 06 - Executive: Constraints
🎙️ Half-Budget, Full Impact
What if your ops budget was cut in half—today—but your KPIs stayed the same?
In this Executive Edition of Practical Prompting, host Alex Kalish turns a high-pressure constraint into a strategy accelerator.
Act I: Household Constraints, Executive Mindset
What can GenAI do with 4 mouths to feed, $80, and a week of dinners? More than you'd think. Alex walks through how a simple one-liner prompt turned into a full dinner plan, shopping list, and prep schedule—in seconds. But the real lesson isn’t about food. It’s about constraint-stacking as a forcing function for smart trade-offs and AI-powered planning.
Act II: Strategy Under Pressure
Alex zooms out to the boardroom: what happens when you treat headcount plans, SLAs, or revenue goals the same way? Hear how one VP used a reusable GenAI prompt chain to simulate outcomes, cut FTEs by 30%, and accelerate throughput—all with KPI integrity intact.
You’ll learn how to:
Frame goals in messy human language—and let GenAI structure the strategy.
Generate decision-ready artifacts like vendor matrices, risk maps, and KPI deltas.
Use GenAI like a co-strategist, not just a summarizer.
🎯 Your challenge: Take one constraint that’s been keeping you up at night, and throw it at GenAI—no polish, no perfection. Just start. Screenshot what you get and tag #PracticalPrompting.
Listen, rate, & review: Email alex@lololai.com (mailto:alex@lololai.com) or tag on LinkedIn with what topic you'd like to see covered. The first ones who do will get a complementary stop sign sticker with "Ask AI First".
Disclaimer: Views expressed are Alex’s own and do not represent any employer; no confidential information is shared.
Connect: alex@lololai.com (mailto:alex@lololai.com)
24 Jul 2025
Practical Prompting 05: Your Journey
Grab your coffee and your passport: this episode shows how GenAI can plan a multi-city European getaway and become the everyday co-pilot you didn’t know you needed.
Act I: Vacation Wizardry
Tabs everywhere, brain in overdrive? Alex demonstrates a repeatable prompt that turns loyalty-point juggling and must-see lists into a polished 10-day itinerary in seconds. Learn the simple role → task → constraints template, the art of micro-iterations, and why you’ll never spreadsheet a trip again.
Act II: The 30-Prompt-a-Day Journey
Follow the progression from “I barely open ChatGPT” to firing off 30+ prompts a day. You’ll hear:
Phase 1 – Sporadic: recipes and random dad jokes.
Phase 2 – Discovery: “Wait, it can do that?” resume rewrites, SQL assists, meeting agendas.
Phase 3 – Habitual: email drafts, stand-up notes, voice-to-prompt workflows, and a five-minute guardrail to stay focused.
Alex shares a habit-stack blueprint and a daily “Ask AI First” trigger that transforms friction points into instant leverage.
Listen, rate, & review: Track your prompts for one week. If you hit 10+ per day, post a screenshot with #PracticalPromptingPodcast and tag @Alex Kalish on LinkedIn. The first 50 listeners get the limited-edition stop-sign “Ask AI First” sticker for your laptop.
Disclaimer: Views expressed are Alex’s own and do not represent any employer; no confidential information is shared.
Connect: alex@lololai.com (mailto:alex@lololai.com)
17 Jul 2025
Practical Prompting 04: You Can Fix It
Episode Description – “You Can Fix It” Grab your phone and your repair tools: this episode turns GenAI into both a pocket-size repair walkthrough and the uses at the workplace.
Act I – The Litter-Robot Lifesaver: A pre-coffee catastrophe: the self-cleaning litter box is flashing red and stinking up the house. Instead of YouTube rabbit holes, Alex snaps one photo, feeds it to GenAI, and gets a three-step repair plan that realigns a wayward sensor and restores feline glory in minutes. The segment breaks down the exact “photo + prompt” recipe so listeners can troubleshoot any household gadget on the fly.
Act II – Scaling the Snapshot Superpower: Now swap the litter clumps for conveyor belts, espresso machines, or HVAC units. Alex shows how the same image-first workflow slashes mean-time-to-repair on the shop floor:
Listen, rate, & review: Send a screenshot of your review to get free access to Alex’s Udemy mini-course Crafting High-Leverage Prompts. Or post a screenshot of your next GenAI win—trip itinerary, killer email, anything—with #PracticalPromptingPodcast and tag on LinkedIn @Alex Kalish. First 50 get the stop sign "Ask AI First" sticker.
Disclaimer: Views expressed are Alex’s own and do not represent any employer; no confidential information is shared.
Connect: alex@lololai.com (mailto:alex@lololai.com)
11 Jul 2025
Practical Prompting 03: Experimentality
Grab your phone and your curiosity: in this episode we turn everyday snapshots into AI-powered wins.
Act I guides you through a photo-based household walkthrough from using GenAI to meal-plan from your fridge, untangle to-do list chaos, self-diagnose that leaking faucet, and more.
Act II scales the magic with a repeatable individual 2-step ritual and a team-based 5-step ritual. It talks about a “one-GenAI-cool-use-per-person” sync format that transforms casual tests into measurable business ROI. One photo, one experiment, one culture shift. Tune in and start compounding your AI gains with Practical Prompting.
Listen, rate, & review: Send a screenshot of your review to get free access to Alex’s Udemy mini-course Crafting High-Leverage Prompts.
Disclaimer: Views expressed are Alex’s own and do not represent any employer; no confidential information is shared.
Connect: alex@lololai.com
11 Jul 2025
Practical Prompting 02: My first 90 days of GenAI
Episode 02 – “My First 90 Days with GenAI”
Follow host Alex Kalish’s leap from curious AI tourist to daily power-user.
Act I: turns GenAI into a pocket coach with mood-ring journaling, five-line reflections, CBT ladders, and future-you postcards that slash mental load .
Act II: maps the exact four-phase ramp—from early fumbling to a workplace flywheel—serving up copy-and-paste prompts so you can shortcut the curve tonight . Tune in for relatable missteps, concrete wins, and a challenge to spark your own AI adoption.
Listen, rate, & review: Send a screenshot of your review to get free access to Alex’s Udemy mini-course Crafting High-Leverage Prompts.
Disclaimer: Views expressed are Alex’s own and do not represent any employer; no confidential information is shared.
Connect: alex@lololai.com
10 Jul 2025
Practical Prompting 01: Stop Waiting for the Perfect Tool
Everyone’s hunting for the perfect GenAI platform, an awesome Agent, some perfect tool. Meanwhile, opportunity is passing them by. In this debut episode, Alex dismantles the “perfect-tool” myth and shows how off-the-shelf apps like ChatGPT can slash hours off operational workflows today. You’ll hear a real-world story from the Pennsylvania government pilot that cut policy-drafting and HR classification time to minutes, and learn the “Rule of 10” ideation playbook for sparking 1,000 GenAI use-cases in two weeks.
Listen, rate, & review: Send a screenshot of your review to get free access to Alex’s Udemy mini-course Crafting High-Leverage Prompts.
Disclaimer: Views expressed are Alex’s own and do not represent any employer; no confidential information is shared.
Connect: alex@lololai.com
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