Asking Good Questions with Edward Roske

Edward Roske
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  • Technology

 In this podcast, we explore the CFO's office's past, present, and future, examining how technology and AI are transforming finance. Join Edward Roske and referents as they discuss innovative ways to enhance the role, optimize processes, and shape the future of financial leadership.  Designed for CFOs and finance leaders, each episode provides actionable insights into leveraging technology to drive growth, improve efficiency, and address challenges. With an engaging tone, the podcast simplifies complex concepts, covering topics like automating tasks, real-time data analysis, and strategic planning. Key themes include the shift from traditional finance methods to innovative, technology-driven processes and real-world examples like scenario modeling and automated reporting. The podcast also highlights future trends, such as generative AI for forecasting and advanced analytics for decision-making, promising to shape financial management. Edward Roske inspires listeners with practical advice and tools to embrace technology confidently. Tune in for strategies to thrive in the evolving financial landscape.

  1. 3d ago

    AI Isn't Failing Because of the Model | Lillian Buziak

    Lillian Buziak runs an AI company in Silicon Valley, so you'd expect the cheerleading. Instead she opened with her Gen Z kids overruling her at home, and halfway through she laid out the squeeze her whole company lives in: if you don't adopt it, you fall behind, and if you do adopt it, you own all these new risks. She cites research (a Forrester or a McKinsey, she can't remember which, and I respect the honesty) that 88% of AI pilots never reach production. They die on governance and on getting the data somewhere the AI can actually see it, all the boring stuff nobody puts in a keynote. "That is real, and that is where you can either succeed or fail." Full disclosure, which I also make on the show: Lillian is the CEO of Caprus AI, which builds AI for finance teams, and I invested way back at the beginning. This episode is not why. Her model for trusting AI runs the same play she runs on actual humans: treat it like your newest intern. Small tasks first, more responsibility as it earns it. Caprus even has a literal internship program now, teaching college kids to use AI and, her words, to ask better questions. Her phrase for the whole thing is "whatever we learn, we teach." She also explained why every billboard on the 101 is AI now, including one that's just a person smiling in a log cabin (I have a theory), what advice 2030 would send back to 2026, what happens when vibe coding runs into enterprise security, and context engineering, which is the unglamorous work of building your company a brain. I'm Edward Roske, and this is Asking Good Questions. New conversations with the people figuring out the human side of AI. If one of these questions stuck with you, subscribe and send it to someone who'd take the other side. The Caribbean AI Summit is October 9-10 in San Juan, Puerto Rico. Come ask better questions with us: CaribbeanSummit.AI LINKS Caribbean AI Summit (Oct 9-10, San Juan): https://CaribbeanSummit.AI Caprus AI: https://caprus.ai Lillian on LinkedIn: https://www.linkedin.com/in/lillianbuziak/ BOOKS & RESEARCH MENTIONED The 88%-of-pilots-never-reach-production stat (her citation, attributed on air to "a Forrester or a McKinsey") AgentCube, Caprus's product (the layer between your data and the AI) Also mentioned: ODTUG (she's the vice president), Oracle AI World, ChatGPT, Claude, AnthropicThis episode of Asking Good Questions is brought to you by Caprus.Ai. Check how we empower the office of the CFO to harness the transformative potential of artificial intelligence (AI) and revolutionize their operations.

  2. 6d ago

    Trust but Verify Applies to AI Too | Elizabeth Ferrell

    Elizabeth Ferrell is the Assistant Corporate Controller and Finance AI Leader at The Kroger Co., which means 450,000 paychecks and the numbers behind the federal filings all run past her. So I opened with the hardest question I had. Would you let AI touch one of those numbers? She would. Trust but verify has been the whole job for her entire career, and she says it applies to humans or AI the same way. The thing I hadn't thought about is that you used to hand-test maybe 10% of the numbers and AI can test close to all of them, and she still runs the manual 10% on top of it. Her way of putting it is that the audit controls are maturing as fast as the AI is. Then the conversation turns human, which is where Elizabeth is at her best. "I'm not looking for different people," she says. "I'm looking to enable the people I have." She runs an exercise on her finance teams where you boil your job down to one sentence, and hers is "put the right number in the right box at the right time." Anybody whose sentence is a list of tasks is in trouble, and her new funnel to leadership is people who can ask the right questions and find the flaws in the AI's logic. Yes, she said that on my show. (She was subscriber number three to this podcast, after my mother and me. I'm told my producer held off until she saw whether we'd make it to three.) Sixty AI use cases turned up in under three weeks, and everything at Kroger is floating in what she calls the AI soup. When I asked why anyone should give up two days for a conference, she got to the line I've been repeating since we recorded: "That's what AI's good at, but it's what we're better at... And so go be it. Go human this thing." I'm Edward Roske, and this is Asking Good Questions. New conversations with the people figuring out the human side of AI. If one of these questions stuck with you, subscribe and send it to someone who'd take the other side. Elizabeth speaks at the Caribbean AI Summit this October in San Juan, which she points out is a lot sunnier than Ohio in October. She's right, and you can come verify that yourself: CaribbeanSummit.AI LINKS Caribbean AI Summit (Elizabeth speaks, Oct 9-10): https://CaribbeanSummit.AI Elizabeth on LinkedIn: https://www.linkedin.com/in/elizabeth-ferrell-606695b/ ODTUG, the Oracle developer and technology user community: https://www.odtug.com BOOKS & RESEARCH MENTIONED ODTUG and Kscope (the Oracle developer and technology user community) Also mentioned: Oracle, Essbase, Excel, MCP, The Kroger Co.This episode of Asking Good Questions is brought to you by Caprus.Ai. Check how we empower the office of the CFO to harness the transformative potential of artificial intelligence (AI) and revolutionize their operations.

  3. Sep 3

    I'm More Worried About Humans Than AI | Idoia Salazar

    Dr. Idoia Salazar advises governments on AI ethics, and I went in expecting the slow-down speech. What I got was her driver's license argument: AI is powerful enough that you should have to learn it before you use it, and right now nobody is teaching anybody. Idoia is the President of OdiseIA, Spain's observatory on the social and ethical impact of AI, and she helped build Europe's first AI regulatory sandbox. She teaches and writes books on top of that. I asked her whether the urgent job of the decade is rewriting AI law. She said school. The skills that survive this wave are human ones, and we're not teaching them fast enough. She is afraid of people. "We are going to become a society very easy to be manipulated. For me, this is one of the biggest risks of artificial intelligence." Later she put it flatter, and that line became the title of this episode. "I'm more worried about humans than the technology." We spend a while on which science fiction movie actually got AI right, which turns into her explaining that the sci-fi you grew up on shapes how your whole culture feels about robots (she'd just come back from Keio University in Tokyo, where the stories people grew up on made robots the friendly ones). People are marrying chatbots now. She has a book coming in November about AI twins. I also made her sit through my Clorox-and-Windex safety test. I ask every new model whether mixing them gets me the best of both. ChatGPT thinks it's funny. Claude gets offended, so these days I go back afterward and admit I was only testing it. (Just in case.) I'm Edward Roske, and this is Asking Good Questions. New conversations with the people figuring out the human side of AI. If one of these questions stuck with you, subscribe and send it to someone who'd take the other side. Idoia speaks at the Caribbean AI Summit this October in San Juan. Her whole Summit talk fits in one breath: do not be afraid, get ready. San Juan this October is a good place to start: CaribbeanSummit.AI LINKS Caribbean AI Summit (Idoia speaks, Oct 9-10): https://CaribbeanSummit.AI Idoia's site: https://idoiasalazar.com OdiseIA4Good foundation: https://www.odiseia4good.org Idoia on LinkedIn: https://www.linkedin.com/in/idoiasalazar/ BOOKS & RESEARCH MENTIONED Idoia's new book on AI twins and the universal AI assistant (out in November) OdiseIA (Spain's observatory on the social and ethical impact of AI) The EU AI Act and Europe's first AI regulatory sandbox The A2A protocol (her HTTP comparison, agents talking to agents) The sci-fi tour: 1984, Animal Farm, Brave New World, Terminator, Her, Back to the Future Part II Also mentioned: ChatGPT, Claude, Keio University in TokyoThis episode of Asking Good Questions is brought to you by Caprus.Ai. Check how we empower the office of the CFO to harness the transformative potential of artificial intelligence (AI) and revolutionize their operations.

  4. Sep 1

    Puerto Rico's First Unicorn Starts at a Hackathon | Pedro Cruz

    Three days after Hurricane Maria, Pedro Cruz lost his job. No electricity, no plan. So he pointed a drone at the SOS messages people had spray-painted on their roads, because the government helicopters kept flying over and the help kept not arriving. That project won an IBM hackathon and became DroneAid. This was back when AI was still "ten years away." Pedro's thesis comes out of that story. A fresh ChatGPT session knows nothing about you. Context is what makes AI useful, and locals are the context. I ended up summarizing it back to him as AI built for Puerto Rico beating AI imported to it. But the line I keep coming back to is darker: nobody is coming to fix the island. "We shouldn't expect it to change. We need to create that change." Singapore did it in 50 years. Pedro's mechanism is the hackathon he's leading at the Caribbean AI Summit: get hundreds of people building, and in a year or two, maybe a unicorn, maybe two. He also co-founded an AR startup (MeshMap, a few million raised), there's an AI-designed Obama statue in Old San Juan that nobody asked for, a surprise pivot into nuclear energy, and a roast where he made me feel geologically old (I'm 52, his parents are 53). And I spent a good minute proposing that Waymo prove itself on an island where the distance markers are in kilometers and the speed limits are in miles per hour. I'm Edward Roske, and this is Asking Good Questions. New conversations with the people figuring out the human side of AI. If one of these questions stuck with you, subscribe and send it to someone who'd take the other side. Pedro leads the hackathon at the Caribbean AI Summit this October in San Juan. Come build the unicorn: CaribbeanSummit.AI LINKS Caribbean AI Summit (Pedro leads the hackathon, Oct 9-10): https://CaribbeanSummit.AI Pedro on LinkedIn: https://www.linkedin.com/in/pedrocruztech/ Pedro's site: https://pedrocruz.io Pedro on Instagram and X: @pedrocruztech BOOKS & RESEARCH MENTIONED DroneAid (Pedro's post-Maria SOS-detection project, IBM hackathon winner) MeshMap (his AR startup; Magic Leap experiences in New York) BrainHi (the Puerto Rico startup that went through Y Combinator) The BONUS nuclear reactor in Rincón (Puerto Rico's 1960s experiment) Also mentioned: ChatGPT, Claude, Pokemon Go, Waymo, FarmVille, the Wayback MachineThis episode of Asking Good Questions is brought to you by Caprus.Ai. Check how we empower the office of the CFO to harness the transformative potential of artificial intelligence (AI) and revolutionize their operations.

  5. Aug 21

    You Can't Prompt Your Way to a Flying Car | Tim Berglund

    Tim Berglund spent twenty years calling AI a promissory note. Always a bright future, never a bright present. (The field was born overpromising. The Dartmouth crew figured they'd nail human intelligence in a couple of months. That was the 1950s.) Then in December 2025 he opened Claude Code and said it on tape: "Okay, this is real." So I asked him what he sees now that he didn't see in the twenty years he spent calling this a trick. Coding got cheap, and cheap coding exposed the true limiting factor, which is that it's hard to make things that don't suck. His words: coming up with a good idea, still hard. Designing a product interface, still hard. Seven months into the agentic revolution, Jira has not suddenly become good. (Check your own tools and tell me he's wrong.) He's completely sold on the tool and completely unsold on the idea that there's a mind in there. It talks like a mind, but it's not one. We dig into why the first machine that uses language the way we do keeps fooling our theory-of-mind reflex, whether AI is making work better or just faster, what the Turing test is worth now that it's been passed and gotten boring, ELIZA pulling the same trick in 400 lines of code back in the sixties, and why his firmware is still handcrafted, artisanal, small-batch C++ (like making your own furniture out of wood). Also in here: the day Claude Opus started calling the other agents its siblings (that terminology did not come from me), the Postmodernism Generator as 1990s proto-slop, the bicycle being invented after photography, and my air-band machine. I have played Ode to Joy on an air piano. It was not quite as much fun as I thought it would be. (The air drums are just clank, clank, clank.) I'm Edward Roske, and this is Asking Good Questions. New conversations with the people figuring out the human side of AI. If one of these questions stuck with you, subscribe and send it to someone who'd take the other side. Tim speaks at the Caribbean AI Summit this October in San Juan, on the real history of AI. He gave me a taste of it in this episode and offered to give me the rest, which I turned down so he'd still have a talk to give. Come find us: CaribbeanSummit.AI LINKS Caribbean AI Summit (Tim speaks, Oct 9-10): https://CaribbeanSummit.AI Tim's site (writing, talks, Substack): https://timberglund.com Tim on X: https://x.com/tlberglund BOOKS & RESEARCH MENTIONED The Dartmouth workshop (the 1950s proposal that kicked off AI as a field) ELIZA, Joseph Weizenbaum's 1960s chatbot (Tim: about 400 lines of code) The Postmodernism Generator (the 90s fake-essay site Tim cites as proto-slop) The Turing test (passed, and passe, per this conversation) The Hitchhiker's Guide to the Galaxy, Douglas Adams (my fault, as usual) Also mentioned: Claude Code, Claude Opus 4.8 and Sonnet 5, Apache KafkaThis episode of Asking Good Questions is brought to you by Caprus.Ai. Check how we empower the office of the CFO to harness the transformative potential of artificial intelligence (AI) and revolutionize their operations.

  6. Aug 19

    With AI, the Winners Will Be the Small Companies | Juan Carlos Pedreira

    Juan Carlos Pedreira told me about a study from this May: 90% of Puerto Ricans only use ChatGPT. Then he told me the winners of the whole AI era will be the small guys. He'd know: he co-founded the Social Business Hub, a digital consultancy in San Juan, and for 15-plus years he's been dragging traditional media companies (Teleonce, Spanish Broadcasting System, Telecinco, and others) into the digital age, and now the AI one. He advises businesses across Puerto Rico, the Dominican Republic, Costa Rica, and Panama, so he sees who's moving and who's stuck. And right now he's running a project where four people do work that used to take five or ten. We get into the two kinds of workers showing up inside every company: the rogue AI person with all the tools, and the one still feeding the fax machine. His dad's IBM XT makes an appearance, along with the accountant who went from "I lost my job" to all in, which Juan Carlos says is happening again right now at super hyper speed. Also in here: why AI belongs with the CEO instead of the IT department, what happens when 800 or 900 million people get handed a very powerful tool without instructions (his numbers), the client Excel report that took a full day and now takes minutes, and my confession that I've got fourteen agents running right now, and that managing them has somehow become a 24/7 job (they do not sleep, which sounded like a feature when I set them up). His two-year prediction: the gap between small and big gets wider, driven by upstarts completely off the radar. I think we're not far from the first one-person billion-dollar company. At one point I told him I had about 45 follow-up questions and genuinely didn't know which one to ask first. Come see which one I picked. I'm Edward Roske, and this is Asking Good Questions. New conversations with the people figuring out the human side of AI. If one of these questions stuck with you, subscribe and send it to someone who'd take the other side. Juan Carlos speaks at the Caribbean AI Summit this October in San Juan. His talk: "AI for Humans: How a Small Business Can Now Out-Compete a Fortune 500 Without Hiring a Single Engineer." Come find us: CaribbeanSummit.AI LINKS Caribbean AI Summit (Juan Carlos speaks, Oct 9-10): https://CaribbeanSummit.AI Social Business Hub (SBH Digital), Juan Carlos's consultancy: https://sbhdigital.com Juan Carlos on LinkedIn: https://www.linkedin.com/in/juancpedreira/ Juan Carlos on X: https://x.com/juancpedreira (on air he calls X his "social media drug") BOOKS & RESEARCH MENTIONED The PR Digital Trends Study 2026 (Estudios Tecnicos + the SME Digital & Innovation Forum, May 2026), the study Juan Carlos cites: https://newsismybusiness.com/puerto-rico-digital-media-use-hits-95-in-2026-study/ "The AI Daily Brief" with Nathaniel Whittemore, the daily AI podcast Edward listens to every day (he blends the name to "the AI Daily Breakdown" on air; this is the real show): https://aidailybrief.ai Anthropic's AI courses (where Juan Carlos points business owners who ask him where to start) Also mentioned: Claude, Claude Code, and Claude Cowork; MCP connectors; QuickBooks; Shopify; LinkedIn Learning; CourseraThis episode of Asking Good Questions is brought to you by Caprus.Ai. Check how we empower the office of the CFO to harness the transformative potential of artificial intelligence (AI) and revolutionize their operations.

  7. Aug 5

    We're Running an AI Experiment on Our Kids | Bivin Sadler

    We're running an experiment on our kids. And we won't see the results for about 20 years. That's Bivin Sadler. He teaches the data scientists at SMU. He's also the dad of an 8-year-old whose default study partner is now an AI. So which is it? Is Gen AI the best tutor a kid ever had, or the thing that hollows out the ability to think? Bivin says it hangs on whether they learned the first principles first. His fix for keeping students actually learning, from kindergarten through college, is an 800-year-old idea: the oral exam. The problem was always the math. Thirty students at thirty minutes each doesn't fit in a semester. So Bivin built Elenkis, a voice AI that runs a real oral exam for every student (yes, the AI asks the questions now), and finally makes it work for a whole school. We get into "trust, but verify" (the same rule he gives his 8-year-old and AT&T's data scientists, which should tell you something) and the stuff you only ever learned by taking the long way around. Plus what actually gets a new grad hired now, which isn't what you'd guess. Whether you're raising a kid on this stuff or teaching one, stick around for this one. Asking Good Questions is hosted by Edward Roske. New conversations with the people figuring out the human side of AI. If one of these questions stuck with you, subscribe and send it to someone who'd take the other side. Bivin joins Edward on stage at the Caribbean AI Summit this October. Come find us: CaribbeanSummit.AI LINKS Bivin's book, "Time Series for Data Science: Analysis and Forecasting" (CRC Press): https://www.routledge.com/Time-Series-for-Data-Science-Analysis-and-Forecasting/Woodward-Sadler-Robertson/p/book/9780367543891 Elenkis, Bivin's oral-assessment platform: https://elenkis.com Caribbean AI Summit (Bivin speaks, Oct 9-10): https://CaribbeanSummit.AI Bivin Sadler at SMU: https://datascience.smu.edu/about/leadership-and-faculty/bivin-sadler/ Bivin on LinkedIn: https://www.linkedin.com/in/bivin-sadler/ BOOKS & RESEARCH MENTIONED "Time Series for Data Science: Analysis and Forecasting" - Wayne Woodward, Bivin Sadler, and Stephen Robertson (Chapman & Hall/CRC, 2022) UNESCO, "Guidance for generative AI in education and research" (2023) Ethan Mollick, The Wharton School - his approach to students using AI in class Khan Academy - Sal Khan's case for an AI tutor for every student Elenkis - Bivin's platform bringing the oral exam back at scale (elenkis.com) Also mentioned: SMU's M.S. in Data Science program, and the AT&T data-science bootcamp Bivin helped buildThis episode of Asking Good Questions is brought to you by Caprus.Ai. Check how we empower the office of the CFO to harness the transformative potential of artificial intelligence (AI) and revolutionize their operations.

  8. Jul 22

    Dr. AI Says That for Puerto Rico, AI Is Life and Death | Nesty Delgado

    Nesty Delgado commanded a Puerto Rico National Guard task force through Hurricane Maria. His line about it stopped me cold. "We were making life-and-death decisions back there, with incomplete data." Today, on the island, they call him Dr. AI. I didn't fully see it until we were in the conversation. For Puerto Rico, AI is a matter of life and death. Economic and cultural, yes. And if the next storm finds us as blind as the last one, literal too. What got me most was the order he puts things in. Values and principles at the top, emotional intelligence under that, tools dead last. Software barely makes his list. (I've written ten books trying to explain this stuff without the jargon. Nesty does it on live TV, which feels like cheating.) We get into shadow AI and the company data walking out the door on personal accounts, the clock that just jumped from 40 percent to 65 percent, why he warns his own competitors, and the Caribbean AI Summit he wants ten thousand people to attend. The Caribbean AI Summit is October 9 and 10 in San Juan, and Nesty presents. CaribbeanSummit.AI Asking Good Questions is Season 3: The Human Side of AI, hosted by Edward Roske. New conversations with the people building AI, and the rest of us wrestling with it. Subscribe and you'll catch every one. LINKS Nesty Delgado: NestyDelgado.com Team 1144: team1144.com AblaTek: ablatek.com Caribbean AI Summit: CaribbeanSummit.AI Find Nesty on LinkedIn, Instagram, and Facebook as Nesty Delgado S3:E2This episode of Asking Good Questions is brought to you by Caprus.Ai. Check how we empower the office of the CFO to harness the transformative potential of artificial intelligence (AI) and revolutionize their operations.

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About

 In this podcast, we explore the CFO's office's past, present, and future, examining how technology and AI are transforming finance. Join Edward Roske and referents as they discuss innovative ways to enhance the role, optimize processes, and shape the future of financial leadership.  Designed for CFOs and finance leaders, each episode provides actionable insights into leveraging technology to drive growth, improve efficiency, and address challenges. With an engaging tone, the podcast simplifies complex concepts, covering topics like automating tasks, real-time data analysis, and strategic planning. Key themes include the shift from traditional finance methods to innovative, technology-driven processes and real-world examples like scenario modeling and automated reporting. The podcast also highlights future trends, such as generative AI for forecasting and advanced analytics for decision-making, promising to shape financial management. Edward Roske inspires listeners with practical advice and tools to embrace technology confidently. Tune in for strategies to thrive in the evolving financial landscape.

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