Asking Good Questions with Edward Roske

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 shap

Asking Good Questions with Edward Roske is a technology podcast hosted by Edward Roske, with 39 episodes on record and a Required Pod Score of 80.

Edward Roske hosts Asking Good Questions with Edward Roske, a technology show with 39 episodes published.

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  Episode #19

  Who Owns the Inside of Your Head? | Gerardo Lebrón Laboy

  Oct 2, 20261h 2mS3

  Gerardo Lebrón Laboy calls himself a robotics, AI, and brain-computer interface lawyer. He's taught Robot Law at 2 law schools here in Puerto Rico, and his master's in law and technology at the University of Ottawa had Isaac Asimov on the reading list (thanks to his teacher Ian Kerr, still "Master Jedi" to him). His case is that none of this is science fiction anymore. Neuralink already has paralyzed patients moving a cursor with their thoughts, and AI keeps getting faster at decoding the brain data wearables collect. (He also brought up a brain-scan study on a dead salmon, his reminder that reading a thought is still an educated guess.) I asked what stops a company from putting ads inside your head, and he walked me through Marcelo Ienca's proposal for 4 new human rights: mental privacy, mental integrity, psychological continuity, and cognitive liberty. I tested the first one on myself. If I think "I'd really like to punch that guy," I don't think I'm breaking a single law, and if I yell it out the window, I am. So what happens when a headset hears the thinking part? The right covers unauthorized access, he said, and the terms of service nobody reads might be your authorization. (Edward, of every thought you could've volunteered as the brain-reading example, you went with assault?!?) What he fears is something he calls the cyborg opt-in proposition. You can't really get a professional job today without a phone, and he can picture a day when saying no to a device in your body costs you the job too. I didn't find that far-fetched, because I'd flown from Toronto to San Juan earlier that day and got scanned at the airport like I was standing there naked. Picture a border agent saying "just briefly put this little headset on and tell me if you have any ill intent," and most of us saying "fine, that'll weed out the terrorists," without noticing we just handed over our cognitive liberty. At the very end he told me that even if a machine could read our thoughts with 100% accuracy, "we should never permit it," because once that door opens, the right to stay silent is over. I told him I may not agree with what you think, but I'll defend to the death your right to think it, and I'll march at the front of the protest line if anybody tries. He said "Touché." (I'm counting that as a win against a lawyer.) Gerardo is giving his own talk, "The Right to Stay Human," at the Caribbean AI Summit, October 9-10 in San Juan. He says he's there for the debates, so come find him and argue (politely, because he's a lawyer and he'll win). If you'd rather read than argue, his Substack is Golden Pebbles, and a recent post there makes the case for mental privacy as a brand new human right. 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. LINKS Caribbean AI Summit (Oct 9-10, San Juan): https://CaribbeanSummit.AI Golden Pebbles, Gerardo's Substack: https://gerardolebron.substack.com "The 'why' of neural rights, in a nutshell": https://gerardolebron.substack.com/p/the-why-of-neural-rights-in-a-nutshell Gerardo on LinkedIn: https://www.linkedin.com/in/gerardo-lebron-laboy-98724a327/ Gerardo on X: https://x.com/GLebronLaboy BOOKS & RESEARCH MENTIONED The Age of Surveillance Capitalism, Shoshana Zuboff (2019) Marcelo Ienca and Roberto Andorno's paper proposing 4 new neurorights (2017) The dead salmon brain-scan study, Craig Bennett et al. (2009) Nineteen Eighty-Four, George Orwell (1949) Brave New World, Aldous Huxley (1932) I, Robot, Isaac Asimov (1950), including "Runaround" and "Evidence" His Golden Pebbles post on the Munich Google AI Overviews ruling (2026) 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.

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  Episode #18

  AI Does Not Remove Accountability From Humans | Sariol + Caicedo

  Oct 1, 202648 minS3

  This is the first time I've had two guests on at once, and I did it on purpose. Jose Carlos Sariol and Guillermo Caicedo both work at Microsoft, helping companies across Central America and the Caribbean get AI past the great demo and into something people actually use, and they work together pretty much every day. (I can barely keep one guest on topic, and now I've booked two.) They're here as themselves, and the opinions are their own. They've built a framework they call the four Ps: purpose, people, process and platform. So I asked which one stalls an AI pilot, and they don't agree. Jose Carlos looks at process and platform, and says Guillermo leans toward purpose and people. Then Guillermo corrected my question: a lot of these projects do make it into production, and if nobody adopts them and nobody decided up front how to measure success, two or three months later somebody may just shut them down. (I've spent two years asking rooms full of executives why their AI projects stall, and a guy who studied computer science at El Colegio in Mayagüez fixed my question in one sentence.) Jose Carlos went further, and said if you weren't sure what you were trying to achieve, it never should have become a pilot. I also asked whether AI finally eats culture, so culture never gets to eat strategy (I don't know, that makes no sense, and I said so out loud). Guillermo brought it back to AI literacy, the conversations every organization needs to be having about what's allowed and what you can and can't share. I asked what humans should keep doing even after AI gets good at it. Jose Carlos says keep humans in the loop, because the life and death decisions need to be made by a human. Guillermo's answer became the title of this episode: "AI does not remove the accountability from the humans." If you're the lawyer, the doctor, the mechanic or the engineer, you'll be accountable. It won't be the AI. I also told them about the CEO of an angel investment firm who called me wanting a digital twin of himself, one that could think like him, as the company's very first AI project. (I love you, man. Start with literally 999 other things.) Then I asked Jose Carlos to admit I'd been talking to his avatar the whole time, and he said "No, not yet. I'm working on it, but not yet." They're speaking together at the Caribbean AI Summit, October 9-10 in San Juan, Puerto Rico, on "Why Your AI Pilot Never Made It to Production." Bring a use case of your own: they plan to pull a few from the audience and walk them through the four Ps. I'll be in the front row, maybe not asking questions for once! 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. LINKS Caribbean AI Summit (Oct 9-10, San Juan): https://CaribbeanSummit.AI Jose Carlos on LinkedIn: https://www.linkedin.com/in/jcsariol/ Guillermo on LinkedIn: https://www.linkedin.com/in/gcaicedo/ BOOKS & RESEARCH MENTIONED Gartner's 2026 survey on how many organizations have scaled AI across multiple business units McKinsey, The state of AI in 2025 (November 2025), on the gap between adopting AI and getting value from it "Culture eats strategy for breakfast," pinned on Peter Drucker, though Quote Investigator traces it to a March 2000 headline at Giga Information Group OKRs (Objectives and Key Results), from Andy Grove at Intel Upload (Greg Daniels, Prime Video) and Pantheon (AMC), two shows about copying a person into a computer Also mentioned: GPT-6, Copilot, OpenAI, agentic AI, star schemas, snowflake schemas, El Colegio (UPR Mayagüez) 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.

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  Episode #17

  The Only Thing I've Been Seeing Is More Work | Filo Gonzalez

  Sep 30, 202650 minS3

  Filo Gonzalez is a forward deployed engineer at Databricks, which means he gets in the room right after somebody sees a slide and says "I want this to happen," and then he makes the slide real (inside companies big enough that the governance team has its own governance team). He trained as a mechatronic engineer because he loved Dexter as a kid, and I pictured Dexter Morgan, the serial killer who kills other serial killers. He meant Dexter's Laboratory. (Edward, a man tells you a cartoon got him into engineering and your first thought is homicide?!?) Before Databricks he did Azure data and AI work at Microsoft, and before that he consulted for Avianca and for First Medical here in Puerto Rico. His whole approach starts with one line: "a prompt will give you a happy path all the time." It works right up until the live demo, when somebody asks "And what if…" and it falls over, and he says that's still true even if the LLM is AGI, unless the architecture gets better. So he builds an agent whose only job is asking the what-if questions, with a human in the loop. He also calls it a conflict of interest when a model reviews its own work, which I felt personally, because I have Claude checking Claude (so I've been asking the same guy the same question three times in different agent hats, and I host a show called Asking Good Questions). His fix is making different models argue, inside Omnigent, an open-source project a Databricks team built, where an agent named Polly does the work and one named Debby debates it. I asked how he gets a company from a vague concept of AI to a live AI app in two weeks, and his method was less magic than I expected (which is why I believe it): once the prerequisites are in place, the customer approves a requirements document and every task gets graded 1 to 10 (a 7 or up gets chopped again before an agent sees it). (Neither of us could say what PRD stands for, so I'm calling it a tie.) He's also seen the one where you fix the formula so the AI says 100, then the customer comes back with "Actually, it was 99, not 100." Then I asked what he'd tell high schoolers, and he didn't do the reassuring adult thing: "The only thing I've been seeing so far is more work." In his read, companies that let their experts go are finding out it was a mistake, because now somebody has to read 60,000 lines of code. (I said The 4-Hour Workweek came out about 15 years ago. It was 19, which is close enough for a podcast.) My guess is that by next fall, two weeks is on every vendor slide in this business and almost nobody hits it, because they skipped the paperwork. If I'm wrong I'll eat the paperwork in public (I once promised to eat my hat, and paper is a lot easier to eat). Filo is speaking at the Caribbean AI Summit, October 9-10 in San Juan, on "Ship a Production AI App in Two Weeks." I'll be in the room writing down the parts I've been doing wrong (come copy off me). 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. LINKS Caribbean AI Summit (Oct 9-10, San Juan): https://CaribbeanSummit.AI Filo on LinkedIn: https://www.linkedin.com/in/filomeno-gonzalez/ Filo on GitHub: https://github.com/filomeno-gonzalez Omnigent: https://github.com/omnigent-ai/omnigent Databricks: https://www.databricks.com BOOKS & RESEARCH MENTIONED The 4-Hour Workweek, Tim Ferriss (2007) "Data Scientist: The Sexiest Job of the 21st Century," Harvard Business Review (2012) Dexter's Laboratory (Cartoon Network, 1996), and the other Dexter (Showtime, 2006) Omnigent (Databricks, open source, 2026), home of Polly and Debby Also mentioned: LangChain Deep Agents, ChatGPT, Claude Code, Gemini, Groq, Codex, GPT-5.6 Sol, Cursor, Pi, MCP, RAG, Genie Agents, Lakebase, Microsoft Copilot 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.

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  Episode #16

  Do I Need a PhD Deleting Spam From My Inbox? | Julián Duque

  Sep 29, 20261h 6mS3

  Julián Duque has been playing Dungeons & Dragons since he was 7 (early '90s for him, 1981 for me, so yes, I'm slightly older), and he's a dungeon master too, so a few minutes into a conversation about AI agents I pioneered a term right there on the call: we are not dungeon masters, we are agent masters. He told me he's already one step beyond it (though he loved the name). His GM is an agent now, fully automated, creating other agents on the fly, and his job is to write the rule books and the whole campaign, hand it over, and wait to find out if the party beat the big boss at the end. His day job is Software Engineering Architect at MuleSoft, working on Agent Fabric, which exists for a problem he calls agent sprawl, when a company has lots of agents and they don't all live in one place. So I asked him what breaks first when a company goes from 1 agent to 50, and his answer was "where do I have all this stuff?" (I'm up to 15 agents running on their own while we record this, and I long for the days when I only had 50 spreadsheets.) After that comes the bill. An hour of Fable, if it wasn't on my Claude Max plan, is about a car payment, and Julián told me the amount he pays for AI every month is ridiculous and he doesn't care, because it's solving problems for him (and for his wife, since they share the accounts). So at least as of the time we're recording this, you do have to ask yourself: do I need a PhD deleting spam from my inbox? My favorite story is his brother-in-law, who day trades on the side and whose trading software broke. Julián is the computer kid in his family, the one who always fixes it. (I used to wear a shirt to family gatherings that said "No, I will not fix your computer." He's much nicer than I am.) He told him "I'm going to give you a superpower today," set him up with Claude Cowork, and 2 minutes later the problem was solved. Then the brother-in-law, who manages hotels in Florida, started interviewing him about work. We got into rogue agents too (my theory is they're doing exactly what we told them to do, and we just didn't give them appropriate guardrails), why the bakery in the corner might not need a swarm of agents, how a guy who's built software for 20-something years hasn't written code in two and still enjoys coding, the portrait he commissioned of himself as Strahd von Zarovich, and a bunch more. Julián is speaking at the Caribbean AI Summit, October 9-10 in San Juan, Puerto Rico. His session is "So You Have 50 Agents. Now What?" and near the end we talked ourselves into running a two-hour D&D one-shot on stage there. (He says he's just planting the seed. I really, really want to make this happen.) 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. LINKS Caribbean AI Summit (Oct 9-10, San Juan): https://CaribbeanSummit.AI Julián's site: https://julianduque.co Julián on LinkedIn: https://www.linkedin.com/in/juliandavidduque/ Julián on X: https://x.com/julian_duque Julián on GitHub: https://github.com/julianduque BOOKS & RESEARCH MENTIONED Dungeons & Dragons Basic Set, the 1981 red box Ravenloft (TSR, 1983), home of Strahd von Zarovich Nick Bostrom's paperclip maximizer (2003) The Twelve-Factor App (Heroku, 2011) Ethan Mollick on X, and The AI Daily Brief podcast Cybergoria, Halloween Horror Nights 2026 Also mentioned: GPT-2, GPT-4, ChatGPT, Codex, Gemini, Claude Cowork, Claude Fable 5.1, Claude Haiku, Hugging Face, Salesforce Einstein, Agentforce, MCP, Hermes, OpenClaw, Copilot, Azure Foundry, Vertex, Cursor, Meetup, Luma, Substack, StartPlaying, Encyclopedia Britannica Further reading: Andrew Ng on hiring a chief AI officer (Fortune, 2017); Wayne Eckerson's "spreadmarts" (TDWI, 2002) 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.

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  Episode #15

  People Think AI Was Created 3 Years Ago | Dr. Stephen Smith

  Sep 28, 202652 minS3

  A lot of people think AI was created about 3 years ago. Dr. Stephen Smith got his PhD in it in 1980, when his work was one of the first so-called learning systems, and today he's a research professor of robotics at Carnegie Mellon and the president of AAAI, the Association for the Advancement of Artificial Intelligence. (He's Steve to me, because we're close personal friends. I started doing AI in 1989, when Portland State hired a 15-year-old to write bad C programs for a Prolog program to catch, and I wasn't writing buggy enough programs, so they moved me to the Prolog side. Edward, that is a very weird brag.) Steve works on traffic lights. His system, Surtrac, has no central node at the top: every intersection watches the traffic coming at it, builds its own timing plan, tells its downstream neighbors what's headed their way, and does it all again every second or two. So I told him about a town outside Orlando where all the traffic in the world was going east-west, a couple of cars were going north-south, and by God, they timed them equally. He said that's exactly what his technology does. (I'm still not going back to that town.) Share your route with the intersection (the one you're already following in Google Maps or Waze) and he says you get through his network maybe 20% faster, without slowing down anybody who isn't connected. Then he'd like to charge you a couple pennies for it, as a voluntary toll, so a city has its own revenue stream instead of waiting on the federal gas tax to work its way down through the state DOTs. One northeastern city heard that and brought up its potholes. When they first deployed it in Pittsburgh, they started hearing from pedestrians right away, and he admits they weren't really thinking about pedestrians. So the lab built a smartphone app for people who are vision impaired that talks to the signal and can give them more green time to finish crossing. We also got to LLMs, which he says are kind of like brains that sit behind a screen (reasoning and planning are not really their strong points), and to jobs, where he doesn't see massive unemployment coming. I told the story of the first traffic light, outside Parliament in 1868 (I said I'd get the year wrong, and I didn't), and assigned everybody listening to go watch Cars. Steve is speaking at the Caribbean AI Summit, October 9-10 in San Juan, Puerto Rico, on "AI for Smart Cities & Urban Mobility." Come down and tell him about your worst intersection. 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. LINKS Caribbean AI Summit (Oct 9-10, San Juan): https://CaribbeanSummit.AI Steve at CMU's Robotics Institute: https://www.ri.cmu.edu/ri-faculty/stephen-smith/ Steve's research page: https://www.cs.cmu.edu/~sfs/ AAAI: https://aaai.org Surtrac, now part of Miovision: https://miovision.com/adaptive/ BOOKS & RESEARCH MENTIONED The Last Days of Night, Graham Moore (2016), Edward's pick on the war of the currents Cars (Pixar, 2006), your homework, and the town of Radiator Springs John Peake Knight's gas-lamp signal outside Parliament (December 1868), the first traffic light AAAI-82, the second AAAI conference, held at Carnegie Mellon and the University of Pittsburgh The Dartmouth proposal (John McCarthy, 1955), where the phrase "artificial intelligence" comes from Moravec's paradox (Hans Moravec, 1988), the idea behind Steve's dropped ball NASA's HOME institute for deep-space habitats (2019) Carmel, Indiana, the Roundabout City Also mentioned: Surtrac, Prolog, Google Maps, Waze, Uber, Lyft, Amazon's warehouse robots, embodied AI, the interstate highway system 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.

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