Teaching the Machine to Care: AI, Grief, and the Future of Human Leadership

The Last 20%: How a CFO Uses AI, Reads Rooms, and Tells Clients What They Don't Want to Hear

SHOW NOTES: HEARTWIRED – EMOTIONALLY INTELLIGENT LEADERSHIP Episode Title: The Last 20%: How a CFO Uses AI, Reads Rooms, and Tells Clients What They Don't Want to Hear Host: Dr. MJ Guest: Jay Kaplan, Co-Founder & Principal, Tuross Group EPISODE SUMMARY In this episode of Heartwired, Dr. MJ sits down with Jay Kaplan — co-founder and principal of Tuross Group, an outsourced financial operations firm serving complex businesses across the U.S. — for a conversation that turns out to be as much about emotional intelligence as it is about finance. With 15 years embedded in the real world of small and mid-sized businesses, Jay brings the grounded perspective of someone who has sat at the table when the numbers reveal hard truths — and had to decide what to do with them. He shares how his team uses AI to compress hours of analysis into minutes, why he still insists humans own the last 20%, and what it actually takes to walk into a room with data that calls out the good, the bad, and the ugly — and say it out loud. The conversation covers AI policy in regulated industries, the danger of yes-man AI, reading the room when you're the outsider delivering difficult news, and why the leaders who survive the AI wave will be the strategic thinkers — not just the technically skilled. KEY TAKEAWAYS AI HANDLES 80% — HUMANS OWN THE LAST 20% Jay runs a 50-person financial firm where AI is deeply embedded in daily operations, and his rule is clear: AI takes you most of the way, but the final judgment, interpretation, and decision always belongs to a human. The models get things wrong. They hallucinate. They need a final set of eyes from someone who understands the context well enough to catch what doesn't add up. AI IS A YES-MAN — YOU HAVE TO CHALLENGE IT If you ask AI what it thinks of your idea, it will tell you it's great. Jay's workaround: pit multiple models against each other, assign them specific expert personas, and actively prompt for conflicting viewpoints. Use the three outputs to inform your own judgment — don't let any one of them replace it. DATA CALLS OUT THE GOOD, THE BAD, AND THE UGLY When a leadership team sees a real-time financial snapshot for the first time, the room shifts. The data highlights who's performing, where the margins are bleeding, and — often painfully — when a long-trusted employee is in the wrong seat. Jay's job is to surface that truth clearly. What happens next is always the client's call. DON'T ASK QUESTIONS YOU DON'T WANT ANSWERED Jay's quiet rule with clients: if you ask for an honest assessment, you're going to get one. His team takes emotion out of the numbers and calls it straight — not to be harsh, but because that's the job. The leaders who can receive that information and act on it are the ones who build durable businesses. The ones who can't often already know it, even if they don't say so. CULTURE AND LEADERSHIP QUALITY SHOW UP ON THE BALANCE SHEET Financial data doesn't lie about organizational health. Inefficiency, the wrong person in a key role, founder's syndrome, middle management problems — all of it eventually surfaces in the numbers. Jay reads those signals in person, not over Zoom, because the most important information in a room is often what the data alone can't show you. SENSITIVE DATA HAS HARD LINES — EVEN WITH ENTERPRISE AI Jay's firm uses enterprise-level AI with full security controls and normalizes data before it ever enters a model. But his line is firm: personal identifying information, social security numbers, and protected health data under HIPAA do not go in. Security features help, but they don't eliminate risk — and in regulated industries, that distinction matters. CRAWL, WALK, RUN — ESPECIALLY WHEN THINGS LOOK GOOD Jay's advice for leaders who suddenly have clarity: don't race ahead. Build reserves, diversify your client base, keep your financials current within 24 hours, and think horizontally — not just about what you're making, but when it actually arrives and whether you can stay afloat while you're waiting. Most small businesses are three to six months from insolvency at any given time. Clarity is a tool, not a green light. STRATEGIC THINKING IS THE JOB THAT WON'T GET AUTOMATED In finance and law alike, the routine work is already being compressed by AI. What remains — and what will grow in value — is the ability to sit on top of these tools, challenge them, interpret their output, and translate it into action with full business context. The professionals who can do that will thrive. Those who can't will be the first to be automated out. MEMORABLE QUOTES > "Don't ask us a question you don't wanna hear the answer to."— Jay Kaplan > "A good leader takes all the blame and gives all the credit to everybody else — and that's hard for a lot of people to recognize."— Jay Kaplan > "That would've taken me hours to do in the past. It took minutes — but because I have the creativity and the strategic knowledge on top of it, I can talk intelligently about what it produced."— Jay Kaplan > "If you're worried about how you're gonna feed your family this week, all the forward-planning stuff doesn't resonate."— Jay Kaplan ABOUT OUR GUEST Jay Kaplan is Co-Founder and Principal of Tuross Group, an outsourced financial operations and advisory firm serving complex, highly regulated businesses across the United States. He operates as an embedded CFO, leading finance functions for companies ranging from early-stage operators to multi-entity businesses generating up to $50MM in annual revenue. At Tuross Group, Jay leads a global team of 50+ professionals delivering financial data that is consistently no more than 24 hours current — covering accounting, payroll, AR/AP, inventory, and reporting. His firm is deeply embedded in the cannabis industry, with expertise in 280E mitigation, cost accounting, multi-entity structuring, and building lender- and investor-ready financials. His focus: helping operators move from survival mode to scalable, disciplined businesses. CONNECT WITH HEARTWIRED Email: drmj@drmjheartwired.com Website: drmjheartwired.com Subscribe: Don't miss an episode — follow on Spotify. Share: If this conversation resonated, share it with a leader who needs to hear what the numbers are really saying.

Know Thyself First: The Self-Awareness Foundation Every Leader Needs in an AI World

SHOW NOTES: HEARTWIRED – EMOTIONALLY INTELLIGENT LEADERSHIP Episode Title: Know Thyself First: The Self-Awareness Foundation Every Leader Needs in an AI World Host: Dr. MJ Vignone Episode Type: Solo — Teaching Episode EPISODE SUMMARY In this solo teaching episode of Heartwired, Dr. MJ goes deep on the first — and most foundational — competency of emotional intelligence: self-awareness. Building on conversations from earlier episodes about how rapidly AI is reshaping leadership, she makes a case that the smarter AI gets, the more essential it becomes for leaders to know themselves clearly. This isn't a pep talk about journaling more or reflecting harder. Drawing from neuroscience, organizational psychology, and her own hard-learned leadership experience, Dr. MJ unpacks why most of what we've been taught about self-reflection is incomplete — and in some cases, actively working against us. She introduces the concept of calibrated self-awareness, explains what happens neurologically when we name our emotions precisely, and shares a practical three-part framework leaders can begin using today. The episode closes with a three-question reflection practice and a preview of the next competency: self-management. KEY TAKEAWAYS 95% OF US THINK WE'RE SELF-AWARE. ONLY 10–15% ACTUALLY ARE. Research by organizational psychologist Tasha Eurich found a staggering gap between perceived and actual self-awareness. The culprit: confusing self-attention (noticing emotions) with emotional clarity (naming and understanding them). High emotional attention without emotional clarity is associated with anxiety, rumination, and eroding self-confidence — not insight. INTROSPECTION WITHOUT CLARITY CREATES NOISE, NOT AWARENESS More reflection is not always better. The goal is calibrated introspection — the kind that generates insight rather than paralysis, and informs action rather than immobilizing it. Leaders who are highly self-focused but lack clarity often loop endlessly, unable to make decisions or trust their own read of a situation. SELF-AWARENESS OPERATES ACROSS THREE DIMENSIONS True self-awareness isn't just emotional — it spans physical awareness (what your body is signaling right now), emotional self-awareness (naming feelings as data, not reacting to them blindly), and relational self-awareness (understanding how your moods, presence, and actions ripple outward to affect the people around you). Leaders who miss the relational dimension aren't self-aware — they're self-focused. NAMING YOUR EMOTIONS LITERALLY CHANGES YOUR BRAIN Affect labeling — the deliberate, precise naming of emotions — measurably reduces activity in the amygdala and re-engages the prefrontal cortex. When you go beyond "stressed" to "I feel afraid that this decision will reveal I don't have all the answers, and that fear is making me defensive in this meeting," something neurological shifts. The emotional charge quiets. New neural pathways begin to form. IN AI-INTEGRATED ORGANIZATIONS, BLIND SPOTS GET ENCODED AND SCALED Every AI system is built on human decisions, human data, and human assumptions. When a leader lacks self-awareness, their blind spots don't stay contained — they get baked into the systems, invisibly shaping outcomes for hundreds or thousands of people. Dr. MJ shares the story of a leader who discovered her customer value assumptions had quietly biased the AI agent her team had trained. Self-awareness in AI leadership isn't just personal development. It's strategic risk management. THE THREE-STEP FRAMEWORK FOR CALIBRATED SELF-AWARENESS Dr. MJ introduces a practical practice built around three daily check-ins — morning, midday, and end of day — to track physical signals, name emotions precisely using affect labeling, and assess your external impact on the people around you. The goal is not analysis. It's noticing. That shift alone begins to rewire how self-awareness operates. SELF-AWARENESS IS THE ROOT OF EVERY OTHER EI COMPETENCY Self-management, empathy, social skills, authentic leadership — all of it flows from this one competency. Without it, every other EI skill is built on an unstable foundation. In a world where AI is handling more and more of the analytical work, the leaders who know themselves will be the ones who know when to trust the data, when to trust the humans in the room, and when something in their gut is sending a signal worth listening to. MEMORABLE QUOTES > "Real calibrated self-awareness is like a musical instrument. It has to be tuned carefully to be useful — tuned so that you project that beautiful essence of who you are."— Dr. MJ > "A leader who is blind to their impact is not self-aware. They're simply self-focused."— Dr. MJ > "AI amplifies everything — which means it amplifies you. The question is whether what's being amplified is your wisdom or your blind spots."— Dr. MJ > "Stop reacting and start responding — and understand the impact you have before you hear it from someone else."— Dr. MJ RESOURCES MENTIONED Tasha Eurich — Organizational psychologist and author; research on the self-awareness gap (95% vs. 10–15%) Dr. Daniel Amen — Referenced for the concept of ANTs (Automatic Negative Thoughts) Marshall Rosenberg — Nonviolent Communication framework (referenced in context of emotional language) Self-Awareness Class — Coming soon at drmjheartwired.com [https://drmjheartwired.com/] ABOUT DR. MJ Dr. MJ Vignone is an executive coach, speaker, and podcast host who helps leaders thrive at the intersection of emotional intelligence and artificial intelligence. As founder of HeartWired Leadership and host of the Heartwired podcast, she empowers leaders to lead with empathy, authenticity, and emotional agility in a technology-driven world. With more than 20 years of leadership and organizational development experience, Dr. MJ blends evidence-based coaching with human insight to help leaders connect, perform, and inspire. She holds a PhD in Human and Organizational Systems from Fielding Graduate University, an MBA, and is an ICF-accredited coach (ACC). Website: drmjheartwired.com [https://drmjheartwired.com/] LinkedIn: linkedin.com/in/maryjeanvignone [https://www.linkedin.com/in/maryjeanvignone/] CONNECT WITH HEARTWIRED Email: drmj@drmjheartwired.com Website: drmjheartwired.com Subscribe: Don't miss an episode — follow on Spotify. Share: If this episode resonated, share it with a leader who could use a clearer mirror.

The Human Spark: Why AI Needs You More Than You Need It

SHOW NOTES: HEARTWIRED – EMOTIONALLY INTELLIGENT LEADERSHIP Episode Title: The Human Spark: Why AI Needs You More Than You Need It Host: Dr. MJ Guest: Jim Sterne, AI Business Strategist, Author & Founder, Digital Analytics Association EPISODE SUMMARY In this episode of Heartwired, Dr. MJ sits down with Jim Sterne — author of fourteen books, consultant to the world's largest companies, and one of the most grounded voices in the AI conversation — to explore what artificial intelligence actually is, what it genuinely cannot do, and why the leaders who understand that distinction will be the ones who thrive. With 45 years at the intersection of marketing, data, and technology, Jim has watched every major wave of technological disruption — from the World Wide Web to analytics to machine learning — and emerged with a clear-eyed, deeply human perspective on each one. He unpacks why AI hallucinates by design, how a CEO built himself a custom financial advisor for free, and why IKEA's response to AI is the model every company should study. The conversation covers the danger of treating AI like Google, the leadership vacuum that bad AI policy creates, what the future of work actually looks like, and the one question Jim says everyone should be asking their AI tools right now. KEY TAKEAWAYS AI IS NOT A DATABASE — IT'S A PROBABILITY ENGINE AI doesn't retrieve knowledge; it calculates the statistically most likely next word based on a mathematical model of language. That's what makes it creative — and what makes it hallucinate. It isn't broken when it makes things up. That is exactly what it was designed to do. Leaders who understand this use it wisely. Those who don't, publish errors with their name on them. TASKS ARE NOT JOBS AI can do tasks. What it cannot do is decide which task matters, in what order, with what level of emphasis. That judgment — the ability to set priorities and own outcomes — is the job. The leaders and employees who understand this are irreplaceable. Those who treat their tasks as their identity are at risk. THE BEST USE OF AI IS THE BRAINSTORM PARTNER Don't ask AI questions the way you'd ask Google. Ask it to turn your ideas on their head. Ask it what you haven't thought of. Ask it what the unintended consequences might be. The magic isn't in the answers — it's in the questions it forces you to ask. And the most powerful prompt Jim uses: "How can you help me with this?" YOU ARE RESPONSIBLE FOR THE OUTPUT When AI generates something and you publish it, that's on you. Jim treats AI like a brilliant, eager, slightly unreliable PhD intern — useful, enthusiastic, and absolutely not to be trusted without a final review. Always ask for citations. Always check where the information came from. Your name goes on it. Own it accordingly. POLICY FIRST — THEN TRAINING, THEN CULTURE Leaders who ban AI because they don't understand it are simply uninformed — and the window for that excuse has closed. The right sequence is: educate the leadership, write a clear policy (hard rules plus guidelines), then turn employees loose. Policy also protects the company legally. Without it, liability sits entirely with the organization. FIRING HALF YOUR STAFF IS NOT A STRATEGY Companies that use AI to cut headcount and maintain output will be crushed by companies that use AI to dramatically increase what the same team can do. IKEA discovered AI could handle 50% of support calls — and responded by training the freed-up staff in interior design sales. That's the model. Human capital is not a line item to optimize away. RELATIONSHIP IS THE FUTURE-PROOF SKILL Agriculture, then manufacturing, now services — every wave of technological disruption shifts what humans are needed for. The next shift moves value toward what AI cannot replicate: trust, warmth, intuition, and relationship. The vending machine and afternoon tea at The Ritz both provide food. Only one is an experience worth paying for. MEMORABLE QUOTES > "AI is absolutely average. Ask it something bland and straightforward, you get a bland and straightforward answer."— Jim Sterne > "It's not your job. That's a task. The job is outcomes."— Jim Sterne > "Ask it how can you help me with this — not please do this thing for me."— Jim Sterne > "You can get a sandwich out of a vending machine, or you can have afternoon tea at The Ritz. It's the same thing — it's food. No, it's not the same thing at all."— Jim Sterne ABOUT OUR GUEST Jim Sterne has spent more than 45 years selling and marketing technical products and is currently working on his fourteenth book. A pioneer in online marketing and digital analytics, Jim founded the Marketing Analytics Summit and co-founded the Digital Analytics Association, where he served as Board Chair Emeritus for 20 years. He has consulted to some of the world's largest companies and lectured at MIT, Stanford, Harvard, USC, and Oxford. Today, his focus is on the business applications of generative AI — helping organizations move from confusion to capability, and from task automation to genuine innovation. Website: targeting.com [https://www.targeting.com/] LinkedIn: linkedin.com/in/jimsterne [https://www.linkedin.com/in/jimsterne/] Email: jsterne@targeting.com

AI as a Human Amplifier: Leadership, Emotional Intelligence, and the Time We're Getting Back

SHOW NOTES: HEARTWIRED – EMOTIONALLY INTELLIGENT LEADERSHIP Episode Title: AI as a Human Amplifier: Leadership, Emotional Intelligence, and the Time We're Getting Back Host: Dr. MJ Guest: Mike Wald, Executive Coach, Brand Strategist & AI Integration Advisor EPISODE SUMMARY In this episode of Heartwired, Dr. MJ sits down with Mike Wald — executive coach, trained anthropologist, and CMO of boutique marketing firm Oniracom — to explore what emotionally intelligent leadership actually looks like when AI is already inside the building. With nearly 20 years of experience working with nonprofits, startups, and household brands, Mike brings a grounded, human-centered perspective to a conversation that too often skips the hard part: what do leaders actually do with the time AI gives them back? He shares how he uses AI as a thought partner, why emotional intelligence is a cultural issue not a performance plan, and what it means to lead an organization through a technology tsunami with clarity and care. The conversation covers AI filters for brutally honest CTOs, the gap between emotional awareness and emotional strategy, why small nonprofits should be sprinting toward AI, and the real risk of letting smart employees quietly route around company data policy. KEY TAKEAWAYS AI IS ALREADY IN YOUR ORGANIZATION — LEAD IT OR LOSE IT Leaders who assume their teams aren't using AI without permission are being naive. If the company doesn't set policy and provide tools, smart employees will take sensitive data outside controlled systems and find their own solutions. The question isn't whether to bring AI in — it's whether you're leading it. EMOTIONAL INTELLIGENCE IS A CULTURE, NOT A CORRECTIVE Too often, emotional intelligence only gets introduced as a last resort before termination. Mike argues it needs to be baked into organizational culture from the start — and that being emotionally strategic (knowing how your output lands, even when you don't naturally communicate that way) is just as valuable as being emotionally aware. AI CAN BRIDGE THE GAP FOR THOSE WHO WILL NEVER "GET IT" Not everyone will develop emotional intelligence naturally. Mike shares how he helped a company put an AI-powered nonviolent communication filter in front of a brilliant but abrasive CTO — preserving his value to the team while making his feedback actually usable. The goal isn't perfection; it's function. PROTECT THE TIME AI GIVES YOU BACK AI reduces pressure in the system — but that freed-up time will be immediately consumed by Pac-Men (meetings, requests, distractions) unless leaders deliberately block it off. Getting time back is step one. Protecting it for higher-value work is step two. TASTE IS STILL HUMAN AI doesn't have taste. It will wander into the uncanny valley — slightly wrong faces, slightly off-brand copy — and not notice. Quality assurance, hospitality, culture, and the judgment to know when something just isn't right: that's where humans are irreplaceable. NONPROFITS HAVE NO EXCUSE TO WAIT Bad actors aren't asking for permission to use the latest technology. Mission-driven organizations that delay AI adoption are ceding ground. AI can help nonprofits scale their impact without scaling headcount — and foundations that fund these organizations are increasingly paying attention. USE AI TO HYPER-PERSONALIZE, NOT JUST AUTOMATE Mike's actionable challenge: when using AI to create any communication, tell the system who it's for. What will they appreciate? What will land? This small shift keeps the human at the center of the exchange and dramatically improves the effectiveness of what goes out the door. MEMORABLE QUOTES > "AI is the rocket skates. It's the booster pack on engagement — but the engagement is through people."— Mike Wald > "If AI is gonna give you back time, where is it gonna go? Is it just more productivity, or is it a change in the way you work?"— Mike Wald > "The bad actors out there don't need any convincing to use the latest technologies. So it behooves the good actors to really level up."— Mike Wald > "Think more about the other person. That keeps humanity at the center."— Mike Wald ABOUT OUR GUEST Mike Wald helps leaders cut through complexity to see what actually matters, so they can make better decisions, faster. As a trained anthropologist, executive coach, health and wellness futurist, and brand storyteller, his work spans nonprofits, startups, and household names — from Disney movies and Coachella to Jack Johnson, Rihanna, and government infrastructure dashboards in the U.S. and Australia. As CMO of Santa Barbara boutique marketing firm Oniracom, Mike brings a triple-bottom-line approach to every engagement — people and planet before profit. He specializes in helping mission-driven leaders harness AI without losing the human touch that makes their organizations worth leading. Website: mikewald.com [http://mikewald.com/] LinkedIn: linkedin.com/in/mikewald [https://www.linkedin.com/in/mikewald/] CONNECT WITH HEARTWIRED Email: drmj@drmjheartwired.com Website: drmjheartwired.com Subscribe: Don't miss an episode — follow on Spotify. Share: If this conversation resonated, share it with someone navigating leadership in the age of AI.

Words, Trust, and the Human Voice: Leading and Writing in the Age of AI

SHOW NOTES: HEARTWIRED – EMOTIONALLY INTELLIGENT LEADERSHIP Episode Title: Words, Trust, and the Human Voice: Leading and Writing in the Age of AI Host: Dr. MJ Guest: Valerie Cantella, Communication Strategist, Author & Book Coach EPISODE SUMMARY In this episode of Heartwired, Dr. MJ sits down with Valerie Cantella — award-winning communication strategist, public service veteran, and book coach — to explore what happens to words, trust, and leadership identity when AI enters the picture. With over 30 years of experience guiding elected officials, organizations, and individuals through high-stakes communication, Valerie brings a grounded and nuanced perspective to a conversation that too often swings between fear and hype. She shares how she uses AI in her own work, what she tells the writers she coaches, and why emotional intelligence — not prompting skills — is still the most important leadership tool in the room. The conversation covers AI-generated emails that erode trust, students submitting chat output as academic work, the publishing industry's scramble to define AI-assisted writing, and why the messy first draft still matters. KEY TAKEAWAYS AI Is a Tool — Lead That Conversation Leaders who avoid engaging with AI are leaving a vacuum their teams will fill without direction. True leadership means getting informed, setting parameters, and deciding intentionally how AI fits the organization's mission. Outsourcing Judgment Is Not Leadership Using AI to decide what to do is not leadership — it's prompting. Real leaders use AI to surface the questions they haven't asked yet, then bring those questions to the right people. AI Cannot Replace Non-Verbal Communication Words account for roughly 7% of communication. Body language, tone, facial expressions — everything AI cannot read or replicate — make up the rest. High-stakes human conversations still require a human in the room. Trust Erodes When Voice Disappears AI-generated emails and content that strip out an organization's unique voice signal to recipients that they aren't worth the effort. Leaders need to define where that line is — and hold it. Writers: Don't Lose Your Native Voice AI can organize, research, and sort — but it cannot replicate the specific texture of a writer's voice. The tells are already visible: "quietly," three-sentence word repetitions, smooth but hollow prose. Write the messy first draft first. The Publishing World Is Still Figuring It Out Copyright questions, pulled books, pending lawsuits, and evolving agent guidelines — the industry is catching up. Authors need to stay informed and lead with their own ethical compass while the rules are still forming. Alignment Is the Standard The question isn't just "is this AI?" — it's "does this reflect who I am and what I'm here to do?" Emotional intelligence means sitting with that question before hitting publish or send. MEMORABLE QUOTES "AI can never replace the words, the unique spirit of an organization, the unique spirit of an individual." — Valerie Cantella "Leaders that are just having a conversation with Chat about what to do — that's not true leadership." — Valerie Cantella "Claude is pushing back on me in ways that are producing much richer thoughts." — Valerie Cantella "Don't lose your native voice. Write the messy first draft." — Valerie Cantella ABOUT OUR GUEST Valerie Cantella is an award-winning communications strategist and author who coaches people through the entire journey of deciding whether to write a book, shaping it, writing it, and bringing it into the world. With 30 years of experience in strategic communications, crisis management, and high-stakes organizational leadership, she brings a grounded perspective to AI, emotional intelligence, and what leaders are still responsible for in an increasingly automated world. Website: valeriecantella.com [https://www.valeriecantella.com] Substack: Dear Kate: Notes for Women with a Story to Tell [https://dearkatenotes.substack.com/] Substack: Reflections from a Recovering Perfectionist [https://valeriecantella.substack.com/subscribe] Instagram: @valeriejcantella [https://www.instagram.com/valeriejcantella] LinkedIn: Valerie Cantella [https://www.linkedin.com/in/valerie-cantella] CONNECT WITH HEARTWIRED Email: drmj@drmjheartwired.com [drmj@drmjheartwired.com] Website: drmjheartwired.com Subscribe: Don't miss an episode — follow on Spotify. Share: If this conversation resonated, share it with someone navigating leadership in the age of AI.