Lead with IT

Kathryn Guarini

Lead with IT is a podcast about how technology shapes strategy, accelerates growth, and creates competitive advantage in every industry, at every scale. Hosted by Kathryn Guarini — technology executive, board director, educator, and PhD scientist — each episode features real conversations with leaders and innovators exploring what it means to put technology at the center of how organizations think, decide, and grow. Topics span the full journey: elevating technology into strategy, building trust by design, and making tech fluency a leadership imperative. The stories are specific, the takeaways are practical, and the perspective is clear: organizations that lead with IT set the pace. Those that don’t, fall behind.   Don’t just use IT. Lead with IT.

Episodes

  1. 3d ago

    Scaling Technology Companies with Amena Ali | #10

    In this episode of Lead With It, Kathryn Guarini talks with Amena Ali about leading technology companies through transformation, scaling, and successful exits. Amena reflects on her experience as a repeat CEO and explains that what consistently drew her to new companies was the challenge: understanding the business, identifying what needed to change, and helping the organization reach its next stage of growth. Amena explains that one of her first priorities as CEO was understanding the customer deeply. She describes conducting listening tours with customers, partners, founders, investors, and employees to understand why the company exists, what problem it solves, and how the product can make customers’ lives easier. Kathryn and Amena also discuss the importance of connecting technology teams directly to customer problems. Rather than building technology simply because it is exciting or new, Amena emphasizes starting with the problem, observing customers closely, and helping engineering teams understand what they are solving and why it matters. The conversation then turns to founder-led companies and what changes when a successor CEO comes in. Amena explains that founders bring passion, grit, and deep market knowledge, but growing companies often need new perspectives and harder questions to reach the next stage. The goal is not to discard what made the company successful, but to preserve those strengths while challenging assumptions that may no longer serve the business. In this episode: ● Leading companies through transformation and scale ● Starting with the customer and the problem ● Connecting technology teams to business value ● Asking better questions as a CEO ● Transitioning from founder-led leadership ● Preserving founder strengths while challenging assumptions ● Building companies for long-term value ● Creating optionality instead of simply preparing to sell ● Moving from operator to board member ● Building trust through consistent communication ● Why every company is now a technology company ● Using AI to improve efficiency, creativity, and customer experience Amena’s message is that strong leadership is less about having every answer and more about asking the right questions, understanding the customer, building trust, and creating a healthy business that can adapt as markets and technology evolve.

  2. Oct 14

    Building Innovation on Purpose with Chris Heemskerk | #9

    In this episode of Lead With It, Kathryn Guarini talks with Chris Heemskerk about how organizations can build innovation deliberately instead of treating it like something that happens by chance. Drawing from his experience at Google and his work advising companies across industries, Chris explains why innovation needs the right structure, culture, incentives, and strategic alignment to succeed. Chris shares how Google created dedicated space for experimentation outside the pressure of the core business. That separation gave teams room to test new ideas without having them shut down too early because of short-term revenue expectations. He also explains that innovation can take many forms, from breakthrough products to incremental improvements in processes and business models. Kathryn and Chris also discuss how companies should measure innovation. Chris warns that organizations can become distracted by too many disconnected bets or metrics that do not align with corporate strategy. He believes leaders need to clearly define where the company wants to play, what problems it wants to solve, and then measure whether innovation efforts are moving toward those goals. The conversation then turns to AI. Chris explains that AI can speed up experimentation and prototyping, but many companies are still using it opportunistically rather than strategically. He encourages leaders to focus on a few meaningful AI bets that create a defensible advantage instead of spreading resources across too many disconnected projects. In this episode: ● Why innovation should be built intentionally ● Creating space for experimentation ● Core, adjacent, and transformational innovation ● Why psychological safety matters ● Aligning incentives with innovation goals ● Building innovation culture beyond slogans ● Measuring innovation without creating the wrong behavior ● Connecting innovation bets to corporate strategy ● Why AI increases the urgency to innovate ● Choosing fewer, stronger AI bets ● Balancing innovation teams with company-wide responsibility ● Why innovation needs structure and discipline Chris closes by arguing that innovation should be treated as a real professional discipline, with clear structure, talent, leadership, and accountability. At the same time, Kathryn emphasizes that innovation cannot belong.

  3. Oct 7

    Leading Transformation Through Technology with Anjana Harve | #8

    In this episode of Lead With It, Kathryn Guarini talks with Anjana Harve about technology leadership, transformation, AI, and how leaders can turn technology into business advantage. Anjana reflects on more than 25 years across different industries and explains why her career became less about following a perfect plan and more about pursuing opportunities to learn and create impact. Anjana explains that when she enters a new organization, she starts by listening. Rather than immediately applying a playbook from a previous company, she spends time across teams and functions understanding the culture, problems, opportunities, and perspectives already inside the organization. Small proof points can then help build confidence and momentum for larger change. They also discuss how the role of the technology leader has evolved. Anjana believes CIOs and CDOs can no longer simply enable business strategy—they increasingly need to help shape it. That requires thinking like a business leader first, communicating complex technology in understandable terms, and focusing on business outcomes rather than only traditional technology metrics. A major theme is that successful transformation ultimately depends on people. Anjana shares an example of bringing roughly 50 separate technology teams together into one global organization. Instead of forcing the change, she built the case, brought stakeholders along, and allowed hesitant groups to experience the benefits before changing reporting structures. In this episode: ● Why careers do not need to follow a straight path ● Listening before leading change ● Building momentum through small wins ● How the CIO role is evolving ● Thinking like a business leader first ● Focusing technology teams on business outcomes ● Why people determine whether transformation succeeds ● Bringing global teams together through change ● Where AI can create measurable business value ● Why AI transformation requires leadership engagement ● Rethinking processes from a blank sheet of paper ● Taking risks and staying curious Anjana closes by encouraging leaders to stay curious and take risks. Her advice is to push yourself beyond what feels completely comfortable, accept that mistakes are part of learning, and continue looking for opportunities to create meaningful impact.

  4. Sep 23

    Rethinking Organizations for the Age of AI with Claudine Gartenberg | #7

    In this episode of Lead With It, Kathryn Guarini talks with Claudine Gartenberg, associate professor of management at the Wharton School, about how AI is changing organizations, strategy, leadership, research, and the way people work together. Claudine shares how her career started in physics before moving into consulting, business strategy, and organizational research. She explains that what fascinated her was not just technology itself, but how groups of people come together to accomplish things that no individual could do alone. A major focus of the conversation is the difference between AI hype and AI reality. Claudine explains that some organizations are already using AI in ways that would have seemed impossible only a few years ago, including autonomous agents that can identify customer needs, design solutions, and integrate them into the business. At the same time, many companies are still struggling with the human and organizational challenges that come with adoption. Kathryn and Claudine also discuss why AI is an architectural shock to companies. It is not just a tool that makes one task faster. It can force leaders to rethink jobs, workflows, communication, metrics, culture, and the way teams are designed. The conversation also explores leadership. Claudine explains that real AI transformation requires strong leaders with conviction, vision, and the ability to give people something to hold on to during uncertainty. Kathryn connects this to broader transformation work, where leaders need to point toward a future that people want to help build. Later, they discuss AI’s impact on research, education, writing, peer review, and trust. Claudine shares concerns that AI generated content is overwhelming systems built for humans and creating new problems around quality, validation, and institutional trust. In this episode: ● Why AI transformation is really an organizational challenge ● How Claudine moved from physics to management research ● What separates AI hype from real business change ● How AI is affecting academic publishing and peer review ● Why institutions may need to be rebuilt for the AI era This episode is a reminder that AI adoption is not just about using better tools. Kathryn and Claudine explore how the real challenge is redesigning organizations, protecting human judgment, building trust, and leading people through a period of major change.

  5. Sep 16

    Technology, Mission, and Strategic IT with Keith Goodwin | #6

    In this episode of Lead With IT, Kathryn Guarini talks with Keith Goodwin, CIO of Make-A-Wish America, about enterprise transformation, nonprofit technology, AI, cybersecurity, and what it means for IT to become a true business partner. Kathryn and Keith begin by discussing his 30 years at IBM, where technology was used to centralize processes, create common data, and give leaders a single version of the truth. Kathryn points out that this foundation matters because companies cannot make strong decisions if they do not trust their data or have visibility into the information they need. The conversation then moves into Keith’s role at Make-A-Wish. Kathryn highlights how a clear mission can help organizations move faster, because everyone understands what the work is ultimately meant to support. Keith explains how technology connects to revenue, medical referrals, wish granting, volunteers, partners, and the systems that help deliver life changing wishes. A key theme is the shift from IT as an order taker to IT as a strategic partner. Kathryn explains that IT leaders should not simply wait for someone to request an app or platform. Instead, they need to understand the business strategy, build trust, and help shape the best path forward. Kathryn and Keith also discuss AI and cybersecurity. Keith shares how Make-A-Wish started with AI policy, guardrails, and secure enterprise tools. Kathryn connects that to a larger challenge: AI can improve productivity, but it also creates new risks around sensitive data, public models, cyber threats, and faster exploitation of vulnerabilities. In this episode: ● Why trusted data comes before advanced technology ● How IT supports mission driven work ● Why nonprofits still need business rigor ● How IT moves from order taker to partner ● Why AI needs policy and guardrails ● How cybersecurity risk is changing ● Why technology strategy must support business strategy This episode is a reminder that technology is not separate from the mission. When IT is trusted, strategic, and connected to the business, it can help organizations move faster, serve better, and create real impact.

  6. Sep 9

    Make Work Optional with Phil Palumbo | #5

    What does it really mean to make work optional, and how can technology help business owners, founders, and wealth managers get there? In this episode of Lead With IT, Kathryn Guarini speaks with Phil Palumbo, founder of Palumbo Wealth Management, about finance, independence, technology, AI, and the responsibility of putting clients first. Phil explains why he believes the word retirement is outdated. Instead of chasing an arbitrary age, he encourages people to think about the number, assets, and cash flow they need to make work optional and create flexibility in their lives. He also shares why he left large Wall Street institutions after two decades and started his own firm. For Phil, independence meant removing conflicts of interest, building around the client, and choosing technology that could better support the way he wanted to serve families and founders. Kathryn and Phil also discuss how technology, cybersecurity, data protection, and AI are shaping wealth management. Phil shares how he uses AI throughout the day for research, marketing, content, cybersecurity, and compliance, while also being careful about hallucinations and protecting client information. In this episode: ● What “make work optional” really means ● Why retirement can be the wrong target ● Why Phil left Wall Street to start his own firm ● How independence creates more flexibility with technology ● Why cybersecurity and data protection matter in wealth management ● How AI is being used in a financial advisory business ● The risks of AI hallucinations and client data exposure ● Why staying behind on AI is a competitive risk ● Why client-first leadership still matters most If you are thinking about wealth, business, technology, or the future of financial advice, this episode is a reminder that the goal is not just to retire. The goal is to build enough freedom, flexibility, and trust that work becomes optional.

  7. Sep 2

    Executive Presence In the Age of AI with Ann Keil Dux | #4

    What happens when AI can make your work cleaner, faster, and more polished, but you still have to show up as a human leader? In this episode of Lead With IT, Kathryn Guarini speaks with Ann Keil Dux, an Emmy Award-winning investigative journalist, executive presence coach, and strategic communication advisor. Ann shares what years in live television taught her about communication, pressure, trust, and staying connected to yourself when everything around you is moving fast. She explains why many leaders perform confidence instead of accessing who they really are, and why that disconnect can cause audiences to lose trust. Kathryn and Ann also discuss why technical expertise is not enough on its own. Leaders need to know their audience, tell the story clearly, and connect the facts to what people actually need to understand. As AI makes presentations, memos, and content easier to create, Ann explains why the human side of communication matters even more. If everyone can produce polished work, the difference becomes how leaders speak, listen, connect, and make people feel. In this episode: ● Why people perform confidence under pressure ● How leaders lose access to themselves ● Why facts alone do not create trust ● Why technical experts need storytelling skills ● How AI raises the bar for human communication ● Why emotional intelligence matters in leadership ● What executive presence really means ● Why presence is about how you show up in the room ● How breathing helps leaders communicate under stress ● Why authenticity is deeper than “letting it all out” If you are a technical leader, speaker, or executive trying to communicate with more clarity and presence, this episode is a reminder that the best communicators do not just know the information. They know how to make people feel connected to it.

  8. Aug 26

    AI Can Amplify, Unlock, And Reimagine Work | #3

    What if AI is not just a tool to make work faster, but a force that can change what work becomes? In this episode of Lead With IT, Kathryn Guarini explores the current state of artificial intelligence, the opportunities it creates, and the real challenges leaders need to take seriously. Kathryn brings multiple perspectives to the conversation: builder of AI tools, former IBM Global CIO, board director, educator, everyday AI user, and parent. She shares how her experience ranges from building AI capabilities earlier in her career to deploying AI at IBM scale for hundreds of thousands of employees across the world. The episode breaks down the evolution of AI from broad artificial intelligence to machine learning, deep learning, generative AI, and agent AI. Kathryn explains how AI has moved from rule-following systems to models that can learn from observation and even learn by doing. She also addresses the concerns that come with this moment, including skepticism, ethics, privacy, intellectual property, job impact, bias, explainability, cybersecurity, energy usage, and the role of AI in education. While those concerns are real, Kathryn also points out that many of these problems are being actively addressed as quickly as they surface. The heart of the episode is Kathryn’s framework for how businesses can think about AI: amplify, unlock, and reimagine. AI can amplify human work by making existing tasks faster and more consistent. It can unlock possibilities humans could not reach on their own. And it can reimagine entire categories of work by changing what the work itself looks like. In this episode: ● Why AI creates both opportunity and concern ● Kathryn’s experience building and deploying AI ● How IBM used AI at global scale ● The difference between AI, machine learning, deep learning, generative AI, and agent AI ● Why AI systems learning by doing changes the conversation ● The technical, ethical, and business challenges leaders need to watch ● Why AI concerns are being addressed in real time ● How AI can reimagine the future of work If you are a leader, builder, educator, board member, or business owner trying to understand where AI fits, this episode gives you a clear framework for thinking about the technology, its risks, and its potential. Connect with Kathryn Guarini and tune into more conversations on Lead With IT.

  9. Aug 19

    Trust By Design | #2

    What if trust is not something you fix after technology fails, but something you design into innovation from the start? In this episode of Lead With IT, Kathryn Guarini explores the idea of Trust by Design: four ways leaders, technologists, product managers, funders, users, and decision makers can build trustworthy innovation with intention. Kathryn explains why this matters now more than ever. Technology is being adopted faster than ever before, and when systems grow this quickly, failures can spread globally and instantly. The consequences are not just technical. They can affect real people, reputations, finances, operations, regulators, and entire businesses. She walks through major examples of trust failures, including the Boeing 737 Max crisis, the 23andMe data breach, the Taylor Swift Ticketmaster ticketing collapse, and the CrowdStrike outage. Each example shows what can happen when trust is treated as something to repair after the fact instead of something designed in from the beginning. Kathryn then shares three specific practices leaders can use to reduce failure and build trust earlier: pay your customers, break it before your users do, and open the black box. These practices are not abstract ideas. They are concrete ways to involve real users, stress-test systems before they fail publicly, and create transparency around how technology works. In this episode: ● Why trust must be designed from the start ● How fast technology adoption increases risk ● Why technology failures now spread globally and instantly ● What leaders can learn from Boeing, 23andMe, Ticketmaster, and CrowdStrike ● Why user insight needs to happen earlier and more often ● What “pay your customers” means in trustworthy innovation ● Why teams should break products before users do ● How Netflix’s Chaos Monkey changed reliability testing ● Why AI and technology need more transparency ● How “open the black box” can help users trust technology If you are building, funding, adopting, or overseeing technology, this episode is a reminder that trust is not optional. When you design trust in from the start, you do not just avoid failure. You build solutions people can believe in and count on. Connect with Kathryn Guarini and tune into more conversations on Lead With IT.

  10. Aug 13

    Welcome to Lead with IT | #1

    What if the biggest strategic advantage in your business is not just your product, your market, or your people, but how early technology shapes your decisions? In this first solo episode of Lead With IT, Kathryn Guarini introduces the philosophy behind the podcast and the leadership shift she believes every organization needs to make: technology can no longer be treated as a support function. It must be part of strategy from the beginning. Kathryn shares her background as a PhD scientist, technology executive, board director, and educator, with experience spanning research, product management, IT leadership, the C-suite, and the boardroom. Through that lens, she explains why every company today is, in some way, a technology company. From banking and retail to pharmaceuticals and small businesses, technology now shapes how companies find customers, serve needs, build products, run operations, and compete in the market. As AI, cloud systems, security tools, data, and automation become more embedded in every business, leaders have a choice: lead with IT or fall behind. Kathryn also shares examples from her work at IBM, including the massive IT separation behind the Kyndryl spin-off, and her board work with Regeneron, where technology plays a critical role in accelerating drug discovery, clinical trials, FDA approval, and patient impact. This episode is a call for leaders to stop thinking of IT as an order taker or back-office function and start using technology to define what the business can become. In this episode: ● Why every company is now a technology company ● What it means to lead with IT ● Why technology must shape strategy from the beginning ● How AI and digital systems are changing every industry ● Why IT cannot be treated as a back-office support function ● What Kathryn learned from leading technology at IBM ● How technology can create competitive advantage in biopharma ● Why future leaders need technology fluency If you are a CEO, board member, executive, founder, or emerging leader trying to understand how technology shapes growth, speed, trust, and competitive advantage, this episode will help you see why leading with IT is no longer optional. Connect with Kathryn Guarini and tune into more conversations on Lead With IT.

  • 10 Episodes

About

Lead with IT is a podcast about how technology shapes strategy, accelerates growth, and creates competitive advantage in every industry, at every scale. Hosted by Kathryn Guarini — technology executive, board director, educator, and PhD scientist — each episode features real conversations with leaders and innovators exploring what it means to put technology at the center of how organizations think, decide, and grow. Topics span the full journey: elevating technology into strategy, building trust by design, and making tech fluency a leadership imperative. The stories are specific, the takeaways are practical, and the perspective is clear: organizations that lead with IT set the pace. Those that don’t, fall behind.   Don’t just use IT. Lead with IT.

Information

  • Creator
    Kathryn Guarini
  • Years Active
    2026
  • Episodes
    10
  • Rating
    Clean
  • Copyright
    © 2026 Kathryn Guarini
  • Show Website
    Lead with IT