Tech Whisperers: Inside the Playbooks of the Best Digital Leaders

Generative AI has taken the world by storm, opening up whole worlds of opportunity for technology leaders to simplify their processes and empower their teams to grow and innovate.But those opportunities do not come without some major concerns. With potentially serious issues like data privacy, response accuracy, and security, how can technology leaders successfully embrace this technology while mitigating the potential risks? And what will tech leadership look like in an AI-enabled world?To help us answer these questions, we’ve invited Dr. Lisa Palmer, a leading AI strategist and international speaker, and Anna Ransley, a powerhouse CIO whose career spans companies like Godiva and Heineken and who has spent this summer advising boards and C-suites about generative AI. With their help, we are unpacking everything you need to know about GenAI adoption so that you can apply it to your tech leader playbook.Tune in as we explore:The technological advancements that enabled AI’s current boomAggressive vs. cautious approaches to AI adoptionWhy CIOs should take a proactive stance in leading AI adoption and educating their teamsHow to choose which old processes to automate vs. which ones to replaceWhy technology leaders need a variety of perspectives in their team to adopt AI successfullyHow job displacement will be offset by new opportunities Why social engagement and collaborative learning will help teams navigate the AI journey

Many of our most inspiring leaders are people who know their values and stick to them, no matter the cost. For CIO legend Chris Hjelm, values-based leadership is his entire foundation. Drawing from his experience at companies like FedEx, Orbitz, and Kroger, we are unpacking Hjelm’s tech leadership playbook to uncover the truth about the cost of values-based leadership, building and maintaining executive presence, the importance of self-assessment, and so much more.  Tune in as we explore:Why values-based leadership and relationships are crucial to leadership successHow to build and maintain executive presenceHow and why it's important to develop your team members’ communication skillsThe secrets to leading and managing effectively through a crisisWhat makes someone a likely candidate for future leadershipThe necessity of self-care and stress management Featuring submitted questions from:Nick Kaufman, Vice President at Kroger TechnologyAnnette Hater, VP, Global Head of Technology Strategy & Portfolio at TapestryLeon Chism, Fractional CPTO/CPO & CTO CoachRyan Kean, CIO at Total Quality Logistics

If you’ve heard an episode of Tech Whisperers before, you’ve heard of the TechLX leadership development program. At our most recent graduation for TechLX participants, Dan sat down with SelectQuote CIO Floyd May. In 2018, SelectQuote’s revenue was around 230 million, but since then they have grown to just shy of a billion dollars by leveraging new technology to streamline the insurance buying process for their customers.May is a CIO that leads with humility, often letting his results speak for themselves, and he is always looking to learn and grow while helping his team do the same.Tune in as we explore:What it means for leaders to model honest communication, balance tasks and relationships, and balance innovation and stability in tech infrastructure.How to use the Hedgehog Concept to differentiate your organization and gain a competitive advantage.How discipline and proper structure will be the key to adopting and leading with generative AIWhy new leaders need to develop their personal network to secure career advancement

From entry-level employees all the way up to the boardroom, the journey to digital maturity impacts all aspects of organizations that pursue it. This, along with the high stakes that come naturally with organizational change and innovation, have driven increased demand for digitally savvy board members.So who better to talk about this than the CIO of the National Association of Corporate Directors, Rona Bunn. Anyone who is on a board or aspires to join one knows of the NACD, which serves as the leading authority on boardroom practices.Tune in as we explore:How an outcome-focused mentality can keep motivation high when the journey gets toughHow Rona is leading her team to increase their impact across the NACD and its customer baseWhy CIOs have a responsibility to drive the implementation of competencies and practices for digital transformationWhat communities of practice are and how they help organizations acquire new competenciesHow data governance committees help organizations leverage data properly to create high-quality data productsThe IT Maturity Curve and how it breaks down the relationship between IT and the business

Companies are investing trillions of dollars into digital transformation initiatives, but research tells us that 70% of digital transformation initiatives fail. How can today’s digital leaders set their companies up for success and ensure that these major investments don’t go to waste?We’ve invited three powerhouse leaders to unpack their digital transformation research findings and share the most important steps leaders can take to ensure success.Dr. Susan Nakashima, Retired IT Executive & Adjunct Professor at Pepperdine UniversityDr. Michael Seals, Chief Digital Officer & SVP of Strategy at Hussmann CorporationDr. John Hill, Chief Digital Information Officer at MSC Industrial SupplyTune in as we explore:How a digital acuity deficit in established leaders prevents successHow leaders can clearly articulate what success looks like and how it can be measuredHow creating a psychologically safe environment promotes learning and prevents knowledge-hiding behaviorsThe key areas of transformational leadership that digital leaders should embraceThe first steps to creating a psychologically safe environmentResources:Dr. Michael Seals’ Dissertation on Digital Transformation Levers of ControlDr. Susan Nakashima’s Dissertation on Creating Psychological Safety

What does it look like for a tech leader to be successful at innovating with products, services, digital, strategy, and employee engagement? Join us as Anupam Khare, SVP & CIO at Oshkosh Corporation, unpacks his leadership playbook, sharing insights from his experiences and the impact his organization has created for this Fortune 500 company that delivered $8.3 billion in revenue in 2022. We discuss:How Oshkosh Corp. embeds innovation into its products and the way it conducts businessThe keys to a successful rebranding strategyStrategies for leading regular team meetingsWhy Anu says it’s important as a leader to invest your time and energy into value first, technology secondThe initiatives that helped Anu win multiple ORBIE AwardsFeaturing mystery questions from:Greg Carstensen, VP of Infrastructure at Oshkosh CorporationChrista Ogilvy, Executive Director at InspireCIO

We’re thrilled to have a top-notch, Hall of Fame CSO as our first cybersecurity executive to join us on the podcast. Deneen DeFiore, VP & CISO at United Airlines, has figured out how to provide clarity in a sea of complexity while managing the multiple business priorities of her mission-critical role.Deneen sat down with Dan Roberts to unpack her leadership journey and philosophy and discuss how she balances the need to secure the business with the need to enable business agility and innovation.Tune in as we explore:How great cyber leaders balance the nuances of collaboration, business operations, and risk tolerance while enabling agility and innovationThe rise of generative AI and the risks it bringsWhy CISOs need to be expert communicators and storytellersThe urgency to build a pipeline of cyber leaders who possess both technical and management skillsThe role of self-care for leaders, particularly when pressure and burnout are high

When we think of a top leader that is serious about creating future-ready leaders, cutting through the noise to identify the right issues, and who climbed the ladder through vision, goal-setting, and meticulous planning, we think of none other than Segra CEO, Kevin Hart.In this episode, Dan sits down with Kevin at Segra’s in-house studio in Charlotte, North Carolina, to unpack Kevin’s amazing career journey and the lessons he has learned along the way. We discuss:Advice for CIOs aspiring to be CEOsWhy investing in leadership development brings increased ROIHow Kevin implemented a 5-year centralization strategy while working at CoxHow to narrow your focus to identify the core problems that need solvingKevin’s journey from CIO to CEOFeaturing mystery questions from:Rose Chambers, CIO at SegraPatricia Martin, SVP Integration Management Office at Cox Communications

As work culture has shifted to quicker employee turnover, people like Panera Bread CIO, John Meister are becoming a rare species: seven years at Accenture, 15 years at Mastercard, and now approaching his 10th year with Panera.In this episode, we are unpacking John’s leadership playbook and exploring how stability, intentionality, dedication, and hard work have helped John have successful tenures at each company that he has worked with. We discuss:How ownership of a problem contributes to innovationHow to work with ever-changing leadershipExplaining new technology concepts to senior leadershipHow AI technology like ChatGPT is changing the way technology teams are workingHow to develop resiliency and why every leader needs itFeaturing audience questions from:Anita Klopfenstein, CIO at Little CaesarsGary VonderHaar, EVP, Operations & Technology at MastercardNaomi Hamilton, Director of Human Resources at Panera Bread

How does someone go from being a KGB spy and one of the most wanted men in America to becoming a fully-fledged American citizen and a top-notch CIO? Jack Barsky, author of Deep Undercover: My Secret Life and Tangled Allegiances as a KGB Spy in America, joins Dan to talk about his incredible journey and the best leadership principles he has picked up along the wayWe discuss:Jack’s experience as a KGB spyHow Jack left the KGBBest practices for professional networking Advice for leaders joining a new organizationFeaturing audience questions from:Robin Dreeke, Founder & CIO of Forged by TrustKelly Lyman, CIO at ExelonGreg Flay, VP for Technology and Data at Austin Energy