Partnering Leadership

Senior executives can spend years thinking rigorously about strategy, talent, capital allocation, and organizational performance while giving surprisingly little strategic thought to their own careers. That gap sits at the center of this Partnering Leadership conversation with Kelly O. Kay, Managing Partner of the Global Software Practice at Heidrick & Struggles and co-author, with Jeffrey Sanders, of Show Up to Win: How to Land the Leadership Role You Want. Drawing on decades of executive search experience, Kelly offers an unusually candid look at how senior leadership opportunities actually develop, how executives are evaluated, and why an impressive track record alone does not guarantee continued career momentum.

Kelly challenges the transactional way many executives approach career decisions. A call from an executive recruiter does not have to mean deciding whether you want a particular job. It can be an opportunity to understand how the market sees you, build relationships with influential executives, directors, and investors, learn about another industry, or develop the fluency required to operate at a higher level. Those conversations can create options years before an executive actually needs them.

The conversation also gets inside the mechanics of senior-level hiring. Kelly explains why previous accomplishments must be translated into the specific challenges facing a new organization rather than simply presented as proof of future success. He shares how executive interviews have evolved from question-and-answer sessions into substantive executive dialogues, why self-awareness can make a candidate more compelling rather than less, and how reputations formed years earlier can quietly influence opportunities an executive may never know existed.

Mahan and Kelly also explore what happens after an executive lands the role. Kelly explains why a new CEO needs people willing to tell them what others may be reluctant to say, and why understanding the organization you are joining matters as much as convincing it to hire you. The discussion reinforces an important theme throughout Show Up to Win: career management is not something executives should suddenly begin when they are ready to leave. The relationships, reputation, judgment, and market understanding that create future optionality are built over time.

The episode closes with a practical discussion about AI and executive career management. Rather than using AI simply to research a company or generate polished answers, Kelly explains how senior executives can use it as an interview coach to role-play likely questions, sharpen their thinking, and prepare for the priorities of a particular interviewer, company, and role. It is a timely example of how technology can strengthen preparation while leaving the most consequential part of the process distinctly human.

Actionable Takeaways

• You’ll learn why career management should begin long before you are considering a move and how that creates greater optionality over time.
• Hear how to rethink the executive recruiter’s call and why a conversation can be valuable even when you have no interest in the job.
• You’ll learn why past performance is necessary but insufficient and how to connect your experience to what a new organization actually needs.
• Hear why executive interviews should feel less like selling and more like an executive dialogue that reveals how you think and what you would contribute.
• You’ll learn why acknowledging a capability gap can strengthen your candidacy rather than make you appear less qualified.
• Hear how reputations quietly shape opportunities before you even know your name is being considered.
• You’ll learn why aspiring CEOs need to develop the ability to think and communicate at a different altitude.
• Hear why every new CEO needs a truth teller willing to surface realities others may be reluctant to share.
• You’ll learn how to use AI as an interview coach to pressure-test your thinking and prepare for the people and priorities in the room.
• Hear why you should never simply put your leadership story on “play” and tell it the same way to every audience.

Connect with Kelly O. Kay

Kelly O. Kay at Heidrick & Struggles

Kelly O. Kay LinkedIn

Show Up to Win: How to Land the Leadership Role You Want 

Connect with Mahan Tavakoli:

Mahan Tavakoli Website 

Mahan Tavakoli on LinkedIn 

Partnering Leadership Website

AI is rapidly improving what people can produce. But is it also weakening the capabilities that make people valuable in the first place?

In this episode of Partnering Leadership, Mahan Tavakoli speaks with Eric So, Stanford-trained behavioral researcher, longtime MIT professor, and author of The Collision: What AI Does to Us. Eric explores a question that sits underneath much of today’s excitement about artificial intelligence: not simply what AI can do for us, but what sustained reliance on AI may be doing to how we think, learn, judge, and work.

Eric explains why AI represents a more consequential shift than previous cognitive tools. Calculators automated pieces of thinking. AI increasingly offers to perform the entire chain, from interpreting a problem to generating an answer. That creates a new risk: people can produce polished work while bypassing the struggle that develops understanding and mastery. The result can be better output without deeper capability.

The conversation then turns to what this means inside organizations. Eric introduces the idea of “signature thinking skills,” the forms of judgment and expertise that distinguish one professional from another. He argues that organizations should be careful not to incentivize AI use for its own sake, because doing so can encourage employees to outsource precisely the capabilities they most need to preserve.

Eric also challenges the common assumption that strong human judgment combined with strong AI will automatically produce better results. His “dream team fallacy” highlights how anchoring, complacency, and overreliance can make human-AI collaboration worse than expected. That leads to a counterintuitive design principle: sometimes organizations need to preserve friction so people continue to think, question, and remain engaged rather than becoming passive recipients of machine-generated recommendations.

Finally, the conversation examines what happens when cognitive outsourcing moves from the individual to the organization. Eric raises concerns about lost apprenticeship, weakened institutional memory, reduced knowledge transfer, and the erosion of trust when people increasingly turn to AI instead of one another. At the same time, he makes clear that the goal is not to reject AI. The opportunity is to use it in ways that expand human capability, reinvest the time it saves into higher-value thinking, and make people better off, not merely faster.

Actionable Takeaways

• You’ll learn why Eric So believes AI is fundamentally different from calculators, search engines, and other tools because it can increasingly take over the full chain of thinking, not just one step in it.
• Hear how to distinguish between using AI to amplify your work and outsourcing the “signature thinking skills” that actually define your professional value.
• You’ll learn why polished AI-generated output can create a dangerous illusion of mastery, and why being able to explain or defend an idea may reveal more than the quality of the artifact itself.
• Hear how incentive systems can unintentionally push employees to overuse AI, and why rewarding outcomes rather than raw AI activity may lead to better organizational behavior.
• You’ll learn why “great human + great AI” does not automatically produce better performance, and how anchoring and complacency can undermine the value of human judgment.
• Hear why introducing deliberate friction into AI interactions can sometimes improve reasoning, retention, and the quality of human-machine collaboration.
• You’ll learn how short-term efficiency gains from reducing junior roles may create longer-term risks for expertise, succession, and organizational memory.
• Hear how to think about AI as a cognitive trainer rather than simply an answering machine, and why reinvesting the time AI saves may be more important than using it to produce more of the same.

Connect with Eric So

Eric So Website

Eric So LinkedIn

Connect with Mahan Tavakoli:

Mahan Tavakoli Website 

Mahan Tavakoli on LinkedIn 

Partnering Leadership Website

What separates leadership as an idea from leading as a daily practice? For Dr. Thom Mayer, the distinction matters. Leadership can become a collection of concepts, titles, and aspirations. Leading is what people actually do, especially when circumstances are uncertain, the stakes are high, and there is no playbook to follow.

Dr. Mayer has spent much of his career in precisely those environments. He served as the command physician at the Pentagon on September 11, 2001, and is the longtime Medical Director of the NFL Players Association, where he helped lead the transformation of the league's approach to concussion diagnosis and care. Drawing on these experiences and others, he wrote Leadership Is Worthless...But Leading Is Priceless: What I Learned from 9/11, the NFL, and Ukraine.

In this episode of Partnering Leadership, Dr. Mayer and Mahan explore why leadership should not be reserved for people with senior titles or treated as something employees earn later in their careers. They discuss what changes when organizations expect people throughout the enterprise to see themselves as leaders, why the people closest to the work often hold knowledge senior executives need, and what organizational charts can obscure about where real influence resides.

The conversation also examines trust as an operating requirement rather than a leadership platitude. Dr. Mayer shares how relationships led to his role with the NFL Players Association, how influence rather than formal power helped change deeply embedded practices around concussions, and why innovation ultimately moves at the speed of trust. His experiences offer a useful lens for executives trying to create organizations in which people can challenge assumptions, exercise judgment, and act without waiting for permission from above.

Throughout the conversation, Dr. Mayer draws lessons from elite athletes, crisis response, medicine, and his own leadership journey. From studying failure with the discipline of an NFL team to helping people discover where their "deep joy" intersects with the world's needs, this episode challenges leaders to think less about the language of leadership and more about the behaviors, relationships, and responsibilities through which leading actually happens.

Actionable Takeaways

• You'll learn why Dr. Mayer argues that "leadership" and "leading" are fundamentally different, and why that distinction matters far beyond the executive suite.
• Hear how arriving at the Pentagon on September 11 with "Command Physician" written across his vest shaped Dr. Mayer's understanding of leading when there is no precedent or playbook to follow.
• Discover why leaders may need to spend less time looking upward in the hierarchy and more time listening to the people closest to the work, especially when decisions depend on knowledge executives don't possess.
• You'll hear why Dr. Mayer believes an organization's real culture isn't found in its stated mission, vision, or values, but in what people actually do when circumstances become difficult.
• Hear the remarkable story of how a personal relationship led Dr. Mayer to become the first Medical Director of the NFL Players Association, and why he advises leaders to build relationships rather than obsess over building résumés.
• Learn how Dr. Mayer used influence without formal power to help challenge the NFL's approach to concussions and advocate for the players and families whose interests he represented.
• Explore why innovation may depend less on the intelligence or creativity available inside an organization than on whether people trust one another enough to experiment, challenge assumptions, and take risks.
• Hear what studying thousands of elite NFL athletes taught Dr. Mayer about examining mistakes, learning from near misses, and turning failure into fuel for better performance.
• Discover what happened when an NFL coach told a player, "I'm not paying you to think," and what the player's remarkable second career reveals about talent, identity, and finding new ways to contribute.
• You'll learn a practical approach Dr. Mayer uses to help people identify where their deepest sources of energy and meaning intersect with work that matters.

Connect with Dr. Thom Mayer

Thom Mayer's Website
Thom Mayer LinkedIn

Connect with Mahan Tavakoli:

Mahan Tavakoli Website 

Mahan Tavakoli on LinkedIn 

Partnering Leadership Website

When AI can generate plausible ideas and polished content in seconds, producing more of it is not a competitive advantage. For CEOs and senior executives, the more consequential question is whether they have an idea worth advancing, an audience for whom it genuinely matters, and the credibility to influence how others think and act.

In this episode of Partnering Leadership, Mahan Tavakoli speaks with Bill Sherman, a leading authority on thought leadership and coauthor of The Thought Leadership Handbook: How the Experts Elevate Their Big Ideas and How You Can Too. Drawing on more than two decades of advising executives, authors, and organizations, as well as hundreds of conversations with thought leadership practitioners, Bill explains what separates meaningful thought leadership from content marketing, personal branding, and the growing volume of AI-generated noise.

The conversation explores how leaders can turn expertise into ideas that travel beyond them. Bill shares why reaching more people is often the wrong goal, how leaders can become deeply relevant to the right audience, and what it takes to make an idea simple enough to remember without stripping away the depth that makes it valuable. He also explains why thought leadership should not reside only with the CEO and how organizations can enable more people to advance important conversations with customers, partners, and their industries.

Mahan and Bill also examine the role of credibility in a world of abundant intelligence. AI may provide instant access to knowledge and recommendations, but consequential decisions still raise questions of judgment, sourcing, and accountability. When the stakes are high, who stands behind the recommendation may matter as much as the intelligence used to produce it.

Bill also reflects candidly on why he waited so long to write a book despite helping others develop and scale their ideas. His experience reveals the uncertainty, sacrifice, and sense of responsibility involved in moving from private expertise to public contribution. This conversation offers a grounded examination of how leaders can use ideas not simply to gain attention, but to create meaningful and lasting impact.

Actionable Takeaways

• You’ll learn why thought leadership is not about being known by everyone, but about becoming deeply relevant to the people whose thinking and decisions you hope to influence.
• Hear how to distinguish genuine thought leadership from content marketing, personal branding, and ideas that merely repeat what others have already said.
• You’ll discover why simplicity does not require oversimplification and how the strongest ideas can be understood by a new manager while still challenging an experienced CEO.
• Hear why understanding a problem makes you an expert, but helping others understand and apply what you have learned is what allows an idea to scale.
• You’ll learn how leaders can move thought leadership beyond the executive suite by enabling employees across the organization to advance valuable conversations with customers and stakeholders.
• Hear how AI-generated content changes the thought leadership landscape and why credibility, attribution, and accountability may become more valuable as intelligence becomes more abundant.
• You’ll discover why a smaller, actively engaged audience can create more business impact than a large following that pays little attention.
• Hear why meaningful thought leadership requires giving substantial value before asking for attention, opportunity, or commercial return.
• You’ll learn what finally convinced Bill Sherman to write his own book after decades of helping other experts develop theirs, and why people with hard-earned insight may have a responsibility to share it.

Connect with Bill Sherman

Bill Sherman LinkedIn

Thought Leadership Leverage

Connect with Mahan Tavakoli:

Mahan Tavakoli Website 

Mahan Tavakoli on LinkedIn 

Partnering Leadership Website

Most leaders understand that strategy requires choices. Fewer are prepared for what follows: disappointing people, committing resources under uncertainty, and accepting responsibility when the consequences are significant. Those pressures are not unique to the battlefield. They show up whenever CEOs and senior executives must choose a direction while facing incomplete information, competing stakeholders, and no risk-free option.

In this episode of Partnering Leadership, Mahan Tavakoli speaks with Matt Cavanaugh, a military strategist, combat veteran, former West Point professor, and author of Who Wins Wars? Lessons in Leadership, Power, and Supreme Command from Washington, Grant, and Eisenhower. Drawing on more than a decade of research, Cavanaugh examines what separated these commanders from the capable opponents they faced and what their decisions reveal about leadership under pressure.

Rather than treating victory as proof of brilliance, Cavanaugh looks closely at moments when outcomes remained uncertain and leaders made consequential choices. He explains how Washington survived repeated tactical defeats, why Grant refused to follow the accepted rhythm of Civil War campaigns, and how Eisenhower weighed conflicting advice before one of the most consequential military operations in history.

Their success depended on more than courage or military expertise. Each leader had to absorb competing perspectives, manage political relationships, understand adversaries, work within constraints, and then exercise judgment. The conversation explores the balance between openness and conviction: listening broadly enough to see the situation clearly while still accepting the responsibility to choose.

Cavanaugh also considers what these lessons mean in an age of artificial intelligence. AI can expand the information available to leaders and strengthen their thinking, but it cannot carry the human consequences of a decision. For leaders facing higher stakes and accelerating change, this conversation offers a historically grounded examination of how judgment develops, why strategic and tactical excellence are not the same, and what it takes to lead when there is no obvious answer.

Actionable Takeaways

• You’ll learn why strategy inevitably disappoints someone and what that means for leaders who mistake broad agreement for strategic clarity.
• Hear how Washington, Grant, and Eisenhower developed superior judgment rather than simply possessing it from the beginning of their careers.
• You’ll learn how to distinguish strategic leadership from tactical excellence, including why an organization can execute exceptionally well and still lose the larger competition.
• Hear how Eisenhower evaluated sharply conflicting recommendations before D-Day and accepted personal responsibility for a decision with enormous human consequences.
• You’ll learn why emotional intelligence is a strategic capability, not merely a tool for maintaining relationships or improving morale.
• Hear how great leaders combine openness with conviction, taking in competing ideas before choosing a direction and staying with it through criticism.
• You’ll learn why no strategic leader succeeds alone and how Washington, Grant, and Eisenhower used advisers, councils, and trusted colleagues differently.
• Hear how effective leaders work within political and resource constraints without allowing those limitations to become excuses for inaction.
• You’ll learn how AI can amplify strategic thinking while leaving consequential judgment with human leaders who remain responsible for the outcome.

Connect with Matt Cavanaugh

Matt Cavanaugh on X @mlcavanaugh

Connect with Mahan Tavakoli:

Mahan Tavakoli Website 

Mahan Tavakoli on LinkedIn 

Partnering Leadership Website

What happens to the way we design organizations when intelligence is no longer scarce? That is the provocative question at the heart of this conversation with Brian Solis and Dave Wright, co-authors of Infinite: How Visionary Leaders Transform Today’s Business Into AI-Forward Companies. Drawing on decades of experience at the intersection of technology, strategy, innovation, and enterprise transformation, Brian and Dave challenge executives to think beyond AI adoption and productivity gains toward a much larger opportunity: rethinking how organizations create value.

The conversation explores why simply layering AI onto existing workflows may leave much of its potential untapped. Organizations were largely designed around scarcity, particularly the scarcity and cost of human expertise and capacity. AI changes that assumption. Brian and Dave discuss what becomes possible when leaders stop asking only how AI can make today’s work faster and begin asking what the organization could do that previously wasn’t possible.

A central tension throughout the episode is the difference between efficiency and reinvention. Dave shares a compelling example from IKEA that illustrates how productivity gains from AI can become the starting point for entirely new sources of value rather than simply cost reduction. Brian builds on that idea by challenging executives to examine the legacy assumptions, structures, and even “sacred cows” they may be protecting. The question is not simply where AI can be deployed, but where intelligence can be applied to rethink work, customer value, and future growth.

The discussion also gets into the harder leadership questions surrounding AI transformation: employee fear, trust, learning and unlearning, resource allocation, and the pressure from boards and shareholders to demonstrate ROI. Brian and Dave explain why AI transformation cannot simply be delegated to technology teams or pursued through disconnected pilots. They explore what it takes to create enough clarity and trust for people to challenge poor uses of AI while also experimenting with fundamentally different ways of working.

For CEOs and senior executives, this conversation offers a useful reframing of the AI opportunity. The advantage may not go to the organizations that deploy the most AI or generate the largest number of productivity gains. It may go to those that learn how to convert new intelligence and capacity into better workflows, new sources of value, and the ability to continually reinvent themselves.

Actionable Takeaways

• You’ll learn why an AI strategy shouldn’t really be about AI and what Brian and Dave believe executives should focus on instead when deciding where AI belongs in the organization.
• Hear why using AI to make existing work faster may capture only a fraction of its potential, and how shifting from optimization to reinvention changes the questions executives should be asking.
• Discover what changes when intelligence moves from scarcity toward abundance, including why organizational structures and workflows designed for the previous era may increasingly become constraints.
• Hear how IKEA turned AI-driven efficiency into a new source of growth, offering a powerful example of what can happen when organizations deliberately reinvest capacity rather than simply bank the savings.
• You’ll learn why trust around AI requires more than encouraging adoption. Brian and Dave explain why people also need the freedom to challenge AI and say when it is not the right tool for the job.
• Explore the concept of “learning velocity” and why the ability to learn and unlearn at speed may become an increasingly important organizational capability as AI continues to evolve.
• Hear why disconnected AI pilots often struggle to produce meaningful enterprise ROI, and why resource allocation and executive-level direction become critical when productivity gains appear across different parts of the organization.
• You’ll learn why traditional AI metrics can be dangerously misleading, and why measuring the performance of the entire workflow can reveal whether AI is actually creating better outcomes or merely generating more activity.
• Consider a provocative resource-allocation question: if AI effectively gave your organization hundreds of additional people’s worth of capacity, what would you choose to do with it?

Connect with Brian Solis and Dave Wright

Brian Solis LinkedIn

Dave Wright LinkedIn

Infinite: How Visionary Leaders Transform Today’s Business Into AI-Forward Companies

Connect with Mahan Tavakoli:

Mahan Tavakoli Website 

Mahan Tavakoli on LinkedIn 

Partnering Leadership Website

As uncertainty rises, people often look to leaders for greater certainty. Yet the more complex the environment becomes, the less credible it is for any one person to claim they have the answers. The leadership challenge is no longer simply making better decisions. It is creating the conditions for better questions, broader participation, and stronger collective judgment.

In this episode of Partnering Leadership, Mahan Tavakoli speaks with Larry Robertson, leadership advisor, Fulbright Scholar, and author of Great Question: The Art of the Ask and Getting More of What You Really Want. Drawing on his research into entrepreneurship, creativity, and leadership under uncertainty, Larry explains why questioning is not merely a communication technique. It is a core organizational capability that helps leaders test assumptions, recognize emerging threats, and see opportunities before they become obvious.

The conversation examines the difference between asking more questions and building a genuinely questioning culture. Larry challenges leaders to consider whether the questions inside their organizations are authentic or simply statements disguised as questions. He also explores who is permitted to ask, which questions receive serious attention, and whether senior leaders are willing to be changed by what they hear.

Mahan and Larry also address the growing role of artificial intelligence. AI can identify patterns and generate predictions from what has already happened, but that raises a consequential leadership question: What happens when the assumptions embedded in historical data no longer hold? Their discussion reveals why human curiosity, contextual judgment, and intellectual humility may become more important as AI becomes more capable.

Throughout the conversation, Larry offers memorable ways to strengthen leadership judgment, from learning to “quiet your cleverness” and “listen atmospherically” to distinguishing functional questions from the great questions that shape strategy and direction. This episode provides a practical and timely examination of how CEOs and senior executives can lead without pretending to possess certainty they do not have.

Actionable Takeaways

• You’ll learn why rising uncertainty should produce more and better questions, even as employees, boards, and stakeholders increasingly pressure leaders to provide definitive answers.
• Hear how the expectation that senior leaders should have all the answers can weaken organizational judgment and prevent essential information from reaching decision-makers.
• You’ll discover how to distinguish authentic inquiry from questions that are actually statements, challenges, or tests of allegiance.
• Hear why a questioning leader and a questioning culture are fundamentally different, and what must change before people throughout an organization feel able to challenge assumptions.
• You’ll learn what leaders can uncover by observing who asks questions, which questions receive attention, and where questioning quietly stops within the hierarchy.
• Hear how to distinguish functional questions that help operate the business from larger questions that can reshape its strategy, direction, and future value.
• You’ll discover why intellectual humility does not require leaders to minimize their expertise, but does require them to recognize when that expertise may no longer fit the situation.
• Hear how “quieting your cleverness” and “listening atmospherically” can help experienced executives notice context, signals, and perspectives they might otherwise miss.
• You’ll learn why AI’s reliance on historical patterns makes human questioning especially important when technologies, markets, and customer expectations are changing.
• Hear how forward-looking reflection can improve future judgment rather than merely helping leaders interpret decisions they have already made.
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Connect with Larry Robertson

Larry Robertson Website

Larry Robertson LinkedIn

Connect with Mahan Tavakoli:

Mahan Tavakoli Website 

Mahan Tavakoli on LinkedIn 

Partnering Leadership Website

In this episode of Partnering Leadership, Mahan Tavakoli speaks with John Kotter, professor emeritus at Harvard Business School, co-founder of a management consulting firm Kotter International and a pioneer in organizational change. John Kotter is the author of 22 books on change, including his most recent book, Change: How Organizations Achieve Hard-to-Imagine Results in Uncertain and Volatile times. John Kotter talks about the struggles leaders and teams face when it comes to change and how to transform organizations to adapt to change effectively and rapidly.

Some highlights:

-John Kotter on the role of human nature on our resistance to change

-The essential components for initiating change in the organization

-Understanding the Survive and Thrive mode and how it impacts our ability to change

-The power of Guiding Coalition to help bring expertise, energy, and perspective across the organization

-The difference between management and leadership

Connect with John Kotter:

Change: How Organizations Achieve Hard-to-Imagine Results in Uncertain and Volatile Times

John Kotter - Kotter International Inc

John Kotter on LinkedIn

John Kotter on Facebook

John Kotter on Twitter

Connect with Mahan Tavakoli:

Mahan Tavakoli Website 

Mahan Tavakoli on LinkedIn 

Partnering Leadership Website

AI adoption is often treated as a technology challenge: choose the right tools, train people to use them, and drive implementation. Dr. Gleb Tsipursky argues that this framing misses the harder problem. Unlike previous technology shifts, AI can trigger fear about job security, challenge professional identity, and create social stigma around how work gets done. For organizations trying to move from experimentation to meaningful business impact, understanding those human dynamics may matter as much as the technology itself.

In this episode of Partnering Leadership, Gleb Tsipursky joins Mahan Tavakoli to discuss his new book, The Psychology of AI Adoption at Work: From Resistance to Results. Drawing on behavioral science research, thousands of survey responses, focus groups, and more than 100 consulting engagements, Gleb explains why traditional approaches to technology adoption often fall short with AI. The conversation examines the very different reasons employees resist, quietly embrace, or even hide their use of AI, and what those behaviors reveal about organizational culture.

The discussion moves beyond adoption to a deeper question facing CEOs and senior executives: what happens when AI changes not only how quickly work gets done, but also how people understand the value they bring? Gleb explores professional identity, shadow AI, the critical role of middle managers, and why organizations may need to rethink where they begin their AI efforts. He also challenges the instinct to start by automating the highest-value activities, offering a counterintuitive approach designed to build trust, experimentation, and broader adoption.

Mahan and Gleb also explore a growing leadership challenge: AI can dramatically increase output while making judgment more important. If AI increasingly generates reports, analysis, presentations, and other knowledge work, the differentiating human capability may shift from producing the first draft to evaluating whether the output is actually good. That raises important questions about how organizations develop early-career talent, redesign onboarding and apprenticeships, and build judgment when AI performs more of the work through which judgment was traditionally developed.

Finally, the conversation looks ahead to an emerging workplace in which employees may increasingly manage AI agents rather than perform individual tasks themselves. Managers, in turn, may need to manage people who manage agents while coordinating increasingly complex human-machine workflows. The result is a conversation not simply about getting employees to use AI, but about the capabilities, culture, management practices, and continual learning organizations will need as AI becomes embedded in how work gets done.

Actionable Takeaways

• You’ll learn why AI adoption creates psychological challenges that traditional technology implementations often do not, and why treating AI like another CRM, ERP, or software rollout can lead organizations to misdiagnose resistance.
• Hear how fear, professional identity, and social stigma can produce very different forms of AI resistance, requiring more nuanced responses than simply mandating adoption or providing additional training.
• You’ll discover why some employees may already be using AI extensively while deliberately hiding that use from colleagues and managers, and what this “shadow AI” behavior can cost organizations in shared learning and business impact.
• Hear why starting with the highest-value work may not always be the smartest path to AI adoption. Gleb explains why beginning with tasks employees actively dislike can create an unexpected path toward broader experimentation and acceptance.
• You’ll learn why executive behavior matters in establishing the social norms around AI use, including how openly sharing successful AI applications can help shift AI from something employees conceal to something teams learn from together.
• Hear why middle managers may become one of the most important leverage points in AI adoption, translating executive intent into the everyday behaviors, experimentation, reinforcement, and learning that determine whether adoption actually takes hold.
• You’ll explore why judgment may become more valuable as AI becomes better at producing work. The conversation examines the difference between generating an answer and knowing whether that answer is good enough to act on.
• You’ll hear why AI creates a significant challenge for developing younger professionals, particularly when technology begins performing the work through which previous generations accumulated experience and learned to recognize quality.
• You’ll learn how the role of employees and managers could change as AI agents become more capable, moving from personally executing individual tasks toward directing agents, evaluating their output, managing handoffs, and improving human-machine workflows.
• Hear why there may be no final state of “AI maturity.” Instead, organizations may need to build the capacity for continual learning as AI capabilities, workflows, and the skills required to manage them keep changing.

Connect with Gleb Tsipursky

Disaster Avoidance Experts Website

Dr. Gleb Tsipursky LinkedIn

Connect with Mahan Tavakoli:

Mahan Tavakoli Website 

Mahan Tavakoli on LinkedIn 

Partnering Leadership Website

Welcome to the Summer Leadership Reset on Partnering Leadership.

We have more access to ideas than ever before.

More books. More podcasts. More articles. More insights.

The challenge isn’t finding more information. It’s spending enough time with the ideas that can change how we think, decide, and lead.

I have seen this in my own life. The books and conversations that have influenced me most aren’t the ones I rushed through and moved on from. They are the ones I returned to, wrestled with, and understood differently as my own experiences changed.

After more than 450 Partnering Leadership conversations with CEOs, researchers, authors, and leadership thinkers, there are a few I continue coming back to because the ideas become more valuable the more we sit with them.

Throughout July and August, I’ll be sharing 10 of those conversations.

They explore some of the questions I see leaders wrestling with most: adapting to change, building trust, making better decisions, rethinking work, using AI wisely, and creating organizations ready for what comes next.

Whether you are listening for the first time or revisiting these conversations, I hope they help you find an insight you can apply and a question worth thinking about long after the episode ends.

—Mahan

Connect with Mahan Tavakoli:

Mahan Tavakoli Website 

Mahan Tavakoli on LinkedIn 

Partnering Leadership Website