In this episode of From the Top with Chad Hesters, host Chad Hesters connects with Donald Thompson, a multi-exit entrepreneur and award-winning CEO, to explore his career path spanning software, marketing, and corporate leadership. Their conversation unveils insights on why being "underestimated" can be a strategic advantage and how "hustling with humility" allows leaders to accelerate their professional development. They dive deep into psychological safety as a critical risk management tool, strategies for professional persistence in conservative cultures, and the evolving role of AI in shaping modern employee engagement.

Donald Thompson is an award-winning CEO, multi-exit entrepreneur, and Managing Director for the Center of Organizational Effectiveness at Workplace Options, bringing decades of experience in building high-performance teams and scaling businesses. Recognized as an Entrepreneur of the Year, Forbes Next 1000 honoree, and three-time Inc 5000 Chief Executive, Thompson has guided companies from bootstrap phases to successful acquisitions by Adobe Systems and private equity firms. In this episode, Thompson shares transformative insights on employee engagement, inclusive leadership, and navigating organizational culture in the age of AI—providing C-suite executives with practical strategies for building trust, reducing turnover, and driving psychological safety without compromising performance standards. His philosophy of "hustle with humility" and commitment to empathetic yet excellence-driven leadership resonates deeply with strategic decision-makers seeking to cultivate engaged, loyal teams that speak up when it matters most.

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"Anything that you're gonna do big and significant requires a team to execute it through. You can have an individual vision, but in order for that vision to have value at scale, you have to be able to be resilient." - Donald Thompson

"Winning through people is going to be the enduring element of business success both now and the future." - Donald Thompson

"You endure pain because the promise is so much greater." - Donald Thompson

"I turned that lack into kind of a limited resource to really be a competitive learner." - Donald Thompson

"Hustle with humility is finding people to help you with the things that you need to work on." - Donald Thompson

"The risk factor is that most leaders are making decisions on a lower percentage of insight than they have in the organization because people are afraid to speak up." - Donald Thompson

"Psychological safety is, do you create an environment where the best ideas surface in time for you to execute them properly?" - Donald Thompson

"Every time I enter a discussion, I have seniority power in most rooms that I'm in, so it sounds like a dictate even when I'm just trying to add to the dialogue." - Donald Thompson

"When you are an elite leader, an elite performer, then that means there's always more to grow, learn, and improve." - Donald Thompson

"AI is not the technology. It is about how do we adopt this technology in a manner that doesn't create fear but creates enthusiasm and opportunity to have a better, more profitable future." - Donald Thompson

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In this episode of From the Top, host Chad Hesters sits down with Jonny Gray, a senior global sports executive and advisor, to explore leadership in one of the world's most complex, high-stakes industries. Drawing from a 21-year military career commanding at battalion level and subsequent roles as CEO of the International Tennis Integrity Agency and head of sports consulting at major advisory firms, Gray provides a masterclass in navigating the collision between commercial pressures, regulatory demands, and the fundamental unpredictability of athletic competition.

Jonny Gray is a Senior Global Sports Executive and Advisor with over two decades of leadership experience spanning the British military, risk consulting, and international sports governance. With a distinguished 21-year career in the UK infantry culminating in battalion command during operations in Iraq, Gray transitioned into the commercial sector, eventually establishing himself as a thought leader in sports integrity, regulatory frameworks, and organizational change management. He served as the inaugural Chief Executive of the International Tennis Integrity Agency and currently leads sports advisory practices across multiple firms while serving as a bid monitor for the UK's Women's World Cup 2030 campaign. In this episode, Gray shares critical insights on leading complex, high-stakes global sports organizations—exploring how military-trained resilience, adaptive leadership, and change management principles translate into navigating the modern sports landscape's evolving regulatory, commercial, and integrity challenges.

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"Leadership is about people. Leadership is about inspiring people to come into work every day and do more than perhaps they would want to do or to do something to act in a way that is about the team, about the organization, as much as it is about themselves." - Jonny Gray

"People want a leader who sets very clear goals, and makes everybody understand what their role is, what their part of the plan is in delivering those goals." - Jonny Gray

"No plan survives contact with the enemy. A sport's similar—you can have a great plan, but what happens when the whistle blows can change that." - Jonny Gray

"The ability to be flexible, great principle of war flexibility, adaptability, all of that, I think, are essential to a modern leader in sport." - Jonny Gray

"There's a tension between the commercial imperatives and the athletic purity—that's a big conversation happening in sport right now." - Jonny Gray

"When you come into an organization as a new leader, do not assume everybody is just on board with whatever it might be that you're trying to do." - Jonny Gray

"Taking time and effort to understand the dynamics and agendas in play, then trying to bring people with you as much as you can, is really difficult." - Jonny Gray

"Good leadership traits are perhaps more important in sport than in other sectors—you may not have to be a great leader to run an automotive assembly plant, but certainly in sport, leadership's more important." - Jonny Gray

"I think people want to be inspired—they want a clear sense of mission, purpose, design, and then the resources and tools to do the job." - Jonny Gray

"Change will mean that perhaps some jobs are going to go or other people are going to come in over people, and not everybody sees change as exciting—many see it as threatening." - Jonny Gray

Episode Highlights:


[00:14:47] Understand Match-Fixing and Integrity Threats as Evolving Organized Crime, Not Relic Issues –

Gray reveals that modern match-fixing operates through international criminal networks using sophisticated approaches (sponsorship deals, spot-fixing individual games rather than whole matches) targeting lower-paid athletes in lower-tier competitions. The problem compounds because betting deregulation creates billions in global wagers, allowing criminals to spread bets below detection thresholds while generating massive returns. For C-suite leaders in sports, entertainment, or any high-stakes industry with integrity vulnerabilities, this insight reframes risk: assume bad actors are already probing your organization, that their approaches are subtle and disguised as legitimate partnerships, and that detection requires systematic monitoring, not reactive investigation. Implement regular integrity audits, educate employees on social engineering tactics, and establish anonymous reporting channels—treating integrity breaches as organized crime rather than isolated lapses. This mindset shift moves you from reactive (catching problems after they occur) to proactive (making your organization an unattractive target).


[00:22:00] Distinguish Leadership from Management to Avoid Toxic Organizational Cultures –

Jonny Gray emphasizes that military training taught him a critical distinction: management allocates resources and handles technical processes, while leadership inspires people to act beyond self-interest for organizational mission. Many commercial leaders conflate these roles, creating blame cultures when external outcomes (like missing playoffs) shift responsibility downward. C-suite executives managing teams in volatile environments often default to management—controlling processes—when staff actually crave inspired leadership with clear purpose. To apply this, spend your first 30 days identifying which team members respond to vision-setting versus resource optimization, then deliberately shift your communication style to lead (inspire mission) rather than manage (allocate tasks). A CEO who frames a market downturn as a collective challenge to solve together builds resilience; one who assigns blame accelerates toxic dynamics. For leaders navigating complex, unpredictable industries, this distinction directly impacts retention, morale, and organizational adaptability.

[00:28:24] Recognize That Emotional Stakeholder Investment Creates Unique Leadership Pressure Unknown in Traditional Business –

Gray points out that sports leaders face a stakeholder dynamic absent in most industries: fans will riot, burn vehicles, and demand executive heads online if performance falters—creating emotional intensity unmatched in typical corporate environments. No automotive or software executive's stakeholders riot if quarterly earnings miss. This amplifies pressure on leadership teams exponentially and requires distinct psychological resilience. For executives in consumer-facing, mission-driven, or publicly scrutinized industries (healthcare, education, nonprofit leadership), this dynamic applies equally. Build resilience by explicitly acknowledging that external passion and criticism aren't personal failures but signatures of high-stakes work. Create peer support structures where leadership teams process collective pressure without internalizing blame. Communicate transparently with passionate stakeholders about decision rationale, even when unpopular—transparency doesn't eliminate criticism but prevents it from feeling like secret incompetence. Leaders who normalize the emotional intensity of high-stakes work and separate their personal worth from quarterly outcomes survive and thrive; those who take criticism personally burn out rapidly.

[00:30:53] Build Organizational Resilience by Accepting What You Cannot Control –

Gray shares that sports leadership uniquely mirrors military command because the whistle blows and things change—external forces (competition, market conditions, or in sports, actual game outcomes) always have a say in your plan's success. Leaders who struggle with this reality create toxicity; those who accept it build resilient teams. Many C-suite executives operate under the illusion that excellent strategy guarantees results, leading to burnout and blame when markets shift unexpectedly. To build resilience, explicitly communicate to your team that flexibility, adaptability, and pivot capability matter as much as flawless execution. Frame setbacks not as failures but as recalibration opportunities—the same mindset military leaders use when battle plans change mid-operation. When your leadership openly models acceptance of uncontrollable factors while maintaining clear vision, team members internalize that resilience comes from adaptability, not perfection. This transforms high-pressure environments from demoralizing to energizing.

[00:35:02] Lead Star Talent by Creating Collective Mission, Not Individual Management –

Gray explains that managing high-ego, high-earning superstars succeeds not through negotiation or accommodation but through reframing their role within collective mission—just as a military commander positions each soldier's role within platoon strategy. Elite athletes (like elite executives) need to understand they're part of something bigger and have a specific, valued role to play; prima donna management typically fails. For C-suite leaders managing high-ego executives, board members, or founder-led teams, this principle applies directly: establish non-negotiable mission clarity, define each person's specific contribution to that mission, allocate appropriate autonomy within their domain, and hold firm on boundaries. A CEO managing a charismatic VP of Sales who thinks rules don't apply succeeds by clarifying role boundaries and mission contribution, not by attempting to manage personality. This approach respects individual capability while maintaining organizational coherence, preventing star talent from destabilizing team dynamics or creating toxic cultures around their exceptionalism.

[00:36:37] Conduct Organizational Due Diligence Before Implementing Change; Don't Assume Buy-In –

Gray's most potent lesson: when entering a new leadership role, he initially assumed stakeholders would simply accept directives once he arrived, only to discover hidden agendas, threatened employees, and covert resistance. Change is universally threatening to those comfortable with status quo—some fear job loss, others wanted your role, and many see disruption as existential risk. Before rolling out transformation initiatives, invest 30–60 days understanding organizational dynamics: who benefits from current state, who loses, where power truly resides, and what informal coalitions exist. Then explicitly communicate why change matters and create pathways for people to participate rather than resist. Executives who skip this step waste 6–12 months fighting invisible opposition; those who invest upfront encounter far less friction. For leaders parachuting into mid-market firms or leading restructures, this due diligence transforms change from a top-down imposition into a collaborative evolution, dramatically increasing adoption rates and reducing sabotage risk.

Episode Resources:

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Xenia Wickett is the founder of Wickett Advisory, a boutique consultancy providing executive coaching, geopolitical advisory services, and strategic leadership facilitation. With an extraordinary career spanning roles at the U.S. State Department, White House National Security Council, Harvard Kennedy School, and Chatham House, she brings unique insights into global leadership and complex decision-making. Her expertise combines deep understanding of geopolitical dynamics with practical leadership development, having served as Dean of the Academy for Leadership in International Affairs at Chatham House and led strategic initiatives at major institutions worldwide.

In this episode, Wickett shares valuable perspectives on the importance of cultivating curiosity and determination in leadership, the balance between specialist and generalist approaches, and how leaders can navigate increasingly complex global environments. Her combination of diplomatic experience, academic credentials from Oxford and Harvard, and extensive work with global executives makes this conversation particularly relevant for senior leaders seeking to enhance their strategic thinking and leadership capabilities in today's dynamic business landscape.

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Xenia Wickett reveals that curiosity and determination, not technical expertise, are the fundamental drivers of leadership success. In today's complex business environment, leaders must constantly explore new information sources and persist through challenges. While specific skills can be learned, the ability to remain intellectually curious and resilient is crucial for long-term growth. Leaders should actively cultivate a mindset of exploration and steady resolve, even when facing unfamiliar territories. For C-suite executives, these traits enable adaptation to rapidly changing business landscapes while maintaining strategic focus.

Modern leaders must balance specialist expertise with broad generalist capabilities to succeed. The ability to connect developments across sectors and geographies has become increasingly valuable as business environments grow more interconnected. Mid-career executives should actively expand beyond their core expertise to develop a more comprehensive leadership perspective. This broader viewpoint allows leaders to better understand how different business elements affect each other globally. CEOs and senior leaders who can effectively translate between specialist and generalist perspectives are best positioned to guide organizations through complexity.

Successful leaders recognize they can't be experts in everything and instead focus on building strong networks of diverse expertise. This approach requires both confidence in one's core knowledge and humility about limitations - a balance that enables better decision-making. Leaders must cultivate relationships with subject matter experts while maintaining enough understanding to ask intelligent questions and integrate various perspectives. For C-suite executives, the ability to leverage external expertise through strong networks is often more valuable than trying to develop comprehensive internal knowledge.

Drawing from extensive research across sectors, Wickett identifies four essential elements for leadership success: skills, knowledge, network, and self-awareness. This framework helps leaders systematically develop their capabilities while recognizing their natural strengths and limitations. For executives, the key is finding the right balance of these elements based on their specific context and organizational needs. Senior leaders should regularly assess their development across all four pillars to ensure continued growth and effectiveness.

Wickett introduces a powerful distinction between experimenting and prototyping as approaches to innovation in risk-averse environments. By framing initiatives as experiments rather than prototypes, leaders create space for multiple attempts and learning from failure. This approach helps organizations maintain innovation while managing risk expectations effectively. The strategy particularly benefits C-suite executives working in conservative industries or cultures where failure is traditionally viewed negatively.

Today's business environment requires leaders to simultaneously understand broad global trends and make specific operational decisions. This dual focus helps executives better navigate uncertainty while making practical day-to-day choices. Senior leaders must develop the ability to translate macro insights into micro actions that drive organizational success. For C-suite executives, mastering this macro-micro connection is crucial for effective strategic planning and execution in an increasingly complex world.

"The two characteristics of mine that I think have got me to where I am aren't South Asia expertise, aren't ability to communicate or to analyze. It is curiosity and determination." - Xenia Wickett

"I never knew what I wanted to do when I grew up. I still don't. I'm early fifties, and I still don't know what I wanna do when I grow up." - Xenia Wickett

"In the context in which we're now operating in this hugely complex environment, yes, we need specialists, but it's the generalists who can translate from one sector to another." - Xenia Wickett

"The best leaders are the ones who will say, I cannot know everything." - Xenia Wickett

"Confidence in the stuff you know, humility in the stuff that you don't." - Xenia Wickett

"If I'm not learning every day, then maybe I'm doing something wrong." - Xenia Wickett

"Regrets come from the stuff you don't do, not from the stuff you do. Because the stuff you do, you learn from." - Xenia Wickett

"Always experiment, don't prototype. Experiment with ten experiments all at the same time. And then once you've figured out what works, then prototype." - Xenia Wickett

"If you can't listen, you're unlikely to be able to gather the best information to make the best decisions." - Xenia Wickett

"What makes America so incredibly strong is it has a culture of failure actually makes you a success." - Xenia Wickett

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Publications

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In this episode of From the Top, host Chad Hesters connects with Laurent "LT" Therivel, former CEO of UScellular, to explore his diverse career path spanning military service, consulting, telecommunications, and corporate leadership. Their conversation unveils valuable insights about career development, leadership philosophy, and maintaining work-life balance in demanding executive roles.

About the Guest(s):

Laurent "LT" Therivel is a seasoned executive leader and former CEO of UScellular, where he successfully led the company's strategic transition and eventual sale to T-Mobile. With a distinguished career spanning military service as a Marine Corps officer, strategic consulting at Bain & Company, and various leadership roles at AT&T including CEO of AT&T Mexico, LT brings unique insights into organizational transformation and strategic leadership. His career highlights include turning around AT&T Mexico's $3 billion operation from negative EBITDA to profitability and maintaining strong employee engagement during UScellular's transition period. In this episode, LT shares valuable perspectives on modern leadership challenges, balancing stakeholder interests, and maintaining work-life equilibrium while pursuing executive ambitions, making this conversation essential for C-suite leaders navigating complex organizational transformations and strategic decisions.

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Episode Highlights:

Laurent Therivel shares the Marine Corps principle of "people lead first," emphasizing that effective leadership starts with establishing clear mission objectives and taking care of your team. Senior executives often struggle with balancing strategic direction while empowering their teams to execute. The key is to establish clear organizational intent and goals, then focus on removing obstacles rather than micromanaging execution. Leaders should provide the "commander's intent" - a clear vision of what success looks like - then step back and let their teams determine how to achieve it. This approach, demonstrated during Therivel's turnaround of AT&T Mexico, resulted in transforming a $300M EBITDA loss into profitability by empowering teams while maintaining strategic clarity.

Therivel recounts a pivotal failure early in his career where achieving business objectives without building consensus led to his dismissal as COO of a startup. This highlights a common challenge for results-driven executives who prioritize outcomes over organizational buy-in. Rather than imposing changes unilaterally, leaders must invest time sharing ideas, gathering input, and building support across the organization. The approach not only leads to better decisions through diverse perspectives but creates stronger engagement and implementation. This lesson proved crucial in Therivel's later roles, particularly during UScellular's two-and-a-half-year acquisition process, where strong cultural alignment maintained team engagement even after the deal announcement.

In today's environment, business leaders face unprecedented expectations beyond traditional corporate metrics, requiring a delicate balance of stakeholder interests. Leaders must now address social issues and ESG concerns while maintaining business performance, often without direct authority over these broader challenges. The key is adopting a balanced, transparent approach that considers all stakeholder perspectives when making and communicating decisions. For executives, this means clearly articulating how decisions impact shareholders, customers, and employees while maintaining strategic focus. The success of this approach was demonstrated at UScellular, where clear stakeholder communication maintained strong engagement through major organizational changes.

Therivel emphasizes the critical importance of proactive family communication in managing career progression, particularly regarding geographical mobility and work-life balance. Leaders often fail by treating family discussions as afterthoughts rather than strategic priorities requiring advance planning and clear parameters. Early alignment on career flexibility, including geographic moves and time commitments, allows executives to confidently pursue opportunities without creating family tension. The approach involves establishing clear timeframes and boundaries, exemplified by Therivel's agreement with his wife about mobility until their daughters reached high school. This strategic alignment enables leaders to make decisive career moves while maintaining strong family relationships.

"Find opportunities that can leverage your strengths, be candid about your weaknesses, and ideally find people that are amazing at it and can fill those gaps in for you." - Laurent Therivel

"People look to business leaders as not just, hey, I want a good place to work and deliver for the shareholders. There's expectations around ethical leadership, moral leadership, and being a great place to work." - Laurent Therivel

"If you have a strong culture and if you have a mission oriented culture and you reinforce that and people truly believe in what it is that they're doing, they'll see it through with you." - Laurent Therivel

"When you actively dislike you, it's a problem. And I was lucky in that I learned that lesson when I was in my thirties, and so I had time to recover." - Laurent Therivel

"The two key words in managing and operating a business today, one is complexity and the other one is balance." - Laurent Therivel

"When you decide to take a social stance or when you decide to lean in to a social issue, if you communicate and explain it to your team in a way that takes all of the stakeholders into account and explains the balancing act that you're trying to strike, people will give you the benefit of the doubt." - Laurent Therivel

"The more flexible you can be, the more chances you have in front of you, the more opportunities you have to advance your career." - Laurent Therivel

"Every other move was pretty deliberate, pretty structured, but, no, I did not have the twenty year plan or the thirty year plan that I've just crisply executed against." - Laurent Therivel

"You end up making better decisions than you would on your own because you have a whole bunch of people providing thoughts and providing guidance." - Laurent Therivel

"The communication has to happen so far in advance. What kind of life are we trying to build together? What are the trade offs?" - Laurent Therivel

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Notable Organizations Mentioned:

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About the Guest(s):

Gordon Dee Smith is the CEO of Strategic Insight Group (SIG), a private intelligence agency serving global investors, law firms, and industrial organizations. As a specialist in intelligence, foreign policy, and global change analysis, he has advised on over $120 billion in investment transactions and worked in more than 100 countries. Smith combines deep expertise in transactional intelligence and geopolitical risk analysis with significant media production experience, including creating and hosting the documentary series "A World on the Brink." His unique insights into global complexity, societal change, and strategic decision-making make him an invaluable advisor for C-suite executives navigating today's uncertain business landscape.

Chad Hesters is the host of From The Top with Chad Hesters and is associated with Boyden, a global executive search firm with 75 offices across 45 countries. As a leader in global executive search and consulting, he brings practical perspective to discussions about leadership and organizational strategy in complex international markets.

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Dee Smith reveals how today's global system is the most complex human-created system in history, making traditional prediction and planning methods increasingly ineffective. This unprecedented complexity affects business leaders across all sectors, with many unable to perform to budget due to heightened uncertainty. The key to navigating this environment lies in abandoning the assumption that we can fully understand or control outcomes based on past patterns. Leaders must instead adopt continuous monitoring and flexible adaptation strategies, constantly scanning for subtle changes that could have major downstream impacts. This new approach requires developing robust indication and warning systems while maintaining clear organizational values and operating principles.

Leaders must fundamentally shift from a traditional "understanding-based" mindset to one focused on continuous adaptation and assumption testing. The old approach of basing decisions primarily on historical patterns is becoming increasingly dangerous as the past becomes less predictive of the future. Organizations need to develop sophisticated horizon-scanning capabilities and remain highly sensitive to subtle changes that could signal major shifts. This requires establishing systematic monitoring processes while maintaining strong organizational values as an anchor. Implementation means regularly challenging assumptions and being willing to adjust course quickly when new information emerges.

Smith emphasizes the critical importance of actively cultivating dissent within leadership teams rather than surrounding oneself with yes-people. Executive teams must create an environment where challenging ideas and pointing out potential weaknesses are not just accepted but encouraged. The key is ensuring dissent remains constructive and focused on organizational success rather than personal agendas. This approach requires leaders to model humility and openness to criticism while maintaining clear direction and purpose. For C-suite executives, this means actively seeking out and seriously considering perspectives that challenge their own views.

The two most crucial leadership qualities for navigating today's complex environment are healthy skepticism and genuine humility. These traits enable leaders to question assumptions effectively while remaining open to new information and perspectives that challenge their existing views. Rather than projecting certainty, effective leaders must acknowledge the limitations of their knowledge and remain adaptable. This combination helps prevent the dangerous overconfidence that often leads to major strategic errors. The most successful leaders will be those who can balance confident decision-making with intellectual humility.

Smith shares insights on how leaders should approach decision-making and respond to inevitable mistakes in an increasingly unpredictable environment. He emphasizes making decisions based on the best available information while remaining open to contradictory evidence and alternative viewpoints. When mistakes occur, leaders must model transparency and learning rather than defensiveness or denial. This approach requires creating organizational cultures that view errors as learning opportunities rather than failures. The key is maintaining credibility through honest acknowledgement of mistakes while demonstrating clear learning and adaptation.

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From The Top with Chad Hesters is brought to you by Boyden and handcrafted by our friends over at: fame.so

From The Top with Chad Hesters is brought to you by Boyden and handcrafted by our friends over at: fame.so