Leading in global sports today demands a fundamentally different skill set than managing traditional business where unpredictability isn't a risk factor, it's a certainty baked into every decision.
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.
What You'll Learn:
- How to distinguish leadership from management in high-stakes environments—and why this distinction matters more in sports than any other industry. Leadership inspires people toward collective mission; management allocates resources. Most executives conflate the two, weakening organizational resilience.
- The framework for building team resilience when your stakeholders riot in the streets if you lose—a uniquely sports-centric challenge. Leaders must cultivate flexible mindsets, clear vision, and the emotional fortitude to adapt plans mid-execution when "the whistle blows," not just survive setbacks but thrive through them.
- Why match fixing in modern sports is more sophisticated than most leaders realize—and how betting deregulation has weaponized it. Understanding that organized crime now coordinates global spot-fixes across minor tournaments using subtle sponsorship arrangements helps executives grasp the true scope of integrity risks they're managing.
- The critical error leaders make when entering a new organization: assuming buy-in when facing resistance. Gray's hard-won lesson: spend time understanding organizational dynamics, hidden agendas, and people threatened by change before rushing to implement your vision. Not everyone wants transformation—some are actively working against it.
- How military leadership principles translate directly to sports and commercial leadership—especially adaptability, flexibility, and the understanding that external forces (competitors, market conditions, the opponent) always have a say in your plan's outcome. The principle "no plan survives contact with the enemy" applies equally to boardrooms and playing fields.
- Why commercial competency alone fails in sports leadership—and what truly separates successful leaders from those who burn out. Successful sports leaders understand that outcomes on the field determine everything, accept this reality without taking it personally, and build organizations that thrive despite circumstances beyond their control.
About the Guest(s)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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Quotes"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:
LinkedIn Profiles:
- Jonny Gray: https://www.linkedin.com/in/jonnygray/
- Chad Hesters: https://www.linkedin.com/in/chadhesters/
Organizations & Companies:
- Ankura – Expert services and advisory firm specializing in sports practice
- Howden – Insurance company with sports and entertainment division
- International Tennis Integrity Agency – Regulatory body for professional tennis
Government & Institutional Bodies:
- Royal Military Academy Sandhurst – UK military training institution (equivalent to US West Point)
- Ministry of Defense Whitehall – UK Defense Department
- The Pentagon – US Department of Defense
- Professional Soccer Association – English football regulatory body (first statutory independent regulator)
Sports Organizations & Events:
- 2012 London Olympics – Hosted in London with terrorism risk management oversight
- English Football Association – Governing body for professional soccer in England
- US Women's World Cup 2030/2035 Bid – UK bid monitoring role
- NCAA (National Collegiate Athletic Association) – US college sports governing body
- NFL (National Football League) – US professional football league
- Premier League – Top tier English professional soccer league
- US Open – Professional tennis tournament
- FIFA – International football federation
