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Game On: What IT Leaders Can Learn from Pickleball

    Home Insight Game On: What IT Leaders Can Learn from Pickleball
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    silhouette of a person playing pickleball

    Game On: What IT Leaders Can Learn from Pickleball

    By Josh Kaplan, VP of Client Solutions | Insight | Comments are Closed | 5 January, 2026 | 0

    I admit it. I’m hooked on pickleball! But as I’ve spent more time on the court, I’ve noticed the principles that make great pickleball players are crazy similar to what makes great IT leaders successful in dealing with today’s tech challenges. 

    THE KITCHEN LINE 

    In pickleball, the “kitchen” is where games are won and lost. Success requires positioning yourself at that crucial seven-foot line. You need to be close enough to capitalize on opportunities but disciplined enough not to overstep. 

    For IT leaders, this is the daily tightrope walk between innovation and keeping things stable. Push too hard on emerging technologies without proper foundation, and you’ve faulted. Systems crash, security gaps emerge, users revolt. Stay too far back in legacy comfort, and you miss the competitive advantages that could transform your business. 

    The best IT leaders master this positioning. They’re close enough to emerging AI capabilities to pilot meaningful use cases, but are disciplined enough to ensure data governance and security aren’t compromised. They invest in cloud transformation while maintaining the systems that keep revenue flowing today. It’s about finding that kitchen line where both coexist.  

    DOUBLES STRATEGY

    Pickleball is predominantly a doubles game, and the best pairs don’t just play alongside each other. They play with each other. One player sets up the shot; the other finishes it. Communication is constant. Coverage is coordinated. 

    This reality hits IT leaders hard. You cannot build every capability in-house anymore. The scope is too vast, the specializations too deep, the pace too relentless. Cloud architecture, cybersecurity, data engineering, AI/ML, legacy modernization, digital experience. Each requires expertise that takes years to develop. 

    The IT leaders who excel are those who’ve stopped thinking about “us versus them” and started building doubles strategies. They know when their internal team should take the forehand, when to let specialized partners handle the backhand, and how to communicate constantly to ensure nothing drops between you. 

    THE THIRD SHOT DROP   

    Here’s where pickleball gets counterintuitive. After the serve and return, the best players don’t smash the ball hard. They execute a soft “third shot drop” that arcs gently into the kitchen, forcing a reset. 

    IT leaders face enormous pressure to deliver fast. The business wants that customer portal yesterday. The board wants to see AI ROI now. Every vendor promises quick wins and rapid deployment. 

    But the best IT leaders know when to slow down the game deliberately. Before rushing into that ERP migration, take time to clean the data. Before deploying that AI model, ensure your data infrastructure can support it. Before promising the moon, set realistic expectations and build incrementally. 

    This patience isn’t weakness; it’s strategic wisdom. The leaders who master the third shot drop avoid the spectacular crashes that come from smashing too hard, too fast. 

    READING THE SPIN

    Every pickleball player learns to read spin. That’s the subtle rotation that changes how the ball bounces and where it’s really going. Miss it, and you’re swinging at air. 

    IT leaders today are reading more spin than ever. Remote work fundamentally changed security perimeters. AI is rewriting job descriptions and skill requirements. Regulatory frameworks are tightening while business demands for agility intensify. The talent market keeps shifting. 

    Each trend carries spin that changes its trajectory in unexpected ways. That “simple” cloud migration becomes complex when you account for data sovereignty requirements. That productivity AI tool introduces intellectual property concerns. That cost-cutting initiative undermines the retention of knowledge your people carry. 

    The IT leaders handling these challenges successfully have trained themselves to read the spin early. They’re anticipating where the ball will actually land, not where it appears to be heading. 

    THE RALLY

    Pickleball isn’t about hitting one spectacular shot. It’s about sustaining the rally. Staying in the point, returning consistently, waiting for your opportunity to emerge. 

    This might be the most important lesson for IT leaders right now. The challenges aren’t going away. The pace isn’t slowing down. IT leadership has become an endurance sport. It’s not about that one brilliant strategy or perfect implementation. It’s about showing up consistently. 

    The leaders who sustain these rallies don’t rely on heroics. They build systems that work, teams that trust each other, partnerships that hold up under pressure, and cultures that can absorb setbacks without breaking. 

    WHY THIS MATTERS

    Pickleball attracts people across generations because it rewards strategic thinking as much as athleticism. You don’t have to be the fastest player on the court. You just have to be the smartest about positioning, patience, partnership, and persistence. 

    The same is true in IT leadership. You’re facing talent shortages, budget pressures, accelerating technology change, security threats, and businesses that simultaneously demand innovation and reliability. 

    You can’t solve these problems by working harder or moving faster. You solve them by positioning strategically at the kitchen line, building doubles partnerships that extend your capabilities, knowing when to slow the game down deliberately, reading the spin on emerging trends, and staying committed to the long game. 

    The spectacular plays are fun, but championships are won through showing up consistently, positioning strategically, and having the discipline to make the right play at the right time. 

    GAME ON!

    At ConsultNet, we partner with IT leaders navigating these exact challenges. We provide the flexible talent solutions, specialized expertise, and scalable delivery models that help you play the long game successfully. Whether you need contract resources to handle surge capacity, managed services to extend your capabilities, or executive search to build your leadership bench, we’re here to be your doubles partner. Learn more at consultnet.com.

    Industry Trends, Business Insights, Workforce Solutions

    Josh Kaplan, VP of Client Solutions

    Josh Kaplan is a visionary enterprise sales leader with nearly two decades of experience driving growth and building high-performing teams and top producers in the talent and solutions industry. As the leader of the ConsultNet Client Solutions in the east coast region, Josh has doubled the team’s growth by focusing on solutions-driven strategies and delivering exceptional results for both clients and the organization.

    Prior to this role, Josh served as Regional Managing Director at Randstad Digital for over seven years, where he revitalized markets, developed top-tier talent, and earned prestigious accolades, including Top Growth Market in 2022 and Top-Selling Managing Director in 2020, as recognized by the former CEO.

    Josh’s leadership style sets him apart: he leads with authenticity, coaches with intention, and consistently delivers results. Known for his consultative approach and genuine investment in people, Josh’s impact extends far beyond metrics. Whether mentoring rising leaders, collaborating with C-suite executives, or driving large-scale initiatives, he remains laser-focused on creating meaningful, results-oriented solutions.

    Colleagues and clients praise Josh for his ability to balance optimism with precision, fostering growth and empowering those around him. His deep understanding of the evolving, tech-driven business landscape—combined with his commitment to team development—has solidified his reputation as a trusted leader and long-term strategic partner.

    More posts by Josh Kaplan, VP of Client Solutions

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