Executive Coaching in Chicago
Lead with authority in America’s most diversified economy. John Mattone Global delivers proven executive coaching for Chicago leaders managing Fortune 500 complexity, high-stakes derivatives markets, and the talent demands of the nation’s third-largest business hub.
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Leadership Challenges Facing Chicago Executives
Every market has its own leadership landscape. Here are the challenges that make Chicago distinct.
Multi-Generational Workforce Retention
With Illinois facing 379,000 unfilled jobs (up 56.6% from 2021) and 10,000 baby boomers retiring daily nationwide, executives must simultaneously retain institutional knowledge from departing workers, engage millennials who expect continuous development, and attract Gen Z talent in a market where remote work has eliminated geographic barriers.
Digital Transformation While Maintaining Human Connection
Chicago executives face relentless pressure to drive AI integration and technology-driven productivity gains across industries from financial derivatives to healthcare to manufacturing. With 59% of senior leaders feeling drained by work demands, leaders must deliver measurable digital ROI while avoiding burnout in their teams and managing the shift to hybrid work models.
High-Stakes Risk in Global Markets
CME Group’s $207 trillion daily clearing volume, United Airlines’ global route network exposed to fuel volatility, and ADM’s agricultural commodities subject to climate and geopolitical shocks require leaders who can manage extreme risk. Leadership failures cascade rapidly in interconnected systems, demanding clarity and composure under pressure.
Executive Presence Across Matrixed Organizations
With 24 Fortune 500 headquarters managing global operations from Chicago, executives frequently lead in complex matrix structures requiring influence without direct authority. Research shows only 10–15% of executives exhibit the strategic thinking aptitude needed for ambiguity, and while 95% of CXOs rate their leadership highly, only 35–40% of their reports agree.
Succession Planning and C-Suite Turnover
Succession planning is the top pain point for 66% of HR decision-makers, with nearly 60% of executives expecting to change roles within three years. Only one in three companies has a formal succession plan for executive roles, and just 14% of HR professionals report strong bench strength, leaving most organizations vulnerable to leadership gaps.
Why John Mattone Global for Chicago
Fortune 500 Leadership Expertise
JMG has coached senior executives at Fortune 500 companies across Chicago’s diverse industries, from financial derivatives to healthcare to advanced manufacturing. Our methodology addresses the specific complexity of leading global operations from America’s most diversified economy.
The World’s #1 Executive Coach
John Mattone has been ranked the #1 executive coach globally seven times (2019–2025) by Global Gurus. Chicago executives get access to the same Intelligent Leadership® methodology trusted by Fortune 500 CEOs worldwide.
Deep Bench of Top-Ranked Coaches
Six of the world’s top 20 executive coaches work under the JMG banner. Clients aren’t limited to a single coach. They get access to a team with unmatched depth and expertise.
Measurable ROI
JMG’s proprietary LeaderWatch® tool tracks quantifiable improvements in leadership effectiveness. Clients typically see 27–31% gains across key leadership competencies within six months.
Igniting Breakthrough Leadership Performance & ROI
John Mattone Global's coaching doesn't just promise growth. It delivers measurable, transformative change. By leveraging our exclusive LeaderWatch® tool, we track real, quantifiable improvements.
Agility with Change & People
Improvement
Creativity & Innovation
Improvement
Building & Sustaining a Positive Team Culture
Improvement
One-On-One Communications
Improvement
Overall Leadership
Improvement
6 of the World's Top 20 Executive Coaches. One Firm.
Global Gurus 2026 rankings. More top-20 coaches than any other firm in the world.
#1John Mattone
#2Dr. Aldo Civico
#5Mark Nation
#9Dr. Barbara Dalle Pezze
#10Dr. Vincent Pieterse
#16Puja Talesara

John Mattone & Intelligent Leadership®
John Mattone is the world's #1 ranked executive coach by Global Gurus, a distinction he has held seven times. His proprietary Intelligent Leadership® methodology combines inner-core development (values, character, mindset) with outer-core skills (strategy, communication, execution) to produce measurable, lasting transformation.
JMG's approach is built on proprietary tools like the MLEI® and STLI-360® assessments, which give leaders a data-driven baseline and a clear roadmap for growth. Combined with the LeaderWatch® tracking system, every coaching engagement delivers documented, quantifiable results.
Learn About Intelligent LeadershipWhy Chicago Executives Need World-Class Coaching
Chicago anchors the third-largest metropolitan economy in the United States, with a GDP of $955 billion and a projected metro area nominal GDP of $920 billion in 2024, reflecting 3.8% growth from 2023. The region is home to 32 Fortune 500 company headquarters and 14 Global 500 companies, ranking Illinois fifth nationally. With 24 Fortune 500 headquarters located directly in Chicago, the city represents the second-highest concentration of these firms after New York. The metropolitan area employs 4.78 million people with an unemployment rate of 4.2%, and supports over 249,000 active businesses. This density of large-scale corporate leadership creates extraordinary demand for executive coaching.
Key Industries
Major Companies
Schedule Your Consultation
Book directly with Nicholas Mattone or Trevor Maloney. No sales pitch, just actionable insight on your highest-impact leadership lever.

Nicholas Mattone
CEO of JMG | Executive coach and leadership strategist

Trevor Maloney
Chief Growth Officer | IL Master Coach and advisor to global C-suites
Frequently Asked Questions
How does executive coaching deliver ROI for Chicago Fortune 500 companies?
Executive coaching consistently delivers extraordinary returns for corporate leaders, with multiple Fortune 500 studies documenting 529% to 788% ROI. A MetrixGlobal study found coaching produced a 529% ROI through measurable improvements in productivity (60% of participants), employee satisfaction (53%), and customer satisfaction (53%). When employee retention benefits were included, ROI jumped to 788%. For Chicago companies like McDonald’s, United Airlines, and Abbott operating in competitive global markets, these returns translate to millions in annualized financial benefits.
What makes Chicago’s business culture unique for executive coaching?
Chicago’s business culture blends Midwest pragmatism with world-class sophistication. Unlike coastal markets driven by venture capital hype, Chicago executives value proven results, operational discipline, and substance over style. The city’s heritage as an industrial and trading hub instilled a work ethic centered on accountability, collaboration, and getting things done. Chicago’s economic diversity (no industry exceeds 14% of workforce) means executives must be versatile, leading across functions and industries.
Why is executive coaching critical for Chicago’s financial services leaders?
Chicago’s role as the global derivatives capital (CME Group’s $207 trillion daily clearing, 20% of global commodities volume) creates leadership challenges unlike anywhere else. Executives must balance extreme cognitive demands with intense psychological pressure, inspire quantitative teams, communicate complex strategies to boards, and maintain emotional resilience under relentless scrutiny. Coaching helps financial leaders develop self-awareness, decision-making frameworks, and influence skills required for the world’s most sophisticated markets.
How does executive coaching support succession planning in Chicago’s Fortune 500 companies?
With 66% of HR decision-makers citing succession planning as their top pain point and only one in three companies having formal plans, coaching directly addresses this crisis. Rather than reactive external searches, coaching helps organizations build internal pipelines by identifying future leaders early and providing targeted development through stretch assignments. For organizations like United Airlines, Abbott, or McDonald’s, robust succession planning ensures business continuity and reduces the massive costs of leadership turnover.
What results can Chicago executives expect from JMG’s coaching programs?
JMG’s Intelligent Leadership® methodology delivers measurable results tracked through the proprietary LeaderWatch® assessment tool. Chicago clients typically see 27–31% improvement in key leadership competencies within six months, including strategic thinking, executive presence, team leadership, and stakeholder communication. The methodology has been validated with over 1,000,000+ leaders globally and adapts to Chicago’s distinctive mix of Fortune 500 corporate leadership, financial markets intensity, and Midwest business values.

