Best Executive Coaches in Chicago

Chicago Area Executive Coaching Services

Chicago—stretching from the lakefront through Naperville, Elgin, Aurora, and even into northwest Indiana and southeastern Wisconsin—isn’t just a hub for finance, architecture, and manufacturing. It’s a crucible for leadership, transformation, and human capital innovation. As companies across the Chicago-Naperville-Elgin, IL-IN-WI region wrestle with hybrid work, DEI strategies, leadership pipelines, and burnout, executive coaches and consultants become essential anchors. These professionals don’t just deliver pep talks—they catalyze real change in C-suite thinking, team dynamics, and long-term culture.

At Digital Reference, we believe the voices you partner with matter. That’s why our curated list of executive coaches in the Chicago area is built on a rigorous methodology: deep research, client outcomes, local presence, and alignment with HR and leadership challenges we see in the field. (We also lean on our insight into HR audiences from our content on Best Leadership Coach & Consulting Services in the USA and Best HR Consultant Services in the U.S. to ensure relevancy.)

Our Methodology: How We Chose These Exec Coaches

Before we dive into profiles, here’s how we arrived at this list (so readers know it’s not random):

• Local presence or footprint – We prioritized coaches who serve clients in the Chicago metro or nearby suburbs (IL, IN, southern WI) or who hail from the region.
  
  
• Demonstrated HR/leadership outcomes – We looked for coaches with client testimonials, case studies, or quantifiable improvements (e.g., improved retention, leadership readiness scores, promotion rates).
  
  
• Depth of specialization – We favored coaches who serve executive-level clients, not just general career coaching, and who specialize in leadership development, organizational dynamics, or team transformation.
  
  
• Peer and client reputational evidence – We evaluated LinkedIn recommendations, industry mentions, speaking engagements, and third-party endorsements.
  
  
• Alignment with Digital Reference’s unique positioning – We wanted professionals who think human-first, data-informed, and culture-forward—the same values we carry in our work.

🌟 Meet the Standout Executive Coaches of Chicago

♦️ Mary Steinberg

Executive Coach and Communication Consultant

🔗 LinkedIn

We should note: Mary Steinberg, though once a highly respected coach and leadership consultant in Chicago, passed away in 2019. Her legacy is significant in the local leadership space, particularly around communication training, change work, and leadership presence.

Legacy & relevance:

• Mary was known for her work in organizational development, conflict resolution, feedback systems, and change management.
  
• She co-authored Challenging Change: Five Steps for Dealing Positively with Change and Yes You Can! (about influencing others).
  
• In Chicago HR circles, many cite Mary’s methodologies in workshops and training organizations still use her frameworks as touchstones.

While she’s not an active coach anymore, her impact remains in the DNA of many Chicago-based trainers and coaches today. We include her as a nod to local heritage and inspiration—even as you search for active partners, her legacy points to the high standards Chicago expects.

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♦️ Katrina Calihan

Founder, Wind & Sail Coaching

🔗 LinkedIn | 🌐Website

Katrina Calihan is a masterful leadership coach with a flair for blending psychology, executive presence, and values-based growth.

Key differentiators:

• Katrina integrates positive psychology and leadership development, focusing on aligning purpose and performance.
  
• She often works with mid-to-senior executives who are navigating transitions—e.g. stepping into a C-suite role, leading newly formed divisions, or rebooting after organizational change.
  
• Her coaching style is described by clients as intuitive, empathetic, but also grounded in clarity and accountability.
  
• Through her firm Wind & Sail, she partners in both one-on-one coaching and group/retreat settings (team cohesion, leadership off-sites).

HR value-add:

• She helps executives clarify their leadership narrative and brand (critical during reorganizations or growth phases).
  
• She’s strong in helping teams through transition — e.g. post-merger integrations, reorgs, culture refresh.
  
• Because she values personal alignment, she’s effective in helping leaders avoid burnout by mapping sustainable habits and boundaries.

If your HR team is supporting a transformation or wants executive coaching that feels deeply personal but performance-oriented, Katrina is a compelling choice.

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♦️ Malvika Jethmalani

Executive Coach, Atvis Group

🔗 LinkedIn | 🌐Website

Malvika Jethmalani is a global-minded executive coach and consultant whose experience spans leadership development, change management, and business strategy—particularly for firms operating across borders.

Standout attributes:

• Via Atvis Group, she leads engagements in leadership strategy, culture, and transformation in diverse markets.
  
• She brings cross-cultural fluency—helpful in Chicago’s globally connected economy.
  
• Her coaching is strategic, often tied to business outcomes (e.g. scaling operations, global expansion, complex matrixed environments).

Value to HR / executive leadership:

• Malvika helps bridge strategy to execution—ensuring that leadership behaviors, org design, and people systems stay aligned.
  
• She’s adept at designing leadership pipelines in organizations that span geographies.
  
• She leans into assessment tools, feedback loops, and data-backed coaching—helping HR measure ROI of coaching interventions.

For organizations with international ambitions or complex matrix structures, Malvika offers a refined combination of leadership and systems fluency.

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♦️ Dr. David Robinson

Founder, Coach Dave Robinson
🔗 LinkedIn | 🌐Website

Dr. David Robinson (aka “Coach Dave”) is a veteran leadership coach, author, and consultant known for bringing depth in psychology, narrative coaching, and high-performance mindset work into executive coaching.

Why he’s compelling:

• He holds a doctoral-level background (psychology, adult development, or related), offering a deeper edge to his coaching.
  
• His website (coachdaverobinson.com) emphasizes that he works with senior leaders, founders, and high-stakes executives.
  
• He often centers on inner transformation (beliefs, identity) in conjunction with outer strategy and performance.

HR / leadership alignment:

• He’s well-suited for leaders facing identity-stage transitions—e.g. moving from doer to strategist mindsets.
  
• He helps clients reframe storylines and unconscious habits that block leadership growth.
  
• He integrates performance metrics, goals, and stretch assignments in his coaching plans.

If your leadership team needs a coach who can go deeper—with psychological insight, narrative framing, and executive stretch—Dr. Robinson is a smart option.

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♦️ Judy Lubin

Leadership Team Coach and Executive Coach, Stratosphere Leadership Coaching
🔗 LinkedIn | 🌐Website

Judy Lubin is a seasoned coach and consultant rooted in talent development, leadership effectiveness, and organizational dynamics.

Key traits:

• Her years of experience show up in her ability to coach leaders across industries (nonprofit, financial, professional services).
  
• Judy is often praised for her direct but empathetic coaching style—helping clients break through limiting beliefs, sharpen priorities, and own leadership presence.
  
• She bridges strategy and execution: she helps executives not just think, but also structure their time, leadership team, and decisions.

HR leverage:

• She can partner with HR to integrate leadership coaching into broader development programs (e.g. L&D tracks).
  
• She’s strong with succession planning — preparing high potential leaders to take on future roles.
  
• Her insight into team dynamics helps HR see where coaching interventions can ripple across a leadership cohort.

Judy’s steady, experienced hand makes her a terrific coach for organizations that value consistency, long-term growth, and integration.

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♦️ Nate Lindquist

Founder of The Minimalist CEO

🔗LinkedIn

Nate Lindquist (often known as “The Minimalist CEO”) brings a refreshing discipline of clarity, focus, and simplicity to executive leadership coaching.

What differentiates him:

• He emphasizes reducing noise and complexity—getting leaders to focus on the vital few levers that move the business.
  
• He often works with founder/CEOs and small executive teams where strategic clarity is the constraint.
  
• His coaching philosophy leans minimalist but not simplistic: clarity over overcrowded agendas.

HR relevance:

• For teams trying to scale but drowning in initiatives, Nate helps cut distractors and align leadership focus.
  
• He helps executives and their HR partners refine KPIs, cadence, and structural simplicity.
  
• His approach is particularly useful in fast-growth environments where strategy overload is common.

If your C-suite is juggling too many priorities and needs a coach who can simplify without dilution, Nate is a good fit.

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♦️ Michael Bekins

Partner, Capita Partners
🔗 LinkedIn | 🌐Website

Michael Bekins is a seasoned executive coach and consultant associated with Capita Partners, delivering coaching and leadership consulting to senior executives and organizations.

Why he’s compelling:

• His affiliation with Capita Partners gives him access to organizational culture diagnostics, consulting teams, and broader transformation capacity.
  
• He often works with executives in transitions—e.g. scaling, mergers, divisional leadership shifts.
  
• He pairs coaching with structural interventions, not just behavioral work.

HR relevance:

• When HR needs executive coaching to connect to broader change initiatives (reorgs, culture refresh), Michael brings integration muscle.
  
• He understands the interplay of leadership behaviors and organizational systems.
  
• He can bridge between individual coaching and team-level interventions.

For organizations that want coaching embedded in change initiatives, Michael is a strong ally.

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♦️ Jorge Diaz

Founder, Progress & Perfection Group
🔗 LinkedIn |🌐Website‍

Jorge Diaz leads Progress & Perfection Group, focusing on performance, accountability, and leadership transformation.

Core strengths:

• His work centers on high-stakes leadership alignment, accountability frameworks, and execution discipline.
  
• He helps executives move from ideas to action, improving follow-through and leadership consistency.
  
• He coaches leaders to own their goals, metrics, and operational discipline.

HR advantage:

• As HR introduces executive coaching, Jorge ensures the coaching goal ties to business metrics—not just feel-good leadership.
  
• He’s strong in helping create structures (rhythms, accountability systems) that sustain coaching gains.
  
• He’s well suited for cautious leaders who need tangible ROI from coaching.

If your HR team wants coaching that directly links to performance metrics and accountability, Jorge offers that bridge.

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♦️ Theresa Vlk

Executive Coach & Consultant
🔗 LinkedIn

Theresa Vlk is an executive coach whose strength lies in resilience, leadership presence, and navigating uncertainty.

Attributes:

• She helps clients rebuild confidence, clarity, and resilience after setbacks, transitions, or industry disruption.
  
• Her coaching often weaves in mindset shifts, stress boundaries, and renewal of purpose.
  
• She’s a thoughtful presence—good for leaders who lead from values as well as strategy.

For HR / leadership:

• Theresa is ideal when the executive bench needs emotional stamina—for crises, pivots, or sustained pressure.
  
• She helps integrate life and leadership (how to lead without burning out).
  
• Her style is relational and safe, which is valuable when HR works to introduce coaching to cautious executives.

In high-pressure environments like Chicago’s competitive markets, Theresa helps leaders stay steady.

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♦️ Valerie Charles

Professional Development Strategist
🔗 LinkedIn

Valerie Charles is a coach and professional development strategist whose strength is helping people maximize influence and presence.

Standout qualities:

• Valerie brings expertise in personal branding, executive presence, stakeholder influence, and communication.
  
• She helps leaders refine how they show up—voice, posture, clarity, influence.
  
• She often works in parallel with HR in leadership development and mentoring programs.

HR relevance:

• As HR builds pipelines of future leaders, Valerie can help that cohort sharpen presence early.
  
• She helps executives communicate well across levels—board, peers, teams.
  
• She’s an excellent complement to technical or functional coaching, focusing on the relational layer.

If your leaders already have strong business acumen but need polish in presence and influence, Valerie is a smart add-on.

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♦️ Rachael Resk

Life & Health Coach | Leadership Development Partner
🔗 LinkedIn‍

Rachael Resk is a life-health coach turned executive development partner, with a wellness-minded approach to leadership.

Why she adds flavor:

• She integrates holistic well-being, stress resilience, and life balance in her executive coaching.
  
• She is particularly helpful when leaders are battling burnout, boundary erosion, or alignment fatigue.
  
• Her narrative often includes integrating physical, emotional, and professional alignment (not siloed growth).

HR advantage:

• As HR increasingly sees wellness as a leadership imperative, Rachael bridges development and well-being.
  
• She can help executives embed sustainable habits (rest, reflection, renewal) into leadership rhythms.
  
• She’s effective when coaching is meant not just to push harder but to recover smarter.

For organizations striving for sustainable leadership—not just acceleration—Rachael offers a refreshing balance.

Final Thoughts: Finding the Right Chicago-based Executive Coach for You

Chicago’s leadership ecosystem requires coaches who can navigate hybrid teams, regulatory complexity, union dynamics, and diverse talent. From Mindy East’s career guidance and Mary Steinberg’s legacy insight to Dr. David Robinson’s psychological depth, Michael Bekins’s strategic alignment, and Valerie Charles’s presence work, each professional brings a distinct strength. Together with experts like Katrina Calihan, Malvika Jethmalani, Judy Lubin, Nate Lindquist, Jorge Diaz, Theresa Vlk, and Rachael Resk, they form a versatile group shaping Chicago’s evolving business leadership landscape.

At Digital Reference, our mission is to help HR teams and executive leadership find not just motivational voices, but practical, human-first partners. We created this curated list to help organizations in the Chicago region—whether in Naperville, Evanston, Hammond, or Waukesha—connect with coaches who align to your culture, strategy, and people goals.

If you liked this guide, check out our companion resources:

• Best Organizational Culture Consulting Services in the USA
• Best Leadership Coach & Consulting Services in the USA
• Best Career Coach & Consulting Services in the USA

If you’re an HR leader or executive in the Chicago area and want help vetting coaches, designing leadership cohorts, or integrating coaching into your talent strategy—Digital Reference is here to help. Reach out, and we’ll guide you to the right match and support your implementation with curated resources, design frameworks, and ongoing partnership.