Executive Coaching for Driven Entrepreneurs

Unlock Your Potential for Effective and Successful Leadership

Who do you want to become as a leader? What do you want your organization to accomplish? You have grand visions and desires, but how do you achieve them? If you’re frustrated because you don’t have a clear path to success, then you need executive coaching from Bob Kauffman at Critical Thinking for Success.

For over 50 years, Bob has helped people turn their lives around and become successful leaders of national corporations. His unique approach combines cognitive neuroscience with storytelling to produce practical solutions for any leadership problem. He will give you the courage, tools and motivation you need to achieve your dreams.

Illustration of an executive achieving his goals through executive coaching

Meet Your Executive Coach: Bob Kauffman

Bob Kauffman of Critical Thinking for Success

Bob Kauffman is a remarkably effective master therapist with a deep and total grasp of human experience. His multiple decades of leadership coaching for executives have given him an extensive skill set for solving his clients’ problems.

Often, Bob diagnoses root issues within minutes of listening to clients and helps them understand their problems with illustrative stories. He then creates custom plans with exercises to help overcome struggles. As a result, many experience positive life changes and relief within the first session!

Bob’s approach is rooted in years of study and mastery in social work, cognitive behavioral therapy, bioenergetics, neurolinguistic programming and more. He combines his knowledge with a deep sense of empathy to bring about profound results. Because of this, he has provided executive coaching and employee assistance for some of the top corporations in the country, including BorgWarner, Harcourt Brace, Neiman Marcus, NutraSweet and more.

Overcome All Roadblocks to Leadership Success

Bob specializes in helping executives overcome a wide range of personal and professional problems. He will use his unique combination of caring and competence to coach you through any of the following:

Achieve Your Goals

Find the confidence and motivation you need to take risks and move down a clearly defined path to business objectives.

Plan and Strategize

Develop your cognitive skills to become more streamlined, organized and purposeful in how you operate your business.

Delegate Responsibilities

Determine how to best take the weight off your shoulders by assigning tasks to your team and focusing on your strengths.

Anxiety and Depression

Learn effective strategies for overcoming anxiety and depression and receive treatment to improve mental functioning.

Relationship Conflicts

Identify the causes of dysfunction in professional relationships and receive ongoing coaching to resolve them.

Debilitating Phobias

Discover the sources of your fear and receive the tools, treatment and exercises you need to overcome it.

Crippling Addictions

Figure out what is behind the addictive habits that undermine your productivity and how to break the cycle.

Employee Assistance

Bob will also work with your team members to help them improve how they work individually and with others.

Executive Coaching Case Studies

Bob has helped many professionals achieve their full potential with his executive coaching services. Click below to read the full stories of some of the impressive people Bob has trained:

Joe Bongiovanni

Founder and CEO of Frontier Marketing LLC

Joe was struggling with an underperforming sales employee and overall team development at his digital marketing company when he first met Bob. Bob’s unique approach quickly identified and addressed the planning issues hampering the employee’s performance.

Recognizing Bob’s expertise, Joe hired him to coach his entire team. Bob’s intervention transformed the team dynamics, providing much-needed guidance and skills training. Joe’s leadership also evolved under Bob’s mentorship. He became more purposeful and effective in planning, goal setting and hiring.

Nicole Loftus

Founder and CEO of Locker Diligence and Pop Venture

Nicole credits Bob Kauffman for her impressive achievements as a successful entrepreneur. She was trapped in an unhappy marriage and living a life that didn’t align with her ambitions when she met Bob and turned her life around.

Bob swiftly diagnosed the root cause of her issues: the suppression of her true aspirations and potential. His coaching equipped Nicole with the necessary tools and exercises for her personal and professional development. Bob gave her the confidence, strategic planning abilities and networking skills she needed to start one of the fastest-growing companies in the country.

Michael Pinelli

Principal at Synergy Construction & Development Company

Michael faced challenges in his business due to a lack of formal executive coaching and difficulties in managing his responsibilities. Impressed by Bob’s successful work with the Marines, Michael sought his assistance, hoping to replicate similar results in his business.

Bob’s intervention was transformative for Michael. He identified the root causes of team dysfunction and guided Michael in improving his planning and delegation skills, which alleviated Michael’s workload. Bob’s neurofeedback therapy further enhanced Michael’s cognitive health, enabling him to focus on his strengths and enjoy his work more.

Dr. Bob Wright

Co-founder of Live Wright

Dr. Wright met Bob as a field student and was immediately struck by his brilliance and sterling reputation. Bob played a crucial role in Dr. Wright’s development, especially when he struggled with self-doubt and criticism during his Master of Social Work studies. Bob believed in Dr. Wright and helped him discover his full potential.

Dr. Wright became Bob’s business partner, and together they helped numerous clients turn their lives around. He recalls Bob’s exceptional skill in diagnosing and treating phobias and providing valuable life advice. He has no doubt he would not be the successful coach and consultant he is today without Bob’s help.

Choose Your Executive Leadership Coaching Package

Receiving leadership development and coaching from Bob Kauffman is a life-changing experience. It won’t take Bob long to help you identify your executive coaching needs and provide custom solutions to your problems. He will direct you to the right path, and his ongoing support will ensure you persevere in the right direction.

Bob offers these three executive leadership coaching packages for aspiring professionals:

Premium Coaching


  • Full year of coaching
  • Multiple sessions per week
  • 24/7 phone support

Standard Coaching


  • Full year of coaching
  • 1 session per week
  • 24/7 phone support

Light Coaching


  • 6 months of coaching
  • 1 session per week
  • Limited phone support

Contact Bob Today to Transform Your Life

Bob Kauffman provides the proven executive coaching services you need to achieve true greatness. Whether you want to start a multi-million-dollar company or transform your organization, Bob will provide the confidence, tools and inspiration you need to make it happen.

Bob provides these leadership coaching services at Critical Thinking for Success in Chicago. Please contact our offices today to schedule an initial meeting with Bob.