“A man will be imprisoned in a room with a door that's unlocked and opens inwards; as long as it does not occur to him to pull rather than push.” ? Ludwig Wittgenstein
President/Founder of Holly M. Teska Coaching & Consulting LLC
Co-Host of Uplifting Women Podcast
An experienced thought leader passionate about guiding successful transformations, supporting and developing authentic leadership, managing careers, and promoting business success through exceptional leadership.
I have been an executive coach and business leader for nearly 20 years. I work with senior-level leaders with the desire and the stamina to take their organizations and themselves to the next level. I help leaders think about and respond differently to the challenges they face in today's volatile, uncertain, complex, and ambiguous (VUCA) environment. Change is fast and constant. Great leaders need a partner to tell them the truth and support them in making courageous decisions. I am that partner.
My experience in strategic implementation, leadership, executive coaching, and talent development are the cornerstones of my work in helping organizations and leaders become the very best versions of themselves.
My superpower is helping individuals develop awareness, align their intention with perception, experiment, reflect, and adapt. The leaders I support develop new competencies to achieve professional and organizational success and the personal fulfillment of having a career supporting their life purpose and passions.
Client success is what fuels me, and excellent execution is what delivers results.
Timeline
Top 15 Coach in Milwaukee 2025 by Influence Digest
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Global Head of Leadership Excellence, AIIR Consulting
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Head of Leadership Consultants, Sr. Exec. Coach, AIIR Consulting
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Director of Coaching, Senior Executive Coach, AIIR Consulting
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Client Success, Workfolio
Top 19 Coach in Milwaukee 2022 by Influence Digest
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Executive Partner, Pappas DeLaney LLC
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Executive Coach, LAK Group
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President, Uplifting Women
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President, Holly M. Teska Coaching & Consulting LLC
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Managing Principal, Executive Coaching, LAK Group
Career Strategies for Women
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Managing Principal, NoAmer Coaching & PMO, North America Talent Management Leadership Team
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VP, Principal Consultant Americas West Region, Right Management
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M.B.A., Ottawa University
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Vice President, Regional Coaching Leader, Midwest & North Central Regions
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Certificate in Sales and Sales Management, Cardinal Stritch University
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B.S., Management, Cardinal Stritch University
Proud Accomplishment
Proud Accomplishment - NAMED A TOP 15 COACH IN MILWAUKEE March 2025 BY INFLUENCE DIGEST
Experience Highlights
President/Owner
Holly M. Teska Coaching & Consulting LLC
Co-founder, President & Co-Host
Uplifting women - the podcast
Head of Leadership Consultants & Senior Executive Coach
AIIR Consulting
Executive Partner
PaPPAS dELANEY llc
Client Success
Workfolio
Executive Coach
LAK Group
Managing Principal, Executive Coaching
LAK Group
Managing Principal, North America Coaching & Project Management Office
Right Management
VP, Principal Consultant - Americas West Region
Right Management
VP, Regional Coaching Leader - Midwest & North Central Regions
Right Management
VP, Client Services Consultant
Right Management
Proud Accomplishment - NAMED A TOP 19 COACH IN MILWAUKEE 2022 BY INFLUENCE DIGEST
Global Head of Leadership Excellence
AIIR CONSULTING
Education Highlights
M.B.A.
Ottawa University
B.S., Management
Cardinal Stritch University
Certified Master Corporate Executive Coach (MCEC)
MEECO Leadership institute
Associate Certified Coach (ACC)
International Coach Federation (ICF)
Certified Integral Coach
New Ventures WEst
Certificate in Sales and Sales Management
Cardinal Stritch University
Trained Coach Supervisor
Goldvarg Consulting
Causes
Association of Corporate Executive Coaches
EXECUTIVE ADVISORY COMMITTEE MEMBER
Association of Corporate Executive Coaches
2021 Conference Committee Chair
The Honor Foundation (honor.org)
Coach serving serving transitioning U.S. Special Operations Forces (SOF)
ICF Coaches for Good
Volunteer
Interests
Uplifting Women Podcast
co-host and founder - available on apple podcasts, spotify and other podcast outlets
Card Making & Watercolors
One of my first coaches helped me to understand the importance of creative outlets in my development
Spoiling my loving Daug (Pug/Dachshund Mix)
SAMMY who thinks he runs the house - and he probably does!
Skills
Marketing
16
Finance
13
Project Management
15
Social Media
6
ACCOUNT MANAGER
7
Public Speaking
15
COACHING
15
LEARNING AND DEVELOPMENT
15
TALENT MANAGEMENT
15
EXECUTIVE COACHING
10
MANAGEMENT CONSULTING
20+
SUBJECT MATTER EXPERT
15
CLIENT SERVICES
20+
Questions & Answers
Why did you choose to become a Coach?
For as long as I can remember, I have always been curious about "the why" of most things. Whether it's learning a new job or task, or understanding how someone came to make a particular decision.https://influencedigest.com/coaching/top-coaches-milwaukee-2025/ For me, it has always been about getting to the "why" that sits behind the what and the how. If I can support others in finding their own "why," I believe it helps them connect with their purpose and motivation in life. For me, coaching is more than a profession; it's a way of showing up in my life and a way of connecting with others to find a joyful, productive, and meaningful existence. It gives me great satisfaction and pride to have others allow me to be their guide to finding their "why."
What is Coaching?
Coaching is for anyone that wants to take a deep look into themselves and understand how they may be holding themselves back. Many of us operate on "auto-pilot" and coaching helps us awaken to all we can be.
Describe your greatest accomplishment.
My family is my happy place. Seeing our children as accomplished adults, as good people in the world gives me great joy and a sense of great accomplishment. We did well in raising them. Watching them raise our grandchildren brings great pride. It's definitely my husband's AND my greatest accomplishment and we are extremely proud of the people they have become.
What tools do you use?
I am trained as an Integral Coach. As such, I serve my clients in dealing with what is in front of them at this moment in time while simultaneously supporting them in developing as a complex, multi-faceted leader and human being over time. We must face what is with us here in the short term in a way that feels doable and safe AND provide a longer-term, lasting impact, which is the more complex, more profound work that helps us evolve in our way of being in the world. It requires creating a container for experimentation and reflection so that the client experiences richer, longer-lasting personal growth, and development.
Assessment tools are essential for clients that wish to take a deep dive into their personality, motivations, competencies, and stress behaviors. They are also critical for getting feedback and perceptions from others. I am certified in a wide variety of assessment tools, including Hogan Assessments, Management Research Group, CDR Assessments, Tallasure, Leadership Navigator, and others.
What are your long-term goals?
I believe we are all called to be leaders in some way and I want to help everyone who accepts that calling step into their leadership potential in the fullest way possible. We spend a lot of time working... we should find purpose and joy in our work and fulfillment in how we spend our lives. Our world needs many good leaders. I want to support others in being the best leader they can be.
Images
Find Uplifting Women Podcast on your favorite podcast app or at www.upliftingwomen.net/episodes
Co-Hosts of Uplifting Women Podcast - Kristin Strunk & Holly Teska
Find Uplifting Women Podcast on your favorite podcast app or at www.upliftingwomen.net/episodes
Co-Hosts of Uplifting Women Podcast - Kristin Strunk & Holly Teska
