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Cultivating Leadership & Designing Careers

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Individual coaching

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What We Do

Working alongside clients to design authentic career paths, effective leadership practices, and courageous workplace cultures is in our DNA. We leverage a mix of evidence-based practices from the fields of counseling, organizational psychology, and leadership education to equip our clients with customized strategies to meet their individual needs. We hope to have the opportunity to serve as your fiercest supporter and thought partner in achieving your career, leadership, life, and/or small business goals.


While we love our home-base in Chicago, (en)Courage Coaching is poised to serve clients across the US and UK leveraging video-conferencing and the return of travel!

what we do

What We Do

Working alongside clients to design authentic career paths, effective leadership practices, and courageous workplace cultures is in our DNA. We leverage a mix of evidence-

based practices from the fields of counseling, organizational psychology, and leadership education to equip our clients with customized strategies to meet their individual needs. We hope to have the opportunity to serve as your fiercest supporter and thought partner in achieving your career, leadership, life, and/or small business goals.

 

While we love our home-base in Chicago, (en)Courage Coaching is poised to serve clients across the US and UK leveraging video-conferencing and the return of travel!

what we do

The Attention We Give

Lessons from Listening for a Living

What if the most life-changing gift you could offer someone wasn’t advice—but your full attention? In this personal and powerful talk, executive coach Katie O’Malley shares the childhood moment that shaped her relationship with listening. Blending humor, vulnerability, and science, she introduces the AIR Method—a simple framework to focus attention, clarify intention, and offer meaningful recognition. In a world full of distractions, Katie challenges us to listen not just to respond, but to truly understand.

ted talk

Katie O'Malley, M.Ed., BCC

Founder & Principal Coach

Katie O’Malley is an Executive Coach and Leadership Educator with twenty (20) years of professional experience serving the nonprofit, education, and corporate sectors. Across these workplaces, Katie noticed her strengths and values consistently steered her toward the support and development of others. In 2012, Katie translated this observation into action, earning a Master’s Degree in Counseling and Board Certification in Coaching.

Who We Are

what our clients are saying

“My time working with Katie was tremendously helpful in revitalizing my career trajectory! Beyond the practical steps of updating my resume, polishing my LinkedIn, and identifying potential future roles, she helped me really dig into the question of what I want for myself. Her positive and direct approach, combined with her broad knowledge base, made the sessions really enjoyable and productive. I’m so glad I made the investment!”

Hannah Birky

Project Manager in Commercial Real Estate

“I wholeheartedly endorse Katie and (en)Courage Coaching. Initially, I had reservations about partnering with a coach to navigate my career journey. However, Katie’s expertise, approachability, and exceptional coaching abilities quickly put me at ease. She serves as an illuminating and positive force, providing invaluable guidance to help you explore potential career paths or enhance your performance in your current role.”

Jordan Lemick

Retail Marketing

“Katie at (en)Courage Coaching was a dream to work with! She exudes positivity and professionalism. I left each of our coaching sessions feeling energized and excited. Katie is incredibly knowledgeable and has a tailored approach to coaching individuals. I am so thankful for her guidance and would recommend her to anyone looking to improve their professionalism or evaluate a career move. Katie’s guidance was invaluable and I’m so thankful I was able to work with her!”

Lindsay Swindell

Executive Director in Healthcare

“Katie at (en)Courage Coaching is simply the best! She is an exceptional leadership coach, who truly cares about her clients and helps them reach their highest potential.

Under Katie’s guidance, I learned to optimize my strengths, understand my weaknesses, and gain more self-awareness. Katie’s personalized coaching sessions really targeted the areas that were specific to my needs. She is easy to talk to, trustworthy, and provides realistic and thoughtful solutions. I have become a more confident leader and learned a great deal about myself through our coaching sessions.

I highly recommend Katie to any professional seeking leadership coaching. You will just wish you would have started working with her sooner!”

Katie Larsen

Orthodontist & Business Owner

“The speaker at this session was great! She took a topic that could be uncomfortable and vulnerable and made me feel comfortable and ready to learn. She had us reflect and gave us actionable steps to bring mental health awareness and resources back to our organizations. I would love to see her present again!”

HR Indiana Conference

Attendee

“Katie was AMAZING!! Best speaker at the conference. Her content was so relatable and informative, her delivery and interaction with the audience was so engaging!”

SHRM Inclusion Conference

Attendee

news and blog posts

TED Andover is in the books!

LEGO Serious Play at NCDA

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Turing The Page on 42, LFG 43!

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