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Building Courageous Cultures

Episode #1081: In this episode of the Arete Coach Podcast, Katie O’Malley, an Executive Coach, Leadership and Development Expert, Board-Certified Coach, Senior Associate Director of Leadership Development at the University of Chicago Booth School of Business, and President of (en)Courage Coaching and Consulting, discusses what it means to have courage, how to build a courageous culture, the difference between coaching and counseling, and Katie’s work with Lead(HER)ship, a women’s development program.

About Katie O’Malley

Katie O’Malley is an Executive Coach, Leadership and Development Expert, Board-Certified Coach, and Senior Associate Director of Leadership Development at the University of Chicago Booth School of Business. Katie is also the Founder and Executive Coach of (en)Courage Coaching and Consulting where she helps business leaders and executives live their most authentic and courageous lives in the Chicago area. She works alongside her clients to design authentic career paths, executive leadership practices, and courageous workplace cultures.

Before entering the coaching industry, Katie gained 15 years of professional experience serving in the nonprofit, corporate, and education sectors. Those years ultimately led her to earn her master’s degree, receiving an M.Ed. in counseling and her board certification in coaching. Along with her coaching practice, she is also a Senior Associate Director of Leadership Development at the University of Chicago Booth School of Business where she teaches and coaches students on leadership coaching. Among her many accomplishments, she has developed the Women’s Leader(HER)ship Program at the Booth School of Business and became a certified examiner with the Hogan Assessments Program.

Katie has a passion for creating courageous business leaders and continues to impact the lives of business leaders through her executive coaching and consulting today.

Key highlights

Coaching vs. counseling

Timestamp 03:23

In Katie’s career path to coaching, she achieved her master’s degree in counseling. However, she realized that she didn’t want to “be constrained by insurance companies” and their delegation of how she “could be of service and support” to her clients. Because of this, she transferred her skills to executive coaching where she could help others without diagnosis and focus on their strengths. Severin comments on her departure from counseling and states that, unlike counseling, coaching is “all about the possibility” or “courage you want to take for your future.” Katie agrees and explains that coaching focuses on the strengths of clients and not the weaknesses. However, she does recognize that as a coach, she sometimes needs to make referrals to mental health professionals for specific challenges and issues her clients face.


Timestamp 13:51

At the Booth School of Business, Katie created the Booth Women Lead(HER)ship Program. She made this program to help “women disrupt and navigate the challenges that they face in the workplace as women.” The program helps participants recognize that they are each other's support, not competition. The women involved in this program are put into small “squads” that are encouraged to take care of each other. As part of the program, participants are given a Gallup StrengthsFinder test to find their strengths, and they are also introduced to women-owned businesses. Katie advises those that are doing a women’s leadership development programming to ensure the “community aspect” of the program is evident and that “the brave space for” participants “to come forward and say what’s truly on their mind and the challenges they’re facing is available to them.”

Nothing is permanent

Timestamp 26:07

One of Katie’s mantras is “nothing is permanent.” She explains that she uses this statement often because when you go through “hard times” it can feel like “I am never going to get out of this environment” or “mindset.” She explains that although it may feel like this, “your brain and your environment are lying to you. Everything is possible if we just allow ourselves to take the blinders off and imagine what else is out there… any circumstance or environment that you find yourself in that’s having a negative or toxic impact on your life, that’s not gonna be the environment that you have to be in for the rest of your life.”

Defining courage

Timestamp 30:05

When asked how she defines courage, Katie uses a painting as a visual aid. This painting features “the wall street bull and also the wall street girl just facing off against each other.” To Katie, this painting is a symbol of courage because “it’s standing up when it’s difficult, when it’s challenging, when you know the outcome may not even benefit you, but it’s the right thing to do.” Severin agrees and shares a story that courage is sometimes “what is needed now to survive and define your future.” He states that “courage is the ability to go forward, but sometimes it’s the ability to stand up, get off the ground, and not only defend your ground, defend your values, and become the very person you need to be.”

Courageous cultures

Timestamp 37:55

In her coaching and consulting, Katie often helps business leaders build courageous cultures. She explains that a majority of the workplace is “what behaviors get rewarded, what behaviors get punished, and what behaviors go unchecked and just let roam free.” She shares that when there are inconsistencies in these three areas, it can be difficult to “be courageous in a workplace” because “you don’t know what kind of response you’re gonna get in return.” To help build consistency, Katie helps business leaders develop their mission, vision, values, and practices.

Not everyone is your client

Timestamp 46:51

When asked what she wishes she had learned earlier on, Katie explains that because she was recovering from “people pleasing” and needing “to be liked as a coach” she had to learn that “not every prospective client is meant to be your client.” She shares that instead of trying to please everyone, coaches should “focus in on helping the people that most resonate with us because that relationship matters so much to a client’s ability to make change and develop.”

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