Katie O'Malley

Evaluator
DISC Type : dsc

Founder + Principal Coach at (en)Courage Coaching + Consulting

Chicago, Illinois, United States

Overview

Katie OMalley is an Executive Coach and Leadership Educator with 20 years of experience, founding (en)Courage Coaching to foster authentic career paths and courageous workplace cultures. A Board Certified Coach with a Masters in Counseling, her work is informed by her background in nonprofits and higher education, including instructing MBA students at Chicago Booth.

Outside of her coaching practice, Katie is a passionate advocate for workplace wellbeing and psychological safety. She enjoys sharing her insights through writing and speaking engagements, including a recent TEDx talk. Her professional activities reflect a deep personal commitment to helping others find alignment between their work and values.

Interesting fact: Katies TEDx talk introduces her "AIR" (Attention, Intention, Recognition) formula as a simple yet powerful framework for transformative listening.

Personality Overview

Hard To Convince

Fast But Analytical

Thorough Evaluator

They have a unique set of diverse traits where they are decisive and methodical but can sometimes be extra cautious and skeptical  They are not very likely to become strong advocates of your product or service They focus on the results, but can still be quite procedural and analytical about how to get there

Topics They Care About

Effective Listening
Her TEDx talk and proposed SXSW session focus on reclaiming the human art of listening, introducing her AIR (Attention, Intention, Recognition) framework as a key leadership tool.
Courageous Workplaces
A core theme in her coaching, she aims to help leaders prevent toxicity and build psychologically safe environments where employees can thrive.
Authentic Leadership
She coaches clients on designing authentic career paths and aligning their leadership practices with their personal values to foster genuine connection and impact.

Media Appearances

Katie has no verified media appearances

Work History

2-2018
Founder + Principal Coach at (en)Courage Coaching + Consulting
7-2021 - 6-2022
Senior Leadership Coach at The University of Chicago Booth School of Business
3-2017 - 6-2022
Instructor | Leadership Effectiveness & Development (BUS31701) at The University of Chicago Booth School of Business
1-2020 - 4-2022
Leadership Coach | Leadership Practicum (BUS31402) at The University of Chicago Booth School of Business
9-2016 - 3-2017
Instructor | Leadership for Social Change (EDP369K) at The University of Texas at Austin

Education

Certificate from Barcelona School of Economics
2013 - 2015
Master of Education (M.Ed.) from DePaul University

More Information

Social Presence :

Prographics :

Exp : 11 Location : Chicago, Illinois, United States Job Level : Leadership Designation : Founder + Principal Coach at (en)Courage Coaching + Consulting
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Insights For Selling To Katie

During A Call Or A Meeting

DO's

  • Use phrases like ‘the ROI of this’, ‘X% more’ etc.
  • Keep a professional, business-like approach; especially if you tend to get informal quickly
  • Help them weigh the risks by sharing objective proof points instead of anecdotes and examples

DONT's

  • Avoid making strong statements, instead invite them to agree with you by asking them questions
  • Avoid self-deprecating references or general informality, it could decrease their trust in you
  • Don’t focus on relationship, focus purely on the merit of your product

When Cold Calling

When Writing An Email

While Negotiating & Closing

    The secret to closing fast with Katie is

  • ROI matters the most to them, followed by process and finally proof of results
  • Will you ever get a clear answer from Katie

  • They might hesitate a little, but will go ahead and say no when necessary (or asked)

Insights For Deal Planning

    How fast (or slow) will Katie move?

  • They are unlikely to move very fast, especially when it comes to new products or services
  • Can Katie take some risk or not?

  • They have relatively low risk-appetite and are not very likely to go for something unproven and risky

You And Katie

Personality Compatibility


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