Katie O'Malley

Career coach · Chicago, IL · in person and virtual

Credentials they list: CCE BCC, Hogan

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"We help individuals and businesses build authentic careers and courageous workplace cultures." (in their words, on their website)

Services

ServiceWhat is includedPrice
Community Workshops
Open to the public		 Live workshops · Practical tools for confidence, clarity, and career growth on request
Career Coaching
Individuals looking to pivot career, leave toxic environment, or re-enter workforce		 Enhance self-awareness · Align career move with strengths, values, aspirations · Job exploration · Compensation negotiation on request
Leadership Coaching
New managers to seasoned leaders and business owners		 Deepen self-awareness · Build leadership practice · Uncover strengths, derailers, drivers on request
The Lego® Serious Play® Experience
Teams and organizations		 Hands-on problem solving · Break communication barriers · Tap collective intelligence on request
Leadership Development Accelerator
Teams and organizations		 11 sessions · Six 90-minute team workshops · Five 30-minute one-on-one coaching sessions · Build interpersonal and intrapersonal effectiveness on request
Workshops & Retreats
Teams and organizations		 1 session · Skill-specific workshops on collaboration, delegation, conflict on request

As published on their website, read Sep 30, 2026.

How they compare

Computed by Callings from the prices and experience coaches publish. Not a rating.

Where they fit

StudentsEarlyMidManagerDirectorVP / C-suite
Resume and LinkedInnoyesyesyesyesyes
Interviews and offersnoyesyesyesyesyes
Job search strategynononononono
Career direction and changenoyesyesyesyesyes
Leadershipnoyesyesyesyesyes
Personal brandnoyesyesyesyesyes

How they work

Process
Discovery: complimentary consultation to explore goals and fit · Strategy: create personalized coaching roadmap · Transformation: regular 1:1 sessions to build clarity and confidence · Elevation: celebrate development and plan future
Assessments
Hogan Assessments, Intercultural Development Inventory
Before coaching
Executive Coach and Leadership Educator, Nonprofit, education, and corporate sectors (20 years)

Do it yourself, or hire a coach?

Doing it yourselfUsually enough whenA coach earns the fee when
Resume4 to 8 hours for a strong base, then about 30 minutes per posting. Callings can tailor it to each job.You are staying in the same field and level and have recent results to cite.You are changing field or level, coming back after a long break, or many applications brought no interviews.
Interviews3 to 6 hours of practice out loud per interview process. Callings can prepare you for each job you track.Early rounds in a format you know.Final rounds, panels, a new kind of role, or you tend to freeze.
Career directionWeeks of reading and conversations about roles that fit. Callings can show your strengths and the pay for each role.You already have two or three target roles.You do not know what comes next, or you want structure and a formal assessment.

Times are our estimates. Try Callings.

Questions to ask before hiring

  1. What does it cost in total, and what is included? (no published price)
  2. If I land a job partway through, what happens to the sessions I have not used? (multi-session package)
  3. What are your cancellation and refund terms? (no refund terms on their site)
  4. Which body issued your credential, and can I check it there? (credential listed)
  5. Who do you usually work with, and how long does a typical engagement last? (always worth asking)

What they publish

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