Kathleen O’Connor

Leadership coach · Chicago · in person and virtual

Credentials they list: Hogan

Visit their websiteCompare similar coaches

"Kathleen helps individuals reflect on their talents and interests in order to create a tangible vision for the future." (in their words, on their website)

Services

ServiceWhat is includedPrice
Encore Career Coaching
individuals no longer energized by their work and not ready for retirement		 confidential coaching sessions · reflective assignments · personalized roadmap to achieve happiness and fulfillment · plan to prepare for second half of life · manage transition to evolved identity and purpose on request
Executive Coaching
leaders individually or with their teams		 coaching grounded in data (360° feedback, personality assessments, stakeholder interviews, observation) · involves internal stakeholders at beginning, middle, and end · flexible duration from a couple of sessions to several months · source and manage pool of coaches for large projects on request
360° Feedback Debriefing
leaders and organizations		 help leaders understand and take action from feedback · use of 360° surveys, personality assessments, stakeholder interviews 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 LinkedInnononononono
Interviews and offersnononononono
Job search strategynonoyesyesyesyes
Career direction and changenonoyesyesyesyes
Leadershipnonoyesyesyesyes
Personal brandnononononono

How they work

Process
reflect on talents and interests · create tangible vision for future · build personalized roadmap · prepare for and manage transition to new identity and purpose
Assessments
360° feedback, personality assessments, stakeholder interviews
Before coaching
internal HR consultant

Do it yourself, or hire a coach?

Doing it yourselfUsually enough whenA coach earns the fee when
Job searchA target list, a weekly plan and steady outreach. Callings builds the weekly plan and tracks every application, free.Interviews are coming in.Three months without traction, or a senior search that runs on your network.
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.
LeadershipPeer groups, feedback from your manager, reading.You have a mentor who has done the job.A first management role or a bigger team, often paid for by the employer.

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. What are your cancellation and refund terms? (no refund terms on their site)
  3. Which body issued your credential, and can I check it there? (credential listed)
  4. Who do you usually work with, and how long does a typical engagement last? (always worth asking)

What they publish

Similar coaches

Chosen by our matching from coaches who serve the same people with the same kinds of help. Nobody pays to appear here.