Deanna Cowling

Captain
DISC Type : DS

Founder & Executive Advisor at The Holos Lab

Chicago, Illinois, United States

Overview

Deanna Cowling is an Executive and Leadership Advisor with over 16 years of experience, specializing in guiding senior leaders through complex transitions. As the founder of The Holos Lab, she also serves as an Executive Coach at Northwesterns Kellogg School of Management and The Honor Foundation.

Deanna recently became a member of the Union League Club of Chicago, drawn to its legacy of civic leadership and service. She has a unique academic interest in global health, having co-authored a pilot study on ethnomedicine across 11 countries during a Semester at Sea program.

She provides specialized coaching to U. S. Navy SEALs and the Special Operations community to help them transition into civilian careers.

Personality Overview

Output-Driven

Dynamic But Sincere

Long-Term Thinker

Reading between the lines and seeing beyond your words comes naturally to them.  They exhibit a rare combination of being result-oriented but patient at the same time. They are very professional in their approach and can weigh multiple perspectives together.

Topics They Care About

Leadership Transitions
Her core advisory work focuses on guiding senior executives and organizations through high-stakes career inflection points, enterprise change, and leadership succession.
Veteran Career Support
As an Executive Coach for The Honor Foundation, she helps elite military leaders from the Navy SEAL and Special Operations communities transition into impactful civilian careers.
Strategic Decision-Making
Acts as a strategic thinking partner to leaders, helping them move beyond reactive decisions toward long-term clarity, alignment, and stewardship.

Media Appearances

Deanna has no verified media appearances

Work History

4-2025
Founder & Executive Advisor at The Holos Lab
6-2025
Keynote Speaker & Executive Advisor | Leadership, Strategy & Institutional Transformation at The Holos Lab
11-2023
Executive Career Coach at Northwestern University - Kellogg School of Management
11-2017
Executive Coach at The Honor Foundation
9-2018 - 7-2019
Coaches Tribe Advisory Board (CTAB) Member at The Honor Foundation

Education

Master of Education (MEd) from DePaul University
2014 - 2015
Professional Graduate Certificate from Mississippi State University

More Information

Social Presence :

Prographics :

Exp : 3 Location : Chicago, Illinois, United States Job Level : Leadership Designation : Founder & Executive Advisor at The Holos Lab
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Insights For Selling To Deanna

During A Call Or A Meeting

DO's

  • Use phrases like 'your team deserves', 'best in class' etc.
  • During followups, use phone or text if needed, they should be fine
  • Suggest clear next steps with confidence, don't be vague or hesitant

DONT's

  • Don't shy away from asking hard questions, but be extra polite
  • Don't get into pricing discussions early on, steer conversation towards proven results
  • Avoid putting conscious effort into relationship-building

When Cold Calling

When Writing An Email

While Negotiating & Closing

    The secret to closing fast with Deanna is

  • Strong proof of impact and their conviction will matter the most, but they wouldn't want to act unilaterally either
  • Will you ever get a clear answer from Deanna

  • They will say no if they are not convinced but you will have to prompt them.

Insights For Deal Planning

    How fast (or slow) will Deanna move?

  • They will want to understand things well but can move fast once they have a clear picture.
  • Can Deanna take some risk or not?

  • They have good risk tolerance but are likely to think it through once or twice.

You And Deanna

Personality Compatibility


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