Ron Cheshire, MBA, PCC

Doer
DISC Type : ds

Co-Founder | Executive Coach for Leaders & Teams | Co-Author at The Co-Leadership Group l Le Co-Leadership Groupe

Greater Montreal Metropolitan Area, Canada

Overview

Ron Cheshire is a Professional Certified Coach and Co-Founder of The Co-Leadership Group, drawing on over 30 years in business and investment management. He focuses on elevating leaders and uniting teams through personalized coaching journeys. Colleagues and clients often describe him as passionate, driven, and an excellent mentor.

He successfully transitioned from a career in finance, where he once grew a firm’s assets from $370M to over $3B, to becoming a dedicated executive coach and co-author.

Personality Overview

Long-term Focused

Strategic Planner

Risk-Accepting

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 Development
His entire practice is built around elevating leaders and activating strengths for high performance, backed by 30 years of business experience.
Action Learning
He co-authored the book "Codevelopment Action Learning for Business" and champions it as a method for teams to co-create solutions and accelerate progress.
AI & Human Trust
In recent posts, he explores the limitations of AI, arguing that while it's a useful tool, it cannot replace the human trust required for effective teamwork.

Media Appearances

Ron Cheshire – The Co-Leadership Group Profile. Featured in The Co-Leadership Group

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Ron Cheshire – Personal Website Home. Featured in roncheshire.com

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About Ron Cheshire – Personal Site. Featured in roncheshire.com

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Work History

1-2020
Co-Founder | Executive Coach for Leaders & Teams | Co-Author at The Co-Leadership Group l Le Co-Leadership Groupe
8-2017
Executive Coach for Leaders & Teams at Ron Cheshire
7-2016 - 12-2019
Vice President & Portfolio Manager, Client Services and Business Development at Foyston, Gordon & Payne Inc.
9-2010 - 2-2016
Vice President, Business Development and Client Servicing at Triasima Portfolio Management
8-2008 - 12-2009
Managing Director & Portfolio Manager at Captiva Capital Management

Education

EMBA / MBA pour cadres from Concordia University
Bachelor of Arts / Baccalauréat ès arts (Économie) from Carleton University

More Information

Social Presence :

Prographics :

Exp : 31 Location : Greater Montreal Metropolitan Area, Canada Job Level : Leadership Designation : Co-Founder | Executive Coach for Leaders & Teams | Co-Author at The Co-Leadership Group l Le Co-Leadership Groupe
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Insights For Selling To Ron

During A Call Or A Meeting

DO's

  • Ask them at the end if they see a strong value prop in your product; expect an honest answer
  • 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 get into pricing discussions early on, steer conversation towards proven results
  • Don't go over them unless you are left with no other option
  • Avoid putting conscious effort into relationship-building

When Cold Calling

When Writing An Email

While Negotiating & Closing

    The secret to closing fast with Ron 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 Ron

  • 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 Ron move?

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

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

You And Ron

Personality Compatibility


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