Chris MacKinnon

Questioner
DISC Type : c

Director of IT at Winnipeg School Division

Winnipeg, Manitoba, Canada

Overview

Chris MacKinnon is a people-first IT Director at Winnipeg School Division with over 25 years of experience in sectors like education, healthcare, and retail. He focuses on aligning IT strategy with educational outcomes, modernizing infrastructure, and developing his teams potential. Chris is a 2019 CIO Leadership Award recipient and holds a Business Administration diploma from Red River Community College.

He is a reflective leader who values trust, vulnerability, and gratitude as foundational elements for effective teams. His personal philosophy emphasizes that leadership is built on small, consistent actions and that showing appreciation strengthens professional relationships. He believes in creating a supportive environment where people feel valued and empowered to grow.

In April 2025, he mentored students in a hands-on project to evaluate real-world cybersecurity contract proposals for the school division.

Personality Overview

Cautious & Analytical

Systematic

Value Seeker

While they don't hesitate to ask questions, they are generally risk-averse and tend to be late adopters.  They prefer to analyze every situation thoroughly.
 They are more likely than others to negotiate on pricing and terms.

Topics They Care About

People-First Leadership
Emphasizes empathy, trust, and vulnerability as core tenets of his leadership style, frequently writing about these concepts as essential for team success.
Educational Technology
As IT Director for Manitoba's largest school division, he is focused on aligning technology strategy with educational outcomes to support over 30, 000 students.
Cybersecurity in Education
Advocates for robust security and actively mentors students on modern cybersecurity issues, involving them in real-world evaluations for the school division.

Media Appearances

Winnipeg school division investigating explicitly altered images of students shared online. Featured in Global News

See Now

Work History

1-2024
Director of IT at Winnipeg School Division
8-2023 - 1-2024
Vice President Information Technology at Princess Auto Ltd.
11-2021 - 7-2023
Director, Information Services at Canadian Museum for Human Rights
4-2013 - 11-2021
Director Of Technology Services at Hanover School Division
4-2012 - 4-2013
I.T. Operations Manager at South Eastman Health

Education

1992 - 1994
Business Admin from RRC Polytech
1992 - 1994
Business Administration Diploma from Red River Community College

More Information

Social Presence :

Prographics :

Exp : 13 Location : Winnipeg, Manitoba, Canada Job Level : Mid-senior Designation : Director of IT at Winnipeg School Division
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Insights For Selling To Chris

During A Call Or A Meeting

DO's

  • Emphasize on objective proof of ROI, help them do a thorough evaluation
  • Back up any claims with data and numbers
  • Emphasise more on facts and measurable benefits

DONT's

  • Don’t overhype the product/pitch, keep it measured
  • Avoid rushing them, be polite and patient
  • Don’t depend too much on anecdotal evidence, it reduces their confidence

When Cold Calling

When Writing An Email

While Negotiating & Closing

    The secret to closing fast with Chris is

  • Confidence that the product provides ROI, effective pricing and process adherence matter the most to them.

  • Will you ever get a clear answer from Chris

  • It doesn’t come naturally to them but they can say no if they are not convinced.

Insights For Deal Planning

    How fast (or slow) will Chris move?

  • They can move at a reasonable pace while making their decisions if they have the necessary information.

  • Can Chris take some risk or not?

  • They can take risk if they are convinced that they have analyzed the circumstances well.


You And Chris

Personality Compatibility


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