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About Holly Simmons

Holly Simmons

Your Thinking Partner

Hello and welcome! I'm Holly and I'm so pleased you've stopped in to learn about the work I do with business families.

I bring enthusiasm, candor, and strategic thinking to my work. I strive to understand your needs with the aim to deliver a tailored experience that results in growth and transformation in your business and family.   


I have two personal mantras.

1. Plan for your future self.

2. Notice the good.


If you're curious about what these mean, let's talk about it when we connect. 

My Core Values


Human Side of Family Business

Clear thinking requires courage rather than intelligence."

~ Thomas Szasaz

Holly Simmons is a professional business coach, facilitator, and trainer working with growth-minded family businesses that need a partner in continuity planning, leadership development, communication, inclusive strategic planning, and effective family meetings.


Holly uses a strategic approach to align values and purpose, develop people and roles, and strengthen communication throughout the business and family systems.


Holly Simmons is a Family Enterprise Advisor (FEA™), a Licensed Associate of TotalLeader® Solutions, is an independent Certified Coach, Teacher and Speaker with Maxwell Leadership, and a Maxwell DISC Certified Consultant.

Over her 25+ year career, Holly has worked in numerous sectors including manufacturing, industrial services, construction, software development, distribution, and luxury goods & services. Her extensive background in marketing brings a unique understanding of how people think, make decisions, and move to action.

Holly is passionate about volunteering in her community. She is the Board Chair of Hamilton Health Sciences Foundation and has volunteered in numerous capacities in a variety of organizations over the course of her career.

By focusing on communication, leadership development, and problem-solving, Holly’s aim is to increase the social and intellectual capital of business families.



JD Creaghan Group Inc_

J.D. Creaghan Group is a business growth advisory that provides full strategic support for the unique challenges business owners face while leading and growing their companies. The team consists of seasoned strategists that deal with key areas of privately held or family run business. With focus on a 4 Stage Function Model, the goal is to build high performing Stage 4 companies. We assist with Scale, Sale, or Succession. 

TotalLeader Solutions Logo

TotalLeader® Solutions provides a leadership content and framework system to coaches, advisors, and leaders. Based on the Human Side of Business and 4 Stage Function Model, TotalLeader® Solutions includes leadership assessments (LeadershipStages™), coaching tools, exercises, workshop materials, published books and an online Leader Library™.

Family Enterprise Canada Logo

Family Enterprise Canada is the national community for business families and designated Family Enterprise Advisors. It connects, supports, inspires, educates, and speaks for the Family Enterprise community in Canada.

Maxwell Leadership Certified Team Member Certification Logo

Maxwell Leadership is a global community of over 40,000 leaders, influencers and high achievers. Maxwell Leadership members touch every industry where true leadership is needed, tied together by a genuine commitment to lead through positive influence. The Team uses a comprehensive curriculum crafted by John Maxwell and his teaching team and is one of the top leadership coach certification programs in the world.

Burlington Chamber of Commerce Logo

The Burlington Chamber of Commerce is the voice of business in Burlington. The Chamber membership consists of businesses in Burlington and the surrounding area, representing thousands of employees. It serves businesses at the local, regional, provincial and national levels with the goal of making Burlington a better place to do business and a better place to live.

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