Canadian Contractor

Kaitlin Secord   

The Dilemma: Old school, new school

Canadian Contractor editor pick

Stirling, a passionate and skillful custom homebuilder, has a lot on his plate. While on the jobsite, he is responsible for managing a team of tradespeople, ensuring projects stay on schedule and within budget while also acting as a liaison to clients. He was also tasked with taking over leadership of the company when its owner and founder, Frank, decided to retire.

Frank oversaw the company for decades and built it from the ground up with hands-on leadership. Upon his retirement, he passed the reins to Stirling, recognizing his dedication to the company and the importance of maintaining its reputation.

The transition of power has not been smooth, however, as the two have different visions for the future of the company. Stirling wants to transition the company to modern tech and tools, whereas Frank is adamant that keeping things traditional is best.

During the period of transition, the two have struggled. Frank questions Stirling’s decisions to adopt new methodologies and technologies, while Stirling feels Frank’s approach will limit the company.


Stirling is feeling defeated and is unsure of how to resolve their conflict while respecting Frank’s years of dedication to growing the company to what it is.

What should Stirling do?

  1. Stirling should keep Frank in the dark – he handed over ownership of the company, so he doesn’t need to be involved in business decisions.
  2. Stirling should assert himself as the company’s new lead decisionmaker and communicate with Frank that he can provide opinions but not make final decisions.
  3. Bring in an external mediator to help the two figure out the best course of action that satisfies both of their interests, as well as the company’s.
  4. Stirling should give leadership back to Frank – it was his company after all.
  5. Something else.

If you have a solution to Stirling’s dilemma, email your entry to and put “Old school, new school dilemma” in the subject line. Include your email information in your response. Please don’t post your response in the comments section on our website.


Stories continue below

Print this page

Related Stories

Leave a Reply

Your email address will not be published. Required fields are marked *


This site uses Akismet to reduce spam. Learn how your comment data is processed.