Building a digital evolution champion

Last updated on August 26th, 2022

I am a huge fan of basketball. Specifically, I’m a die-hard Toronto Raptors fan. Last season, I sat on my couch every night they played, and was very fortunate to witness them winning their first NBA championship.

Lately, I’ve been missing live sports in a large way, and that longing for sports has crossed over into my professional life. I’ve started drawing parallels between sports and business-related topics. At first, I thought I needed to focus harder on the business side because my kids won’t stop eating and I need to keep my job to afford their food, but then I started to realize that the reasons for success in sports and success in business are very similar: make a plan, follow through on that plan with conviction and hard work, throw in a little luck, and success will come.

One of the questions I’ve been asking lately is: What is the sports equivalent of digital transformation?

At first, I determined that building a championship team by signing high-priced free agents might be the answer – spending a bunch of money to achieve success. However, the more I thought about it, I increasingly realized that my conclusion was a bit off, and that the following rang true:

  • Building a championship team through free agency is akin to a digital transformation: You expect a quick turn-around from your huge financial outlay.
  • Building a championship team by drafting well and having a prepared, aligned team culture is akin to a digital evolution: You expect there will be a slow climb to success through methodical progress and measured spend. Slow, but always moving forward.

So, the question has now become: What is the sports equivalent of digital evolution?

To properly determine if my analogy is apt or daft, a correlation must be drawn between the data-specific organizational structures of a successful small-midsize business and a winning sports franchise:

Organizational Charts

The similarities are obvious:

  • A clear, structured hierarchy headed by leadership that balances performance alignment goals with one consistent and centralized initiative: Satisfy the key external customer.
  • A functional middle level tasked with taking in tactical output from specialized departments and converting it into strategic advantages
  • A strong, defined level of professionals given the responsibility of deriving, analyzing, securing, and visualizing data to support strategic decision making

So, knowing that the organizational structures are akin to one another, four aspects of a successful digital evolution should be considered: TARGET, TIME, TALENT, and TENACITY:



Typically, sports franchises have one clear objective: a championship. Every decision made considers how much closer a team is to a title after that choice. Digital evolution doesn’t usually involve such a steely focus on one sole outcome. If anything, the end game of a digital evolution is ever-changing. New technologies, shifting priorities, change in leadership – these aspects all contribute to the moving goalposts of a digital evolution (yes, another sports analogy….).


This is the key parallel between a successful digital evolution and a championship sports franchise. More specifically, the requirement for patience. Digital evolution requires many short steps in a long journey. Faulty choices can be traced back to the most recent checkpoint to minimize damage and mitigate risk. Likewise for a sports team having the internal rigour to build slowly through good drafting and strong team culture.

Michael Jordan is, arguably, the best basketball player ever, and he didn’t start winning championships until after the Chicago Bulls had patiently put a team of role players and complimentary systems around him (not to mention, a Hall of Fame coach!).


Many see this as the most elusive aspect of developing a digital strategy that meets expectations. Does a company’s current employee base have the necessary skills to contribute to a successful digital evolution? Furthermore, is there an adequate level of leadership talent to guide the company through the inevitable missteps and challenges? If the answers to the preceding questions are anything but “yes”, a company needs to address their skills gap. This can be done through organic improvement (hard/soft skills training, growth opportunities, etc.) or external acquisition of resources to augment the current company roster (additional hiring, contractors).

Sports teams have similar considerations. At all times, they are evaluating their talent and leadership. Are the players talented enough to win a championship? Is the right coach in place to lead those players? Are there replacements available to bring in via free agency or trade?


Building a sports franchise towards a championship requires unending focus on the end goal. Hard decisions (see: Toronto Raptors trade for Kawhi Leonard) and pitfalls will come about, but they are inevitable, especially considering the time required and the scope of the journey. The same applies to a digital evolution. Missteps and mistakes are inevitable and will take place along the way, but a company should not allow them to divert attention from desired outcomes.

Tenacity is particularly important in the “doing” phase of a digital journey:

Many organizations swirl in an endless loop of “doing” digital things – an illusion of being digital – rather than making changes to business, operating, and customer models.

The “endless loop” referred to in the quote above is an important consideration. When the focus is placed on the individual tasks, it can be disheartening, but when consistent emphasis is put on established end goals, every task is seen as a smaller part of a much larger quest.


In sports, winning franchises are built patiently and methodically. Challenges are inevitable, blockers are overcome. Digital evolution is no different. A company needs to confirm its current state, visualize aggressive – yet reachable – end goals, and determine how to reach them. A company culture that encourages using missteps as lessons is vital as there will be abrasion on the journey. All in all, digital evolution is a long road that leads to championship-level success if you keep driving and refuse to be deterred by distraction.

About the Author

Ryan Wicklum is the Manager, Business Development at The Owl Solutions, a supply chain data analytics company. His background in Operations and Supply Chain Management spans over 20 years, having held progressive roles at Magna International, Clearpath Robotics, and Arctic Wolf Networks.

Ryan lives and works in Kitchener, Ontario.

Contact Ryan Wicklum

Share on social:

Automate root cause analysis and predict defects in real time

How is that possible?