Great Teams Don’t Need Superstars: How a Former Athlete and Teacher Is Transforming Business Automation

Posted by on June 12, 2019

I grew up playing sports: basketball, softball, track. Through sports, I’ve learned many life lessons, especially about the power of good coaching and teamwork.

I’ve played on teams stacked with superstars who couldn’t gel, and we ended up with losing seasons. We were unable to harness the synergy for team success. 

I’ve also won with teams who, individually, were less talented but were able to capitalize on each other’s strengths. The whole was greater than the sum of its parts; or, as they say, teamwork makes the dream work.

Leading digital transformation is like preparing a championship team. It takes great coaching; an effective, well-communicated strategy; willing players; and plenty of patience. Consider these lessons learned from leading digital transformation:

Lesson 1: Lead by Coaching

Technological innovations can be difficult to understand and even harder to implement. You need a leader who can coach the company through transitions and guide them to the right solutions. At Cherwell, we call the person with that job our “CTO,” and the “T” stands for “transformation” not “technology” because the challenge includes so much more than technology.

CTOs must come alongside executive management to help them understand how investing in technology (and supporting it with training) will improve the business in every office and department: C-suite, HR, sales, finance, operations, even IT. CTOs should develop plans and shared vision with each executive on how digital transformation will enhance outputs and increase revenue.

And coaching doesn’t end there.

You’ll need to convince employees that this change will help them, too. How do you do this? Start by listening. Listening to their challenges and issues will help you to:

  • Better understand internal processes and pain points
  • Inform the development of solutions with respect to process and technological changes that can specifically address employee concerns
  • Develop training that speeds transition to new processes and technologies
  • Track adoption to make sure processes and technologies work as planned

Lesson 2: Strategy Before Play

You’ve met with the executive team to establish a vision. You’ve listened to the employees to determine their challenges. Now you need to find the applications or software to fit the company’s needs…but wait! You wouldn’t send your players on the court without deeply understanding how each of them plays and how their specific roles function together as a team. 

Before rushing to apply digital solutions, savvy CTOs ensure that they deeply understand the processes they aim to support. Skipping this step may lead to simply creating a more expensive broken process.

I recently encountered a situation where a digital sales application was implemented on top of outdated processes and failed methodologies. The digital “transformation” created more paperwork, and it required 80 percent of the work to be done manually. Recalibrating, we worked with executives and employees to improve underlying processes. With the same application deployed on an updated view of the holistic process, we were able to reduce paperwork and transform the process to be 80 percent digital.

Lesson 3: Capitalize on Culture

The famous quote attributed to Peter Drucker reminds us, “Culture eats strategy for breakfast.” In the course of an effective transformation (digital or otherwise), strategy and culture are tightly aligned with an organization’s capabilities to produce something new and different.

While change—and new technology—can seem intimidating and overwhelming, those negatives are minimized in a culture that values and rewards innovation and improvement, growth, and goals (both organizational and individual). As you engage with execs and staff, consider your company lingo and what is counted as a win or as a failure. Be intentional about encouraging and rewarding the change that you want to see happen and don’t harp on failure—highlight what can be learned.

The CTO’s role is not about setting new standards, implementing new software, and demanding compliance. It is coaching and guiding teams of individuals to produce something entirely new. A new product. A new revenue stream. A new path.

Essentially a catalyst for change, a successful chief transformation officer guides their company through a maze of technological and procedural innovations to enhance speed and effectiveness in every facet of business.  Like a championship coach, leading transformation takes teamwork, strategy, and culture, not just technology.  

To learn more about digital transformation and how Cherwell can help your organization succeed, contact me at