Kobe Bryant and Derek Jeter on leading your digital transformation

Digital transformation is not an IT project.

That was a theme echoed throughout the 2017 SAPPHIRE NOW & ASUG Annual Conference last month. While the path to transformation will vary among organizations, as well as the technologies they deploy to get there, one common thread should run through them all. Digital transformation is business transformation. It’s not just about adding new technology to fix one archaic process or speed up a single department. Digital transformation should underpin the modernization of your entire business and strategy.

And that takes more than IT.

As guest speaker Michael Dell, chairman and chief executive officer of Dell Technologies, explained during the first day’s keynote, digital transformation has to start with the CEO. That doesn’t mean IT has no role at all. Your IT department should be an integral player in key technology decisions and strategy – and may even need to take on an expanded role.

But CEOs need to take the lead in ensuring the entire organization is aligned to the digital transformation strategy. That means putting the right people and processes in place, from top to bottom, so that the entire organization is in lockstep on the transformation journey.

Get to the sports stuff – I know, I know

On the last day of the conference, SAP CEO Bill McDermott was joined by two entrepreneur/philanthropist/authors, Derek Jeter and Kobe Bryant. You may also know them as five-time World Series champion and New York Yankees captain, Derek Jeter, and five-time NBA Champion with the Los Angeles Lakers, Kobe Bryant. Pick your profile.

The three sat down to discuss lessons learned (good and bad) over the course their historic 20-year careers. Each legend shared personal leadership mantras that helped them rally their teams, stay focused and win big – mantras that any business leader can use to bring their organization together in support of successful digital transformation.

What Derek and Kobe can teach us about leading digital transformation

Get to know who you’re leading

Transformation is about people. As Jeter explained, people may listen to you, but that doesn’t necessarily mean they respect you. You’ve got to take the time to get to know who you’re leading and understand what motivates them. Only then will you know what it takes to get your team to play in harmony.

Bryant agreed and said he struggled with this early on in his career. Over time, he learned to take the time to understand his teammates’ ambitions and goals, and how those goals related to his own. Once he got to know his players, he knew how to drive them forward.

Leaders looking to get their organizations to work in harmony need to do the same. As Bryant said, if you have an employee acting counter to the vision of the organization, you have to first understand the “why” behind it before you can find the best solution.

No two individuals are alike. What motivates one person to get on board with a new process or technology may not be the same for someone else. Do people want to be challenged? Put at ease? Inspired? Listening to staff and getting to know what makes your organization tick will reveal how to rally everyone around transformation.

Preparation is key

When asked how they were able to stay so good for so long, to play at the highest level so consistently, both athletes boiled it down to a focus on preparation. For Jeter, physical and mental preparation ensured he was ready to play regardless of the opponent, weather conditions or stadium. Preparation helped him focus on the game and not let any scenarios distract him, foreseen or unforeseen.

For Bryant, it was about building good habits. NBA life can be grueling, living out of suitcases and bouncing from hotel to hotel. To stay focused and prepared, establishing and (more importantly) sticking to a routine was critical.

In short, have a plan for your digital transformation. Think of all the scenarios that could derail your progress and find solutions in advance to work through those issues. And be consistent and disciplined with your communications and checkpoints. Make sure the goals and benefits of your digital transformation are constantly reinforced throughout your organization.

Competition eliminates complacency

Both Bryant and Jeter share an above-and-beyond-average competitive spirit. Whether one championship or five, both always wanted more. But how did they maintain that success year after year?

For Bryant, winning always meant that someone else lost. He knew that in the off-season there was always someone else in the gym getting stronger, ready to come back next year and fight for the championship. So Bryant kept any celebration short and sweet before he went right back to work.

Jeter credits his drive to a short memory. Good game or bad game, he was never happy with something he accomplished in the past. It was always about moving on and winning the next game.

Digital transformation leaders shouldn’t forget the competition either. Every organization today is using technology to improve the way they create new products and services, provide customer support and analyze performance. Transformation should be continuous. Take time to enjoy the successes and milestones along the way – but keep driving.

Everyone else is.

CEOs may take the lead, but they aren’t the only leaders

Even Jeter admits that all 25 players on the Yankees roster weren’t on the same page 100 percent of the time – that was never true. What made the difference for the Yankees was that there were enough people at the leadership level pulling in the same direction. When leadership sets the example and direction, people will follow.

The same applies to digital transformation initiatives – CEOs can’t do it alone. They need leaders from all levels of the organization, across IT, finance and all departments, to rally their own teams and push the entire organization toward the future.

That’s how you become a champion.

Danielle Simer

Danielle Simer

Danielle Simer is a marketing portfolio manager at Hyland. Her mission is to share best practices and evangelize the power of enterprise content management (ECM) as a tool to automate... read more about: Danielle Simer

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