How to Be a Great Leader During Digital Transformation

Jessica Thiefels

07 July 2019

Digital transformation is necessary if businesses want to stay competitive and innovative. New technology now levels the playing field and gives organizations of all sizes the ability to grow at a pace never previously attainable. 

However, digital transformation can also be a very complicated process. It involves the assessment of people, processes, data, applications and more because the introduction of technology affects every area of your business.

The shift can be especially challenging for organizations resistant to change. In this CIO article, Howard Tiersky, CEO and founder of FROM, explains his experience with this: 

“Being in the business of helping companies through their digital transformations, I have observed that many of the companies that struggle digitally do employ super-sharp and visionary executives who see what needs to be done. However, those executives face massive challenges when it comes to enacting the kinds of changes that are necessary in order to make that digital leap.”

As a leader, it’s your job to steer the ship of change, rather than slow it down.

Here are a few key areas you should focus on to innovate and enact digital change.

Own the Digital Transformation 

Barry Ross of Ross International puts it best: “You can’t delegate digital transformation for your company… you and your executives have to own it! Executives need to engage, embrace and adopt new ways of working with the latest and emerging technologies.” 

This means, before bringing it to the team, you need to be prepared with a vision that you can own, and that the company will want to own as well. Figure out how to steer the ship before asking everyone to jump on board. 

Additionally, don’t forget to stay open-minded if you want to own digital transformation. For example, if you’re hesitant about an idea from the CEO, own the hesitancy and find a solution before fighting back or resisting the change. 

Being a great leader means being ready to adapt. If you can own the plan, or come up with a better one, you’ll get everyone on board and allow the company to grow.

Be Forward Thinking

First and foremost, you must start with a plan to handle foreseeable challenges, which benefits both you and your team. “Clarity of the issues allows the team to objectively break down the risk factors, anticipate potential outcomes with a clear line of sight, and identify a path toward the real issues they should be really solving for,” says Glenn Llopis, leadership expert and best selling author, in this Forbes article.

Llopis explains that this eliminates the “guesswork and makes change management less about dealing with potential adversity and more about seeing and seizing the opportunities that are right in front of you."

However, it’s nearly impossible to anticipate everything that could go wrong by yourself. Instead, connect with the various teams involved and ask for their insights—but don’t stop there. In an article entitled, Six Principles of Great Leadership, communication experts at Hubgets suggest asking, “And what else?”

Why? “This short and unexpected question will push people out of their comfort zone and make them voice the thoughts they otherwise would’ve kept to themselves out of a natural need of playing safe. But those undervalued thoughts could be the gold mine; the outstanding ideas that give birth to innovation.”

Compile the teams’ responses into a list of different scenarios and how they could play out. As you collaborate with these internal leaders and employees, ask yourself:

- Where are the gaps? 
- Who can I involve in each stage for support? 
- How can we fix the problem before it happens?

Keep Agility at the Forefront of Your Planning

Executing digital changes requires both you and your team to be agile every step of the way, suggests Scott Terrell, CIO of HealthMarkets. He explains, “The fast pace of technological change and the demanding nature of consumers for an optimal experience makes it critical for organizations to be nimble and alert. You have to prepare your team to be agile and pivot quickly when needed.”

This means everyone needs to be on board, and ready to move quickly and efficiently. Make time to gauge any potential challenges and resistance among employees and provide your team with the tools they need to move fast, act accordingly and complete the project. 

For example, if there are concerns about connecting with you, and other members of leadership, to execute changes quickly, an internal chat tool can be a simple solution. This makes it easier for employees to get in touch with you as soon as they need to, rather than waiting for you to respond to an email. 

Move Ahead 100 Percent

Digital transformation is not something you can do halfway, explains George Brady, EVP of technology at Capital One. In an article on Medium, he says, “After more than four years leading a comprehensive digital transformation at Capital One, I’ve learned a few tough lessons and I’ve got a lot left to learn as we continue on our journey. For one, you simply can’t do a digital transformation halfway. It involves taking an honest look at your current systems to see what’s broken, scrapping what’s not working and choosing the simplest path forward.”

It might be tempting to stop in the middle of a major overhaul because you’ve come up against what feels like an insurmountable roadblock, or you’re dealing with pushback from board members. 

Instead of giving into the fear of a potential setback, keep Brady’s advice in mind: Get honest about what’s working, don’t be afraid to change systems and address what’s broken. Sometimes, to move forward, you have to scrap what’s been done and start over.

Be a Great Leader in the Age of Digital Transformation

Managing your teams through digital transformation will likely be one of the most challenging, yet rewarding tasks you face in your career. As a leader, you have the ability to propel your organization into the future and be a part of something that’s innovative, ever-evolving and significant. Use these tips to prepare for this important time in the company’s history and ensure success. 

Jessica Thiefels

Jessica Thiefels is an entrepreneur and founder and CEO of Jessica Thiefels Consulting. She’s been writing for more than 10 years and has been featured in top publications like Forbes, Fast Company and Entrepreneur. She also writes for Business Insider, Virgin, Glassdoor and more. Follow her on Twitter @JThiefels and connect with her on LinkedIn.

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