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Turbulent times call for leadership. That especially applies in a digital world with constant change and transformation. Solo entrepreneurs and big businesses try to outmaneuver each other online to gain any slight advantage.

Rachel Miller, Matthew Owen, Mark Boothe and Winnie Sun are leading digital competitors but—coming from different markets—not with each other. Together they talked about what it takes to be a digital leader in a digital world.

Miller is the marketing lead for SAP, a cloud business software company. As she describes her work, “I woo people for a living.”

With more than 25 years’ experience transforming companies, Owen partners with small and mid-sized businesses. His keys are quality, reliability, agility, creativity and personality.

As senior director of digital marketing at Instructure, Boothe has led a team, managed a budget, executed campaigns and built influencer programs.

Sun, the “Wealth Whisperer,” is a financial professional who contributes regularly to CNBC, Forbes and Good Day LA.

“Digital leadership means keeping up the innovative ways to continue to market your business,” she said. “I hope to evolve our current content to live on more platforms and continue to push the interactive envelope.”

Grab on to intelligent marketing for great results

Owen places particular emphasis on productivity.

“Since I tend to work with technology startups, digital leadership means building the company from the ground up with the most efficient workflow possible,” he said. “Assembling the correct tech stack from Day 1, can future proof an organization that wants to scale.”

Boothe does his best work by paying attention.

“Digital leadership is all about listening to your audience and then creating experiences that match what they want,” he said. “Listen and then create equitable, personalized and relevant experiences for those you care about.”

Ask people questions

In his view this is a lot more than most others are doing.

“To build a successful digital practice, companies need to more heavily emphasize listening and engaging,” Boothe said. “Use surveys, focus groups, calls and more. Do anything you can to really understand the ins and outs of what your customers need.

“Make sure your analytics practice is rock solid,” he said. “No matter what solution you use—Adobe Analytics Cloud is my favorite, but there are lots of options—look at the voice of customer stuff like what Qualtrics offers.”

Podium messaging tools are another Boothe favorite because they help more with listening to and understanding what customers need.

“Just having the data does not make someone successful,” he said. “Analysis paralysis is a real thing. You have to set goals and objectives before that data is even gathered so you know what value you are trying to get out of it.”

It’s often all too eBay to get enamored with numbers and forget about people.

“Effective digital leadership is leveraging technology to achieve business goals while also emphasizing a company’s greatest asset—its human workforce,” MIller said. “Powering individuals with best-fit technology to achieve maximum productivity and connectedness is the ‘new normal.’”

Artificial intelligence brings us back to the human touch

Much as in other professions, those at the head of digital technology learned the basics along the way.

“One becomes a digital leader by trying and testing new tech,” Sun said. “It’s being a pioneer and directing what you do next versus waiting for something to come to you. Leadership evolved by experience, learning and the people you surround yourself with.”

Practice and learn

Miller believes leaders are made by learned behavior.

“Some traits, like empathy, can be innate,” she said. “Other elements such as being courageous and self-aware are skills that need to be deliberately practiced.”

As Owen concurred, “Even with natural talent, you always need to be learning and improving. During your career you must develop digital skills and leadership skills. With enough time, you’ll naturally move into digital leadership.”

Boothe laid down these markers to become a digital leader:

  • Listen to your customers. Use data in the right way.
  • Create experiences based on what you learned in Step 1.
  • Test different platforms and experiences.
  • Keep listening.
  • Keep testing.

Those tie into top skills leaders need to have:

  • Empathetic Listener.
  • Powerful Explorer: Don’t be afraid of new and different.
  • Focused Tester: Test everything, and let the data make the decisions.

Digital leaders also need to find ways to implement and encourage others to take an active role in digital leadership strategies.

“It all starts and ends with you and your enthusiasm,” Sun said. “When you’re excited about trying something new, that flows to your team. It’s important for you to roll up your sleeves and try and fail, too, instead of just having your team ‘go at it.’

“As a leader in anything, you have to put in the time,” she said. “You need to be researching, learning from others and collecting data points. Then your team has the highest chance of success in the projects you’re working on together.”

Change for a reason

Eyes and mouths must be in sync.

“Leading people into the unknown requires vision and  communication skills,” Owen said. “People don’t like to change. They need to know why they’re changing and what the end goals are.

“Successful digital transformation projects require a leader who can communicate those goals,” he said.

Good alignment puts your values top of mind

Leaders need to describe the road ahead as they see it.

“To successfully implement digital leadership strategies, you need vision, communication skills and ultimately an open mind to experiment and pivot to secure best-fit technology and practices,” Miller said.

Blazing trails forces leaders to weigh uncertainties.

“There are business risks, but I have always chosen calculated and cautious risks,” Sun said. “It’s important to be financially sensible in how you go big. I know a risk is worth taking because I’m investing not only my own money, but also that of our company.”

New ventures incur particular post-traumatic stress.

“Anytime you start a business, it’s a big risk,” Owen said. “All the downstream risks seem smaller by comparison. So far it’s worked out well, but as they say, past performance does not guarantee future success. Ultimately, you just have to accept risk. It’s never going away.

“I’ve had my share of success and failure—spectacular instances of both,” he said. “I carry emotional scars from each of them. I didn’t realize the damage done until later in life. I might need some sort of entrepreneurial therapist: failure PTSD perhaps.”

Effective digital leadership strategies can make teams more productive and increase revenue.

“It’s very challenging to provide world-class solutions and products using outdated technology and strategies,” Miller said. “There’s a strong ‘walk the talk’ element that’s needed to differentiate as a true digital leader.”

In charge of tools

Those who succeed have a good grasp of talent on hand.

“Digital leadership strategies mean that you know what to do with the tools that you have and who can run the tool, keep it running, and what factors to facilitate success,” Sun said. “Tools don’t run by themselves—ever.

“Leaders need to be able to separate productivity from profitability,” she said. “Just because it works, doesn’t mean you should do it. If it works and it brings in profitability, then it’s worth repeating until the next productivity star comes along.”

Opportunity awaits the innovators

The end result will boost everyone’s efficiency.

“Digital leadership can help increase revenue by improving convenience, speed and customer support, which makes customers increasingly satisfied with your product or service,” Owen said. “They will be a great source of word-of-mouth referrals—still an important channel.”

With more and more companies working remote for the long term, entrepreneurs need to clearly display their vision in a virtual work setting.

“I’m a big believer in over-communication,” Sun said. “It can alleviate a lot of misunderstandings and keep a team moving in the same direction. Whatever work environment the future holds for you, keep your focus on making the best for each situation.”

That will test leaders’ adaptability.

“Know your audience, and provide your vision in a variety of formats: email, PowerPoint, video,” Miller said. “Don’t type out everything you’re going to say onto a slide. This isn’t 2005.”

Familiar-looking app

Several apps, tools and technologies are most helpful on the journey to success.

“The best tool is the person you see in the mirror,” Sun said. “As good as digital tools are, they can never really reach their full potential without you directing and strategizing how best to use the tool. Once you reach that point it’s amazing.

“I like tools that allow you to set and forget, but always introduce new functions to help you up your game,” she said. “Right now our focus is on live-streaming tools.”

Owen added more core tools for personal and business success:

“Hands down, collaboration and communication tools are integral to my team’s success,” Miller said. “It’s real time for the win.”

Artificial Intelligence, Leadership, and Talent Management

One of the most important leadership skills is to know when a strategy does not work and how to fix it.

“I use a financial gauge,” Sun said. “If I don’t feel that I’m gleaning at least a multiple value on the cost I’m paying for the tool, it’s time to pivot—and pivot quickly. Pay for digital tools on a monthly basis until they’re proven.”

Keeping an open eye will detect many impending problems.

“It’s important to have real-time monitoring processes in place as well as monthly or quarterly reporting,” Miller said. “Then data-based decisions can be made versus just ‘feeling really good’ about a product, solution or strategy.”

Motivation through recognition

People are motivated for success by success. Digital leaders commemorate their wins and recognize a job well done by themselves and their team.

“It’s important to celebrate your wins regularly,” Sun said. “Small celebrations make a big difference. We’ve overcome a lot to get to where we are. It’s important to be grateful for the silver linings, reflect on hopes for coming years and give thanks to your team.”

As Owen noted, a simple thank you will go a long way.

“For sustainable success, make sure your compensation structure is aligned with business goals so everyone shares monetarily in the wins,” he said. “That’s a guaranteed way to create more wins.”

To avoid needless delays, Miller recommended to “always give credit where credit is due—immediately.”

Visual information is more important now than ever before, emphasizing informative but “aesthetic” visual content.

“Visual information is so important because most of us appreciate visual design,” Sun said. “Be bold, make design personal, but make sure it stays true to the brand. Design can walk a fine line between awesome and messy.”

Owen leans toward Canva for creativity. 

“It’s a surprisingly versatile tool that can help you easily create compelling and informative visual content for a variety of platforms,” he said. “I highly recommend it.”

Turn on a dime

Marketers have learned to be ready to rapidly pivot at any time, relying on their strong digital leadership plans.

“It was important to have experience in self-managing a lot of things my team has helped run,” Sun said. “You need to have exposure to all different fronts to run and market your business. You have to be able to stay nimble, pivot and win against the odds.”

Miller discovered something more important than a digital leadership plan.

“Have flexibility built in and contingency plans to make sure the business keeps running even when the world stops,” she said.

Social media listening keeps you plugged in

Following up later might be too late.

“Social media can be used as a listening tool, making sure you have an up-to-the-minute grasp of your market’s conditions,” Owen said. “By listening in real time, you can craft plans for various business scenarios, and even A-B test them prior to pivoting with the right tech.”

Digital is not always about dazzling projects, but about transforming people and ways of working, sometimes on short notice. 

“We’ve had to quickly move from a very traditional business to a completely digital business,” Sun said. “Fortunately, half of our business had already moved in that direction. So, the transition was relatively smooth.

“For the future, we want to continue to become more remote friendly,” she said. “We have a great office and work environment, but we need to embrace remote work to give our team the work-life balance we all crave. We will only be stronger by keeping this focus in mind.”

Better fan experience

Owen found that part of his success has come from being a good sport—or having one.

“One of my favorite projects has been the implementation of facial authentication for touchless express entry to FirstEnergy Stadium, home of the Cleveland Browns football team,” he said. “Wicket will transform the fan experience, starting with quick access to your seats and favorite merchandise.”

Being a chief technology officer, Owen has solved a wide array of business problems.

“They all have one thing in common,” he said. “Somewhere the flow of information within the organization is disrupted. Data needs to be accessible to the right people at the right time.”Quote about faith in people

Whatever technology they use, the best digital leaders stay focused on meeting customers’ needs.

“We help our clients leverage their time and life by taking over the heavy lifting of managing their finances and wealth,” Sun said. “Yes, we do this very well. We had been using visual communication for some time, so this transition just meant taking it up a few notches.

“When I started in the business, my greatest tools were my phone and car,” she said. “Now, it’s my camera, laptop and the internet. This will continue to evolve, but the key skills of effective communication will remain. We need to keep practicing to stay relevant.”

Sun never forgets who she really works for.

“Using technology and digital tools is great as long as they’re used with the intention of enhancing your client experience,” she said. “Being people-based will never steer you wrong.”

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Jim Katzaman
Jim Katzaman is a manager at Largo Financial Services. A writer by trade, he graduated from Lebanon Valley College, Pennsylvania, with a Bachelor of Arts in English. He enlisted in the Air Force and served for 25 years in public affairs – better known in the civilian world as public relations. He also earned an Associate’s Degree in Applied Science in Public Affairs. Since retiring, he has been a consultant and in the federal General Service as a public affairs specialist. He also acquired life and health insurance licenses, which resulted in his present affiliation with Largo Financial Services. In addition to expertise in financial affairs, he gathers the majority of his story content from Twitter chats. This has led him to publish about a wide range of topics such as social media, marketing, sexual harassment, workplace trends, productivity and financial management. Medium has named him a top writer in social media.

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