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What comes to mind when you think of these people? Christopher Columbus, Ferdinand Magellan, Marco Polo, and Ernest Shackleton. Go ahead… think for a moment… (Jeopardy music playing).

Okay, you’re probably waiting for the connection. What does today’s digital transformation have to do with great explorers?

As I try to better understand these people and their contribution to society, I think of visionaries who are convinced there is more out there in this world, and they will do most anything to unveil the “what if discovery.” They would probably say their journey was the most important part of their tenure as explorers, not the end destination discovery that was attached to their name in history.

Untold and unseen pieces of our world today were discovered because of curiosity, and insatiable desire to innovate, explore and see where the journey leads.

These heralded explorers and others also could motivate those around them to participate in something greater than themselves. Something not seen or experienced before. The exploration of uncertainties is the mindset we need to adopt today to find out how digital transformation fits into our businesses, our departments, our roles, and our future. Wow, now that’s a challenge.

Let’s start by looking at digital transformation one step at a time so you can begin a process that will be helpful.

The Digital Transformation Journey Starts Here

We all know digital transformation is important. After all, it seems a lot of social posts, blogs and influencers are deliberating on how to start the transformation process. Truth be told, not many businesses know what it means for them. They’re not sure if they need to do this digital transformation thing at all. And if they decide to move forward with it, where to begin, how to think, how to benchmark progress, and where does it lead?  Hmm… So many uncertainties.  That’s why we’re here, right?

Journey Map

Let’s say you work for a company that understands the need to do something but they’re not quite sure what. That’s pretty much all of us, right? Let’s start with goals. Like any good project initiative, it’s always good to know what you are trying to achieve, even if you are not exactly sure what the end destination looks like or where it will end up.

First: clearly define what you are trying to accomplish by embarking on a digital transformation journey.

Ask yourself a few questions. If you are to be successful in this journey, what must happen? And what tactical and strategic outcomes are expected? This is not a blog full of questions you can’t answer. These questions are a starting point for your teams to start chewing on, dissecting and to begin unraveling keys to what’s next as they relate to digital transformation and your business model now, and for the future.

Let’s go back to what the explorers did at this point in their journeys. If they got overwhelmed, ran into a roadblock or couldn’t find the answers they needed, well, when the going got tough, the tough dug in a little deeper and didn’t let setbacks get them down. When it did happen, they re-tooled, dusted themselves off and tried again.

You will probably find that your digital transformation journey is not an easy plug-and-play exercise. It’s hard work. It also takes a lot of thinking outside the normal boundaries of everyday workflow which is taxing on the brain and the teams involved. But keep going. What you learn throughout this process is priceless.

After you finish defining what you are trying to accomplish (overarching goal), now it’s time to create a general structure for generating new ideas.

Here are a few helpful tactical objectives:

  1. Create an idea think tank of people that will participate in and engage with the process of unveiling your digital transformation
  2. Problem Identification
  3. Clear Purpose of Exploration
  4. Adopt Start-up Principles
  5. Key Takeaways for Next Steps
  6. Digital Disruption


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Idea Think Tank

Create an employee group that represents as many generations as possible. Preferably 4-5 if you can. Your think tanks need different types of people contributing to the thought process, creativity, technology, business process, monetization, people interaction, behavior, ideation, sustainable future possibilities, and customer experience to name just a few.

The connectivity and collaboration between these generations is the secret sauce most businesses don’t think about.

Multi-generation collaboration brings out the best ideas that would never have emerged before if just the senior executives of your company were sitting in a conference room tossing ideas around. Because digital transformation is connecting today to the future, you need the future sitting on your think tank team.

Each generation brings a unique frame of reference; business, communication preferences, e-commerce, social media, political, historical, technological; but it is the ability to work in a consolidated, collaborative way across the generations that is truly powerful.

The more experienced people bring perspective within the business, the industry and throughout their entire work exposure. A seasoned veteran’s perspective is valuable when it comes to scaling ideas, problem-solving, and relating to existing business and industry challenges.

However, younger Gen X, Millennials and Gen Z professionals each bring new perspectives to solving problems, thinking ahead, interacting and connecting. Your think tank needs these unique perspectives for your digital transformation to excel. Think of your multi-generational think tank as a facilitator of change, coming up with ideas, concepts and potential paradigms that just might be the next key drivers your company needs.

The goal of the think tank is to collaborate, connect and harness all these varied perspectives and the thought capital generated from it to begin the digital transformation journey. Remember to explore just like the famous people we talked about did. Search for the unknown, create a new way of conducting business and redefine what will make your company successful and sustainable for the future. There’s no visible or known path to digital transformation because each company is truly unique. Let your minds think freely, you have to dream, create, re-organize and at some point, make it real, actionable and own it.

Photo by Startaê Team on Unsplash

Problem Identification

Everyone likes to identify a problem. That’s the easy part. It’s finding out the solution to the problem is where the challenge lies.

In the problem identification section, you want to start identifying problems that can only be solved using ways your company doesn’t currently employ. I know, that’s rather cerebral. Let’s break it down further.

Three areas that are commonly known for problems are the customer journey, their pain points and their experience along that journey. Try unpacking these to see what you discover. If you can dive into these and figure out what’s happening, and not happening that’s a great start. Next, seek out what’s called adjacent innovation, then see how you might be able to adopt a variation of that in your company. Now you might be on to something. Recap: Identify the problems and look for adjacent innovation to help solve the problems. Roger Park, EY Innovation Leader calls Adjacent innovation: “taking an idea from one area and seeing if it will work in another.”

This type of innovation viewpoint is relatively common in businesses that are the front-runners in innovation. Start looking at other industries and how are they evolving. Then start thinking about how you can adapt what you discovered. If it is a solution to your problem, you just might be able to then write it into your digital transformation plan.

Clear Purpose of Exploration

If an organization’s focus is to do amazing things for customers, and if that purpose is clear to your think tank, then no matter what a person’s age or background, they’ll have a clear sense of why they are chosen to be on the think tank team and how to contribute. This is a great start.

During the exploration process, think like your customer, not like an employee. After all, It’s the customers you need to create next-generation growth with. Focus on connecting and engaging with that customer at a deeper level. Our younger generations which will be the generations of buying power are who we need to think about. Explore all possibilities that come up in your think tank sessions, even the ones that don’t seem possible.

Adopt Start-up Principles

Encourage trial and error, as well as failure. What? Failure? Who thinks like this? If you’re on a think tank team, you need to think of failure as an option, because most of your ideas are not going to be sustainable for future growth and the failures are the ones you learn from the most. Hmm… just like life.

Additionally, make sure to allow for the ability to recover quickly from failure. This is important. Putting all your resources in one area with no failure recovery plan is not smart. A failure recovery plan is a means by which your team pivots off that initiative, once you’ve collaboratively gathered all the intel from it and moved to another initiative deemed more viable.

Also, don’t wait too long to call it a failure. Remove the ideas that don’t appear to be worth keeping. Draining resources because you are emotionally attached to the project is not the goal here. When you fail, you want to do it fast. I know, who plans for failure? And who plans on failing quickly? It’s just not in the mindset of today’s business leaders. Although, universities will tell you that failure is critical for success. In fact, “Fail fast and fail often” is prescribed by an MIT student initiative.

Initially planning for failure means starting a few different initiatives or concepts at the same time to see where they lead — learning and capturing valuable data along the way. Then, at a certain point, a discovery will be made and most likely only one idea is viable and the other will fail (or less viable). Discoveries are not just positive; they are also leading to failures. But that’s okay.

Take what you learned from the failed ideas, shift that learning and resources to the concept that you believe to be “the next big idea” and run with it from there. It’s like a business research project, only way cooler, and more iterative.

This may sound easy, but it’s not. Pivoting quickly off the failed idea is tough, especially when you’re invested in a potential business, industry or world-changing idea that doesn’t exist yet. Remember to learn from what you’re working on, continue to dialogue with your team, record the findings, successes, and missteps; and apply all of those to the concept that the company thinks will be the winner. That’s the key here.

Key Takeaways for Next Steps

Before your think tank chooses an idea and begins running with it, make sure to use extreme discipline when selecting. Don’t just say “this is a great idea, let’s do it.” That is a recipe for wasted time and resources. Make sure you’ve got enough data and research behind you to validate your selection. Of course, we said earlier to plan for failure. Also, make sure to have an action plan for when/if a failure does occur. Just because you picked an idea doesn’t mean failure won’t happen later.

So, let’s say your digital transformation idea is the winner and it appears to be the real deal. At some point, someone needs to think about scaling this idea beyond the concept and research stage to the enterprise and rollout stage. This just might be the most important thing of all because you’ve tapped into the gem you’ve been looking for. Now it’s time to make it a reality.

With larger, more decentralized companies, this is very challenging. This initiative will need to be clearly communicated to all the stakeholders, which means people, departments and divisions. Widespread, clear communication will help create more project value across the company and share the vision, clarity, and expectations moving forward. I’ve been on teams when this was not executed well, and teams become highly dysfunctional and unproductive. And you can only imagine what happened after that.

Digital Disruption

Lastly, we know digital disruption has become commonplace, especially with the integration of technology disruptors such as IoT, predictive analytics, machine learning, and predictive modeling. If none of these factor into your next plan for digital transformation, you may want back up the train and re-think. Today’s most successful companies are new players that know how to do business with these forms of technology as well as older, more mature companies that once relied on traditional business models and have been forced to re-think how they do business to survive. Digital transformation is here to stay because the digital economy is a way of survival for modern, sustainable businesses; it’s also the DNA of our future customers.

Exploration Continued…

Those celebrated individuals like Columbus, Magellan, Polo, and Shackleton explored new frontiers and set the stage for business leaders even today. Their moxie and poise in the face of skepticism is part of what helped them continue their journeys, even when catastrophe struck. They failed, often many times. But they continued and learned from their journeys.

Your digital transformation journey will be exciting and unique, challenging and informative, heart-breaking and thrilling; and potentially industry or life-changing. Regardless of where your journey leads, remember the process and learning along the way. All of it combined will help ignite your next exciting business adventure and also provide a platform for which to seek out new ways to innovate. Digital transformation is not a project. It’s a means of conducting business, and a way of thinking that will help create sustainable growth.


Scott MacFarland is the Director of Marketing for HMY Yacht Sales in Jupiter, FL. He’s an advocate of exciting new ventures, digital marketing, transformative learning, and how to continue to be at his best in today’s digital workplace. Scott has had the opportunity to work with some amazing business leaders, all of which were instrumental in his perspective and desire to continue growing through business change.

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