The Pitfalls and Path Forward to Digital Transformation
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The Pitfalls and Path Forward to Digital Transformation


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Clearly, digital transformation is no longer an option, but an imperative. The risk is no longer merely getting left behind, but being eliminated altogether. The digital revolution forced every organization to reinvent itself, or at least rethink how it goes about doing business. While those investments are projected to top $6.8 trillion by 2023, they’re often made without seeing clear benefits or ROI. Although these failures have multiple causes, they are generally the result of underestimating the various steps or stages required to successfully execute a transformation strategy. But even the best technology will go to waste if you don’t have the right processes, culture, or talent in place to take advantage of it.

I previously bought my parents an Alexa, hoping they’d use it to streamline the tedious and analog (or what I believed to be) process of playing music, checking the weather, or setting the kitchen timer… anything. A year later, it’s collecting dust never to have been opened. When I ask why, they shrug their shoulders as if to not hurt my feelings and that they ‘prefer to be stuck in their ways’. Ah, boomers.

There’s the dilemma with innovation or ‘digital transformation’ for transformation’s sake. It can be presented and even force-fed on someone but any technology is only as good as it’s compatibility with the user and it’s ability to make their life (or jobs) more efficient.

Conversely, my parents bought my wife and I a digital picture frame (which admittedly still sits unopened – I swear not out of spite), after a friend gifted them one. They proudly display it in their home (and have gifted it time again to other couples) a limitless carousel display of their offspring. It’s a simple, yet personal source of pride for them and clearly taps into their value points which prioritizes an infinite barrage of family memories. Simple to most, and yet a major innovation from their dusty old ‘static’ picture frames scattered about the home.

Lesson learned, innovation for innovation’s sake can be futile. When led with humanistic insights and considerations, it can transform even the most stubborn of laggards.



It can be problematic when companies decide to embark on a digital transformation agenda without having a clear definition, let alone vision, for what it means. To merely, ‘follow the tide’ for the sake of self-preservation, is a precursor for failure. It must be led with intention, just like any strategic business decision. How are we going to navigate these uncertain waters? How will we make up the gap between ‘us and them (industry leaders)’? What happens when things don’t go according to plan – which is an inevitability?

The one unnegotiable to keep you clear and committed on this journey – your North Star – is the essence of your brand. The WHY of your existence, and subsequently driving the HOW and WHAT you will deliver to make good on that core principle. If you aren’t clear, committed, and intentional about this before you make that digital transformative leap, I assure you, things only get muddier from here.

If you’re not fundamentally clear and concise with your organization’s thesis for being and doing at the forefront, the rest will be a red-lined mess.

In most cases, you’ve got to measure twice (or more) then cut once. Because once you make that first cut commitment to transformation, it becomes exponentially costlier and more complicated to pivot. So do yourself the favor of being mindful and intentional about investing in your brand’s strategy before you make that inevitable leap.



The old adage ‘we are drawing in information and starved for knowledge’ has never been more applicable.

To better understand oneself, you’ve got to be willing to be vulnerable and look under the hood of your organization. Exposing, assessing, understanding the good, bad, and ugly. Everything from brand identity and communications, to web & social performance, SEO, content strategy, UX/UI, sales pipeline, and the list goes on… Nothing is too sacred for deeper inspection.

You may consider yourself ‘transformed’, because you’ve got a shiny new website, TikTok channel, or optimized CRM that checks that box. All good steps, but without a comprehensive and unifying strategy of how they will work in concert, these are merely tools and tactics that wind up driving you, not the other way around. And consider this, not every brand MUST check ALL of the boxes of the new ‘digital standard’. Because every organization is unique, and there are differences between types of businesses, industries, and cultures; the fundamental meaning of transformation is not about replacing old technologies with new ones, or capturing high volumes of data, or hiring an army of data scientists, or trying to copy some of the things Google or Amazon advise you to do. Be intentional about what technologies you are embracing that will actually help move the needle for your business, not simply following what ‘the other guys’ are doing. That’s a hamster wheel where nobody wins.

The essence of digital transformation is to become a more nimble, innovative and responsive organization in today’s competitive marketplace. But it begins with understanding the current and future needs and opportunities specific to your brand. Measure twice, cut once.

Future-proofing against the tide that is already among us.

But first, you must be ready and willing to unlock, or perhaps redefine your purpose, passion, and clarity for the transformative path that lies ahead. So, are you?


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