Type above and press Enter to search. Press Esc to cancel.

February 21, 2022 | 5 Mins Read

If You’re Striving for Digital Transformation Perfection, You’re Doing it Wrong

February 21, 2022 | 5 Mins Read

If You’re Striving for Digital Transformation Perfection, You’re Doing it Wrong


By Sarah Nicastro, Creator, Future of Field Service

I read a Harvard Business Review article last week written by Harmit Singh, Executive Vice President and Chief Financial Officer at Levi Strauss & Co., sharing four lessons from the company’s digital transformation. It’s an excellent article, ripe with self-awareness and nuggets of hard-earned wisdom any business leader can benefit from. What stood out to me, though, was the point Singh made around perfection – to not let “perfection be the enemy of good.” 

For the retailer, the focus on perfection is innate and Singh shares that overcoming the instinct to apply that same principle to the company’s digital transformation was one of its biggest challenges. We’ve talked before about how digital “transformation” is really more of a journey, and if you liken the digital journey to any journey of self-improvement the way in which striving for perfection can be detrimental becomes clear. IDC expects global spending on digital transformation to reach $6.8 trillion by next year, and for those investments to make their intended impact, companies are well-served to recognize the need to release visions of perfection. 

In his article, Singh shares how the 168-year legacy of Levi means that the company was going into this journey with a lot of deeply rooted beliefs, practices, processes, and habits. This is the case for so many organizations who start out thinking that the digital journey means layering on more modern, sophisticated technology only to find that it is far more a journey of reshaping not only the company’s identity but its culture, mindsets, structure, and processes. This, my friends, is why we began using the term digital transformation over ten years ago and are still discussing it today – it is far more complex in practice than any headline can properly convey. 

Singh shares his top four lessons learned, which again are well worth reading. What I want to share, though, are my thoughts on the five areas where visions of perfection prohibit attainable progress with digital transformation.

#1:  Legacy Lingers

Any company who has embarked on their digital journey can tell you that the hardest parts have far more to do with people than they do with technology. And so much of that is related to legacy thinking, beliefs, feelings, and patterns. And it’s important to recognize that is okay – it is to be expected. We can’t charge ahead into a new way of work and simply expect to snap our fingers and erase the legacy that has made the company what it is; nor should we want to. Rather, we need to acknowledge up front that overcoming legacy thinking and behaviors that don’t fit into the digital journey will be a challenge and we need to plan accordingly. Focus on progress rather than perfection. Be respectful of the ways in which change can be hard for your teams and put ample effort into change management to help their transition into the new company ethos be smoother. 

#2: Agility Muscles Must be Built

Singh talks about how the concept of becoming more agile was particularly challenging for Levi, as it is for many others. But it is absolutely imperative as the pace of change is never going back to a former speed. Technology today simply doesn’t fit into anything but an iterative process, and companies who are unfamiliar with the approach can really struggle to make progress because of this fact. And I’m not only talking about agile as a methodology, but also as a mindset. Before we can flex our agile muscles, though, we must build them over some time. A big part of this that Singh discusses in his article is normalizing failure. The agile mindset – and process – is one of continual improvement, in which trial and error is normal. This is often at odds, though, with the legacy culture of the company – and leadership needs to understand the importance of empowering employees to work differently without fear. 

#3: Look Ahead, Not Beside

Yes, it is important to pay attention to what your competition is doing when it comes to all aspects of differentiation, including digital. However, your digital journey can veer far off course by measuring your progress against someone else’s journey rather than your own improvement. Singh talks about how it can be difficult not to panic when you feel “behind” the competition – but this sort of sideways attention only detracts from the forward progress you must make to keep pace. There will be a time to study competitors but being distracted by their journeys when it comes to what is a very company-specific transformation is a waste of effort and energy. 

#4: Data Mastery Takes Effort

One of the key objectives of digital transformation is to create and leverage far more data than you’ve ever had before. This is powerful, but it can also be overwhelming – and sometimes company let this overwhelm paralyze them from making forward progress. You don’t have to perfect data use from the start, in fact I’d argue it is impossible – you will always be finding new ways to use data to glean insights that help the business and your customers. But you should know, from the start, that becoming adept at converting data to intelligence takes an investment and must be a part of your digital transformation strategy. Singh shares that, “To realize the full potential of the data, employees must embrace new tools and develop data savviness. We don’t expect that to happen overnight, given employees are comfortable using systems that have worked for them for years. We realize with training and a clear picture of how the systems simplify and supercharge their work flows we’re creating an innovative and responsive culture around data savviness.”

#5: Stay Open to the Journey

Part of a more agile mindset is realizing that while you may start your digital transformation journey with an “end goal” in mind, the reality is that the end goal is always evolving. For people, like me, who really relish the satisfaction of crossing a project off the list, this can be a tough pill to swallow. However, the companies who have the most successful digital transformation stories have recognized that being too fixed on your initial vision of success can prohibit you from seeing and incorporating valuable learnings along the way. As Singh says, “Success doesn’t always look like what you initially thought. I’ve seen this throughout my life both professionally and personally, and this is especially true in business. The place we end up is different from what we set out to be, and often, the journey becomes even more valuable than the actual outcome.”