In the sequel to Alice in Wonderland, “Through the Looking Glass,” Alice steps through a mirror and enters a world in which logic is entirely reversed. Up is down, down is up, and running as fast as you can only makes you stay exactly where you are. If the latter effect — frantically running and yet going nowhere — feels familiar, it might be because it mirrors (no pun intended) the experience so many organizations have with digital transformation. The faster we try to run, the more we seem to stay exactly where we are.

Despite our collective energy and investment (and despite the fact that it’s about to enter its second decade as a top-of-mind IT trend!), digital transformation still feels difficult. There are, of course, many reasons why this remains the case, but let’s start with the most obvious: digital transformation is difficult. No amount of buzz, no list of best practices, and certainly no single technology is going to change that. Fundamentally transforming how you organize your team, develop your products and engage with your customers isn't going to be easy.

But that doesn’t mean we shouldn’t work to find solutions that enable forward progress. So, let’s examine five key reasons why digital transformation often feels so difficult, and discuss some of the steps you can take to alleviate the challenges they present.

Lack of Trust

I can’t tell you how often in the past decade I’ve heard an executive say, “I know we should, but I just don’t trust it.” The reality is, we know what we should be doing. We know we should switch to agile development. We know we should automate once-manual processes such as testing, integration and even database management. We know we should prioritize our mobile properties alongside (if not ahead of) our web properties. We know we should invest as much (or more) in our digital experience as we invest in our products themselves. 

We know we should, but we just don’t have the trust.

If we’re ever going to truly accelerate our efforts to drive digital transformation, we have to trust the technologies and processes that power it. If that seems like a leap, think back and recall all of the now-common technologies and processes we once didn’t trust. We didn’t trust that customers would transact online (no one will ever trust their credit card number to a website, was a common refrain). We didn’t trust that BI and analytics could deliver valuable insights (data is for statisticians, not business leaders, I was so often told). Now, just about every company in the world is driving transactions online and running some form of data analysis to better understand how their business and customers behave.

From CI/CD and continuous testing to AI and machine learning, the tools that power digital transformation are there. Now it’s time for us to trust them. (And no, they won’t steal your jobs!)

Related Article: When Digital Transformation Transforms

Lack of Expertise

Part of the reason we so often lack trust is we also often lack expertise. Digital transformation not only requires you have the right tools and processes, but that you have the expertise to successfully implement, manage and refine those tools and processes. And expertise requires experts. 

Is it realistic for every company to hire an (often-expensive) expert every time it invests in a new tool or implements a new process? Probably not. But this is where it’s time to start demanding more from your vendors. Make it clear you’re not about to invest in their technology or platform unless they can also provide hands-on expertise (i.e., experts) who can help you succeed with it. Trust me, if they’re serious about winning your business, they’ll find a way to make it happen.

Learning Opportunities

Related Article: 4 Digital Transformation Hacks

Lack of (Proper) Training

While the tools and processes are undoubtedly there, the training necessary to make use of those tools and processes usually isn’t. Now, you might be thinking, we have training sessions, so we’re fine here. But there’s a big difference between offering training and offering proper training. Namely, repetition.

No one wants to hear this, but training employees on a new technology or process once just isn’t enough. Training them twice probably isn’t either. Remember, you’re asking your team to fundamentally alter the way they go about delivering products and engaging customers. That takes repetition. Training in the age of digital transformation is an ongoing endeavor. If you’re not continuously training your employees to reinforce behaviors and get them comfortable with new concepts, then you’ll inevitably run into the following barrier.

Related Article: Digital Proficiency: Literacy, Fluency, Mastery

Lack of Adoption

The ills of shelf-ware are well documented, so I won’t belabor the point other than to say that lack of adoption is usually about the inadequacy of training rather than the inadequacy of the technology sitting on the shelf. Employees aren’t about to start using tools they don’t trust (there’s that word again) or understand. So, if you find yourself sitting on a mountain of shelf-ware, the adoption of which could be the catalyst for your stalled digital transformation efforts, it’s time to train and evangelize. Consider forming a center of excellence (COE) responsible for encouraging and simplifying the adoption of new technology throughout your organization. If you’re not resourced to create a COE, start by appointing one or two of your best and brightest employees to play the role of internal evangelist. Or better still, lead by example and start playing it yourself.

Related Article: Goodbye Digital Transformation, Hello Cathedral Thinking

Lack of Positive Reinforcement

Digital transformation is hard. Not everything is going to go as planned. But if you want to keep your team motivated and keep your initiatives moving forward, you need to identify and celebrate the successes you do have and treat the inevitable missteps as exciting learning opportunities rather than failures. 

If that sounds a bit like stepping through the looking glass, well, sometimes that’s what it takes to keep from running in place. 

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