Digital Transformation Falling Flat? Bring in the Pirates

IT leaders should reflect on how and why digital transformations fail and tap nonconformists who are not afraid to think outside the box as a start.

Guest Commentary, Guest Commentary

March 17, 2020

5 Min Read
Image: Pixabay

Over the course of my career, I've been fortunate to work with clients who have seen tangible and sustainable results on their journey towards transforming their organization.  But recently, and with greater frequency, I've observed a few unfortunate trends: 

  • Fragmented, piecemeal efforts at digital transformation vs. integrated and scalable digital initiatives;

  • New technology initiatives (e.g. AI/machine learning, IoT, blockchain) that spark excitement and proof-of-concepts but yield few new applications because IT teams are bogged-down with keeping the lights on and erasing technical debt;

  • Companies unable to capitalize on new data, in new ways, to meet new challenges, because it would require headcount that had not been budgeted for the support and maintenance of the application.

I am an avid reader of biographies (from “John Adams“ by David McCullough to “Last Train to Memphis: The Rise of Elvis Presley“ by Peter Guralnick) and I tend to draw on their life experiences when I am at a crossroad or in my professional career, when I start to observe problems or trends that need a course correction.

In addition of being an avid reader, I am passionate about helping my clients reimagine, refine, and reinvigorate their business processes, systems, and data in order to better serve their customers. And when I am witnessing firsthand, which has also been cited by many others in our industry, companies failing at digital transformation, it’s time to draw from those biographies and their lessons learned.  

Walter Isaacson's biography “Steve Jobs“ taught me that valuable lesson about why digital transformations may be failing. Isaacson tells how Jobs cherry-picked a team of about 20 “pirates” (as he called them) and relocated them to a small building three blocks away from Apple's main campus. The book describes how Jobs actively recruited rebels and swashbucklers -- talented but audacious individuals -- who could move fast and get things done.

These modern times require us to change how we think, develop and deploy digital services and solutions. But the thing about digital transformation is that it often requires great change within the company -- sometimes fundamentally new ways of thinking about the business. Yes, it may involve new technologies, but it may also dramatically redraw the way people do their jobs. While this often leads to higher productivity and better decisions, it’s still a hard thing for many companies (and their employees) to swallow. 

That’s why we need our pirates: people who are willing to not simply challenge the status quo, but to unshackle themselves from how things “have always been done.” But it’s unlikely they'd be called pirates at your company (unless your CEO is Jack Sparrow). So, you may better know them as “Innovation Teams” or “Skunk Works” teams, or something similar.

If a company doesn’t have a plan for this type of “pirate” strategy, they need to stop making excuses for why their digital transformation efforts hit roadblocks or why their adoption of the latest digital technology is failing their employees, shareholders, clients and/or customers.

If you're ready to get started and ready to embrace a “Skunk Works” approach to digital transformation, you'll need to learn from some common mistakes and misconceptions before putting the following techniques in place to achieve success:

Pirates need freedom from today’s daily tasks:  Skunk Works (aka Digital Lab, Innovation Center, Product Incubator, etc.) must have enough autonomy to avoid being sidetracked by existing business need. It must operate as an offshoot of the main organization, protected from cultures and processes that inhibit progress and have a platform to create, develop and concept-test new opportunities, products and services.

Innovation projects starts before traditional projects: First, innovation projects tend to start with loosely-defined goals and the processes used are more experimental and exploratory; Second, teams must be multi-disciplinary; the right balance of strategists, product experts, technologists, program managers and IP experts to showcase real innovation and; Third, innovation teams need to learn to fail fast and fail smart in order to progress to more attractive options.

Set up measures, monitor objectives and be accountable:Having senior management buy-in with set agreed-upon objectives in place for the Skunk Works to achieve its goal or display value within an agreed timeframe will ensure the operation is successful and sustainable.

Continuous feedback and collaboration: Naturally, regular feedback is provided to the organization, providing transparency into the team's activities, and what it plans to deliver and achieve. But what is also needed is for the Skunk Works to highlight the changing market—new threats, as well as opportunities that digital provides the organization—while making improvements to make the product or service better in advance of competitors.

Synthesize the team: The team needs to connect theoretical, abstract notions of innovation and drive high levels of engagement to inspire the company and distinguish yourself against competitors.

Host guest members: Allow employees outside of the Skunk Works team to take part, based on a rotation schedule and a discipline. This approach can provide transparency into “what’s in the works” and prevent any misconceptions that arise as a result of the Skunk Works team's isolation from the rest of the company.

We must improve the predominant process of how we conceive, develop and deploy applications. And if we do not shift to a Skunk Works strategy for digital transformation, all the digital applications we create will be added to our list of legacy applications tomorrow.

So, let’s take a page from aeronautical engineer Kelly Johnson: Set a stretch goal, frame it with intelligent constraints, select a special team, secede from the main operation, and get to work. And no excuses: our employees, shareholders, clients and customers are counting on us.


Todd Chusid is a Senior Digital Strategist at Anexinet. He has a proven, 15-year track record of taking end-to-end ownership and delivering diverse technologies on web, mobile and ecommerce solutions. Chusid’s mission is to help clients reimagine, refine, and reinvigorate their business processes, systems, and data to enable more engaging and productive interactions with customers, partners, and employees through digital transformation and mobile devices.


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