Chart Your Voyage: How Pirates Lead Digital Transformations

One year ago we explored the question of when it was time to live the pirate life. Today, we are going to explore ways to chart your first pirate voyage. You’ve convinced your executive team that change, in this case a “digital transformation,” will bring tremendous value. What was once a pirate project has burst into the mainstream with companies projected to spend billions (trillions?) of dollars on transformative projects over the next few years.

So what is a pirate to do when the seas are awash with investment? When the corporate armada is suddenly on-board yet somehow rudderless and adrift? When you’ve been given a compass, spyglass, and every hope and prayer that you will navigate the fleet to Transformation Island unscathed and under-budget?

The exciting news is that your pirate instincts are exactly what is needed to navigate these unchartered waters. Digital transformations have new twists and turns depending on the organization. Fortunately, smart consultants follow the scent of any reusable idea (a.k.a. treasure) floating in the breeze and “Digital Transformation” is a pungent example. As a result, the resourceful pirate has many safe harbors of research freely available to help chart a path into unfamiliar waters.

Do The Reading

Pirates read…a lot. Without direct orders from the Royal Navy and propelled by burning curiosity, pirates continually need to chart new paths and learn new skills to navigate uncertainty. Here is a list of seven go-to articles to fuel your strategic thinking before drawing a dotted line to the oversized “X that marks-the-spot” for your digital transformation.

McKinsey & Co.

These articles provide the best introduction to different frameworks Data Strategists can use to frame complexity. Start with “Ten Red Flags..” and pay special attention to how data initiatives are organized by impact and feasibility. The venn diagram illustrating both the multitude and intersection of analytical roles is very versatile. I’ve used it as a wake-up call for overly ambitious executives, and as a way of highlighting gaps in an organization. Lastly, make note of the diagram illustrating the centralized vs. decentralized organizational structure. It’s especially helpful when paired with the articles from HBR listed next.

The Harvard Business Review

“What’s Your Data Strategy” begins with a true and sobering statement: “CDOs’ tenures are often difficult and short.” This article introduces two potential data strategies, offensive and defensive, based on the intended use of an organization’s data. While I find the article a bit too (delightfully) abstract to put into immediate practice, the framework is an invaluable tool to negotiate the responsibilities shared between the business and IT. The second article is an urgent reminder of the specific skills critical to data success, and a helpful guide to the crew you will need to recruit.

Harvard Data Science Review

The Harvard Data Science Review is a new publication that belongs in the bookmark list of any and every data professional (pirate). “How to Define and Execute Your Data and AI Strategy” integrates many of the principles outlined in the lists above from McKinsey and HBR, with the additional benefit of a practitioner’s detailed perspective. This is especially evident in the Operating Model section of the article which introduces an almost Agile view of the data and business functions in an organization.

Sketch a Map

To be fair, at some point you will start feeling seasick from reading about data strategy and digital transformation. And it’s at this point when the seasoned pirate recognizes that it’s time to take action and put pen to paper. Sketching a map includes balancing risk vs. reward, and building consensus. A clear map to treasure is not enough. The people you engage provide the wind that powers your sails and the rudder that keeps you on course.

Balancing risk vs. reward begins by marking treasure with a big letter “X” wherever you think it may be found. That’s easy and unfortunately many companies (and doomed pirates) stop there. Building consensus is about sharing the map of possible treasure sites, and inviting your colleagues and crew to weigh in on both the risks and the rewards. Worthy topics for our next article. Until then just remember: good pirates do the reading. Now get started!