My Digitalization Cheat Sheet

July 8, 2022

Over the years when I’ve been working in all sorts of roles where I have been a smaller or larger cog in a piece of machinery aiming to advance digital capabilities, I’ve slowly been forming a structure in my head to help me navigate the many layers of a successful (or failed) digital journey. When successful, most parts of the structure have been addressed. When failed, the structure provides a troubleshooting tool to figure out what bits were missing. 

The other day I decided to try to put the structure into a simple picture – My Digitalization Cheat Sheet. For me, it serves as a map when I discuss with clients where they are and what they need to develop to progress on their journey. 

Without further ado, here’s the Cheat Sheet: 

The model has two parts. The outer hexagon lists what I call the 5 Ds of Digitalization. They can be seen as a high-level roadmap of activities, starting from Discover and, if effectively completed clockwise, ending in successful Digitalization. As is often the nature of this kind of model, it’s iterative. A new round of the 5 Ds can (and probably should) be initiated. The 5 Ds can also be applied on all levels, from strategically shifting a company’s direction away from obsolete business models and products, to figuring out a new set of features for your latest app. 

The inner triangle addresses the eternal challenge of changing people’s habits. As I have already elaborated on in an earlier post, digital transformation happens when the changed behavior among customers and employees exploiting new technology leads to realizing the potential value this technology enables. 

Creating new habits 

Let’s start with habits. When I talk about this, I often use the example of a child who is just about to start learning to brush their teeth. As an adult, I understand why brushing my teeth is important; I am able to do so because I have been shown how to do it and have practiced, and I want to do it – for me, not brushing my teeth is simply just not an option. In short, I’ve made brushing my teeth a good habit. Given my experience and skills, it’s now my job to coach my child to gain an understanding of why she should brush her teeth. I also need to teach her the mechanics of toothbrushing. Finally, I must motivate my child to keep doing it. All parents know about this. It can be many years before we don’t have to ask, cajole, threaten, and do anything else we can come up with to make sure that those teeth get brushed. Then, one day, the child has fully transitioned into a person who happily and voluntarily brushes her teeth every morning and evening. 

When it comes to changing people’s behavior, we’re all two years old. Frankly, we can’t be bothered with this toothbrushing thing. We don’t understand the point of it. We’re scared we’ll fail. We hope the boss won’t notice we’ve skipped the brushing for a month now. We can’t find the damned toothbrush when we need it. 

For every D in the 5 Ds of digitalization, then, we must keep in mind that the end goal of Digitalization won’t happen before people change their behavior and create new habits. For every D we must identify who needs to be coached through the “understanding – ability – will” cycle. We must never fail to allocate time and resources to accomplish this.  

The 5 Ds of Digitalization 

In this blog post, I will focus on the strategic journey of a firm that has not yet embraced digitalization. Other trajectories through the 5 Ds will be the subject of other posts perhaps.


This is where key stakeholders are impacted by impulses that will prod them into discovering the new. On the highest level, it can be the board of directors or the executive team that collectively come to the realization that their digital capabilities are weak and ineffective. Often, their journey to establish new habits will be painful and slow. A lifetime of experience from bygone years can seem totally inadequate to help them even understand what they are supposed to do to become “data-driven” or “digital”. Here, the obvious remedy is to enroll fresh blood that can guide and coach these teams to a new place.


Oh, the number of times grand proclamations have come to nothing! To decide is not to rush through a board meeting on Zoom nodding approval to the new vision. To decide is to deeply commit to the new direction; to make sure all stakeholders have a reasonably coherent understanding of what it means; to stand up for the decision when the going gets tough. The failure to decide in this deep way is one of the most common reasons organizations fail to bring their strategy to fruition.


Once a new understanding and, most importantly, a firm and articulated will to change has been established, the organization must design a new future for itself. This is a multi-layered effort, one which often only reaches halfway to its target. I don’t care to count the number of strategy documents I’ve been privy to that have had lofty goals of digitalization and becoming data-driven without a shred of elaboration on what that means for the firm and how they are supposed to get there. The vision and goals must always be clearly explained and articulated, and we must always craft a plan describing the activities that will move the firm to its wanted position. I hasten to quote Dwight Eisenhower here: "planning is everything, the plan is nothing", by which he meant that any plan is obsolete shortly after it has been drafted. But the key takeaway is that the planning itself will help clarify important things that must be put into place one way or the other in order to be able to reach the goal. The details will have to be changed time and time again, but the course has been laid.


We’re now ready to start executing our plan. This is where we need to establish a program, identify new competencies and roles, make sure we connect new business processes with relevant IT capabilities, and a myriad other thing. I will lay out my thoughts on this topic in a later blog post lest this one gets too bloated.


This last step is where the rubber hits the road. This is where new ways of working, new ways of interacting with customers, and new software and apps are fully embraced by everyone concerned. To reach this point, all people involved have successfully journeyed through the “understanding – ability – will” cycle. This will be true not only for employees but also for customers, suppliers, and other parties involved in the organization’s new digital outfit. Behind this lies countless hours of training, coaching, communication, follow-up, etc. Without this, Digitalization will not happen.


Feel free to use this cheat sheet as a checklist to figure out where you are and where to go next. I will continue deepening these thoughts in upcoming blogs.

If you ever feel the need to have a sherpa by your side, reach out to us at EMCAP. This is what we love doing!

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