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  • Writer's pictureOliver Nowak

The Top 7 Reasons Why Digital Transformations Fail

What is it? – Digital Transformation is all about the process of reimagining how things are done today through the use of technology. It’s all about creating disruptive change that pushes the business, industry or world in a completely new direction, depending on the scale you’re operating at. We’ve got many examples of this in history; the smartphone or video streaming are just a couple.


But it has become a bit of an obsession. These days if you look on any business’s website or in their annual report you’ll see that pretty much every organisation is going through some sort of ‘digital transformation’. But are they succeeding?


Unfortunately not. The truth is many organisations inevitably get stuck. We all want to be the Apple’s and Netflix’s of this world but very few are. Most get stuck somewhere in the middle and just end up pouring vast amounts of time and money down the drain without so much as creating a small change, let alone transformation.


And here’s why. Digital Transformation can’t solely be achieved by throwing technology at a problem. You have to be willing to reimagine everything from top to bottom and that includes most importantly how your people and processes work today – how you operate.


So let’s dig into some of the key factors that derail successful digital transformation for the vast majority of businesses.


Agile: A Swing and a Miss

Again, exactly the same as digital transformation, most businesses like to say they ‘work in an agile way’. Most businesses have great ideas, they just can’t execute on them. How many stories have there been in history where large corporate organisations had these innovative transformations in their heads but just couldn’t get them to market? Marriott had the same idea as AirBnb long before they came to market but could never get their act together. How much has that cost them today?


Most companies have great ideas for integrating technology into the way their business operates but can’t execute because their organisation isn’t agile enough. It inevitably gets stuck in the blackhole that is IT. And that’s because shifting to Agile isn’t just for IT, it needs to be business-wide.


So where are people going wrong:

  • Trying to run IT in an agile way while running the rest of the organisation in the same legacy way.

  • Not listening to resistance. Teams might be adopting agile job roles and function names but have they actually changed the way they work?

  • Thinking you have to change the whole organisation all at once. You can start a small digital product organisation with product owners capable of executing on certain business change projects while still working alongside the traditional model.


Though we’d all like to think we’re revolutionary enough to adopt Agile overnight, the reality is that it’s an enormous business change process that is going to take time and patience.

Setting the bar too high

Many organisations want to portray this sense that they are the next big thing but in the process put more on their plate than they can realistically digest. Being too ambitious means that individuals lose track of what the overall vision means to them. Lose this connection and you’ll lose momentum overnight.


Don’t aim too far into the distance. Incremental, attainable goals that people feel are realistic are going to get significantly more buy-in than the sexy forward-looking ones defining a vision for the business 5 years from now. As accurate as they may or may not be, no one can imagine themselves living that reality.


Not Defining or Measuring Success

Businesses only implement technology for a business outcome. What is that outcome? And how are you measuring it?


In a data driven world, there is no shortage of things we can measure. But are they the right things? Do they give us an accurate reflection of reality or are they just telling us what we want to see?


Good metrics get us to the root case of the problem quickly:

  • We set off in the wrong direction

  • We started off on the right footing but lost ourselves along the way

  • The landscape has evolved

  • We’re seeing the right behaviour some of the time but not all of the time.

Following a Roadmap Without Learning the Landscape

It’s like following a Tube map to navigate London overground. Is it really that helpful if it doesn’t have the detail? You need to follow a roadmap that takes frequent measurements of your loads and balances. Are you actually where you expect to be? Is your planned next step still the best next step?


This can be solved by simply checking in on your roadmap. Don’t write it up and stash it away in the bottom draw. It should be a living and breathing document.


Decision-Making Efficiency

This can be summarised as too many cooks. If a decision has to be made people often like to be involved and share their opinion. Listening to what people are saying is essential for a successful digital transformation but do it too much and it may take you a few centuries. If a decision needs to be made make sure you do your research but the whole village doesn’t need to be present.


Involving too many people in the decision-making process results in lost time and money, and a higher chance that a decision is made for the sake of making a decision. If you’ve got accurate metrics and a clear roadmap, decisions should come easy.


Underestimating Change Management

The hardest part of digital transformation is the people. No people, no transformation. It’s as simple as that.


Inevitably, the key to this will be patience. Human beings are instinctively habitual. These habits aren’t broken overnight.


What it will boil down to is communication. Clearly articulate the incremental change that you are going to introduce and the pace at which you’re going to do it. No surprises.


This is about creating connection between the individual and the solution. How does each incremental step tie into the overall vision? What’s in it for them?


In my experience this is the most underinvested in component of a digital transformation because it is viewed as non-essential and an area to try and claw some money back. Don’t fall into that trap!


Not Solving Business Problems

The number one killer. Why would anyone spend money on technology if it didn’t solve a problem for them?


Before going near any technology, you need to understand the problems the business is facing.


  • What do people truly need?

  • What’s the right problem to fix?


Only then do we go into solution mode.


  • What does the workflow look like today?

  • How can we make the workflow better?

  • How can technology make workflow better?

  • What solutions can we deliver within the constraints of the technology, timeline & budget?


Before your digital transformation initiative even gets off the ground you need to assess Desirability, Viability & Feasibility.


  • Desirability: This requires research into your end users. Is this solving a problem that is affecting your end users’ ability to do what the business needs them to do?

  • Viability: What does the business need in order to reach its targets and ambitions?

  • Feasibility: Can the solution be delivered within the constraints set by the technology, timeline & budget?


Get all of these right and you’re delivering a strategically aligned, user-centred solution that is technically robust to deliver transformative change.

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