How I approach digital transformation for clients

After many years of working with clients in various industries, I’ve boiled down my top-level digital transformation planning to this simple two-step process.

Digital transformation is a hot topic for every business. With the emphasis on better, faster services companies are racing against the clock to deliver digital initiatives that will boost customer satisfaction and increase business agility, with the ultimate goal to facilitate growth. Over 40% of technology spending will go towards digital transformation this year, with CEOs and CIOs leading the charge to what has been accurately labelled a ‘competitive necessity’ in the modern marketplace. 

Proper planning is key, of course. You need end goals that fit the overall vision for your business, as well as a system in place to keep projects on track. It is a common mistake to think of digital transformation as just a technology problem. On the contrary, it is your people and culture that will decide its success. Do you have key people in the right positions to lead the charge? Are your teams in place and ready to embrace the future of connected work with an open mind? Only when your entire staff are on board and fully briefed on the strategic purpose of digital transformation should you move forward with choosing technology providers and planning the gradual replacement of legacy systems. 

But as important as all this is, it isn’t where you begin. 

You begin with a tightly controlled, detailed vision of what you would like to achieve. We’re talking top-level, blue sky thinking on your ideal transformation, grounded in the reality of what you can practically accomplish within a given timeframe. 

I’ve worked with many clients that find this initial stage difficult. Digital transformation can seem like such a vast, overbearing network of separate processes that it can be easy to get overwhelmed before you even get started. Often I find a simple thought experiment like the one below can go a long way to clarifying what you would actually like to achieve. This two-step questioning process is humbling and extremely simple but will ensure your project starts off on the right foot, and without any of the obstacles that often trip up well-meaning technology executives. 

Before you start any sort of digital transformation, ask yourself these two questions:

1. Can it be done? 

The first question that needs to be asked is ‘can it be done?’

Can your transformation realistically happen within three months, six months or a year? Do you have the resources in place? Do you have the people and systems to make it happen? It’s absolutely critical that you answer this question honestly and with maximum transparency. There’s no point in setting off on a journey that requires an element of chance or divine intervention. Make sure you have a concrete, realistic view of what can be achieved before you decide to put pen to paper on any vendor contracts. And then, when that is done, consider the negative view – what can go wrong? What could make it fail? Covering this difficult ground will reorient you towards a solutions-based focus and will lead you to the next question, which is-

2. How can we do it?

You’ve got a detailed idea of what you would like to achieve – so, how can it be done? What people and teams need to be on board and in place to hit your business goals? What technology partnerships do you need to forge in order to make it happen? Once you have that top-level vision of what is possible you need to start listing the specific action steps that can take your organisation to where you want it to be. Think of these as small, actionable milestones that can be delegated and actioned by specific members of your transformation team in order to achieve the wider mission. You know it’s possible – so let’s do it. 


This two-step thought experiment is undeniably simple; some people may even think it is too simple for what is a complex and technical process. Well, I can tell you in all confidence that that isn’t the case. Small, medium and large businesses can benefit greatly from taking a step back and answering these questions in a candid and honest manner. Not only will you be rewarded with exceptional clarity, but you will also have a clear direction in which to head into the future. 

If you have any questions regarding digital transformation and how you can begin, feel free to email me at


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