Digital transformation. It sounds so grandiose, doesn’t it? Like some sort of beautiful metamorphosis: an ugly caterpillar of old tech magically becoming a beautiful butterfly, resplendent in its new digital wings.

Jon Aizlewood
Jon Aizlewood
5th March 2019

If only it were that magical. The reality is that digital transformation is damned hard.

Having worked with clients and companies of various size and shape over the years, I’ve noticed a few commonalities and trends that seem to pop up. If you’re in the midst of a transformation or about to embark on that metamorphosis of pain, these tips are for you.

1. It’s not about the tech stack

Most digital transformations are borne out of a need to re-platform. Companies suddenly recognise, invariably too late, that the technology platforms on which they spent a lot of money back in the day are now rapidly becoming obsolete. Inevitably the company focuses on the technology. But technology doesn’t make the world go round, people do.

The term ‘people’ here is purposefully broad. It refers to people on both sides of the coin: those who provide the new technology, and those who use that new technology.

In the end, digital transformation is just a fancy metaphor for embracing the shift in customer behaviours towards digital. If your customers can’t find, interact, buy or communicate with you digitally, you’re going out of business.

IDG’s 2018 [State of Digital Transformation]( https://resources.idg.com/download/white-paper/2018-digital-business) survey reports 62% of respondents say delivering an excellent customer experience as measured by customer satisfaction scores defines success as a digital-first business.

Pro tip
If your product isn’t usable — by real people, — then it doesn’t matter if your new tech platform makes unicorns appear: it will lose money.


2. Get a visionary

Transformation projects without a North Star don’t work. To call it a success you’ll need someone who holds the vision in their heads and a resolve to get sh*t done.

This person (or persons) needs support to see out the business goal, without sacrificing user needs in the process. This mystical, overlapping Venn diagram is not easy. It needs significant corporate experience and political nous to come off. Choose your visionary wisely.

Pro tip
Find someone to lead the charge, and — get this — someone who actually gets digital. This sounds a lot easier than it is.

3. Stop being risk averse

Barrelling headfirst into a transformation strategy without the appetite and ability to take risks is like running a marathon without running shoes. You can do it, but why would you?

Risk is an inherent part of change. You need to try new things and be open to new methods and approaches. You need to know that not all changes will work, but some will. An inability to manage or accept risk will only result in half-baked, unfulfilled projects, because senior stakeholders are too reluctant to try something new.

Sometimes ‘up top’ are too afraid to let ‘digital’ do what they do best. Being prevented from providing digital solutions to a digital transformation leads to a compromised and impaired end product.

Pro tip
Avoidance of risk is borne of fear of the unknown. Stakeholders who act as blockers are often unsure of what digital can (or can not) do. Improving an appetite for risk can be as simple as providing better education as to what’s being done, why, and how the business will benefit.

4. Digital literacy is a must

Having a literacy in digital isn’t as simple as knowing what digital things are called. It’s having a deeper understanding of the methodologies, techniques and strategies needed when dealing with a digital product or service, and how these will work in a business context. Knowing what digital can and cannot do is critical to ensuring a successful transformation strategy across any business.

As one respondent put it, “It’s a war between old-school technophobe leaders and the technology innovation that represents a completely different way of doing business.” Forrester — [The Sorry State Of Digital Transformation In 2018](https://go.forrester.com/blogs/the-sorry-state-of-digital-transformation-in-2018/)

A great example here is agile. You know, that word everyone uses in large orgs, but rarely do it right. I know agile was never meant to be prescriptive, but come on, having a standup once a day doesn’t mean you’re suddenly an agile organisation.

Agile needs time and oxygen. It needs to be both a top-down and bottom-up approach. Senior execs need to be as wedded to the idea as the practitioners at the coal face. Agile is a mindset, not a line item.

Pro tip
Ironically, language is the common denominator within digital transformation. Try to avoid terms like ‘sign-off’ which are steeped in historical contexts that no longer exist in the digital realm. Similarly, avoid the wonton use of acronyms and jargon when you can explain it using plain English.

5. Double-down on design maturity

Although hearing the phrase ‘design needs a seat at the table’ makes my skin crawl, the struggle is real. Design at most large organisations (those most likely to be undergoing seismic shifts towards digital) is tokenism at best.

Digital transformation is like an iceberg. 90% of the project is backend systems, re-platforming, evolving tech stacks and the plumbing. But the remaining 10% is what makes all that effort worth it. That 10% is where customers meet, interact with your company and buy from you. Be 100% sure it’ll include both digital and design.

If the senior stakeholders in your business still see design as making it look nice, you’ve got issues, my friend.

Design is about problem solving. It’s about reframing the problems and challenges faced by an organisation and alleviating them through design thinking methods. Though very few organisations today are 100% design mature, those that are striving towards it — alongside digital transformation — will reap the rewards.

Pro tip
Want to measure your design team’s outlook on design maturity? Share our Design Attitude 2019 survey.

6. Ship it

For all the hard work done by teams — often over years — in digital transformation projects, it doesn’t mean a thing if you can’t ship what you’ve created.

Large-scale transformation projects include countless moving parts. Stakeholders, technical requirements, Systems Integrators and many more.

That cacophony of voices and agendas can often counter-intuitively grind progress to a halt, rather than turbo-boost a transformation programme. The net result: your transformation has stopped focusing on shipping your best-in-class product. Instead, you’re just shipping your org chart.

According to Forrester Research, companies will never be truly transformed. It will be an ever-evolving dance of sensing and responding. Companies will continually adjust to changing online and digital behaviours.

Pro tip
Delivery or shipping in this context means continuous deployment. Bursts of activity, effectual releases and incremental growth. This is exactly what agile was made for; yet another reason to consider agile as a business-wide methodology rather than confined to development only.



Digital transformation is hard. It takes a long time. It costs a lot of money. Why waste that investment by taking shortcuts or approaching it the wrong way?

This has been a collection of my thoughts, gathered from working with clients during or at the start of a digital transformation. It’s as seen through a designer’s view. If you have a different viewpoint or would like to comment, find me at @aizlewood.

This post was originally published on Medium