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Digital transformation: Our 12 most popular articles of all time

In 2016, we introduced a comprehensive explainer on The Enterprisers Project called What is digital transformation. Our goal: Help answer some of the most common – and most challenging – questions CIOs had around digital transformation, to help them on their journeys.

To date, this deep dive resource remains among the most popular articles on our site – month after month, year after year. We’ve added to it and updated it frequently, as digital transformation and the CIO’s role in it evolves. And, unsurprisingly to anyone leading digital transformation in their organization, tough questions continue to arise.

As we approach the seventh anniversary of The Enterprisers Project, we thought it would be fun to take a trip down memory lane. Let’s explore how your work with digital transformation has changed and the most important topics to readers at various points in our history – from the early days when organizations wondered who should be in charge of transformation efforts, to today, when a global pandemic has drastically reshaped business agendas and priorities.

[ Culture change is the hardest part of digital transformation. Get the digital transformation eBook: Teaching an elephant to dance. ]

What topics from the past are CIOs still grappling with today? What aspects of digital transformation haven’t we covered that you’d like us to? Let us know in the comments!

2014

How to overcome the culture of “no” in your IT department

Business-minded IT leaders know that saying no all the time won’t earn them a seat at the table. Yet saying yes to every request isn’t the right answer. How can CIOs strike a balance?

2015

4 IT leaders discuss how they are driving digital transformation

Learn why the responsibility for digital leadership is defaulting to the CIO – and how the CIO role is evolving in order to keep up.

2016

How to break the news that a significant IT transformation is in order

How do you break the news to your CEO or Board of Directors when you discover that a significant IT transformation is in order, even if it’s on the order of multiple years or more from start to finish?

CIOs: Fight the fad of hiring CDOs for digital transformation

Companies that hire a CDO have a CIO who is either not doing their job of embracing transformation, or they are not being recognized for it.

2017

Matson CIO: The most painful, gut-wrenching part of leading transformation

CIOs who fail to recognize the organizational disruption caused by transformation early on will quickly learn some painful lessons. I had to fight and overcome my optimistic nature in making the tough organizational decisions required for ultimate success.

Transformational leadership: 5 big mistakes execs make

Working to become a transformational leader who inspires people amid great change? Avoid these common missteps.

2018

When AI meets digital transformation: 4 areas where AI fits now

How can AI help your organization meet digital transformation goals? Let’s examine four current use cases.

Digital transformation: Are you using outdated IT metrics?

Yesterday’s IT metrics don’t show what IT contributes in the digital era. CIOs share 7 ideas to update how you measure success.

2019

Digital transformation strategy: 7 key pieces

Give your digital transformation efforts the best chance to succeed by building a strong strategy. CIOs and other experts share the steps you should focus on.

Why digital transformations fail: 3 exhausting reasons

Fatigue from continuous change is a top reason why more than 70 percent of digital transformations fail. Let’s examine the three factors that cause exhaustion – and how to avoid them.

2020

Digital transformation: 5 ways COVID-19 is forcing positive changes

The COVID-19 crisis is rapidly reshaping the “what” and “how” of digital transformation agendas – for the better. Look how organizations are improving amid dramatic disruption.

Digital transformation: 11 habits of successful teams

Say no to innovation theater. Quantify what success looks like. Encourage widespread agility. Consider these practices of teams beating digital transformation challenges.

[ Get answers to key digital transformation questions and lessons from top CIOs: Download our digital transformation cheat sheet. ]

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As the Enterprisers Project turns 7, check out the digital transformation wisdom and advice that answered our readers’ toughest questions through the years

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