Enterprise Guide to Digital Transformation

Don’t let IT modernization be the bane of your existence. This curated collection of articles will give you more clarity and help you get started.

James M. Connolly, Contributing Editor and Writer

January 27, 2022

12 Min Read
digital metamorphosis of a butterfly
Chan2545 via Adobe Stock

[Editor’s note: This curated guide was updated in January 2022 to reflect new trends today and to include our most recent content.]

In just a few years, digital transformation has evolved from a general concept preached upon by authors and conference speakers into something demanded by business executives and board members.

“Why aren't we doing digital transformation?” And, “We should be doing it now!”

The problem is that those shouting the loudest probably have no idea what digital transformation is, and what it isn't.

Let's take a look at what digital transformation really means, the progress enterprises have made in utilizing the approach, where the benefits lie, and advice on how to achieve those benefits.

The best starting point is in understanding what this transformation is not. Some think that automating a process, providing mobile access, adding a new user interface, or replacing an aging system constitutes transformation. Nope, that's what IT teams have been doing for decades. Those changes are updates, enhancements or upgrades. That technology may be different, but it doesn't really change how business gets done.

Digital transformation begins with a change in thought process for what organization is. It means rethinking how the business operates and how today's technologies enable that change. For example, rethinking the business could mean examining how customer relationships work and can be improved. It might mean exploring how decisions are made, and how those decisions can take place closer to the customer interface or an employee's desk. Or, it could mean reshaping the business itself to abandon dated business lines and launch new data-driven services.

It boils down to identifying how data -- what you already have and what data you can gather – can help the organization run more efficiently and make the customer relationship more valuable for all parties.

Consider how you can better make and sell more stuff while keeping customers happy and buying. Then it's time to consider how evolving technologies such as analytics, artificial intelligence, edge computing and mobile access can enable those business goals.

In this Guide to Digital Transformation, you will find a collection of InformationWeek articles focused on the state of digital transformation, including thoughts on how the concept has evolved, how an enterprise should implement a transformation, the technologies involved, and the results that leading edge companies have enjoyed.

Check out this collection of articles, and more from InformationWeek on other topics such as IT management, careers, analytics, DevOps and cloud.

The State of Digital Transformation

The rate of digital transformation adoption certainly has been growing over the past couple years. Meanwhile the definition of transformation and the best practices have been tweaked.

CIOs to Accelerate Digital Business Transformation in 2021

What did we learn about digital transformation in 2021 and through the pandemic? Compare these predictions with what you have seen in the marketplace and your own organization.

Weighing Doubts of Transformation in the Face of the Future

Deloitte’s 2021 outlook posited enterprises should double down on digital transformation and reskilling. What about those not ready to commit to change?

Digital Transformation Challenges IT Leaders

As organizations strive to improve operations, build the best workforce, establish competitive advantage and improve customer experience, they are increasingly turning to technology and IT leaders for solutions in digital transformation.

How to Assess Digital Transformation Efforts

Not all organizations are succeeding with their digital transformation efforts. For one thing, the focus of their success metrics may be too narrow.

Getting Started with Digital Transformation

Before you run out to buy the hot technologies thinking that they will transform your organization, focus on developing a plan and goals for digital transformation.

Digital Transformation is Not Magic

The goal of digital transformation must be to reach a place where the business is connected end-to-end, from employees and stakeholders to partners, suppliers, and customers. Finding ways to leverage technology in various aspects of a business will improve efficiency, drive sales, and increase profits.


Clear Goals Essential for Results in Digital Transformation

Survey shows that schisms between C-suite expectations and the rest of the organization could hamper returns on plans to go digital.

6 Keys to Digital Transformation Success

Nearly every enterprise is undergoing a digital transformation. Some are more successful than others. Here are 6 factors shared by the successful ones.

Why Customer Experience is the Driver for Modern Commerce Architecture

Since the pandemic, enterprises have upped their digital transformation strategies. To remain competitive today, businesses must adopt a customer-focused architecture.

The ‘It’ Factors in IT Transformation

According to Accenture, three key factors produce an IT transformation that can maximize the value from technology and people to power business agility.

Overcoming Roadblocks to Digital Transformation

While companies must now move at light speed when it comes to innovation, these strategies will help leaders grab the proverbial wheel to drive their workforce into the future.

3 Factors That Should be Driving Your Digital Transformation

To maximize output of any digitalization project, organizations must treat it as a wider business initiative, rather than a targeted IT transformation.

Why a Master Data Strategy Is Key to Digital Transformation

Find out why deploying an effective master data strategy across an enterprise is an important foundation to building a successful digital transformation journey.

11 Digital Transformation Hacks That Get Results

Organizations tend to get different results with digital transformation. To realize business value, first realize that transformation isn't just about tech. Get advice from companies that have been there, and from consultants who have been involved with their customer’s transformations.

6 Ways to Maximize Digital Transformation Success

Enterprise organizations will shift from what is being used to how it is being used. Maximizing what is already in place will become the priority

Technology and Its Limits: Transformation is About People

In the argot of today’s technology world, transformation is about “People + Machine.” The machine alone is, well, just a machine.

The Secret to Digital Transformation Success

Digital transformation is more than technical. It’s also procedural and cultural. It can change how thousands of employees do their jobs, make business decisions, and collaborate across the company. In short, digital transformation can change everything. Here's how CIOs can reduce adoption risk, close skill gaps, and keep teams happy.

What to Not Do in Digital Transformation

For every “do” in digital transformation there's also a “don't”.

How to Fail: Digital Transformation Mistakes

Don't make these nine digital transformation mistakes that will slow down your efforts to be competitive in a new era.

Digital Transformation Strategies Are Failing. Here's Why.

Every company's digital transformation plans got sidetracked by COVID-19, but there are additional reasons why their strategies are not full steam ahead.

How to Avoid Developer Burnout from Big Transformation

Many companies take the ‘big bang approach’ to transformation and it often fails. Worse, though, is that the pressure tech teams and business leaders apply causes burnout among developers.

Watch Out: 7 Digital Disruptions for IT Leaders

Here are seven digital disruptions that you may not see coming.

Learn from the Experiences of Your Peers

Those considering and planning digital transformation initiatives today have the benefit of seeing what their peers in other IT organizations have gone through and accomplished.

NuVasive CIO Details Digital Transformation Project


Spinal surgery product and services supply company NuVasive targeted its surgical supply ordering in Japan for a digital transformation project to streamline operations.

FTD’s CTO Powell on Transforming and the Next New Normal

One year after joining the 110-year-old company, Powell talks about the floral ecommerce retailer’s revamp of its infrastructure.

Strategies You Need to Make Digital Transformation Work

CTOs, IT leaders, and executive management can use these examples to form their own master plans to transform their organizations and win.

Tech Leaders: Steps to Take on Your Digital Transformation Journey

Transformation can sound daunting, but companies that last do it over and over again. Take a gut check, plan, get the right technology -- and go.

Designing Your Roadmap for Rapid Digital Transformation

While business and IT leaders are under pressure to boost their digital transformation plans, they should stop, rethink, and assess before fully diving into a roadmap.

Digital Transformation: How Leaders Can Stand Out

Here are three things leaders in digital transformation are doing to set themselves ahead of the competition in 2021 and beyond.

Realogy CTO Discusses Cloud Transformation for Real Estate

Bringing a major real estate services company with multiple brands in its portfolio to the cloud as part of a digital transformation effort required a multifaceted strategy that continues to evolve.

What Enterprises Can Learn from Digital Disruption

Digital disrupters have changed the rules of competitiveness. Savvy enterprises say they are paying close attention.

Going Up? Otis Elevator Hits Digital Transformation Button

Otis pioneered predictive maintenance before most heard the phrase Internet of Things. Now the 166-year-old company is prepping the elevator of the future. Like IT, the elevator business is undergoing a large-scale digital transformation.

Syngenta Talks Cloud Migration and Digital Agriculture

A research and agriculture technology provider turned to automation software to make its data and resources more digestible for a move to the cloud.

Tips on Digital Adoption and Transformation from Tesla

The former director of learning shares some of the mindset that drives the electric car maker’s strategy for fueling external and internal adoption.

How PepsiCo Put Data to Work Connecting to Customers

Developing a strategy to use first-party data helped the food and beverage giant adopt more nuanced understandings of consumers.

Five Ways to Tackle Digital Transformation Without Downtime

Imagine rebuilding an airplane in flight. That's how you can modernize your enterprise technology. Here are five lessons that an information architect and his team learned on their path to transform their technology and operations.

Organizing for Digital Transformation Success

Remember, you're not just transforming a technology but the company itself. Understand who the project drivers are, and how roles may change.

6 Ways to Get Your Board on Board with Digital Transformation

While cost efficiencies are important milestones, the real value of digital transformation lies in long-term innovation. Here’s how you can get some mileage by making your case.

5 Critical IT Roles for Rapid Digital Transformation

As some organizations look to transform faster than anticipated, putting critical tech roles in place will be the key to a smooth, successful journey.

Digital Transformation: Business Leaders Still Struggling to Cope

What you don't know can hurt you. When it comes to digital transformation, many top enterprise executives may have to learn this lesson the hard way.

Chief Data Officers Help Steer Digital Transformations

Chief Data Officers are prioritizing data quality, ROI from data and analytics investments, and data sharing.

How to Accelerate Digital Transformation with a CDO

Looking to update ordering for ecommerce customers, bakery manufacturing and ingredient supplier Dawn Foods decided to hire a chief digital officer to spearhead the process.

In-House Gatekeepers Help CIOs Drive Digital Initiatives

CIOs and CFOs must forge strong partnerships to execute powerful digital transformation strategies and achieve larger organizational goals.

How CIOs Can Nurture a Culture of Digital Transformation

To foster long-term resiliency and workplace innovation, IT leaders must invest in employees’ skills and create an open and inclusive environment where people feel valued.

IT Meets Finance: How CFOs Drive Digital Success

Chief financial officers now play a key role in guiding organizations through digital transformation so they can survive the current climate and come out stronger on the other side.

What Becomes of CFOs During Digital Transformation?

As some executive roles disappear, chief financial officers must evolve to survive in the new tech landscape created during digital transformation.

CTOs Evolve in Shake Up of Digital Leadership in the C-Suite

Expectations for chief technology officers to deliver game-changing strategies may push CTOs to take on new responsibilities and decision-making powers.

Who Owns Digital Transformation?

Forward thinking leaders know that while specialism may sit within one team, the responsibility to bring those ideas to light and generate ROI is a shared one.

Digital Transformation Technology

Once you know what you want to accomplish, that is the time to weigh the tech options that are available today or coming down the road. How will you use that technology?

Microsoft CEO Nadella Outlines Forward-Looking Tech Trends


Hybrid workplaces, hyperconnectivity, digital business, and cybersecurity may be key priorities for organizations.

RPA Deals Heat Up Amid Faster Digital Transformation Pushes

Automation is a key component in successful digital transformations today, and several big tech vendors are adding these capabilities by acquiring RPA vendors.

One10’s AIOps and Cloud Journey to Software Modernization

CIO discusses how the organization migrated custom solutions to cloud-based applications and AIOps to cut costs and the burden on in-house developers for the cloud security firm.

Overcoming Digital Transformation Challenges with The Cloud

Here’s how cloud computing can enable the future of work, accelerate data strategies, integrate AI and cyber strategies, and innovate for social good.

The Importance of Digital Transformation in Predictive Analytics

Ironically, it’s not that companies don’t have access to the data that that they need -- it’s their inability to deal with the requirements for data transformation.

Why DevOps is Critical to Digital Transformation

Organizations should focus on automation and efficiency to keep pace with pandemic-driven technology transformation.

Should AI Be Part of Your Digital Transformation Strategy?

Digital transformation strategies are common, but many enterprises lack an AI strategy. Where does it fit? Not everyone agrees.

Automation Is a Game Changer, Not a Job Killer

Your employees may view automation as a threat rather than an asset. How can you shift their perspective and empower them to use automation to their own benefit?

Cloud Strategies Aren't Just About Digital Transformation Anymore

Digital transformation may accelerate cloud migrations, but in the pandemic era a number of other factors are driving cloud adoption. The new normal is even more virtual.

What the IBM-Adobe Collaboration Means for Transformation

Adobe Experience Manager running on Red Hat OpenShift and other IBM resources intended to help regulated enterprises meet security demands.

About the Author(s)

James M. Connolly

Contributing Editor and Writer

Jim Connolly is a versatile and experienced freelance technology journalist who has reported on IT trends for more than three decades. He was previously editorial director of InformationWeek and Network Computing, where he oversaw the day-to-day planning and editing on the sites. He has written about enterprise computing, data analytics, the PC revolution, the evolution of the Internet, networking, IT management, and the ongoing shift to cloud-based services and mobility. He has covered breaking industry news and has led teams focused on product reviews and technology trends. He has concentrated on serving the information needs of IT decision-makers in large organizations and has worked with those managers to help them learn from their peers and share their experiences in implementing leading-edge technologies through such publications as Computerworld. Jim also has helped to launch a technology-focused startup, as one of the founding editors at TechTarget, and has served as editor of an established news organization focused on technology startups at MassHighTech.

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