Digital transformation: 10 counterintuitive tips

No two digital transformations look alike - so why do so many organizations try to follow the same rules? Turn common wisdom on its head with these tips from CIOs and tech execs
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Adopt a “fail fast” approach. Put the customer at the center. Minimize your risk through careful planning and preparation. Start with legacy IT modernization. Stay ahead of the technology curve. You’ve likely heard this advice for digital transformation a time or two - or 10, or 20.

But remember, there are no “universal truths,” and common wisdom can – and often does – fall flat for an organization that attempts to fit its digital transformation into the same mold as another company’s.

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

Digital transformation lessons learned from CIOs, CTOs

We asked IT and business leaders who are well down the path with their own digital transformations to share something surprising that they learned along the way. Turns out, some of the advice they got early on wasn’t always helpful – and in some cases even led to major roadblocks on their digital transformation journey.

Read on for their counterintuitive advice for digital transformation.

1. Legacy modernization isn’t always the best first step

The transition to digital has little value if you merely migrate what you are already doing to the cloud.

Ryan Talbott, chief transformation officer, Altimetrik: “In the past, I was advised to start digital transformation projects with a legacy modernization or movement to the cloud to help begin the transition. However, the transition to digital has little value if you merely migrate what you are already doing to the cloud. You will likely have minimal insight, costs will not go down, and you will not gain the speed and flexibility that a real digital native type approach would bring.

“Another ‘universal truth’ around digital transformation that always falls flat for companies is the belief that the strategy needs to be implemented across the entire organization right away. This is why you see stats that claim that 90 percent of digital transformation projects fail. Many organizations aren’t ready to successfully complete a massive digital deployment because it may not support what is needed for different departments in the organization (purchasing, finance, HR, etc.), and the skills needed are not yet present.  Start small digital ‘fires’ where it makes sense, share the lessons learned, and help others get small wins that build the organizations’ desire to more rapidly adapt. Soon you’ll have a bonfire you can be celebrating around.”

2. Don’t call it “digital transformation”

Mark Hill, CIO, Nelson Frank: “Don’t treat digital transformation as an IT project. Digital transformation affects the entire business – it’s about changing processes, not just about new software. If you want to ensure buy-in and proper adoption of your new digital platforms at every level, in every department, you need to frame it in the right way.

“Digital transformation” puts the project in a box.

“You have to sell the blanket impact that it’s going to have across the whole organization, and ‘digital transformation’ puts the project in a box. Though my title is CIO, my role is equally about business change. That’s the approach you should be taking when leading on digital transformation – think like a business leader, not just a tech expert. When digital transformations don’t have the desired results, a lot of the time that’s due to a failure to engage the whole organization. It’s a business transformation, and it should be communicated as such so that those outside of the IT bubble don’t assume it has nothing to do with them and switch off as soon as they hear ‘digital.’”

[ Since some people loathe the phrase “digital transformation,” how can you talk about it? Read also:  Why people love to hate digital transformation. ]

3. You can't “fail fast” your way to transformational change

David Egts, chief technologist, North America public sector, Red Hat: “Common mantras in this world are ‘move fast and break things’ and ‘fail fast.’ I always thought speed was a modern, universal truth until I read about the Open Decision Framework, which Jim Whitehurst described in The Open Organization. With this approach, you want to float an idea early with stakeholders but delay the decision process as long as possible. By giving everyone the opportunity to get a say in a major decision, team members not only feel that they’ve been heard, but they also have a greater sense of ownership of the success of the solution, and you end up with an overall better solution than top-down decision making. You don’t want to use the Open Decision Framework for every decision you need to make as it can take time, but it’s a good way to make better major decisions thanks to transparency and inclusivity.”

4. Treat risk as your friend, not your enemy

With agile methodologies, we gave up on trying to be right and aimed to minimize the cost of being wrong.

Rob Zuber, CTO, CircleCI: “You will never eliminate risk; the best thing to do is embrace it. This advice holds true in every stage of digital transformation. No matter how much time we put into defining requirements, we were always wrong. So with various agile methodologies, we gave up on trying to be right and aimed to minimize the cost of being wrong.

“For instance, deploying to production was something that we considered a high-risk activity that was best managed with careful planning and preparation. That just made it more painful. The evolution of CI and CD means companies can deploy with confidence many times per day without any real consideration. No matter how well you are doing in your development and deployment tooling, something will still break in production. Embracing this risk and building your system such that it will continue to thrive in the event of failures is an evolutionary step that will make all of our services better.”

[ Need a primer? See What is CI/CD? and Getting started with CI/CD: 4 success factors.]

5. Worry less about sharks and more about smaller fish

Matt Mead, CTO, SPR: “There is a lot of talk around ‘disrupting the industry.’ And as a result of this market-disruption mindset, many business folks are concerned that their industry will be drastically disrupted by some other company, and they’ll suffer the negative consequences.

“While it’s true that drastic industry disruption would have a negative consequence for most established companies in an industry (e.g., Uber’s disruption of the taxi industry), worrying about disruption is like worrying about being bitten by a shark. While it could happen and there could be major consequences, it is highly unlikely.

“A more pressing concern should be that smaller companies could cannibalize your business much more subtly and slowly. And if you’re not mindful of this possibility, then one morning you could wake up and feel like swiss cheese because so many companies have chipped away at your market position piece by piece. So don’t worry so much about the sharks; worry more about the smaller fish that can and will nibble away at your value to the market a bit at a time.”

Carla Rudder is a community manager and program manager for The Enterprisers Project. She enjoys bringing new authors into the community and helping them craft articles that showcase their voice and deliver novel, actionable insights for readers.