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Digital transformation: 3 outdated tips to ignore – The Enterprisers Project

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If you’re taking on a big, complicated project that could get hopelessly tangled up with one wrong move, it pays to seek out advice. You’d talk to every expert you knew before building a custom home, for example, and you’d probably read everything in sight before embarking on a 30-day bike trip across the western United States.
CIOs overseeing digital transformation projects have been advised by the best and the brightest – everyone from analysts to consultants to colleagues to peers – and most would say the counsel they’ve received has been helpful. But occasionally, a tip gets passed along that’s outdated or just plain wrong. While it may have made sense at one time, it would steer them off track if they pursued it today.
As your organization adapts its transformation strategies to succeed in a post-pandemic environment, here are three pieces of outdated advice to avoid – and a few counter-tips to follow instead.
Historically, many IT leaders thought that in order to survive in a digital-first era, they had to transform from top to bottom, across every department and product line. This caused many transformation efforts to fail. Companies tried to invest too broadly in the concept and aimed too high in an effort to generate results.
This type of thinking isn’t practical because there will always be limitations on resources and the ability to absorb change. Companies that try to do too much too fast end up with failed projects that weren’t scoped, sized, or prioritized correctly.
A better approach is to dedicate to prioritization. Make sure you take on projects one at a time. Use agile methodologies and lean techniques to select what you’re going to work on first. Then work through each one before moving on to the next thing. In this way, you can incrementally accomplish your transformation rather than trying to boil the ocean.
[ Discover how digital transformation priorities are changing. Get the Harvard Business Review Analytic Services report: Maintaining momentum on digital transformation. ] 
Over the years, organizations have periodically divided up IT groups, with one concentrating on maintaining legacy functions and another pursuing innovation for the future. This practice was resurrected in an effort to achieve faster and more effective digital transformations. Creating a bifurcated IT function may have a place in very large organizations that are pursuing many projects at once, but in the mid-market, it doesn’t work.

This is especially problematic today considering the tight job market for skilled IT professionals. Having one group maintain legacy products and unleashing another to focus on innovation leaves individuals in the first group behind, creating a culture of haves and have-nots. The employees working on new technologies are able to challenge themselves and stretch their skill sets. Meanwhile, workers focusing on legacy technologies are less satisfied with unexciting tasks, making them more likely to leave knowing they’ll have no trouble finding other jobs. The organization ends up needing to hire more workers or reassign those from the innovation group to ensure legacy technologies are still being supported.
Companies are better off creating an agile, collaborative IT organization with cross-functional groups not segmented by technology. Plus, if you’re going to train new people on new technology, a new business practice, a new process, or a new way of doing things, you might as well train more broadly as it effectively costs the same.
[ Also read Digital transformation: 4 outdated notions to move past. ]
For years, the culture of IT has been to move fast, break things, reassess, and retool. This pattern took hold at the dawn of the digital transformation era. After all the breaking and reassembling, measurement was tacked on at the end, to see if the transformation initiative achieved the stated goals.

This is a poor strategy. Instead of waiting and measuring later, it’s better to set up the analytics upfront to validate the transformation process as it goes along.
Transformation doesn’t happen all at once. It’s iterative, and you will need to be able to measure improvement from iteration to iteration. To do this, you need to set up the right architecture for the project, scope out reasonable goals, and instill a process to measure progress step by step. Then you will be able to review measurements periodically and adjust tactics as needed to see steady improvements.
Digital transformation is a major undertaking. As an IT leader, you should continue to seek advice to help prepare for what lies ahead. But don’t be wedded to any one particular piece of advice, because what works today may not work tomorrow, and what works for one organization might not work for another. Validating the advice, testing it, and being willing to adapt are all important elements of a successful transformation process.
[Where is your team’s digital transformation work stalling? Get the eBook: What’s slowing down your Digital Transformation? 8 questions to ask.]
Keep up with the latest advice and insights from CIOs and IT leaders.
Keep up with the latest advice and insights from CIOs and IT leaders.

Keep up with the latest advice and insights from CIOs and IT leaders.
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