What advice would you give CTOs leading digital transformation journeys?

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CIO in Finance (non-banking)2 years ago
My advice to anyone embarking on a digital transformation journey is: Don't try to solve all the problems by yourself. That's been one of the biggest lessons I've learned; with no disrespect to my skills or those of my colleagues, there is outside expertise that can be brought in to help gain the business's confidence and fast-track the transformation. For example, experts in cloud-native technologies, security or automation can augment the effort. Of course, your ability to bring in those experts depends on the budget, among other factors, but the value realization is much quicker and more predictable. With software releases, the delivery team can build a business solution in two weeks; however, they can take 4 weeks to deliver the outcome or make it available to the customers. Inefficiencies like these always draw my attention as this can be easily addressed through technology and automation.

Trying to do it internally can be a high risk due to a lack of skills. Having the proper skills and expert resources is an important aspect of any digital transformation journey. And beyond that, you need alignment to validate your roadmap and gain support so that it's not a surprise to anyone who will be impacted. Finally, from a customer point of view, whatever you do has to be better if not the same.
IT Director in Education2 years ago
Digital transformation in a company (or in our case a school) goes far beyond 1's and 0's. There's a culture involved, a way of thinking and managing processes, that has likely been in place for years and years. The reality is that sometimes "paper" is better because technology breaks but ultimately technology will win because of its infinite resource-saving possibilities. 

As the leaders of digital initiatives, it's not our job to "convince" people that technology is better and force it upon them. It's our job to implement the best solutions for the company. Making changes to processes because of the latest greatest technology will help no one. If it works, keep it, but continue to understand how it could be better if technology was involved or ultimately replacing it without losing what made it successful.

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MSP & IT Director in Services (non-Government)2 years ago
Evaluate the business value and need for specific applications or processes, Gain an understanding of various processes from key stakeholders (as you are going to be catering towards them and their teams)... you may need to get outside professional assistance. Create a plan (might be a multi-year plan) and do it in phases, perhaps easier and less riskier processes first.
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Director of IT in Healthcare and Biotech2 years ago
A few important items that come to mind are 1) thinking about how solutions are created, solutions nowadays need to be built with work from home support - this is an area that will continue to see growth and digital transformation needs to have that as a focus. 2) Rather than focus on technology specific achievements, think about business transformation goals and technology achievements will be supplemented through this approach. Often times, when only technology achievements are sought after, business transformational goals may get missed. 3) Cultural change - digital transformation is a form of transformation which will impact culture - experience and human perception will change, it may be difficult to gain momentum or other challenges may present themselves, having a focus on culture change and including individual contributors to executive leadership is important. 
Senior Director of Engineering in Software2 years ago
Two things need to happen in order to assure success on the transformation:
1 - identify your allies (and invest in converting the detractors)
2 - socialize across the org the changes that you are promoting and drive the enthusiasm.
Everything else will follow. :)

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