What advice would you give CTOs leading digital transformation journeys?

IT Strategy & Roadmap Portfolio, Program & Project Management Business Relationships

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CIO in Finance (non-banking), 51 - 200 employees

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.

CTO in Software, 11 - 50 employees

I have a few ideas here, the first and most essential of which is to optimize your business activities with automations so that you may rethink the way value is provided while also lowering the cost, time to value, and changing the way clients and consumers connect with you. Aside from that, you may allow for a lot of experimentation, promote partnerships, and increase employee participation, and make sure you use digital transformation technologies to help with the change.

IT Director in Education, 11 - 50 employees

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.

MSP & IT Director in Services (non-Government), 2 - 10 employees

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.

Director of IT in Healthcare and Biotech, 10,001+ employees

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 Software, 501 - 1,000 employees

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. :)

CTO in Education, 1,001 - 5,000 employees

It is not about technology. We are in the process of moving to a new ERP/HCM. The biggest hurdle we faced was change management. Employee roles had to change. They need to be included in every phase and have a voice. You must also show that you are listening and you care about what they say. Test. Test. Test. You must have test environments and use them. If those tests don’t work, fix it and retest. Don’t assume the fix is going to just work. Finally, I wish we had a ticket system for users to report issues. We have a ticket system for the technology department. We did not have a ticket system for our payroll department. They were overwhelmed with emails at the start and did not have a good way to track or hand off issues to others to fix.

CIO in Services (non-Government), 201 - 500 employees

Digital Transformation can be extraordinarily disruptive (in the bad way.) Getting all levels prepared ahead of time, from C-Suite, all the way down to each department head and individual employees, is a good start. Under promise, over deliver; and remember, as with all change, there will be people and even entire departments that will hold out to the bitter end, against the changes.

You will be taking cultural and embedded processes that some people have been used to for more than a couple of decades, and you will be changing the way they do their jobs; there's always some attrition and employee turnover by those that can not, or will not change.

And pay attention to workflow! It's overlooked sometimes, but make sure the workflows in each area make sense. It's easy to make things far more complicated than they should be, by concentrating on the tech and not the process.

Senior Director of Information Technology in Healthcare and Biotech, 10,001+ employees

Definitely getting buy ins from leadership but most importantly to the stakeholders at the user level. Adoption could be challenging without user buy ins.

Director of IT in Services (non-Government), 201 - 500 employees

While I am not a CTO, I have been on the Sr. Leadership teams that have led the charge on digital transformation. I look at it as an adjunct or natural progression within continuous improvement.
When I was researching this not long ago, I found an article on Forbes that I found quite helpful:
https://www.forbes.com/sites/forbestechcouncil/2021/09/30/leading-the-digital-transformation-
seven-tips-for-ceos/?sh=6c5d066851c2
Hope it helps you as well.