The Future of Work is Now: Leading a Digital Transformation

The pressure to be the best CTO is immense and many organizations have yet to establish this integral role. If you are a current Chief Technology Officer, every decision you make while leading a digital transformation has an impact on all other parts of the organization. If you are an organization without a CTO, there are solutions to help navigate the uncertain waters of digital transformation.

If Digital Transformations were easy, everyone would do it.

One thing we know for sure, there are a limited number of hours in a day so we must prioritize where we spend our time and energy. Because of the far reaching impact across an organization, large scale change efforts must have proper management for all of the moving parts. To begin leading a digital transformation, start with the ultimate goal - your why. What does this organization need to look like post digital transformation? You will find that the process may change but the goal often will not change. We will discuss goals further in this article.Next, define the key players - who, detailed requirements - how, and timelines - when. Don’t leave out the intangible, but oh-so-important, momentum!

Key Players

Obviously, those doing the technical work and project managers must be included in each phase of the planning and handoffs between phases. But there is one thing we all know to be true, nothing will slow the process of change more than teams of people waiting for an approval. So be sure to include the people who will be needed for approvals to move on to the next phase. They need to be informed that this is a priority and to clear their other commitments for a defined time frame.

Detailed Requirements

Focus on how to deliver the requirements and performance. What technologies and technical skills are needed to accomplish each task? If you have major technical skills gaps during this process, your budget and timeline will be blown. What budgets, hardware, software, and manpower is necessary? To achieve a sustainable and impactful change, not just change for the sake of change, investing in these resources are fundamental.


Define which tasks and phases have dependencies on the other tasks. What can be done in tandem and what must be done to completion before the next can begin? Breaking down a digital transformation into bite-sized pieces and mapping it out over time will give confidence to those you rely upon.


Forget the last year during a pandemic, even small changes can be very challenging and require reassurance! Be thoughtful in addressing real concerns as they will pop up often. Remember that through frustrations come breakthroughs. To make the digital transformation as painless as possible, stay positive and keep your messaging to the teams focused on the goal! Gain momentum by celebrating small wins along the way to the BHAG!

Agility is THE goal before, during and after a Digital Transformation.


Through technology and talent, it is important to position the organization to be able to take action when opportunity presents itself. Don’t just make a transformation to meet the needs of today, but future-proof your organization! As you decide your organization’s goal for the digital transformation, think about how fast businesses and technologies change today and take some best practices from organizations you have seen that have been able to weather storms whether big or small. How were they able to thrive during adversity? How did those organizations demonstrate agility? Your goal will also incorporate many small digital transformation goals along the way. Be sure those are all aligned to the main organizational goal. This new transformation may also require a shift in strategy and KPIs. This is a great time to fill skills gaps through staff augmentation giving you the benefits of managing your digital transformation budget and creating scalability within the organization.


Of course it is important to stick to the plan as much as possible, but be flexible, realistic, and embrace opportunities. “One tip: allow for some departmental or organizational latitude, but stick to your plan. And when you encounter resistance, which you certainly will in 2021, identify your holdouts — and then listen if not embrace what they have to say.” There may be limiting factors that make themselves known during this process. If this transformation does not come to fruition, that does not mean it was a failure. The smaller steps along the way have helped to create a more sustainable organization and you will be better prepared for the next opportunity - maybe two years from now or tomorrow. Some organizations never make it past the planning phase of a digital transformation when they realize the resources it will take. It is important to note that these changes are happening every day in every industry, so eventually the organization will be forced to make the changes. Would you rather plan ahead and do it at your own pace or be forced into one just to keep up with your competitors?


Speaking from experience, leading a digital transformation through to the end, is one of the most rewarding experiences. The impact of the project felt throughout the organization is immense. The benefits of meeting those digital transformation goals and helping to create a more agile organization for all, compound for years to come.

CTO Service

At TECKpert, we understand that some organizations do not have a CTO to lead a digital transformation. To fill that need, we are able to offer a CTO Service for these digital transformations - large and small. Many of our clients prefer the unbiased outsider perspective and the ability to scale their leadership, as well as, their workforce. Let’s collaborate! Reach out today for your free consultation.