Digital transformation: 3 people pain points

Considering the insatiable customer appetite for better and more efficient service, digital transformation is now a bit of an arms race: Companies that resist it risk being left behind by their competitors and customers.

During my long tenure as an IT leader, I’ve found that the biggest challenges in any company change always boils down to people. In today’s world, where the modus operandi is to get things done as quickly as possible, it can be easy to lose sight of the things that will help a project go well.

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

A company shift of any type always relies heavily on the human element – whether it’s securing executive buy-in for funding and prioritization, or heavy time and resource investment from team members to execute. With that in mind, here are three pain points that CIOs should plan for when leading a team through digital transformation.

1. Executive discord

In virtually every major company transformation, there will be key stakeholders you need to convince. Each stakeholder may have a slightly different idea of what is a priority and what is a success, depending on which part of the company they lead. It’s the CIO’s job to translate the benefits of this technological shift into business terms and outline how the project will support metrics that each executive cares about.

This is particularly pertinent (and tricky) in cases of digital transformations that are aimed at improving internal, or “behind the scenes,” systems. When Wire was considering switching our codebase from closed to open source in 2016, we encountered the problem of disagreement over priorities: Some stakeholders felt that it was most important to develop customer-facing features to maintain a steady stream of competitive functionalities for the platform.

Ultimately, what helped us decide was to examine the open source benefits through the lens of several key business objectives:

Company value: The focus and value of our company are based on security. To truly achieve this, we need maximum transparency in our algorithms and code. Open source is the ultimate tool for that.

Team value: Open source attracts great talent to join the “architecture of participation,” where they are able to contribute to a project even if they are external to the company. This ultimately builds great connections in the developer world and leads to amazing talent acquisitions that may not have happened before.

Product value: Last but not least, moving our codebase to open source would help our developers program, enabling fewer errors and a greater level of transparency. I like to compare it to the places where we live: If we know that our partner or mother-in-law is going to visit, our living space is likely to be cleaner and in better shape than when we are alone.

In the product world, this directly translates into lower error rates (meaning a higher level of quality assurance) and a more efficient process of production, which in turn leads to better and faster implementation of change requests from customers.

[ Read also: 8 advantages of using open source in the enterprise. ]

2. Disruption of process and culture

Digital transformation initiatives require not only monetary investments but also a reallocation of human resources and time. Company changes of this scale mean that other projects are put on hold, legacy systems are put under the microscope and either reconstructed or completely uprooted, and new systems are put in place, often requiring retraining and adoption of new skills. Teams are, for lack of a better word, disrupted. Because of this, CIOs can expect some frustration and pushback from their team.

The best solution is perhaps the most obvious one: Listen attentively to concerns, work with the team to find compromises, and treat them as instrumental allies by showing them how this change will ultimately benefit their work.

During our open source project, we found that some developers were (rightly) resistant to stopping their production flow in order to learn new systems and redo some of the work they had already completed.

There was also a significant cultural shift that had to occur. When a company has an open source code base, it creates an environment of extreme transparency, as the code that developers work on is exposed to external commentary and critique. To combat this, we invested further in our team by providing additional learning opportunities and striving to reinforce a culture of open collaboration and progress – in other words, there is no failure, just many opportunities to learn and improve.

We also sought to highlight how open source could benefit our programmers. We did this mainly by emphasizing how open source code can garner helpful external code contributions and contributions in terms of suggestions and debugging, resulting in more creative, efficient, and thorough problem-solving without placing additional stress on the team.

[ Are you leading through change? Get our eBook: “The Open Organization Guide to IT Culture Change,” featuring advice from 20+ IT practitioners, industry leaders, and technologists.]

3. Lack of strategic implementation

Organization is one of the biggest pain points when rolling out digital transformation initiatives.

Many leaders fail to define clear roadmaps, set realistic goals, or implement effective systems to collect internal feedback and the right data for success metric tracking. This not only makes the implementation process more difficult, but it also puts the success of the initiative as a whole at risk.

Effective strategic plans span the whole lifecycle of implementation and are highly scientific in their approach. Breaking the launch of your initiative down into smaller sprints is a good way to make the project feel more attainable and will also allow you valuable time to step back and evaluate how everything is going.

Each of these sprints should follow the same process: Produce a piece of the plan, test, collect data, analyze feedback, evaluate areas of improvement and success, use learnings to develop slight iterations in strategy, and move to the next phase.

At Wire, we utilized a strategic implementation process when updating all of our programming languages (switching JavaScript to TypeScript, Objective-C to Swift, and Scala to Kotlin). We invested heavily in team skills and necessary training, conducted by recognized experts in the field (the first few months were just spent learning the new languages).

We prioritized quality first – each phase of the implementation plan began with extensive testing before anything was fully rolled out. And finally, we made sure to extensively document at every step of the way because even if everything goes well, there is always something you can learn to do better.

It was a massive project that was very delicate and required a lot of team effort and investment. But in the end, the time and rigor paid off because we were able to minimize technical debt and increase programming efficiencies.

A successful digital transformation depends on your ability to galvanize and organize your team. Setting clear goals, empowering your team, and establishing transparent communication and organized implementation plans all lead back to the same idea: Ambition is good, but it’s critical to be able to prioritize and be realistic about what your team can handle – and what is actually necessary to achieve your goals.

[ Get answers to common digital transformation questions and lessons from top CIOs: What is digital transformation? A cheat sheet. ]