Why Empathy Matters in Digital Transformation

Abby Kearns
4 min readMay 1, 2019

An open letter to CIOs navigating a changing world

Imagine being told the job you’ve been doing for decades, and your place within the organization, is changing. Asking your employees to completely rethink who they are and how they fit into their place of work removes a fundamental layer of security — a scary thought for almost anyone.

As an industry, we aren’t giving enough thought to the psychological and lifestyle ramifications of change. It asks a lot of organizations and the people who are proud to work there. The comfort that people enjoy in their day-to-day work — how they accomplish tasks and interact with colleagues or partners — should not be overlooked.

This point really hit home for me when I had the opportunity to sit down with Denise Yu on the keynote stage at our most recent Cloud Foundry Summit. Our conversation was entirely on empathy and why it is so important in open source, as well as product development of any type.

I often liken digital transformation, and the cultural change required to make it work, to massive group therapy. After all, you’re asking people to undo the myriad ways they think about their job, their role, and potential modes of impact in their professional lives. This is a huge undertaking, with a significant impact.

Don’t neglect the emotional toll of change

When businesses neglect these challenges, they don’t only do so at their own peril, but also that of their employees. It’s critical to understand how the impact of cultural change can be both positive and negative. This juxtaposition of excitement about new technology and the radical changes needed to embark on a new approach to work is profound.

We should practice empathy during this time — invest the time and resources to understand concerns and absorb the responsibility we all have to improve the outlook for everyone within an organization. Excitement for the technology is abundant on many levels, but implementing those changes on an operational level is where many organizations run into the most resistance.

If we’re going to reimagine work at the most fundamental level, we owe it to everyone involved to prepare, train and communicate with transparency. Systemic culture change is an undertaking. It won’t be as simple as turning something on or flipping a proverbial switch on a new system. Rote processes and stale models for change management need not apply.

Empower and unlock success from within

I often get asked the question, “what does success look like for someone undergoing change at this scale?” By way of an answer, I often respond with a story about a large home improvement company.

If you have spent more than ten minutes with me I have referenced Home Depot. The home improvement supply store that employs more than 400,000 employees and operates nearly 2,300 retail locations. When a Home Depot employee, working anywhere within the organization including the sales floor, shows interest and aptitude, they can take advantage of a program that Home Depot calls the Orange Method. This education offering includes bootcamps and immersive training sessions that include learning how to write code, deploy apps to the cloud, and getting up to speed on modern technology stacks. Just imagine the opportunities this unleashes for those individuals and the organization.

Home Depot understands it can’t merely hire for innovation and success. By giving employees without a traditional background or technical degree the same access to tech jobs, the Home Depot is emboldening its employees to be part of something bigger and more impactful.

Continuous learning and employee empowerment enriches your team

Continuous learning is fundamentally what is at the heart of digital transformation. Everyone in your organization needs to constantly learn new ways of working and how to leverage the best tools and technologies for your business. While focusing on the technology part is fun, it’s also the easiest part of this shift.

If you’re giving people opportunities to learn and providing them the space and support to grow, they will contribute in more meaningful ways to your organization. Constantly evolving, training and learning new things is a reimagined approach to business that pays for itself.

The second your business stops evolving is the second it will no longer be competitive.

Make your employees a central part of the transformation process. You’ll be giving them an important role in the future of your company and a greater chance of success for your entire business.



Abby Kearns

Technology Executive | Board Director | Angel Investor