For software professionals, it is critical to get a broad and diverse perspective on what is happening within our industry. One of the best ways to do this is to listen to technical podcasts that seek out these voices and allow them to share their perspective on our industry. The Software Defined Podcast is a podcast that provides insight into our industry while allowing guests to join them and share their perspective.

In Episode 244, Kylie Grenier shared about her background and how she got to where she is today as a leader in this space. In this episode, she provided a thorough look into the human mechanisms behind digital transformations and how technology professionals can help drive value in large organizations. She also discusses the cloud space, how it can enabled businesses to launch into their digital transformation, and where that can fail.

As a technologist who works with these software tools every day, my first instinct is to rush into the technical solutions, the cool toys of the day. While it is important to know the technical options available in the marketplace, Kylie advocates for the idea that digital transformation is a leadership and personal challenge first, long before fancy new software comes into play. Coming in and pitting legacy software against the modern cloud will often cause a tension that will put digital transformation off on the wrong foot.

Stepping back from technical solutions, we have to first acknowledge that transformation is a process that begins because the software that has been built is valuable. There wouldn’t be a push to bring it forward into the next generation of the organization if it wasn’t! This acknowledgement is difficult, but requires leadership commitment to use the knowledge and skills of the individuals who built these existing value-providing systems to help inform and deliver this modernization.

As organizations begin a move to the cloud, they often take the approach of starting with simple, low-impact, or completely greenfield applications. Kylie discusses how organizations often stall out as they move past this first happy phase into the meat of the organization. This stall is critically important to identify as the endgame of digital transformation is only enabled through chewing through these difficult challenges. Technology leaders and business leaders, in the end, all want to be able to make better data-driven decisions rather than relying on gut instinct.

Without enabling transformation of the applications that can provide this real insight, fancy new cloud platforms will fall short of the promised goals while probably at the same time missing the desired cost savings. Without enabling transformation of the core business portfolio, you will be left supporting multiple technology stacks, maintaining these dual systems, without any capability to realize the cost savings and simplicity that can come with these modern cloud platforms.

One aspect that Kylie noted as teams get into the meat of transformations is that things often get harder before they get easier. She spoke about how working through upgrades and changes of new systems, starting back with Lotus Notes and Word Perfect, can often make the workflows of existing users more challenging before they become simpler. This is the critical way in which we have to understand technical transformation as a leadership and organization problem. Our systems, no matter how deep in the stack our technology is, are used by humans. Migrations moves the work of humans in a meaningful way that can break the shape of existing organizations. We need to acknowledge that challenge and be open about it before modernization can be successful.

How do we actually do this? When we think about this transformation, we can break it down into three phases. The first phase, migration, acknowledges the good work you have done in the past and defines a base for how it can run into the future. Migration is the foundation of your transformation. The second phase, modernization, is how that good work grows into something useful in the present. Applications and workflows were designed in different eras and we need to appreciate that and determine how to take advantage of this new generation. Finally, transformation is what makes your good work available in the future. With transformation, we can make the hard work of an entire organization be organic in a way that will allow it to live on into the future of the organization. The only way we get to the point of transformation is to honor the work that the organization and acknowledge that it must be moved in this direction to continue to provide the value required for the organization.

The episode brings up a great quote from Dan Millman, author and speaker: the secret of change is to focus all of your energy not on fighting the old but on building the new. Often, we spend lots of our energy in modernization fighting the legacy we see all around us. Instead, we must work to focus the energy of the organization onto the vision of the future. This is what technical leadership must deliver to an entire organization to execute successfully.

As this language turns to the transformative potential of the cloud, every organization is trying to adopt cloud. It is critical to have executive sponsorship to power past the challenges faced with the real meat of the organization. These efforts must have clear and measurable business goals, or they will stall out when the going gets touch.

Kylie advocates that in these situations you find a trusted partner who can bring in that expertise to bring your work into cloud space. One of the reasons I’ve really enjoyed being here at ObjectPartners is that we have this focus, our goal is to embed ourselves into the organization to deliver on desired technical outcomes while also enabling the teams we work with to understand and be effective in these new systems. Digital transformation efforts can be full of pitfalls and challenging personal and political battles, but by addressing these challenges head on and defining the future goals for the organization, an entire workforce can find the motivation and direction to bring its application portfolio into a digitally enabled future.

This post is a reflection inspired by the Software Defined Talk podcast episode with Kylie Grenier and informed by my own experience as both a consultant and full time employee. I’d love to hear from others who have faced off with digital transformation in the enterprise and how they have successfully, or unsuccessfully, navigated the leadership, personal, and (last of all) technical challenges in this space.