Bear with me, folks. If I were in a click-maximization mode I would tell you how to turn on “Together” mode in Teams. Not today. I have been rolling around some seemingly disparate threads that I want to unite in a thought I hope you find valuable: how do we, as technology leaders, advance digital transformation?

Digital transformation. The term reminds me of the “___ is like teenage sex” saying: everyone talks about it, nobody really knows how to do it, everyone thinks everyone else is doing it, so everyone claims they are doing it. (Here is someone who used the analogy for Big Data). As a concept, digital transformation is not new; it is at least as old as COVID-19. How do I know? Because there is another half-joke out there stating that the biggest driver of digital transformation has been COVID-19.

I want to take a detour before I go back to digital transformation. Here are the thoughts I have been trying to connect.

• Digital media and digital policy
• Digital infrastructure
• IT, technology, and roadmaps in organizations

How to connect the dots? And are there even dots that we should connect? Let me expand on each of these items.

Digital Media and Digital Policy

My friend and stand-in for a ZZ Top front man, Mike Wright, posted this article from the Mott Foundation in a Slack discussion. I encourage you to read it. The article focuses on the need for digital policy, now that we have experienced the impact that digital media and information/misinformation campaigns can have on civil society. As a veteran of the technology industry, I have fun mocking US Senators and Representatives as they display their sometimes-complete ignorance about social media. But I stop laughing when I remember that these are the people that will enact regulations for social media companies. How can you regulate what you don’t understand?

And what about Program staff in grantmaking foundations or non-governmental organizations? What do they know about social media and digital policy? What experience can they draw from? I must say that I have been encouraged, as I help roll out Teams in a grantmaking organization, to see the Teams pilot users jump on use of GIFs, memes and emojis. As I said last week, having J. Lo applaud me will be a 2021 highlight no doubt! GIFs and the like are just one part of social media, but witnessing this embrace makes me think that Program staff might be savvier about this aspect of digital transformation than I have given them credit for.

Digital Infrastructure Governs Who Can Participate

John Mohr (MacArthur Foundation), Karen Graham (Tech Impact) and I have for the last couple of years been kicking around the idea of how to ensure grantees have access to the technical tools they need to accomplish their mission. We are all familiar with the image of the struggling non-profit trying to get by with out-of-warranty hardware and software tools. I am working with just such a non-profit now.

And while we continue to iterate on the proper mix of investment and in-kind donations that will prove most effective, we are seeing digital transformation expand the minimum toolset these non-profits need. The Technology Association of Grantmakers posted an excellent piece on this in March, calling for greater investment in digital infrastructure. If digital media and digital policy are prerequisites for achieving outcomes across technical and non-technical realms alike, then do we really have a choice about investing in the digital infrastructure of the organizations whose causes we champion?

Who Drives Technology?

I have seen (and helped shape) many IT roadmaps that included projects to support digital transformation in the organization.

• A community foundation revamps its donor portal, to use technology to serve small-dollar donors at scale while refocusing donor development staff on large-dollar donors.
• An NGO uses public cloud resources to sequence the genome of a strain of wheat.
• An aquarium maintains visitor interest by letting the penguins wander through the empty aquarium building and broadcasting their movements via webcams.

These digital transformation initiatives haven been like earlier initiatives in this sense: a technology leader sees the opportunity to apply technology to a problem or opportunity facing the organization. “Here, let me apply this technology to the problem. Now, isn’t that better?” The initiative starts with someone who knows the technology well. They have then worked to understand the needs of the organization (you know, that whole CIO-as-business-partner thing). With that, they have defined a project that will match technology solution A with organizational problem or opportunity B.

That approach to digital transformation is not going away. It will, however, be supplemented by its inverse. We start with a person who deeply understands a problem space. They also understand enough about technology to believe that there is an opportunity for technology to help. They seek out expert help (that is you, Dear Reader) to define a program.

This newer approach will occur because it must occur. “Digital,” whether infrastructure, media, policy, or something else, is a necessary component of any change program. Organizations need digital to connect with the people they serve, to amplify their messages, and to deliver their services.

Who Owns Technology Adoption?

As digital becomes all-pervasive, who owns digital technology adoption? We all do. During this pandemic we have seen that “digital transformation” might be summarized as (apologies to American Express) “don’t stay home without it.” We have all become both consumers and boosters of technology (at least the stuff we like).

Organizations still need IT and other technology leaders. Not everyone wants to become an expert in the technology they use. But as technology leaders, we will find ourselves acting in turn as consultants, project leaders, change management advisors and security and compliance brokers. We will still catch it when Outlook stops working (whether it was our fault or not). Perhaps our new role in digital transformation is in raising the technology level of every leader in the organization. We can help others learn how to think about technology and its possibilities. We can communicate enough technical knowledge to help others understand what is possible today and what is (still) not.

Maybe that is what “digital transformation” is all about. The “digital” part is about the ways that technology has come to aid (or invade) our lives. And the “transformation” part is, first and foremost, about the transformation of people.

So how do we enact digital transformation? By doing the things we have always done, yes. And then we must go on to coach, cajole, counsel, and encourage the other leaders in our organizations. We can tease out the ways that technology is helping or hindering their work. We can push these leaders to paint a picture of what they would love to achieve. And then we can work with them to get it done.

Who is ready for that?