I started this series after I came across a Gartner article discussing the role of the CIO, and how many of them struggle with communicating with the business, that gave me pause. Reflecting on my performance over the past 20 years of IT leadership, I considered the successes and failures and found four common themes that have served me well.

I have a deep love of history. I have drawn many lessons in strategy, leadership, and communication from the continual pursuit of understanding our collective past. When it comes to communication, few in recent memory were as compelling as JFK. If JFK were a CIO in 2020, how would he talk about roadmaps? Let’s find out.

Tell the story in color

We began this story in Frankfurt, Germany in June of 1963. Kennedy confronted one of the darkest chapters of the cold war with his typical elegance. He discussed the change that had come to the world in proportional terms, communicating the scope of the change in relatable way.

This rhetorical device can also help IT leaders communicate roadmaps. If your roadmap has initiatives that span a long period, talk about them in relation to the life of the business. Unless it’s a recent startup, that makes a 2-year program look like a flash in the pan, rather than a major undertaking. Also, help people understand the power of the initiative. If you are implementing a new data management platform, illustrate in simple terms how much effort it would take to achieve its goals (e.g., every employee running Excel functions 100 times an hour for 100 years to get the work of one day of the data management platform). Finally, be able to speak to the appropriate audiences about financial proportion. Relating the cost of the implementation of an ERP in terms of transactions processed per year, or over its lifetime. At the end of the day, you want to be able to communicate the scale of things in the frame of the big picture, not the small area of spreadsheet cell.

Focus on outcomes

In the late 1950’s, America trailed the Soviets badly in the space race. Again, Kennedy reached into his communication playbook and brought forth an outcome-based vision. On May 25, 1961 he boldly proclaimed, “This nation should commit itself to achieving the goal, before the decade is out, of landing a man on the Moon and returning him safely to the earth.” I think the parallel is easy to see here. As I.T. leaders, we must focus on improving our ability to serve customers, employees, partners, and other stakeholders. Framing those outcomes in our roadmap transforms the conversation from “We need feature X by date Y” to “We will enable Business Function A to serve Stakeholder Group B” more effectively as part of the first milestone of this roadmap. Focusing on outcomes enables all involved to understand the big picture and unleashes the ingenuity of your team.

Reconcile the old and the new

Your organization is changing. At times, your roadmap must tackle the sacred cows in the business you lead. The people who built that sacred cow are probably still around and necessary to achieving the new roadmap. Mind you, the sacred cow could be tech or a set of processes. As an I.T. leader, you must put these sacred cows out to pasture without alienating your core of experts. The trick here is to be sure that everyone understands that while things must be retired, they must also be honored. Our charge is not to demonize peoples’ accomplishment but to put that accomplishment into the proper perspective. As President Kennedy remarked in 1962, “A nation reveals itself not only by the men it produces but also by the men it honors, the men it remembers.” Your organization does too.

Customize and personalize the roadmap

The first rule of communication is “know thy audience.” Some scholars contend that President Kennedy was the first president who built his inauguration speech for mass media. He was aware a shift had occurred in who would be consuming the information. He now had the opportunity to connect directly with Americans in their living rooms and thus created perhaps one of the most famous inaugural addresses in American history. As you go forward, you should not only be thinking about the audience, but also the media utilized. Consider creating video blogs or a podcast to share with your development team, while leveraging the traditional in-person, outcome-based roadmap presentations for your executives. Thinking about how your audience will best consume, reflect, and engage on material should be as important as the material. Launching a roadmap successfully requires organization-wide engagement. Thinking through your personalization strategy is a critical ingredient for getting the buzz going.

2020 has been a whirlwind, but here we are almost halfway through it already. Before we know it, we will begin planning for 2021. Hopefully, this post has given you some food for thought on how you can improve roadmap communications. As, President Kennedy said in February of 1963 “It is not enough for a great nation merely to have added new years to life—our objective must also be to add new life to those years.”