How long are two decades, when it comes to digital government? Well, very long – and with a lot of things happening. At least that is what it feels like, as the rapid pace of technological development presents governments with new opportunities, sure. But also, with challenges and risks, new elements to consider in strategy papers, and different ways of delivering services to citizens. Arvo Ott has seen quite some things happen in this time span. First, as the first Government CIO of Estonia until the early 2000s; then, in his work for e-Governance Academy, where he is a Member of the Management Board. In conversation with Chairman Hannes Astok, we review how the task of managing digital transformation has changed throughout the years. In Estonia and beyond.