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Datadog made a strategic business decision in 2018 to migrate all our infrastructure to Kubernetes. During this process, a large number of our infrastructure teams were trailblazing the platform to make it work for each shape and type of our workloads for multiple cloud providers and accounting for their idiosyncratic runtime differences.
Managing expectations of 2000+ engineers involved in migrating to a new Deployment Platform while the company was undergoing rapid growth, posed one of the biggest challenges of my management career since it introduced the greatest variable – the intersection of software and people.
During this process, a large number of our infrastructure teams were trailblazing the platform to make it work for each shape and type of our workloads for multiple cloud providers and accounting for their idiosyncratic runtime differences. The hard lessons learnt during this effort in the technical realm have been presented on multiple occasions. However, even accounting for the daunting magnitude of its technical side, transforming and guiding human behaviors on the new way of deploying and operating software turned out to be at least just as challenging as reforming our infrastructure.
What we came to realize during this endeavor more clearly was that we, as humans, form habits very easily and don’t like disruptions to what we have become familiar with. When communicating a change to people who are directly impacted by it, assumptions (and therefore disappointments) are often unavoidable, no matter how clear one believes themselves to be when outlining said change.
In this talk, I’d like to share the lessons we learned building a Deployment Platform that involved an eventual migration of 2000+ engineers, from 250+ different teams, making tens of thousands of changes per week to 3000+ different workloads. I will share the importance of understanding the complexity of human motivations and establishing two-way communication channels, listening reflectively by placing oneself mentally into their positions and thinking what words may be more impactful for their particular situation.
