The Boss Who Said “Show Me”
In a previous post, I talked about how much having the right boss has meant to me throughout my career, and nowhere did that truth become more real than during my first months at Microsoft.
When Denny Ramsey hired me to fill Patrick LeBlanc’s previous role on the Higher Ed team, it raised a few eyebrows, including my own. I had spent years managing and developing data warehouse databases and had deep experience with Microsoft databases and products, but I had never once opened Power BI before walking through that door. I seriously didn’t think I was in the running to win the role throughout the process. What I learned afterward was that as Denny moved through the interview process, his thinking about what he actually needed started to shift. He already had strong analytics talent on the team and came to realize what he wanted was someone who could bring automation and architecture expertise, so that is what he hired me for.
Four months in, still drinking from the firehose that hits every new Microsoft employee, learning Power BI as fast as I could and automating a number of system deployments, I sat down with Denny for one of our regular one-on-ones. He talked about wanting to drive more migrations to Azure, and hearing him say that gave me the opportunity to trust my gut. By that point I had met with a large number of customers, and because many of them knew me from the Oracle community, I was hearing things that most people on our team would not. I trusted Denny enough to share what I was seeing, and I told him directly: “If you want more Azure projects, we need to move the Oracle databases to Azure too. They’re in the way. They’re like an anchor holding these customers back from making the move, because this is a data ecosystem, not a collection of isolated environments.”
He pushed back, telling me they had already tried migrating Oracle databases and it hadn’t worked. I said, and pretty bluntly “You’re doing it wrong.” He looked at me and said, “Show me.”
Denny trusted me enough to let me go prove a solution to a problem I was convinced existed, even though doing so meant working well outside the boundaries of my actual role. Over the next few months I started migrating Oracle databases to Azure to run on virtual machines, learning as I went along, and exactly what I had predicted started to happen. Customers who had been sitting on the fence because of their Oracle environments began making the move to Azure. Denny took notice and started asking me to handle Oracle migrations not just for my own customers but for my teammates and other teams across all of Higher Ed at Microsoft. Eighteen months after that conversation, the Cloud Architecture and Engineering team came to me and offered me the chance to make Oracle migrations my official role.
I spent five years leading Oracle work at Microsoft across multiple teams, and none of it would have happened without Denny choosing to trust what I was telling him and giving me the room to go prove it. Being a good boss means trusting the expertise and the lived experience of the people on your team, and when the moment calls for it, being willing to take a real chance on them.
