I have a boss in charge of Product and Marketing who seems reluctant to learn about a product management tool we use, called Pivotal Tracker. My boss started working with us long after we began using the tool.
The main issue is our boss asks us for ETAs on when projects will be started, how long they will take, and a notification for when they are deployed. He also wants to keep track of what is being worked on at a given time. Pivotal Tracker is made to be able to do all those things automatically. Instead of using the tool, during one instance, he made a Word Doc with bug fixes listed out manually. That made us have to update our progress in two locations. All these extra steps, I believe, is a waste of time and gradually slows our workflow.
I am part of a small team of developers, and we have casually told (but not really pushed) him to use this, but I find it difficult, considering I am lower ranked, and I cannot boss him around.
What can I do to ensure he regularly uses this tool, so we don't need to resort to using manual notifications, such as via email?