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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?

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    One of those managers? Facilitate their wish to be told everything. Point the most verbose email outputs of your build, source control and work tracking systems at their email. :D – Nathan Cooper Oct 10 '15 at 8:49
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You said your boss is reluctant to use this tool, however you didnt say unwilling. Since you say this tool can do all the things he wants, perhaps you should take some time and teach him how it works. If you show him how to get all the information he needs, then he might stop interrupting you. A good reporting tool should make reports easy to make and use.

If he still does not want to use the tool, then you are in a quandary. You could go to his boss and explain this situation. Obviously, there are drawbacks and advantages to this situation, but if it is the right thing to do, then you should do it.

In the end, he is the boss. If no one above him forces him to use the tool, then that is that. Adapt and survive.

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    +1, roughly what I would say. I might add, show him how it pays off in the long run. I would assume the software tool requires budget or, best case, front-end resources to set it up. Rather than focusing on "ensuring he regularly uses the tool," show him the positive impact the tool has on the business, and how it's worth the investment to make it work. – S. Grey Oct 10 '15 at 5:13
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Your boss is reluctant, because using your tool is really not his job. It's your job to update him on your status.

That said, there is no need to do double tracking of tasks. All your boss needs is status updates. If your tool is any good, sending status updates at the time and in the format needed and should be trivial.

There is no need to fill out your bosses Word Document if he gets a daily report from your tool. The important part here is "gets". He should not need to learn the tool to pull himself a report. A report should be pushed to him by the tool without any extra work by him. And it's your job to make that happen.

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A lot of managers are reluctant to use software/practices which they have never been used, for obvious reasons. What if adopting it is just a tiny value addition, and takes a significant time/resources for learning it?

But, if you think it would really provide significant value addition to the company and the project, then you have to build a nice POC(Proof of concept), and take it's snapshots, or better make your manager look at it and use it.

When I presented the idea of an automated data workflow pipeline(in place of separate cron jobs for each), my manager was obviously reluctant to adopt it, as he didn't want to make such a drastic change in the architecture and convention unless the proposed idea have a significant value addition.

So, I went ahead and made a basic POC, and made my manager execute the entire flow and he loved it. Thus, I got a green signal to adopt and re-design the architecture.

So, PROVE the value addition. Make him use it, or make him see when the team is using it for a quick POC session.

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