Consider the various planned extensions to your current software[4] that are or may be needed. Instead of planning to add tests for the changes after they've been done, try the following.
[4] You could also try this on a project that doesn't involve software. It will probably mean that you can't automate the tests, but everything else may well apply.
1.
To work with you on this, ask someone who may be able to help more on the business perspective or on the testing aspects.
2.
Choose an iteration time period and stick to it.
3.
Together, write a story about each extension or a part of it. If the story is too big, break it into smaller parts.
4.
For each story, write one or two Fit tests that you can use to decide whether the story has been implemented completely in software or in some other way. This may help refine the story.
5.
Run the planning game. The people who will implement the changes are completely responsible for estimating the time/effort required.
6.
Based on the estimates, choose the stories that will fit into the chosen time period.
7.
As the changes are implemented, test for completion with the story tests.