Should I be using Test::Unit or RSpec? Maybe Cucumber? Should I be testing this functionality as unit tests, functional tests or integration tests? Should I seed the database with fixtures or factories? If I want to use factories, should I use Machinist or Factory Girl? How am I going to test client-side functionality? Selenium tests, or webrat or javascript unit tests? If I'm using javascript unit tests, then do I use Jasmine, or QUnit, or Mocha?
The answer to most of these questions is really just a matter of personal preference, but you can see how easy it is to get overwhelmed even after you've decided to do TDD on Rails.
I told him that I could discuss the options with him for a half hour but the point isn't to pick the best password manager, the point is to use a password manager. There are 10 different companies in this space and telling him about all of them will only create a barrier to entry. The huge wins you get from the macro-optimization of starting far outweigh any micro-optimizations between different providers.
Where TDD shines is giving you a tiny testbench to see that your implementation is heading in the correct direction before you get too far.