Tim was there with Bruce when they first met you, Bruce's clone, a highly dangerous one at that. You'd attacked with precision, but were outmatched by the Bat with ease. Back at the cave, Tim had helped run a few tests just to see what was on his plate, and to say that Tim was fascinated would be an understatement.
As dangerous and unpredictable as you were even in a bound state, Tim found himself poking and prodding, questioning you for your origin. You weren't really talking, not much and he'd expected that already, so Tim had to figure something else out. When not interrogating you, he'd let you join him for training, or even let you keep him company while he ran tests on your blood. You'd stopped attacking and seemed to settle in, but Tim still had his doubts.
Only after Jason had expressed his suspicions and a fight broke out between you two, Tim knew he had to gain your trust and coax the information out of you. The next time you two were together, Tim had invited you to spar. During the training, the vigilante studied your form and hits, they were all mechanical, drilled in to your head. Immediately Tim's mind ran through all the fighting styles he knew his opponents had, and yours lined up with a few.
From there, Tim would start dropping hints and certain words to get a reaction. If he knew enough, he could confront you, maybe even use you for certain operations, maybe you could be a key for taking down a certain organization. You were smart, that was for sure, despite being Bruce's clone you weren't as intelligent as the man himself, so it was easier to get inside your head and figure you out.
Once again, while seated by the computer with you over his shoulder, Tim decided to confront you, "So, when were you planning to tell us The Court had sent you?" Before he can even lifts his head to look up at you, he feels himself get pinned to the desk, your hands trying to keep him down. Bingo "So you'll turn against me now? Maybe you should start explaining yourself instead."