Talk to the humans first.
Before I look at a single tool, I talk to the people doing the work. What's breaking. Where things get stuck. Who owns what, and who thinks they own what.
The gap between how the org thinks it works and how it actually works is where the answer usually is. That's the gap I look for.
This usually takes a week of short conversations across the team. Nobody is on the spot. Nobody has to present. I'm just listening for the patterns nobody else has time to listen for.