This is perhaps the easier of the two loop trails off of the Madrone Trail #4. Both loops have an abrupt 150-200-foot climb from Madrone Trail #4, followed by some relatively flat trail before another quick 150-200-foot descent. But this is a doubletrack, whereas the other Cougar Canyon Overlook Trail #4a is a singletrack.
It's probably better to hike this in the counterclockwise direction as the difficult climb is relatively straight and then you'll have a twisting trail for the descent, but there is no reason it can't be taken clockwise.
Towards the middle of the trail, you'll find an overlook with a great view of the Ice Cream Hill Trail #1b and the fun parts of Spring Branch Trail, which should both be on your to-do list if you've made it this far.