What’s the point of merely holding an advantageous position? Sure, you can use it to control your opponent, as well as to set up an eventual transition to another position or submission… But merely holding the position means that you aren’t using your full potential. Rather, you should try to make your opponent uncomfortable in the process.
For example, that’s why it’s sometimes good to make a transition from the simple Side Control to the painful Kesa Gatame position. Josh Barnett explains how.

THE MOST PAINFUL SIDE CONTROL

Many Jiujiteiros think that transitioning from a “normal” Side Control to Kesa Gatame means to simply “throw” their arm around the opponent’s head. However, if you do this, the opponent will most likely get an underhook on you… Which is a big no-no.
Therefore, as Barnett emphasizes, you should first slide your forearm against the opponent’s arm. That way, you’ll negate them their underhook efforts; all the way up until you decide to make your next move. While there, use your other arm to lift up their head from the mats even more.

Now that you’re in this position, your next move is to shoot that arm through and switch your hips towards the opponent’s head. Slide your leg towards their head and clasp your hand over your thigh to make the other person extremely uncomfortable.
You’re now in a Kesa Gatame position. Position your first leg to “12 o’ clock” and your bottom leg to “3 o’ clock” in order to gain stability; and drive your bodyweight on top of the opponent’s torso.

To see how to do this painful transition in action and to check out an easy to use Armbar finish from Kesa Gatame, check out the video below: