Enneagram 8, The Challenger. Enneagram 8s are often seen as determined, confident and very assertive. They are the best at taking action and actually being in control of a situation. They are the best at being a leader and are able to make quick decisions. They love to take control of situations and to see the big picture. The biggest difficulty is that they can be too aggressive and controlling. They can be a bit too direct and too demanding at times. They also can be a bit rigid and somet