Talk to the middle school kids about the importance of taking initiative. Give examples of work or classroom situations where taking initiative means the difference between success and failure or mediocrity. Real-life examples show students the real effects of initiative.
Set an example for your middle schools kids to show them the positive effects of initiative. If you took initiative at work and were recognized for it, relay the story to your kids. In your home life, you and your spouse can take the initiative to get the dishes done, clean out the garage or reorganize a closet.
Use games and interactive activities to encourage the students to show initiative in everything they do. Set up role-playing situations where the students can act out various outcomes and perceive the differences in the outcomes. Enlist the students' help in creating the game, so that they have a personal investment and motivation in participating.
Organize team-building exercises to encourage middle school kids to work together and learn to trust. In many cases, taking initiative requires you to work with others toward a common goal. Team building activities, such as creating a pyramid, lining up by birth date or falling into the arms of another person, teach teamwork and encourage students to finish a task they begin.
Require everyone to participate in activities or discussions about the topic of taking initiative. If one student is shy or afraid to participate, encourage her one-on-one. Recruit other members of the class to encourage her to participate. Participation not only provides a learning experience, it also encourages her to take the initiative, even when she is unsure or afraid.