Today's students are surrounded by adults who care deeply about their success—but sometimes that support unintentionally prevents them from developing the resilience, responsibility, and independence needed to thrive. This workshop explores how parents, employers, volunteers, alumni, advisory committees, and community members can become partners in building work-ready students rather than barriers to their growth. Participants will examine common ways adults accidentally undermine grit and accountability, learn strategies for promoting productive struggle, and develop practical tools for communicating expectations beyond the classroom. Walk away with ideas for engaging families and community stakeholders in creating a culture where students learn to take ownership, overcome challenges, and develop the mindset skills necessary for success in work, school, and life.