Transition planning is a federally-mandated process that involves systematic planning for life after a child with a disability exits the school district. Family engagement in transition planning is central to ensuring positive post-school outcomes for individuals with disabilities. Using a family-friendly framework for transition planning, such as person-centered planning, enhances family engagement. Innovations in technology have made active participation in transition planning easier than ever before. Educators who can successfully navigate current technologies and encourage technology use with the families they serve can reduce barriers many families face when engaging in transition planning. By enhancing family-friendly transition planning strategies (such as person-centered planning) with technology, educators have a powerful tool to increase student self-advocacy and self-determination while increasing family engagement in the transition process. Early and ongoing communication with families will also increase family engagement throughout the process.