This workshop will explore the various reasons why kids and teens may have a hard time opening up in therapy. Generation Alpha comes with the challenges that accompany technology and the pandemic, along with the enduring challenges including suicide prevention, trauma responses, the need for communication skill building, and trust-building. Understanding the obstacle allows the clinician to employ the most appropriate strategy to engage the youth or elicit the information needed. Participants will leave with a menu of options for encouraging conversations. Conversation cards, the use of games, puppets, whiteboards, humor, homework challenges, and strategic framing will be explored. The power of incorporating siblings and other family members will also be emphasized. Presenter will share her favorite phrases for introductions, assessments, invitations, and explanations.