The Career Decision‐Making Difficulties Questionnaire (CDDQ; Gati, Krausz, & Osipow, 1996) has long been demonstrated as a useful instrument for career counseling practice. Several case studies have demonstrated how and why using the CDDQ facilitates the career counseling process (e.g., Amir, Gati, & Kleiman, 2008; Gati & Levin, 2014; Levin & Gati, 2014). This study explores how an in‐depth analysis of a case study conducted at the item level can provide career counselors with a richer understanding of their clients’ needs. The case study also emphasizes how administering and providing feedback on the CDDQ in career counseling sessions is likely to foster working alliances. The study concludes by presenting an intervention map based on the CDDQ taxonomy.