Context Although left ventricular assist devices as destination therapy (DT-LVAD) can improve survival, quality of life, and functional capacity in well-selected patients with advanced heart failure, there remain unique challenges to providing quality end-of-life care in this population. Palliative care involvement is universally recommended, but how to best operationalize this care and measure success is unknown. Objectives To characterize the process of preparedness planning (PP) for patients receiving DT-LVAD at our institution and better understand opportunities for quality improvement or procedural transferability. Methods Retrospective review of 107 consecutive patients undergoing DT-LVAD implantation at a single institution between 2009 and 2013. Information regarding demographics, advance care planning, and mortality was abstracted from the medical record and analyzed. Findings were compared with a historical cohort who received DT-LVAD implantation at the same institution before the development of PP (2003–2009). Results Mean age of patients receiving DT-LVAD was 64.3 years (SD ± 10.7). At last follow-up, 46 patients (43%) had died. Mean post-DT-LVAD survival in this group was 1.1 years (SD ± 1.2). Eighty-nine percent of patient had palliative care consultation before implantation, and 70% completed PP. Although 66% of patients completed an advance directive (AD) preimplantation, only two ADs (2.8%) specifically mentioned DT-LVAD and none addressed core elements of PP. AD completion rates improved from 47% before our policy on PP (P = 0.012). Conclusion A disconnect was evident between the rigor of PP discussions and the content of ADs in the medical record. We urge that future efforts focus on narrowing this gap.