A holistic approach to diabetes considers patient preferences, emotional health, living conditions, and other contextual factors, in addition to medication selection. Human and social factors influence treatment adherence and clinical outcomes. Social issues, cost of care, out-of-pocket expenses, pill burden (number and frequency), and injectable drugs such as insulin, can affect adherence. Clinicians can ask about these contextual factors when discussing treatment options with patients. Patients' emotional health can also affect diabetes self-care. Social stressors such as family issues may impair self-care behaviors. Diabetes can also lead to emotional stress. Diabetes distress correlates with worse glycemic control and lower overall well-being. Patient-centered communication can build the foundation of a trusting relationship with the clinician. Respect for patient preferences and fears can build trust. Relevant communication skills include asking open-ended questions, expressing empathy, active listening, and exploring the patient's perspective. Glycemic goals must be personalized based on frailty, the risk of hypoglycemia, and healthy life expectancy. Lifestyle counseling requires a nonjudgmental approach and tactfulness. The art of diabetes care rests on clinicians perceiving a patient's emotional state. Tailoring the level of advice and diabetes targets based on a patient's personal and contextual factors requires mindfulness by clinicians.