Many individuals who struggle with career decisions seek professional guidance from career counselors. However, little is known about how to ensure that career guidance sessions are of high quality. Vital factors for a successful counseling process include a positive working alliance and empathy of the counselor. This study investigates how counselors’ behaviors, measured with a behavioral coding instrument, related to positive working alliances and empathy. We introduce a video-based instrument that measures microbehaviors and skills during career counseling sessions. Psychometric analyses were conducted on the basis of 53 video recordings. Double-coded sessions ( N = 18) showed excellent interrater reliabilities for the coded microbehaviors. By using a multitrait-multimethod approach, we established construct validity with another coding instrument, whereas criterion validity was established with respect to counselors’ empathy and working alliance ratings. We discuss theoretical implications of using video-based methods in career sessions to advance process research and present practical applications in terms of assessing quality assurance in career interventions.