Objectives: Despite the need for consultation at a medical institution, some workers currently do not undergo a re-examination or a thorough examination following regular workplace health checkups. This study aimed to clarify the factors leading to the need for a further examination at a medical institution after workplace health checkups and to examine occupational health activities necessary to improve the examination rate. Methods: We conducted a cross-sectional questionnaire survey of workers of companies with over 1,000 employees in the Tokyo and Saitama prefectures, targeting men and women over the age of 20 years. The study consisted of 453 employees (389 males, 64 females) who answered that they had received recommendations such as the need for a re-examination or a thorough examination based on the results of an initial workplace health checkup. We divided the participants into two groups, based on whether they underwent further consultation at a medical institution. The factors that led to a further consultation were verified using a logistic regression model. Results: The odds ratio (OR) for consultations at medical institutions for workers with less than 5 years of work and those with more than 10 years was 2.9 (95% confidence interval [CI]: 1.6–5.2). Additionally, there was a significant association with the presence of a counselor (OR: 2.4, 95% CI: 1.4–4.3) and with periodic visits to a medical institution (OR: 1.8, 95% CI: 1.2–2.7). There were no significant differences in relation to age, sex, type of employment, overtime work, sense of well-being, use of the workplace system, or specific consultants. Conclusions: The factors that led to further consultation at medical institutions were the presence of counselors and periodic medical consultations. It was also observed that employees who have less than 5 years of employment seek medical attention according to recommendations received from medical institutions. Therefore, in order to receive the appropriate medical attention, we should promote further consultation by experts following health checkups and address workers’ medical needs in accordance to their length of employment.