COVID-19 has provided further opportunities for organizations to hold web meetings. This study explored the factors of holding appropriate web meetings. A web survey was conducted with 412 clerical was determined by the following. (1) Concerning the groups which positively or negatively evaluated the web meeting regarding participation, the rate of the group which positively evaluated the web meeting was high. It reached over 80% when the basic information and communications technology (ICT) operation skills were high and the personal computer (PC) usage experience was 20 to 29 years. (2) Concerning the interpersonal evaluation of web meetings, 60% of the assessments were highly positive when the expertise of the communication partner was high. (3) For the technical evaluation of web meetings, 40% of the assessments were high when the ability and confidence in computers were high. (4) For the groups which positively or negatively evaluated the web meeting regarding hosting it, the rate of the group which positively evaluated the web meeting was high. It reached over 80% when the anxiety related to computer operation was low and the communication partner was highly active. Additionally, the results of the decision tree analysis and text mining suggested that individual skills and attitudes that affect technical aspects and communication issues were essential. Striving to improve and solve these problems n the early stages may lead to holding appropriate web meetings from the perspective of participants and organizers.