Purpose: The purpose of this paper is to analyse the relationship between on-the-job learning and information and communication technology (ICT). Design/methodology/approach: Action research methodology was applied to study 62 small- and medium-sized corporations, and to interview over 200 knowledge workers and managers. The qualitative, textual data collected were transformed into 16 variables and analysed by multidimensional scaling. Findings: The paper provides insights into the optimal use of ICT in intra-organizational knowledge transfer and learning. We found that it is essential to use the right combination and number of technologies, aligned with the organization's internal processes. Four different types of organizations with sub-optimal usage of ICT and possible strategies for them to reach the optimal zone were identified. For successful organizational learning, however, more is needed: the individual must also understand the value of learning and must be motivated to take part in it. Research limitations/Implications: On-the-job-learning can be facilitated with ICT tools but only if the organization invests in the right levels of ICT. Too much technology can be as destructive to on-the-job learning as too little. Future research should look at other contexts (size, age, industry, etc.) to validate these findings. Practical Implications: The paper demonstrates the effective use of ICT in knowledge transfer and on-the-job learning. Originality/Value: The paper extends our understanding of human-computer collaboration. It highlights that finding the optimal level of ICT is essential for successful knowledge transfer and on-the-job learning.