Purpose: The purpose of this paper is to highlight the challenges regarding learning in stakeholder relations in profit and nonprofit organizations. Design/methodology/approach: Conclusions and models presented in the paper have been designed based on the systems perspective, critical thinking and critical review of previous contributions. Findings: Organizational learning has been examined in profit and nonprofit organizations, and factors which stimulate this process have been identified. More precisely, factors contributing to organizational learning in board of directors have been critically examined, accreditation as a factor contributing to organizational learning in higher education institutions (HEIs) has been suggested, learning dynamics in university-industry collaborations and inter-professional learning have been examined, as well as organizational learning as a bottom-up approach supported by transformational leaderships. Research limitations/implications: Conclusions and models provided in the paper need further empirical testing and validation. Practical implications: Useful implications for practitioners in profit and nonprofit sector have been suggested based on the critical analysis of previous contributions regarding stimulation of organizational learning in stakeholder relations. Originality/value: Contributions from previous authors have been systemically and critically reviewed, adapted models have been provided and suggestions for practitioners in this regard have been offered.