Serendipity, at the heart of many business innovations and strategic opportunities, is a crucial asset for corporate success. Thus, many corporations are now actively seeking ways to foster serendipity, often by designing workplace environments that encourage spontaneous interactions. However, these strategies often fall short of delivering the expected results. Given this, we argue that the key to harnessing serendipity lies in developing a serendipitous mindset among employees, which can be nurtured through a dialogic approach. Dialogue is inherently forward-looking, encouraging exploration rather than closure. By engaging in dialogue and developing dialogic intelligence, individuals can learn to question assumptions, challenge preconceptions, and critically assess new ideas – skills essential for fostering a serendipitous mindset. To make dialogue-based training more accessible and effective, generative AI (GenAI) can be utilized. Its ability to simulate dynamic, adaptive conversations in a psychologically safe learning environment – free from external pressures – provides an ideal setting for simulating authentic dialogues and developing serendipitous thinking. So far, we have designed a GenAI-based prototype for dialogic intelligence training. Moving forward, following experiential learning pedagogy, we will integrate serendipitous scenarios into the system, ensuring that dialogue-based serendipity training becomes a practical and impactful tool for corporate learning.