Much of organisational development occurs during times of crisis when answers and solutions are urgently needed. The research presented in this paper suggests that, during such times, what matters for organisational legitimacy is understanding stakeholders’ changing needs. This paper proposes that organisational listening become a core function for brands and organisations. Building on theories related to organisational listening, social media and stakeholder engagement in digital marketing, this article argues for incorporating mature online listening into the customer engagement in social media (CESM) framework introduced by Santini et al. (2020). In the practise of organisational listening, organisations employ their processes, structures, technologies and skills to show attention to interpret and respond to their stakeholders. This article concentrates on listening on social media because changes have been most visible in this context due to the lack of gatekeepers, such as legacy media institutions. Times of rapid development make positive changes possible, but when development is rapid, unintended consequences can also follow. In the early years of social media, unintended consequences included banner advertising and targeted advertising, but during the pandemic, issues related to disinformation and spam have arisen. The research described herein views organisational listening as a skill that develops from immature to mature. To illustrate our position, we chose two time periods during which organisational listening practices developed especially quickly. During the late 2010s, stakeholders were introduced to a direct route to brands made available through social media, and many unanswered customer service questions suddenly became visible and were subsequently addressed. Similarly, the COVID-19 pandemic has put pressure on organisations’ communication systems to respond to citizens’ urgent concerns. The analysis of both examples reveals that organisational listening matured significantly in a relatively short time. The illustrations show that organisations under pressure, despite their strategic objectives to promote two-way engagement, often resorted to one-way speaking and direct marketing on social media. However, the prerequisites of engagement, trust and satisfaction are only built if organisations listen. Our findings indicate that organisations rush to engage with stakeholders on social media using one-way speaking and direct marketing, skipping the vital stage of listening and establishing trust and relationships, without which listening cannot become strategic, nor can it mature to its full usage potential. 23 These results call for organisations to take a more strategic approach to organisational listening to attain their desired higher levels of engagement and conversion to action and to generate positive WOM. Modern technology can be used systematically for wider listening and for establishing relations with stakeholders online. However, listening activities must be strategically planned; the non-strategic use of listening technology does not guarantee success and may even backfire. We suggest that communication professionals embrace times of rapid change to best utilise the pressure put on their organisations, as the leaps in growth observed in the current research highlight the importance of communication and organisations’ ability to mature more quickly in an environment of accelerated advancement.