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Transparency—the observability of activities, behaviors, and performance—is often treated as a panaceafor modern management. Yet there is a conundrum in the literature, with some studies suggesting thattransparency may benefit group creativity and others suggesting that privacy may do so. A similarconundrum exists regarding the effects of different social capital types—structural holes vs. networkcohesion—on group creativity. Enterprise social media (ESM) provide a unique opportunity to solve theseconundrums by allowing groups to be “transparent” (non-group members can observe and/or participatein group activities) or “private” (group members and activities are hidden from the community) andenabling groups to develop distinct social capital structures. Using data from 28,083 written interactionsproduced by 109 transparent and 106 private groups in an ESM of a multinational design firm, we foundstrong support for our contingency hypotheses that both transparent and private groups may produce highlevels of creative dialogues, yet in different forms. Specifically, expansion-focused creative dialogues—those focused on combining or expanding existing concepts—emerge in transparent groups, but onlywhen the group’s social capital is characterized by structural holes. Conversely, we found that reframingfocused dialogues—those focused on challenging and rethinking—emerge in private groups but onlywhen the group’s social capital is characterized by network cohesion. Theoretically, these findings canhelp to solve the conundrums in the literature on group creativity and shed light on the role of ESM usein this context. Practically, our findings offer a critical reflection o contemporary initiatives for increasingtransparency, whether through physical design or digital transformation.