In the last decade, conversational search has attracted considerable attention. However, most research has focused on systems that can support a \emph{single} searcher. In this paper, we explore how systems can support \emph{multiple} searchers collaborating over an instant messaging platform (i.e., Slack). We present a ``Wizard of Oz'' study in which 27 participant pairs collaborated on three information-seeking tasks over Slack. Participants were unable to search on their own and had to gather information by interacting with a \emph{searchbot} directly from the Slack channel. The role of the searchbot was played by a reference librarian. Conversational search systems must be capable of engaging in \emph{mixed-initiative} interaction by taking and relinquishing control of the conversation to fulfill different objectives. Discourse analysis research suggests that conversational agents can take \emph{two} levels of initiative: dialog- and task-level initiative. Agents take dialog-level initiative to establish mutual belief between agents and task-level initiative to influence the goals of the other agents. During the study, participants were exposed to three experimental conditions in which the searchbot could take different levels of initiative: (1) no initiative, (2) only dialog-level initiative, and (3) both dialog- and task-level initiative. In this paper, we focus on understanding the Wizard's actions. Specifically, we focus on understanding the Wizard's motivations for taking initiative and their rationale for the timing of each intervention. To gain insights about the Wizard's actions, we conducted a stimulated recall interview with the Wizard. We present findings from a qualitative analysis of this interview data and discuss implications for designing conversational search systems to support collaborative search.