The Circle session every two months brings a captain of industry or a specialist or a thinker into conversation with the Naora members for sixty minutes. The sessions that produce the conversations worth having do not happen by accident.
They happen because the person who is facilitating them has done the specific preparation that converts the potential of the guest into the actual quality of the conversation — the research, the question design, the specific framing that creates the conditions for the guest to say the thing they know and do not usually say in the contexts where they are asked to say it.
The selection of the guest is the first preparation. I spend time between sessions identifying the person whose specific expertise or experience intersects with what the Naora Circle is in the way that the generic expert in the same field does not.
The difference between the founder who has built and exited a significant company and has been honest enough to think carefully about what the exit actually produced in them, and the founder who gives the standard narrative of the exit as the achievement and the next chapter as the strategic pivot: both are founders who have exited significant companies.
Only one of them will produce the Circle session that the members are still thinking about the following week. The selection is the identification of the one rather than the other.
The Preparation
Once the guest is confirmed, the preparation begins in earnest: the background reading, the specific work the guest has produced or been involved in, the interviews and the talks and the articles where the guest has expressed their thinking in the public form.
The reading has two purposes. The first is the factual preparation that any interviewer requires: knowing enough about the guest’s work to ask the question that goes beyond what the Wikipedia entry already contains. The second is the identification of the specific tension in the guest’s thinking, the place where the work or the experience has produced the genuine insight that the conventional framing of their field or their role has not yet accommodated, and that the right question in the right context will produce in the conversation rather than the press release version of the guest’s position.
The questions are written out and then largely abandoned. Not because the preparation was wasted, the preparation is what makes the abandonment possible. The prepared question is the scaffold that the conversation builds from and then dismantles as the guest says something that the preparation did not predict and that the conversation needs to follow rather than redirect back to the prepared structure.
The best Circle sessions are the sessions where the prepared questions were answered in the first twenty minutes and the rest of the session was the conversation that the first twenty minutes made possible. The preparation is the platform. The platform is not the session. The session is what the platform allows to happen.
