1/ I love this question and I believe it's much harder than most CEOs think initially. I think teammates of varying backgrounds and learning styles absorb complex information differently- and I've found that discussing strategy as a team is not straightforward for most.
https://twitter.com/sarjun/status/1359139608466890753
2/ I am a fan of talking about it frequently and in different formats. As CEO I tried to do it every 6 weeks as a co and for the formats to change. Sometimes presentation, sometimes fireside Q&A, sometimes panel w/ heads of teams talking about strategy, small and large groups etc
3/ The repetition helped teammates absorb, think about it and have it ingrained. They also could see evolutions over time- which are inevitable for a startup- and not have those iterations feel like giant pivots (as they may if only talked about strategy 1x-2x per yr)
4/ The different formats helped different learning styles. Some people loved being able to ask questions in Town Hall format. Others strongly preferred small group discussion. Some teammates liked the slides- especially opportunity to review before/after the talk.
5/ Every six weeks may sound like a lot, but I found less and it led to fraying at the edges. To keep it fresh the various formats helped, as did trying to lighten it up. Playing a game, physically moving the location of the talk to different parts of the office, etc.
6/ I don't think there is one right way to discuss strategy but I found consistent repetition in terms of the basic concepts and varying how those concepts were delivered to be helpful
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