There's a few ontologies for describing the phases leaders -- and their startups -- go through, whether it's product-sales-etc. or pioneer to settler. In any case, as companies evolve, so must the leaders -- but can the same person transition across all these phases? When and when not; what are the qualities, criteria, and tradeoffs to be made?

In this episode of the a16z Podcast, originally recorded as an internal hallway-style chat (pre pandemic!) a16z general partner Martin Casado, who co-founded but decided to remain CTO of Nicira -- and previously shared his own journey, lessons learned, and advice for founders about bringing in an external CEO and the question of "to CTO or not to CTO" -- and Armon Dadgar, co-founder (with Mitchell Hashimoto) and CTO of HashiCorp, chat with Sonal Chokshi about both managing their past psychology through these common questions and decisions. They also share their strategies on managing the specific tactics behind it all: Everything from the "dating" process of finding an external CEO to figuring out swim lanes; handling debates and decisions; who presents, who sells. And while the conversation is a brief glimpse into their longer personal journeys, there's lessons in it for startups and leaders of all kinds on the art of hiring and sales, managing credit and conflict, and more...