I think the hardest conversation circles around language choice. One problem with choosing innovative languages is that you can end up on a dead end. Zipcar, for example, used Tcl. While I am a fan of Tcl, it became obvious around 2012ish (IIRC) that this was not the future. There was a first attempt at a migration using rails, but that ended up being ditched for a JVM stack. (I don't know if most of it is still in groovy, but there were also pieces in ruby, kotlin, and java.) We also had a large number of performance and billing problems we needed to solve, and as we were guaranteeing compatibility and interoperability (a big bang switchover was too risky for many reasons), we had a lot of performance and usability issues for years.
It cost far more than management expected in the outset for many reasons, but at the same time, staying on Tcl was unsustainable for developer recruitment and retention purposes. It's something that biases me toward blub languages now as a manager unless you have a very good reason to innovate there.