[Isamu]

Middle and upper management are mostly concerned about risk, because the environment they are in rewards being “done” more than trying something that could have a bigger payoff.

That is, the downside of accepting risk tends to outweigh the upside of achieving a goal at the cost of running over schedule. In that environment.

[b3morales]

Very much this; not least because, having organizational power, they can manipulate the situation to evade the downside. As discussed in the classic Gervais Principle essay: https://www.ribbonfarm.com/2011/10/14/the-gervais-principle-...