The thinking like a poker player is mostly about being upfront about your risk tolerances and then having a culture supporting people who make the best risk adjusted decision, even if it doesn't work out.
Expected Value is complicated because a 50% chance for $100 is the same as a 10% chance at $1000. It's the variance, not the EV that makes a lot of decisions hard.
You (and businesses) need to decide what risk is acceptable, communicate that clearly. Reward people who manage risk in a way that's aligned with the business even when it doesn't work out. Get rid of people who are either take too big risks, and people who don't take risks.