Am I actually empowering my heirs or am I enabling them without realizing it?

The honest test is whether your kid would still know how to handle the situation if you weren't available to handle it for them. Empowerment leaves them more capable. Enablement leaves them more dependent. Kris Kluver, in The Dysfunctional Family Office, asks founders to walk through specific recent decisions. Did you give them tools and let them choose? Or did you remove the obstacle so they didn't have to. The pattern matters more than any single instance. Most founders find a mix when they look honestly. The fix is to start noticing in real time and choosing the harder option. Letting them handle the awkward conversation. Letting them sit with the failed venture. Letting them feel the budget constraint. The discomfort is yours, not theirs.