And it’s management’s job to multiply the senior’s estimate by 5 and +/-50% for good measure. And even then, that’s a rough estimate at best.

Maybe using points for some planning actually works; I’ve never worked at a place that could use it for actual estimates. My estimates are entirely based on gut feel, my feeling of the complexity involved and my feeling of how much the team can get done. Over the last two years (since metastasizing into a CTO) my overall estimates have pretty much always been in the right ballpark. Which is to say, when the CEO says “We’re going to do X, Y, and Z this quarter,” I say “We’ll be able to reach about 50% completion if we work on all of those at the same time,” I’m usually more or less right.

I’ve never worked with a dev who could make significantly better estimates than me (excluding the early years of my career when my estimates were absolutely awful). Most of the devs I’ve worked with just wouldn’t give estimates; if pushed they’d be as vague as they possibly could. The only boss I’ve had who would give definite estimates was always off by an order of magnitude (as in he thought it would be 10x easier than it was, even though he had decades of experience writing code and managing teams).