> He’s still an amazing asset to the team, but in this case he does have some experience that’s hampering him in a new role.

OK, but how much could it possibly "hamper" him if he's still an "amazing asset"? Is it a permanent condition? Or is it just something that you noticed once or twice and made a mental note of?

We all have gaps and shortcomings. Overcoming them is a matter of practice, but if someone is second-guessing and judging every brain-fart, that's not good for anyone.