My routine is to get Speedy out first and bring him over to the trailer where I tack up. Then I go get Izzy. This has worked out well on a number of levels. First, Speedy feels as though his me first ego has been stroked and second, Izzy is comforted knowing Speedy is waiting for him.
It might not be the job I want for Speedy, but a job's a job and everyone's gotta have one.