My Male Sneakers is the world's worst about "reminding" you it's time to go out on the Leash/Harness. My Female Becca doesn't seem to care and just goes along for the company.
When it's time to go (we have fairly regular schedule) he will sit/stand by the Harness/Reel Leashes, look at them, then back at me, then them, and do a little "yip" to get my attention. And he can really be a pest till I either take them, or say a firm NO.
He usually gets his way though.