have him go to a parking lot and practice for a little bit. I'm sure he's like most of us.....with a little practice he'll get a system down. The first time we brought ours home it was similar but without the mailbox. We live on a busy road and wife was out directing traffic for me. There's a little hump in the road and she couldn't see over it.....she had a car go to pass me right as a car was coming over the hump. Got pretty intense there for a second. I'm sure some cuss words were said and fingers given that day. After 2-3 times I could pull it in without any assistance and nail it first try.