I’ve only seen that done once with any degree of proficiency, and that was with the dolly turning with the lead, which must have been the kind with 2 pintle eyes. That eliminates one pivot point.
LTL Linehaul position pulling doubles
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What I loved about those doubles was I could take my 30 minutes in a shopping center parking lot, curled around a light pole like a cat.
Later on I pulled regular trailers and eventually got a gig hitting docks with vans, so I had to back all the time; it was traumatic at first, like being in school all over again.
What I used to go back to when I got frazzled backing --in a place so busy there were multiple supervisors in the lot with vests and flashlights and clipboards, all watching to see how long I took-- is to turn the bottom of the wheel the direction I wanted the trailer wheels to go. If you remember nothing else and your mind goes blank that can help.
Also, I didn't care how many people were waiting, if I wasn't sure I Got Out And Looked. Eventually that got me a little respect because they knew I was unlikely to hit something, even when I was killing them on time.
For me it helps to try something, then sleep on it, seems like the next day goes better, like I learned something overnight by processing the data I gathered. So if you can find some equipment that's similar to practice with, that is likely to help, with both skill and self-doubt.
Might be that a road test at one company teaches you how to pass one at the next company, think of them as practice rather than performance, lots of LTL's out there.
Far as drive tests, it can be all over the map, some have looked at what I've done on my resume and reckon I'll figure it out, some will take me for a drive. Just show up and be open and honest about what you can do but not self-revealing to the point of self-destruction. Show them some good driving, then tell them you need backing practice.
One early test they had no drivers so a shop guy and I got in their big old Kenworth wrecker and went for a spin. Another place I had a 3-million mile safe driver henpecking me over tires touching turn lane markers with a sleeper and 53 in a city, but they still offered it to me.
When it works, it works like magic. When it doesn't there's no fixing it.
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