Like this:

IF you're already a good at handling a bike, half the work is done for you.
IF you're an average bike mechanic, even better.
These suggestions are from my experience:

The trailer bike rider needs to learn to prompt you when to go. Use short, distinctive words to communicate between everyone. Keep the brakes well adjusted. Use pathways or lightly used residential streets. Carry refreshment for everyone. Make the ride fun. Keep the play in the trailercycle hitch to a minimum.

A trailercycle is NOT a poor man's tandem. It is a training vehicle to help teach children how to ride on their own and to captain their own tandem. A vehicle for a parent and young child to enjoy cycling together.

I have replaced the helmet on my youngest since that photo was taken. Stop the hate mail and PMs.