Love your dog
If you want your dog to listen to you carefully, then you should treat him with love and affection. For this, you should not scold your dog and help him understand things with love. You should spend a lot time with your dog as possible and make sure that you take him out for a walk on daily basis. It is of utmost importance that you strengthen your bond with the dog and explain him this new trick of yours. You should talk to him about this new trick and help him understand about it.
Give him a demonstration
In order to help your dog understand the trick, it is of utmost importance that you should give him a demonstration of what you are trying to teach him. For this, you should take out your skateboard to give him a demonstration. You should tell your dog to sit and not to move until you say so and then take a few rides over the skateboard. You must keep talking to him about it and keep taking rides over the skateboard.
Make your dog stand on the skateboard
You should continue doing this until your dog gets familiar with the technique. Remember that you do not want your dog to overrun by a skateboard. Now, you must ask your dog to place his paw on the skateboard and stand firmly on it. Make sure that your dog is comfortably standing on it.
Push the skateboard and give your dog a ride
After your dog has gained confidence and is standing firmly on the skateboard, you must push the skateboard a little and give your dog a smooth ride. You must not push the skateboard with a lot of force as this will scare your dog.