Find the right skateboard. The board should be at least an inch wider than your dogs normal stance. Use one with older ball bearings—you want your board to travel about a meter with each push.
Introduce your dog to the skateboard. Begin with putting your dog in a carpeted room with the skateboard. Place it flat on the ground, wheels up. Praise your dog extensively for any interest it shows in the skateboard. Make noises with the board by spinning the wheels or tapping the surface. Observe your dog's response. After a few minutes, put the board away. Let your dog rest for 20 minutes or so.
Bring the board back down. If your dog seemed fine with the board upside down, put it right side up this time. However, be sure to secure the board so that it doesn't roll around when your dog tries to play with it. Again, praise your dog for any interest in the board.
Roll the board around a little. Observe your dog's reaction—any sign of fear and you should back up a step. Try not to roll the board directly towards your dog, as this can be seen as threatening. Instead, awaken your dog's predatory instincts by rolling the board away from it. Continue for a few minutes, then take a break. Repeat. Continue to the next step when your dog is comfortable around the skateboard. If your dog tries to get on the skateboard at any point, be sure to give it lots of praise and/or treats. Don't forget to hold the skateboard steady.
Begin training your dog to get on the skateboard. Secure the board so that it can't move. Reward the dog the majority of the time that it shows any interest, but focus on interest involving one or more paws on the board. It's okay if your dog doesn't leave his paws on the board yet. Continue this until your dog puts a paw the on the skateboard whenever it's presented.
Begin rewarding your dog only 1/2 the time he shows interest in the skateboard. Reward the majority of the time that he puts a paw on the board, and always when two or more paws are put on the board. If your dog begins to get so frustrated that he whines/barks or stops trying, put the skateboard away and try again later and/or back up a step.
Move the skateboard forward a couple feet once your dog places his paws on it. Initially, your dog will probably move his feet as soon as the board starts rolling. Try to reward your dog with a treat in the moment before he gets off the skateboard. Put the treat directly in his mouth so that he dog doesn't have to move off the board to get it. Move on to the next step when your dog is comfortable keeping two paws on the moving board for at least 4 feet (1.2 m).
Place your dog so he is standing on the skateboard completely. Reward your dog extensively for standing on the still board. Phase out rewards for merely being interested in the board, and only reward some of the time for two paws. Once your dog consistently stands on the board, you are ready to move on.
Roll the skateboard back and forth slowly. Be sure that you are holding the skateboard to keep it from shaking too much. Praise your dog for staying on the board.
Get your dog to mount the skateboard on his own. Tap the board and say the desired command to get your dog to get up on it. Move slightly back from the skateboard so that your dog is required to push forward to get the treat. Reward your dog whenever he does something desirable.
Continue trying until your dog will obey the command without the need of a reward other than praise.
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