Cindy's Answer:
You can't teach him to hold his ground, it sounds like he's a dog that wants to avoid conflict with other dogs. Believe me, many people that write to us have the opposite problem! They have dogs that want to fight or are aggressive to off-leash dogs. I've had both and dealing with a dog that wants to fight other dogs not only is extremely dangerous, it's so stressful.
I would teach your dog that YOU will protect him and keep other dogs out of his space. That in itself will build his confidence. I will do whatever I need to in order to keep off leash dogs from approaching when I'm out walking with my dogs. Usually, I have my dog go behind me or next to me and I challenge the dog with very stern posture and tell them to GO HOME. If the owner is there I give them an earful and tell them to get their dog. I have a can of compressed air and a walking stick. If I need to get more forward to impress that other dog to leave, I will.
I hike every day with my dogs and over the last 5 years, I've only had to hit a few dogs with my walking stick to get them to leave. These dogs wanted to fight, and like I said, I will do whatever I have to in order to keep my dog safe.
When you have a dog that lacks confidence around strange dogs simply showing your dog you've "got his back" and driving away the other dogs will show your dog the two of you are a team and you aren't going to let the other dogs harass him. This often builds a dog's confidence and will help him be less worried in the future.
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