He becomes very worried incredibly quickly. Allowing him to be off lead in a secure area to sniff out treats on different surfaces encourages him to investigate and he's learning that it can be rewarding to be brave.
To help build up his confidence we allow him to be off lead but his handler is present to offer support, he is allowed to choose what to approach, take the time he needs to look at it, move towards various areas and sniff at things.
Allowing Toby the freedom and choice to make his own decisions is a powerful tool to help him learn. As we are close to him, he realises we are available for support and guidance if needed, however, we are not forcing him to do anything. He can do it all at his own pace.
As he becomes familiar with the items in the we have placed in the run we are gradually adding new ones like the umbrella and stuffed dog. You can see he looks at them and even investigates but he doesn't over-react. He is associating them with treats and a positive experience.