When you let him out they will start to toughen up on their own.
I've just come back from Turkey and been walking about bare footed and my feet got really tough

Also now the weather is colder and damper the grass and soil where he will mostly walk will be softer.
if you have not let him out before. It's best to be with him for a few times.
To take him round the garden. I took mine out on a lead for about 2 weeks.
I also make sure they are in at night. Even more so now it's coming up to Bonfire night. There's a lot of Danger out there for our Loved ones!!
Hope this helps.