Kish, it depends on the situation.
Some of the chain stakes I pulled in the past two days would come up through the softer soil underneath and then stop dead against the top 3" of concrete hard dirt.
Instead of breaking my back for the last hoorah, I just use my stake driver and make 3 holes around the stake head to loosen the upper crust. Usually you can pull them out by hand then.
By the way. Do not buy any Mark June's "Pro Grade" earth anchors. What a joke. The welds break, they only set half the time, and when they do they take a good 6" of vertical travel until they bite.
I'm getting rid of every style for next year except my homemade anchors and Fox Hollow super stakes.
I USE A 6' DIGGING IRON WITH A HOSE CLAMP FASTENED ABOUT 18" FROM THE FLAT END. HOOK SMALL END OF LARGE SPRING CLIP TO LOOP ON CABLE STAKE AND BIG END OVER BAR.SPRING CLIP WILL LODGE AGAINST HOSE CLAMP WHEN YOU LIFT UP. GIVES YOU A LOT OF LEVERAGE! PULLED A COUPLE DOZEN OUT THIS YR WITH NO TROUBLE.