Place potatoes in pot and fill with cool water and bring to a boil.
Meanwhile, cut the top of the garlic head so that the cloves are exposed and drizzle with olive oil. Wrap in aluminum foil and place in oven. Roast for 30 minutes, until softened and golden brown.
Once the potatoes have come to a boil, pour out the water and add new water to cover the potatoes. Bring to a boil again, then continue to cook until potatoes are soft. Drain completely. Add butter, milk, and desired amount of garlic. I used about half of the head of garlic.
Mash the potatoes. Season with pepper to taste. Garnish with chives or parsley.