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Season the beef stew meat generously with salt and pepper. Place the beef in a ziploc bag and add the flour. Close the bag and shake until each piece of beef is fully covered in flour. Add more flour if necessary.
Heat the olive oil in a large pot over medium-high heat. Add the beef to the pot and cook just until the meat starts to brown. Since you do not want to fully brown the meat, you may have to do this in 2 or 3 batches. When done, set aside.
In the same pot, add the chopped leek, carrots and celery. Cook the vegetables until soft, stirring occasionally, about 5 minutes.
Stir in garlic, oregano, bay leaf, thyme and tomato paste. Add the meat to the pot; then, add the beef broth and season with salt and pepper to taste. When this begins to boil, reduce heat to medium and cook for about 45 minutes, stirring occasionally. The meat will become tender during the cooking process.
Add the barley to the pot and cook for an additional 30 minutes or until the barley is cooked through. To avoid sticking, stir occasionally. If the soup is too thick, add water until you get the desired consistency.
Remove the soup from heat and garnish with fresh parsley before serving.