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First off, I've been there, and I consider myself a more outgoing person. When I started in my first professional reporter job at 22 years ago fresh out of college (almost eight years ago), I was frightened every time I had to talk to a source. I was even more scared when I had to ask those tough questions. Over time, though, I learned to be comfortable because I learned an important part of journalism: all reporters aren't the same.
When you're in school you're led to believe that all reporters operate the same way. That's the furthest thing from the truth.
I used to butt heads with a former editor because she was much more cut-throat than I am. She'd have no problems calling people and demanding things. She was poised for a fight with a source every time she picked up the phone.
I don't operate the same way. I believe you can draw more flies with honey than with vinegar. It works for me, and I've been told more than once from sources that they like talking with me because they don't feel like they're talking with a reporter. The reason I operate as such is because it makes me just as comfortable as it makes my sources.
You have to find your own way to handle sources that makes you hit a comfort zone. There will be harder days with tougher stories, but if you find a way to handle the job in your own way it'll be easier for you.