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Writing positively about yourself can be hard.  It feels like bragging, which feels rude.  What I've found helps is to frame it as a *specific marketing project*.  It's not that I would go around boasting in general, but this year-end performance self-assessment is where I have to show my value and accomplishments to my employer (via my manager).  If I do it well I might get a better raise.  It's a business proposition.

With that frame of mind, I can block out the nagging feelings of boastfulness and write stuff.

On an application for a program, "tell us why you're a good candidate" is a request for you to write the "pro" side of a self-assessment.  It's a pitch and the reader doesn't know you like your boss does, so approach it with facts and examples.  Tell them about your track record, your accomplishments, and your related experience; that will be more powerful than asserting things about your character.  To me it also feels less "braggy".  When I applied for a program in a different field, I gave examples from my field and explained how they mapped to my target field -- why being good at X in domain A would make me good at doing something similar to X in domain B.

"Tell us about a time when you did X" is what's called a "behavioral" question in job-interview contexts.  People ask those kinds of questions in interviews, and in application essays, because anybody can say "I have these qualities" or "I would do X in this situation", but what you *actually did* in a past situation is a better indicator.  In an interview the question is the beginning of a discussion, and the interviewee best approaches it as an opportunity tell a story.  (A true story, of course!)  On a written application you don't have the back-and-forth of a conversation, but they're still asking you to tell a story.  You've probably told stories from work (with the serial numbers filed off) to friends and family, filling in context where needed.  Approach it like that, but with a more formal style.