View All num of num See all Photos Progressive Insurance www.progressive.com Overview Reviews Salaries Interviews Jobs Photos Benefits 925 Reviews 1.8k Salaries 552 Interviews 253 Jobs Follow Add Interview Follow Add Interview Interview Question Claims Representative Senior Interview Mayfield Heights, Cuyahoga, OH Progressive Insurance I did role playing with a friend to prepare for the interview after finding 30 of the most difficult interview questions on line. I didn't get anything unexpected; however, I am VERY GLAD that I prepared because the interview is extremely extensive and they want very specific examples of how you have handled situations they ask about in your past. work history. You absolutely must be prepared or you may as well not even bother to apply. a few of the questions: 1. Describe a specific time where you had to handle three tasks as one time with a deadline. What action did you take to work through the situation and what was the outcome. 2. Tell me about a specific time when you had to negotiate. What was the situation, what was the action you took and what was the final outcome. 3. Tell me about a specific time when you had a conflict with a co-worker or boss and how you handled it. What was the situation, what was the action you took and what was the final outcome. 4. Tell me about a time when you disagreed with a company policy. What was the situation/policy, what was the action you took, what was the final outcome. The questions are all very, very specific and they are all just like the questions above. Read all the different Progressive interview questions on glass door, write them down and practice them over and over and over with someone else in order to prepare. It paid off for me and I was offered the position. Tags: behavioral See more , See less 8 Answer Add Tags Answer Interviews > Claims Representative Senior > Progressive Insurance Add Answers or Comments To comment on this, Sign In or Sign Up.