Challenging doesn't always mean changing
I always challenged my teams and my peers. Not for the fun of it, but because experience proved me that some extraordinary ideas and insights were behind that challenge of mine.
Few years ago, I had a nice experience challenging the owner of a very nice marketplace that was also organizing some off-line events for its community. The status-quo was that there are no entry fees for the visitors attending his off-line events. He was afraid to change something that worked. But, finally, he agreed to make a test. What happened was that people gain more trust in his event and a new revenue-stream appeared in his P&L.