Colin returned as reserve team coach at the beginning of the 2001-02 season and is now in the process of taking his UEFA Pro License - successfully achieved by Chris Hughton last summer.
Working with players on a daily basis is an area where he feels stronger the more experienced he gets.
"I think so," he pondered. "I think I am definitely more confident about how the week is going to go and how I am going to structure it.
"You are always learning, I learned an awful lot in the first year and I think I've learned just as much this year - but I've had a group to work with.
"From the point of view of having a team together I've learned a lot more than I did in my first season.
"Looking at what we're going to have next year, I'm going to have a good number of boys together as well.
"I would think we will be looking to get them out on loan to give them experience. Then we will get them back here and assess if it's done them any good or if they've stood out."
Colin Calderwood believes that he has improved as a coach over the course of his two seasons back at the club.