But he didn't expect it to happen so quick.
On April 19, Yzerman was named executive vice president and GM of the Red Wings and Holland, who had encouraged the move, was promoted to senior vice president and was to serve as a senior adviser to hockey operations after completing his 22nd season as GM.
On May 7, Holland was by the Oilers.
"I was looking forward to work with him," Yzerman said. "I really enjoy being around him, talking hockey with him, listening to his rationale, how he manages situations. I was really looking forward to that. But I know -- we talked about it -- he loves managing. He has a burning desire to do it.
"I think things happened very quickly, more quickly than even he expected. And I'm happy for him that he's happy."
In a recent wide-ranging discussion with NHL.com, Yzerman elaborated on life without Holland in Detroit, why he doesn't think teams can be built via free agency, and the future of veteran defenseman Niklas Kronwall.
You consider Ken Holland a mentor. What kind of legacy has he left on the Red Wings organization?
"At the end of the day, I understood where he's coming from. Mostly, he's happy about his move so we're all pleased for him. In the Detroit organization, he's done so much for us. Not only building Stanley Cup teams, all of us who have worked with him, he's been a friend, a father figure, a professional adviser to us all, and he's looked out for us all. We're all grateful for everything he's done for us and we're going to miss him."
Holland always stressed the importance of the NHL Draft, as did you when you were GM of the Tampa Bay Lightning. You have the No. 6 pick in the 2019 Draft, how key is it to hit on this selection?
"The Draft is so important. You have to acquire your talent some way. To do it through unrestricted free agency, you're not going to build a team that way. At least I don't think you can build a team that way. How you do it is acquire the young talent and try to develop them. I think we're fortunate to have a small core of the [Dylan] Larkins, the [Anthony] Manthas, the [Tyler] Bertuzzis coming. There's the foundation there and we have to add to it. They're all good young players."
Judging by those comments, should we not expect a big splash from the Red Wings in free agency?
"I've never used free agency to make a splash. I like when people use that term. I'm not trying to make a big splash, I'm trying to build a good team. And I don't think you can build a team through free agency. But collectively and selectively, you can improve your team."
Speaking of Mantha, he had a great performance for Canada at the 2019 IIHF World Championship with 14 points (seven goals, seven assists) in nine games. How big was that for his confidence heading into 2019-20?
'It was great, good for him. I thought all the Detroit players did really well in the tournament. Was happy to see them go and to all play well. For Anthony Mantha, I thought he progressed as he went on this past season. He finished the regular season strong as did all the young players did in Detroit. Now to go over to the Worlds to play with and against some of the best players in the world, I think it's a big confidence boost to play against these guys. I think it's a stepping stone to bigger and better things."