Some 14 players are out of contract at the end of the season, with the likes of Adam Reach, Tom Lees, Kadeem Harris and red-hot youngster Osaze Urhoghide yet to agree deals to stay on at the club.
Monk, who was sacked as Owls boss in November after 14 months in the Hillsborough hotseat, was speaking as part of Sky Sports’ coverage of their 5-0 demolition of Cardiff City on Monday and admitted the uncertainty created is far from ideal for any manager.
“Obviously in my time there that [having players close to the end of deals] is a strategy the club has implemented since the owner has been there but of course it makes it difficult,” he said.
“I had 11 [players] in my last season there and there is 14 again this season. I think there were a lot out of contract in the previous seasons and the problem is it creates uncertainty. It creates uncertainty to players whether they are going to be there or not.
“I know everyone will say you are always playing for your future but it is not quite as simple as that.”
Big-name players such as Steven Fletcher, Fernando Forestieri, Morgan Fox, Atdhe Nuhiu and Sam Hutchinson came to the end of their contracts under Monk last summer.
And the former Owls boss made it clear he did not see the business sense in having valuable assets come close to the end of their deals.
He said: “Players prefer security and then they know what they are working towards and what that club is on board with and, of course, as you get to the later stage of the season there are lots of players out of contract and commitment is what you are asking for. It creates difficulties in that sense and from a business point of view.
“There are young players on there, potential assets, and trying to create a business plan or model, you leave yourself wide open to a lot of things in terms of losing out on certain assets that's for sure.”