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The 34-year-old, who played under McLeish during his first spell in charge of the national team, is due to hold further discussions next week.
McFadden scored a memorable goal as McLeish led Scotland to a famous victory over France in Paris, in a Euro 2008 qualifier in September 2007.
Former Celtic midfielder Peter Grant, currently Head of Youth Development at Fulham, has also been sounded out over a coaching role.
Grant worked alongside McLeish at Birmingham City, Aston Villa and Nottingham Forest, and worked with Scotland Under-20s at last year’s Toulon Tournament in France.
Alex Rae, who served as McLeish’s number two at Belgian side Genk, could also join the national team’s coaching set-up.
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McFadden, capped 48 times by Scotland, assisted Mark McGhee at Motherwell during the 2016/17 season.
McLeish, who quit Scotland in November 2007 after just ten matches to take charge of Birmingham City, signed McFadden from Everton during his time at St Andrews.
Speaking to BBC Radio Scotland, McLeish revealed that he had “spoken to a few people” about coaching positions.
“I’m hopeful that I can make some kind of progress in the coming week,” McLeish told BBC Sportsound.
“I’m coming back to Scotland on Tuesday and I’ll be doing everything I can in terms of getting the guys in, and looking ahead to the friendly games.”
Scotland host Costa Rica on March 23 before travelling to face Hungary on March 27.
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