Michael Jordan apparently second-guessed himself while passing down his basketball knowledge to Kobe Bryant early in his career.

NBA reporter Jackie MacMullan discussed her conversations with Jordan for her podcast the Icons Club during an appearance on The Hoop Collective (6:30):

"Kobe called Jordan sometimes in the middle of the night...and he would be asking him these very specific questions and Jordan would be talking to him and lie back down and say, 'Why the hell am I doing this? Why am I giving this kid all my secrets? I've never done this with anybody else. Why am I doing it for this kid?'"

As MacMullan explained, Jordan was "flattered" by Bryant trying to emulate him as he developed into a superstar. 

Bryant entered the league in 1996, playing for the Los Angeles Lakers during Jordan's final two years with the Chicago Bulls. He earned his first All-Star selection in 1997-98 while Jordan won his final MVP and last of his six NBA titles.

While Jordan was extremely competitive throughout his career, he seemingly had a soft spot for Bryant.

"Losing Kobe was a huge blow for him, they really were very good friends," MacMullan said of Bryant's 2020 death. 

It seems Kobe took advantage of the advice, at least, going on to earn 18 All-Star selections with five NBA titles during his Hall of Fame career.