The pair will lock horns when Hibs travel to Dundee today, with Lennon keen to make sure that the Dens Park side don’t pick up their first points of the campaign.
McCann gave up a secure job as an analyst for Sky Sports to take the reins at Dundee on a permanent basis this summer, after initially guiding the club to Premiership safety at the tail end of last season.
Lennon, who has done his fair share of punditry, admits he admires the 43-year-old for deciding to make the move into the dugout.
He said: “Neil is different, he is sort of learning on his feet.
“He cut his teeth at Dunfermline working with Jim Jefferies, who is a great sounding board. And now he’s taken the plunge, which has to be admired. I was surprised he left the job but I admired it as well.
“So he has rolled his sleeves up and taken it on and good luck to him.
“But no matter where you go, whether you are Brendan Rodgers, Jose Mourinho, myself, whether you’re at East Fife, it’s difficult, every job has its own pressures.
“Neil will have his targets and he’ll want to fulfil them. And knowing the enthusiasm he has for the game, until he gets points on the board he’ll be determined to make that happen.
“He was always very knowledgeable about the game, he played for a long time at some big clubs.
“And while he was doing the punditry he was assistant manager with Jim.”
McCann has joked that there could be some “needle” between both benches today after admitting that both he and Lennon are fiery characters. But Lennon, pictured, does not foresee any issues. He added: “I wouldn’t have thought so. Me, fiery?
“I played against him a few times and he was a great player who had a good career. He was a really class outside left, he went to Southampton and had a good time down there as well.
“I have known him a long time through football and through punditry as well. I wish him well, just not on Sunday.”