Danny and Nicky Cowley have taken the Fratton Park reins for the remainder of the season following Kenny Jackett's departure.
They've been tasked with guiding the Blues into the League One play-offs after a poor run of form led to Jackett being relieved of his duties.
The Cowleys got off to a perfect start on Saturday with a 2-1 defeat of top-six rivals Ipswich at Fratton Park.
Having achieved two promotions with Lincoln City, there's plenty of positivity among supporters that the duo can lead Pompey back to the Championship after a nine-year hiatus.
But speaking on talkSPORT, Jordan is 'not sure' that will happen after the Cowleys were sacked by Huddersfield last season despite keeping them in the Championship.
‘You want to hear them say they're going to be successful but I'm not sure,’ said Jordan.
‘I'm not sure why they went to Huddersfield in the first place. I like Phil Hodgkinson, I think he's a decent chairman, I'm not quite sure why it didn't work out there aside from the fact their win record was very poor.
‘And I'm not so sure about this. I think they talk a very good game and they did very good things at Lincoln.
‘But Lincoln, Portsmouth Huddersfield – Lincoln is a different sized club with different expectations, different governance, different ownership, different ambitions.
‘Portsmouth are a big club waiting to happen again and they have a task on their hands.
‘They will go to Portsmouth and they'll either be good for Portsmouth or not. We'll see over 14 games.’
Ex-England international Trevor Sinclair worked with the Cowleys at Lincoln.
He's confident they can be a hit on the south coast.
Sinclair said: ‘I've worked with them and they're workaholics. Their due diligence, planning and attention to detail are second to none.
‘I was with them when they were at Lincoln. They understand football clubs and involving the community. Lincoln, as a city, got involved in that football club and they understood it enhanced the football club and enriched the environment for players with the interaction with the fans.
‘I was surprised they weren't successful at Huddersfield because they believe in their methods, beliefs what they do will improve players, performances and get results.
‘Both Danny and Nicky are great guys and when you see them working on the training pitch, you understand why players improve.
‘I’m sure Portsmouth and Mark Catlin will feel very privileged at the moment.’
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