There have been a few bumpy moments.
No doubt, there have been one or two rows along the way as well.
Yes, the relationship between chief executive and manager rarely travels a smooth course.
But, a season down the line after appointing Steve Cotterill as boss, David Lampitt insists it has been a ‘pleasure’ working with the 46-year-old.
Not that it’s been plain-sailing along the tough path the pair have trodden as the club have emerged from administration.
Lampitt admits there has been a few disagreements as Cotterill fights to get the best conditions for his team in an unenviable terrain for a manager.
He’s adamant the man from Cheltenham was ‘the only choice’ when completing the process of announcing Avram Grant’s successor last June.
And, 11 months on from that, he remains certain that is still the case.
The common goal of Pompey emerging from a dark period, as fans wait for the protracted takeover of the Convers Sports Initiatives group to be completed, has underpinned the relationship between the pair.
Cotterill is shifting impatiently on that front, with the hope a takeover could be sealed this week.
That has naturally led to some agitated calls between the pair, but Lampitt believes that is indicative of both men wanting the same thing – the best for their football club.
Lampitt said: ‘From my point of view, it’s been thoroughly enjoyable working with Steve.
‘He’s a real character, he’s incredibly passionate about the game and he’s incredibly knowledgeable about the game.
‘I’ve certainly learned a few things from him in the course of the last 12 months.
‘I’d like to think he’s learned a few things from me, too!
‘It’s been a pleasure to work with him.
‘That doesn’t mean we always see eye to eye.
‘We have a mature relationship, though.
‘Chief executives and football managers will not always agree on everything.
‘I think we’ve got a healthy enough understanding that we know we want the same things, ultimately.
‘We both want the success of Portsmouth Football Club and are committed to that.
‘That ambition overrides anything else and we are determined to achieve that.’
Lampitt knows Cotterill has undoubtedly faced more trials than virtually any other manager in his first campaign as boss.
A crazy pre-season, a transfer embargo and squad restrictions – including the contract impasse which forced the absence of Michael Brown and Richard Hughes – have been just some of the issues thrown in his direction.
Cotterill admitted he’s known nothing like it in his time in the game.
But he is certain tackling the incessant obstacle course placed in front of him has made him a better manager.
Lampitt believes negotiating the problems Pompey have had to deal with, and avoiding the short-cuts which have landed the club in the mire in the past, will make future success that much sweeter.
He said: ‘We’ve all had some challenges to deal with this season.
‘Steve has had more to deal with than many managers at many other clubs.
‘That has been the same right across the board, really.
‘There has been an awful lot going on here for everyone to handle.
‘We’ve had to suck up an awful lot.
‘But we have come through that and hopefully that will hold us in good stead moving forward.
‘We all want success and crave it.
‘But, like any success, when you fight hard for it, it becomes more valuable.
‘Sometimes doing things in the right way, the hard way, can be difficult but it can be worth more in the end.’