And the Blues head coach says he's been 'inspired' at learning just how much the club means to the fans.
Cowley was present at the latest Isle of Wight Pompey Supporters’ Club meeting on Wednesday – just days after 900-plus fans travelled to Accrington for the 2-2 draw at the Wham Stadium.
Since arriving at the club in March, initially on an interim basis to replace sacked former boss Kenny Jackett, the 43-year-old has regularly faced up to fans from across the area and beyond at such organised events.
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Despite what has been a far from ideal start to the League One campaign, with his side currently sitting 16th in the table, Cowley has accepted invitations to attend several supporters' club's meetings.
The Blues boss believes attending these gatherings has allowed him to gain a thorough understanding of what the fans want from him and his squad.
And Cowley said it's been a 'privilege' to be able to converse with so many Pompey supporters, who clearly love their club.
He said: ‘I’ve been inspired by how much the football club means to so many.
‘There have been lots of good questions on the team, how the team is playing, certain individuals.
‘It’s been great - it’s a privilege to go.
‘I managed a very small club in Concord Rangers and I think we started with 62 supporters in our first game.
‘I think we had more supporters’ clubs than what we had supporters!
‘It just says so much about this great club and how much it means to so many.
‘I think is always really important that we go out, we speak to them (the supporters) and we listen to them.
‘Ultimately, it’s their football club and it’s a privilege for us to be here and it’s great to understand what they want.’
Cowley has also attempted to utilise his presence at the various forums to offer supporters an insight into his vision and ideas for the club.
He said it's been nice for the Fratton faithful to get a closer examination of him and his thinking rather than just a bite-sized snippet on a match-day.
‘It’s also good for me to come and explain to them how we’re working and what’s going on behind the scenes,’ added Cowley.
‘They only ever see the matc-hday and we all get defined by that 90 minutes at three o’clock on a Saturday.
‘There’s obviously an awful lot of work that goes in and around that.
‘A lot of the work is hopefully going to create a legacy and long-term success for this club moving forward.’