Andy Awford is to hold fresh talks with Jed Wallace to discover where his future lies.
The highly-regarded midfielder yesterday returned from a two-week holiday in the Caribbean.
Before jetting off, initial discussions had taken place over a fresh deal to keep the youngster at Fratton Park beyond the summer.
With Wallace’s contract set to expire on June 30, the Blues are desperate to convince him to remain and avoid a tribunal dictating any potential transfer.
Awford’s close relationship with the Academy product is seen as crucial in on-going negotiations.
And the Pompey boss is planning to meet him in the next 24 hours to canvass the 20-year-old’s current thoughts.
Awford said: ‘I have had a couple of texts from Jed while he has been on holiday and he returned yesterday.
‘We are now going to meet up and have a chat to see what the latest is.
‘The meeting is not going to take place at the Mayfair in London, it will probably be in Starbucks over a cup of coffee. It’s not going to be cloak and dagger!
‘We have a very good relationship, he respects me and I respect him – and I want him to stay, no doubt about that.
‘I understand where Jed’s coming from and if the right club comes in he will be interested, I get that.
‘But I do hope that Jed and Pompey can remain together and achieve success simultaneously – and I will be reinforcing and reaffirming my visions when we meet.
‘I am not going to put a gun to his head, I want players who are here because they want to be here.
‘I would just like for him to explain to me where he is at this moment in time and we, as a club, also need to bring him up to speed and see what he thinks.
‘He’s a lad with great ability and a great attitude, and I want him to stay to help us finish as high up the league as we possibly can.’
Wallace turned down a move to Peterborough in January in preference to seeing out his contract with Pompey.
The likes of Wolves, Leicester and Leeds have also been monitoring the progress of the former Lewes player over the past 12 months.
However, taking his age into account, a tribunal would be required to meet to set a compensation fee payable to Pompey if another club wanted to sign him once out of contract.
Awford added: ‘I have said all along, the problem Jed has got is he needs to have a club ready, willing and prepared to go to a tribunal. That’s his issue.
‘You just don’t know what the tribunal fees are going to be and another club has to be prepared to take that hit and take that risk.
‘Having said that, I am hoping it does not come to that.
‘I want him to stay right here with us.’