Frank Lampard said Mason Mount would sign a new contract at Chelsea "in an ideal world" but accepted the situation may not be so straightforward for the England midfielder.
The 24-year-old is about to enter the final year of his contract and has been heavily linked with a move away from the club he joined aged six.
The parties have been in talks for much of the season over a new deal but have failed to reach an agreement, and it seems increasingly likely that he will leave with Liverpool and Manchester United reportedly interested.
If no extension is agreed it will mean he is free to begin negotiating with other clubs at the start of next year, but Chelsea could look to sell in the summer to avoid the possibility of the academy graduate leaving on a free transfer.
As a youth product any sale would be recorded in Chelsea's accounts as pure profit, which would assist in their bid to remain within Financial Fair Play rules following a mammoth transfer outlay over the last 12 months.
Lampard, who gave Mount his first-team debut during his first spell as manager in 2019 and has frequently voiced his admiration for him, said the club must work to show academy players that there is a path to the senior side regardless of Mount's immediate future.
"It's a hard one for me to comment on because I'm not inside Mason's head and from the club's point of view my role is clearly what it is," said Lampard, who takes his side to face Manchester United at Old Trafford on Thursday.
"In the practical sense it's completely between both sides on that front. I'm not surprised because this is football. Does everyone know that I really like Mason Mount as a lad and as a football player? Yes, sure, of course they do.
"I wish him the best personally and sitting here with my Chelsea top on now, I've seen what Mason has delivered at this club. But we'll see.
"I think, to be fair to this club in the last few years particularly we've seen the hard work of the academy for a long, long time, people like (academy head) Neil Bath and (head of youth development) Jim Fraser.
"(Players) have come through and been very good and now it's delivered in terms of people that are affecting the team, or have been sold on for big money.
"That's been a real positive so I think it's important we try and keep that feeling that younger players can see a pathway to get into the Chelsea team and play for the team they will grow to love, which is Mason, which is Reece James etc.
"Of course in an ideal world those players stay with the club, but again in modern football it isn't always that clear."
Lampard also heaped praise on defender Thiago Silva and pointed to the Brazilian's influence as the team looks to find direction following a miserable season.
Silva signed a new deal in February that will keep him at Chelsea until summer 2024 by which time he will be almost 40.
With so many new youngsters having joined the club in the last 12 months, Lampard said the former Paris St Germain player can be a role model as the team's raw talent matures.
He said: "It's an amazing achievement physically. I played until 38, 39 but the last couple of years in MLS I started to understand that my body was telling me 'don't do it anymore'.
"I've got nothing but praise for the career that Thiago has had and to see him at this level, he's an inspiration to the players, who could and should learn a lot from him in terms of how he looks after himself off the pitch and how he approaches training daily and what he demands from his team-mates.
"That's something that has to rub off at this club more at the minute. He's been special.
"He's demanding and that's a good thing. I wouldn't say he's the most vocal, each to their own personality wise. Some players will be really vocal, he's not that but he's one of these players that leads by example.
"Players that play next to him or with him understand what the levels are. If you don't (give) them you'll get a look or a talk or something. He's not a screamer and shouter but he certainly demands from people around him and I think that's a good thing.
"At this level, you need players like that, and they're not everywhere."
Read More: Frank Lampard: Chelsea must avoid knee-jerk decisions if they are to recover | PlanetSport