The two-time former manager has found himself with the reins at contrasting points of Chelsea's development under different owners, the latter being at the end of last season in a temporary capacity with a bloated squad.
Back in 2019, though, Lampard took over when the club had been handed a transfer ban, resulting in a number of youngsters being promoted to the senior setup.
Many of them have proven to be a success, either in terms of appearances made or money generated from a subsequent sale, but only Reece James remains from the crop that featured at the start of Lampard's first reign.
As well as players wishing to find first-team football elsewhere, new owners Todd Boehly and Clearlake Capital have been open to using the exits of academy graduates to substantially bolster their FFP position.
In terms of academy graduates who remain in Mauricio Pochettino's squad, Levi Colwill, James, Ian Maatsen, Conor Gallagher and Armando Broja are in the Argentine's plans, while there is a question mark over Trevoh Chalobah.
Nevertheless, Lampard has admitted that he expected there to be more of his crop of starlets still at the West Londoners, the likes of Marc Guehi, Fikayo Tomori, Billy Gilmour, Mason Mount and Tammy Abraham having since moved to pastures new.
Speaking to Sky Sports' Monday Night Football, Lampard said: "I'm slightly surprised by it. At that time, I would have expected more players to stay longer, but every player has a different story. Fikayo Tomori, I wanted to keep, but at the same time, I had five centre-backs, and he was in and out of the team, was frustrated and wanted to leave. It happens.
"Within that, I did think that some of the players would stay. I think, in the modern world, the ownerships of club and sporting directors certainly, are not seeing academy players in the same way as what I saw and Chelsea fans may see.
"I think when they come to Stamford Bridge, they feel a real connection with players as they come through. I thought that was a real strength of that time (2019-2021) when I left the club because you could see players that are going to be there for a number of years.
"Maybe they have lost that to a degree. We were talking to Conor Gallagher 20 minutes ago, I like that, a boy that has come through. It's not the be all and end all, you need good players and need to succeed, but I felt that more players would have stayed the course."
Gallagher has been linked with a transfer away from Chelsea, his future in question up until the final day of the summer transfer window.
The England international is now captain in the absence of James and Ben Chilwell, Gallagher leading Chelsea to a 2-0 win over Fulham on Monday night.