Both coming from Launceston's TSL side, the pair played varying roles in the Devils' inaugural Talent League minor premiership before getting selected number two (McKercher, North Melbourne) and 17 (Leake, GWS) respectively.
Webberley stressed that there were many people besides himself that were crucial to the players' development.
"It takes a village to raise a child and our draft team have a lot of people involved, so it's just a great celebration for our state in general," he said.
With McKercher showing promising signs from an early age that AFL was within his grasp, Leake was something of a late bloomer with the recently-turned 18-year-old bolting up the draft order from early-season predictions.
"Both probably had a bit of a different journey, I've had a lot to do with Colby over the past 24 months, whereas James has been a little bit different, he was in our program, then he went back to Launceston," Webberley said.
"He was playing under-18s last season and credit to (Launceston TSL coach) Mitch Thorp, he saw the signs of real potential in James and got him up into the senior team at the back end of last season where he played in a premiership.
"Then he came back into our program this year and just hasn't put a step wrong and he's gone from strength-to-strength throughout the year across multiple positions across the ground, while Colby has always been a high-end talent for a period of time and his last 24 months has been extremely consistent and at a very high level."
While their journeys to AFL football have been different, the teams which they will be joining are even more contrasting, with McKercher's Roos finishing in the bottom four for the fourth-straight season, compared to Leake's Giants who lost their preliminary final against Collingwood by just one point.
While Webberley accepted it would be harder for Leake to break into the Giants' 22, he expected him to see regular game time.
"One of his greatest strengths is adaptability, but for James early on I think he'll settle down at half-back, where it sets him up for how he plays the game," he said.
"He reads the game extremely well defensively, but I think the more comfortable he gets to the level, I think then you'll see that flexibility come to the fore."
Plenty more midfield minutes are likely to head the way of the Kangaroos' first pick of the 2023 draft, and Webberley suggested that McKercher will play a key role in a resurgent season at Arden Street.
"We've seen the emergence of GWS this year and other clubs where when success comes, it can come extremely quickly," Webberley said.
"So I think although North Melbourne may have struggled for the last couple of years in terms of results, I think they've got a really good platform and foundation to launch into the next phase of their development."
As for what Webberley wants them to remember:
"Be yourself and put yourself on show. They're both high on character and they both got selected in the first round for a reason, so I think go there and be a sponge."
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