Woodside will need to, given the magnitude of the task facing the 31-year-old. While Penney is a known quantity through his previous stint with the Breakers, his time with the Tall Blacks and a successful last season in Illawarra, little is yet known about Woodside's ability to replace Cedric Jackson.
But Penney, whose recommendation was key in Woodside coming to the New Zealand club, was confident his mate possessed all the attributes to account for the departure of one of the Breakers' best.
"He's a really high-level European point guard," Penney said. "I don't know what else you could ask for, to be fair. He'll probably say 'I'm not quite Russell Westbrook' but I don't think he was available.
"He plays really hard at both ends of the floor, he's a smart basketball player and a really good leader, really vocal. He should lead the boys round the court really well."
Penney would know. The pair met in Ankara in 2012, strangers in a strange land who quickly became friends. The two men and their partners spent the season "attached at the hip" and developed such a strong relationship that, in 2015, Woodside was able to lure Penney to play together again in Seville. And now the shooting guard has returned the favour.
"We needed a point guard and I said to [coach] Pauli [Henare] and [general manager] Dillon [Boucher], 'what about Ben Woodside?' And they said, 'yeah, can you get him?' and I was like, 'I don't know but I'll try'. We've got a way to convince each other and the timing was perfect."
Perfect for Woodside, who admitted he had put many miles on the clock in his eight-year professional career. Only days after arriving, he was wishing he had found the Australian NBL -- a six-month season of high-quality basketball -- earlier and was grateful to again be playing alongside his fellow guard.
"We developed a great relationship," Woodside said of Penney. "He's a great guy to have down here and we kind of know each other's role on the floor. It seems like wherever he is, I know where he's at, and I think he kind of knows where I'm at. Hopefully that can benefit us."
Woodside believed that type of fluency spread beyond the back-court and throughout the Breakers, acknowledging the high expectations set at the four-time champions but confident the group could reach those lofty levels.
"We mesh well," he said. "We've got a lot of good character guys who want to work hard for each other, and that builds the team chemistry."