The team-building secrets this Sydney to Hobart winning CEO swears by

which examines personality types and how they’re best suited to different roles, including leadership.

He likens his own personality type to that of Captain Cook, always exploring and wondering what extreme challenge – whether it be ocean sailing, or skydiving, his other main sporting interest – he can face next.“Having a highly connected and motivated team is crucial. We use the same apps in our business as the sailing team to achieve that,” Winning says.“We measure crew sentiment, emotion, and how they’re going week-to-week.

But, perhaps surprisingly given his intense schedule, the Sydneysider is not a morning person. With advisory board members stationed in Austin, Texas, and London, Winning works late into the night.He used to catch between 120 and 130 flights each year pre-pandemic. To survive this washing machine of a sleep cycle, Winning trained himself to operate successfully on four hours of sleep for days at a time before banking sleep when he has time to catch up.

Winning doesn’t hesitate when asked if he’s keen to race Andoo Comanche at next year’s Sydney to Hobart: “It’s a great group, it’s a great team, we’re enjoying it, and I think if we can win it again.”The boat’s name – as well as that of his online shopping destination – is a reference to a boat used by his father and grandfather: Yandoo.

Source: News Formal (newsformal.com)

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