In the race to scale, tech companies often focus on innovation, sales, and customer acquisition....
When it comes to building a high-performing leadership team, most CEOs are told to embrace being challenged. But Riccardo Pellegrini, CEO of Knode AI and former Amazon/AWS leader, offers a more nuanced view: challenge only works when it’s paired with judgment, accountability, and the willingness to commit.
In a 2-minute conversation on Wisdom From Wizards, Riccardo shared what he looks for when building a team culture that can question strategy without stalling progress.
“You want people who know what to challenge and when — and who can actually offer a better alternative, not just punch holes in the plan.”
This mindset, he explains, starts during hiring. At Knode AI, Riccardo’s team explicitly tests for this kind of discernment in interviews. It’s not enough to be smart or opinionated. The bar is higher: bring thoughtful criticism, offer a better option, and be ready to row in the same direction once the decision is made.
Riccardo’s framework reflects a rare blend of intellectual rigor and operational pragmatism:
- Challenge with purpose
- Propose superior alternatives
- Disagree and commit once a path is chosen
It’s a powerful leadership principle — especially for tech scaleups facing constant pressure to move fast while staying aligned.
Wisdom From Wizards is brought to you by Caribou Strategic, helping tech scaleups stand out and succeed.
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