Jack Dorsey, Co-Founder of Block, on His Biggest Leadership Mistake: Delegating Too Much.
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Jack Dorsey’s biggest regret at Block was delegating too much: Splitting Square and Cash App under separate CEOs looked like a scaling move, but it quietly turned the company into a holding company instead of one integrated financial platform. Delegation without a unifying thesis is a disaster waiting to happen. But my take is that the second the CEO is not driving the company with their own energy, but rather relies only on structure, entropy wins, and the company gets misaligned.
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](/BigBrainBizness)
Jack Dorsey, co-founder of Block, on his biggest leadership mistake: delegating too much. Reflecting on his time running his companies, Jack admits that over-delegation was the most consistent error he made, especially at Block. “Probably the worst case in any of these companies… just delegating way too much. Especially within Block, because I wanted to set a structure where we had multiple CEOs in this company, but I realized, oh man, we’re just building like a holding company now.” With a separate CEO for Square and another for Cash App, the structure pulled the business apart rather than bringing it together. Jack explains why that fragmentation undermined the entire premise of the company: “The value of our company is not these unrelated things that are growing at different clips. It’s how do we bring them together and really challenge the whole financial network entirely, because we have both sides of the counter. So why aren’t we structured that way?” The consequences went beyond strategy. The siloed setup created deeper organizational problems: “That I think led to just very differing cultures and values and execution levels, and that was a mess.” What stings most for @jack is how long it took him to act on the mistake: “The one thing that I probably consistently would have corrected would be just delegating too much… and I didn’t learn that fast enough. That’s the regret. I didn’t choose to learn from that fast enough. But when your entire company’s legible, it’s a very different equation.” Looking ahead, Jack predicts his future regrets will centre on a different question: whether he’s injecting enough of his own drive and direction into the organization. “My regrets going forward, if I were to predict them, would be: am I actually putting enough entropy into the system, enough of the intent into the system, to actually keep us relevant going forward? And that’s hence the shift.”
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1:00 PM · Jul 22, 202612.5KViews
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