A Decade at Block, Part 1: The Best Leaders Know Which Details Matter
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A Decade at Block, Part 1: The Best Leaders Know Which Details Matter<br>What I learned about the best leaders at Block
Rahul Thathoo<br>Jul 05, 2026
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This is the first in a series of blog posts I intend to write, capturing some lessons I learned after spending over ten years at Block, also known as Square.<br>There is a popular idea that as leaders grow in scope, they should move further and further away from the work. The language around this usually sounds sensible: set context, hire great people, delegate, operate at the right altitude, don’t micromanage, don’t get pulled into the weeds. And there is some truth in all of that. A leader who tries to sit in every meeting, review every decision, or personally inspect every project will eventually become the bottleneck they were supposed to remove.<br>But I think the simplified version of this advice misses something important.<br>The best leaders I worked with were not detached from the work. They were selective about where they went deep. They could zoom out and understand the broader system, but they also knew when a specific detail mattered enough to warrant their personal attention. They understood that some details are just noise, while others are load-bearing. The job was to know which details were worth caring about.<br>That distinction took me some time to properly internalize.<br>When you are earlier in your leadership journey, being close to the details is often straightforward. Your scope is smaller, your team is closer to the work, and your personal knowledge of the product or system is usually one of the reasons you are effective. As your scope grows, the challenge changes. You can no longer know everything, but you still have to know enough. You have to develop a sense for where reality is hiding, where risk is accumulating, and where the official status update is probably too clean.<br>At scale, leadership is not distance. Leadership is judgment. Amazon has a tenet which says leaders are right, a lot. In my sense is they are often right about their judgment of where to go deep and where to not.<br>Staying close to the work that cannot fail
Every organization has a small number of things that truly cannot fail. These might be core product flows, fragile systems, major strategic bets, important launches, or people decisions that will shape the team for years. In those areas, staying too abstract is dangerous.<br>I have seen leaders use “empowerment” as a reason to avoid getting close to uncomfortable details. I have also seen the opposite failure, where leaders involve themselves in everything and accidentally train the organization to wait for their opinion before moving. Both are mistakes, but they are not the same mistake.<br>Some details are genuinely not worth your time. The team should own them, and your involvement will only slow things down. Other details are early warnings. A confusing customer experience, a brittle system dependency, a repeated hiring miss, a team that is quietly losing trust, or a strategic bet that everyone supports in public but nobody can explain clearly in private — these are not “the weeds.” These are the work.<br>The hard part is that these two categories can look similar from far away. A leader has to develop taste for the difference.<br>This is also where org charts can become misleading. Reporting lines, skip levels, ownership boundaries, and escalation paths are useful tools, but when something important is at risk, the formal structure matters less than the truth of the situation. If a core product flow is broken, or a major initiative is drifting, it does not really matter whether the problem is technically “under” you. The responsibility of leadership is to make sure the important work is understood, supported, and moving in the right direction.<br>That does not mean barging in and taking over. In fact, that is one of the easiest traps to fall into. When a leader spends too much time in a critical detail, they can unintentionally steal scope from their team. They can reduce the agency of the people who should be growing through the work. They can create an environment where everyone is optimizing for the leader’s approval rather than for the customer, the system, or the business.<br>The goal is to be close enough to improve judgment, but not so close that you become the owner of everything important.<br>That balance is difficult. It is also one of the central skills of leadership.<br>Hiring is half the job
Another lesson that became more obvious with time is that nothing compounds like great hiring.<br>A strong hire does not just add capacity. They raise the quality of the room. They improve the judgment of the team around them. They reduce the amount of process required because they bring ownership, taste, and clarity. The best people make problems feel more solvable. They create momentum that is hard to...