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.
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.
But I think the simplified version of this advice misses something important.
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.
That distinction took me some time to properly internalize.
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.
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.
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.
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.
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.
The hard part is that these two categories can look similar from far away. A leader has to develop taste for the difference.
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.
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.
The goal is to be close enough to improve judgment, but not so close that you become the owner of everything important.
That balance is difficult. It is also one of the central skills of leadership.
Hiring is half the job
Another lesson that became more obvious with time is that nothing compounds like great hiring.
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 manufacture any other way.
The inverse is also true. Nothing quietly drains an organization like avoiding a hard people call.
Most managers know earlier than they admit when something is not working. The signs are usually there: repeated misses, weak ownership, poor judgment, lack of trust, or a mismatch between what the role needs and what the person naturally brings. But because these situations are uncomfortable, it is easy to delay. You tell yourself the person needs more time, or that the context was unfair, or that the next project will be a better fit. Sometimes that is true, and patience is warranted. But often, the delay is not kindness. It is avoidance.
Over time, I came to believe that great teams are built through two related behaviors: hiring thoughtfully and correcting quickly when needed.
That can sound harsh, but I do not mean it in a ruthless way. In many cases, when there is a real lack of fit, moving on is better for everyone involved. I have seen people struggle in one environment and then thrive in another place that valued their strengths differently. A mismatch is not always a judgment on someone’s talent or character. Sometimes the role, the moment, the manager, the company, or the operating environment simply does not fit.
What is unfair is letting a mismatch linger long after it has become clear. in every case where I think I let things linger longer, everyone suffered: my team, me, the individual in question, as well as the business. In all cases where we made decision to part ways, the individuals in question always landed on a better trajectory than they were on.
Leadership requires enough care for people to be honest with them, and enough care for the team to protect the environment they are operating in. Avoiding the hard call rarely serves either side. It is important to treat people like adults, and not shy away from having tough conversations, as early as needed.
Assuming best intent without losing accountability
Earlier in my career, I was more likely to personalize organizational pain.
If another team blocked something, I might interpret it as politics. If a process made our work harder, I might assume the people behind it did not understand or did not care. If a decision seemed irrational, I would sometimes build a story around the individuals involved rather than the incentives and constraints they were operating under.
That instinct is understandable, but it is usually not useful.
One of the best pieces of management advice I received was to start by assuming best intent. Not because people are always right, and not because outcomes do not matter, but because assuming malice too quickly causes you to misdiagnose the problem.
Most organizational problems are not caused by bad people doing bad things. They are caused by misalignment, missing context, unclear ownership, competing incentives, fear, poor communication, or sometimes plain incompetence. Those are very different problems, and they require very different responses.
If you assume someone is malicious when they are actually missing context, you will create unnecessary conflict. If you assume a team is incompetent when they are actually responding rationally to the incentives around them, you will miss the system problem. If you assume politics when the real issue is ambiguity, you will spend your energy fighting shadows.
Assuming best intent does not mean being naive. It does not mean tolerating poor outcomes, avoiding accountability, or pretending that every conflict is just a misunderstanding. It simply means starting from a more productive place: people are usually rational actors operating within the context they have.
Instead of asking, “Why are they doing this to us?” you ask, “What are they optimizing for that we may not understand?” Instead of starting with blame, you start with diagnosis. Instead of escalating emotionally, you try to uncover the missing context.
Trust and accountability are often framed as opposites, but in practice they work better together. Trust helps you diagnose the problem accurately. Accountability helps you act once the problem is clear.
Clarity beats charisma
Charisma is powerful. A charismatic leader can energize a team, create belief, and make a difficult mission feel possible. That matters, especially in moments when an organization needs momentum.
But over a long enough time horizon, charisma without judgment becomes expensive. In fact, I have seen many charismatic leaders completely fail because they started acting in a way that was strategically misaligned.
The leaders I came to respect the most were not always the most magnetic people in the room. They were the ones with durable clarity. They could reason from first principles. They could separate the important from the merely urgent. They could look at a complicated situation and identify the few things that actually mattered.
Given the choice between a highly strategic, thoughtful leader who is less charismatic and a charismatic leader without depth, I would choose the former every time.
Energy can start things, but clarity sustains them.
This becomes more important as organizations scale because the cost of confusion grows. A small team can survive ambiguity through proximity and constant conversation. A larger organization cannot. If the strategy is muddy, different parts of the company will fill in the gaps themselves. Teams will make local optimizations. Roadmaps will drift. People will stay busy, but the work will not add up.
This is where leadership communication matters, but not in the performative sense. The point is not to sound inspiring. The point is to make the work more legible. What are we doing? Why does it matter? What tradeoffs are we making? What are we explicitly not doing? Where do teams have room to decide, and where do we need consistency?
Charisma can make people feel aligned for a moment. Clarity makes alignment survive contact with reality.
Put smart people together and create the conditions
One of the simplest leadership lessons is also one of the easiest to forget: put smart people together, give them a clear problem, and get out of the way.
This does not mean abandoning the team. It means resisting the urge to over-prescribe the answer before the people closest to the problem have had a chance to solve it.
Strong engineers, designers, product managers, data scientists, and operators often come up with better answers than a leader would have specified from above. But they need the right environment. They need a clear problem, real constraints, fast feedback loops, and enough ownership to make decisions without navigating a maze of approvals.
A lot of leadership is environment design.
If the environment is good, talented people compound. They build trust, move quickly, challenge each other, and develop better judgment through the work. If the environment is bad, even talented people spend their energy navigating confusion. They wait for permission, protect themselves, duplicate work, or optimize for the wrong thing because the system around them is unclear.
Leaders often underestimate how much of their job is simply removing the conditions that make good people less effective.
Sometimes that means clarifying ownership. Sometimes it means reducing the number of priorities. Sometimes it means forcing a decision that everyone has been circling for weeks. Sometimes it means protecting the team from drive-by feedback. Sometimes it means getting the right five people in a room and making sure they stay with the problem long enough to solve it.
The best leaders do not need to be the source of every good idea. They need to build the conditions where good ideas can survive and become real.
Ownership, not compliance
The people I saw grow the most over the years were not the ones who simply did what they were told. They were the ones who acted like owners.
They noticed problems outside their lane. They questioned decisions thoughtfully. They took responsibility for outcomes, not just tasks. They cared about whether the whole system worked, even when only one part of it was formally assigned to them.
Ownership is not the same as random motion. It is not arguing with everything, ignoring alignment, or treating every boundary as bureaucracy. High agency is valuable when it improves the system. It becomes exhausting when it creates chaos. And I saw my fair share of chaos creators as well.
The best people find a way to expand their scope while making the people around them more effective. They challenge without constantly derailing. They push without making everything about themselves. They take risks, but they do so in service of the broader mission rather than their own need to be seen as bold.
That is when careers really take off.
Compliance can make someone reliable, but ownership makes them valuable. The difference is whether they are simply completing assigned work or increasing the organization’s capacity to solve harder problems.
As a leader, one of your responsibilities is to create room for that kind of ownership. If every decision is tightly controlled, people learn to comply. If every risk is punished, people learn to hide. If every disagreement is treated as misalignment, people stop telling you the truth.
The environment has to reward people who think beyond the task while still respecting the need for shared direction.
That balance is where great teams live.
What I believe now
If I had to summarize my leadership lessons from a decade at Block, I would put it this way: leadership is the repeated exercise of judgment under conditions of ambiguity.
It is judgment about which details matter and which ones should belong fully to the team. It is judgment about who to hire, when to wait, and when to make a hard call. It is judgment about whether a problem is caused by people, process, incentives, strategy, or lack of context. It is judgment about when to intervene and when to step back. It is judgment about how to create an environment where smart people can do the best work of their careers.
The higher you go, the less your job is about having all the answers. That part is true.
But it is still very much your job to know where the important questions are.
And often, the only way to know that is to stay close enough to the work to see reality clearly.
Great insights!
I am a great believer of ownership over compliance too. Looking forward to reading more in this series.