The Hard Thing About Hard Things

Every founder starts with a pristine vision that inevitably shatters against the chaotic reality of the market. This collision produces what is known as the Struggle, a permanent state of tension where the leader is in over their head, resources are vanishing, and the initial dream feels like a nightmare. The Struggle is not a failure of leadership but the inherent condition of building a technology company. Operating in this domain requires accepting that there is no formula for survival and no easy answer to complex dynamic situations.

Greatness emerges entirely from how a leader navigates the Struggle. The primary objective is to keep the company alive long enough to find a solution that seems impossible today. Leaders must learn to share every existential burden they can, maximizing the number of brains working on a problem rather than internalizing the collapse.

A fundamental distinction in management is recognizing whether a company is operating in peacetime or wartime. Peacetime occurs when a company has a massive advantage in an expanding market, allowing the leader to focus on broad creativity, cultural exploration, and long term optimization. In peacetime, the organization can afford debate, autonomy, and an emphasis on efficiency.

Wartime triggers an entirely different operating system. A wartime company faces an imminent existential threat from competitors, macroeconomic shifts, or dwindling capital. In this state, survival depends on absolute focus, immense speed, and strict adherence to a single mission. The leader must transition into an authoritative commander, abandoning democratic consensus in favor of making rapid, critical choices to keep the organization alive.

When a company starts losing its major battles, truth is often the first casualty. Leaders frequently feel overwhelming psychological pressure to shield their employees from bad news, projecting a sunny demeanor to maintain morale. This artificial positivity destroys trust. Employees are highly intelligent and usually recognize fatal issues long before leadership addresses them openly.

A functional organization demands brutal transparency. In any human interaction, the required amount of communication is inversely proportional to the level of trust. By telling the unvarnished truth, the leader validates the reality employees already perceive, preserving trust while mobilizing the entire workforce to solve existential problems. Bad news must travel fast, and sweeping failures under the rug only ensures the company will die quietly.

Survival and success depend on taking care of people, products, and profits, strictly in that order. Taking care of the people means building a genuinely good place to work, where politics do not overshadow merit and bureaucratic processes do not choke out creativity. When a company is succeeding, people stay for the financial upside and the prestige. When the economics disappear, the only thing that keeps an employee from walking out the door is the knowledge that they are valued and their work environment is sound.

If a leader fails to maintain a strong internal environment, the best talent will flee at the first sign of a downturn. This triggers a death spiral where a declining valuation pushes more top performers to leave, further diminishing the company. Prioritizing people ensures the foundation holds firm precisely when the product struggles and profits vanish.

Startups operate in a continuous race against time, leading many executives to mistakenly view employee training as an optional luxury. In reality, training is one of the highest leverage activities a manager can perform. A few hours of focused preparation can yield hundreds of hours in increased productivity across a team. Training cannot be optional; it must be mandatory to ensure performance management, product quality, and employee retention.

This effort must cover both functional and management training. Functional training equips employees with the exact historical and architectural nuances of the product, while management training establishes explicit expectations for leadership behaviors. If a company fails to measure the productivity gains from this education, it loses sight of its ultimate goals, creating a chaotic environment where raw talent remains underdeveloped and managers fail to provide structured feedback.

When hiring executives, the most devastating error is relying on consensus decisions. Group interviews naturally orient toward finding flaws, leading the company to hire candidates who lack obvious weaknesses but also lack exceptional abilities. To build a world class organization, a leader must hire strictly for overwhelming strength in the specific areas the company desperately needs, willingly tolerating acceptable weaknesses in the process.

A leader must fully understand the open position before trying to fill it. The most effective way to grasp the requirements of a role is to step in and act as the executive yourself. Once the necessary strengths are identified, the ultimate hiring choice must be a lonely decision made by the chief executive, ignoring the safety of consensus to secure a candidate capable of delivering extraordinary results.

Firing an executive is rarely a simple case of incompetence; it is almost always a failure of the interview and integration system. A leader might have hired for scale too soon, selected a candidate based on a generic job description, or completely failed to integrate the new hire into the existing operational flow. The first step in removing an executive is performing a rigorous root cause analysis to understand exactly how the system failed.

Once the decision is made, the execution must be clean, decisive, and highly prepared. The leader must inform the board to secure support and approve a severance package, then communicate the decision to the executive using absolute, non negotiable language. The overarching goal is to remove the executive swiftly while entirely preserving their dignity, followed immediately by communicating the change to the rest of the company to prevent rumors and confusion.

When a company fails to hit its financial targets and must reduce headcount, the execution of the layoff defines the surviving culture. Delaying the decision causes devastating leaks that paralyze the workforce. The leader must move with absolute speed, taking public responsibility for the failure rather than framing the layoff as a performance cleanup. Trust is the ultimate currency, and blaming the exiting employees instantly shatters the trust of the people remaining.

The most critical operational rule of a layoff is that managers must personally fire their own direct reports. Outsourcing this heavy burden to human resources or external firms is an act of cowardice that ruins managerial credibility. After the layoff is executed, the chief executive must be highly visible and present, facing the surviving employees to answer questions and establish a clear path forward.

Intelligence is a critical asset, but when highly intelligent people lack reliability or basic teamwork, they become active threats to the organization. A leader will inevitably encounter brilliant employees who manifest as heretics, flakes, or jerks. The heretic uses their massive intellect to actively look for faults and build a case against the company rather than fixing its weaknesses. The flake possesses immense potential but cannot be trusted to deliver work consistently.

The jerk is particularly destructive at the executive level, using abrasive and asinine behavior to cripple cross functional communication. While a leader might occasionally tolerate a highly disruptive genius if their individual contribution is irreplaceable, this mitigation requires massive personal energy. The organization cannot function if toxic brilliance is allowed to pollute the broader culture.

Corporate culture is not established through motivational speeches or standard office perks. True culture is a behavioral design point intended to influence how employees operate when nobody is watching. To embed a core operational value, a leader must implement mechanisms that are trivial to execute but possess significant shock value.

A highly visible, provocative rule forces employees to confront and internalize the company's underlying philosophy daily. If a company demands extreme frugality to maintain low prices for customers, creating desks out of cheap wooden doors sends an unmistakable message that words alone cannot convey. Effective cultural programming requires designing unexpected, slightly bizarre constraints that perfectly align with the ultimate mission of the business.

The most difficult skill an executive must master is managing their own psychology. The immense pressure of running a complicated human organization causes many leaders to either internalize every failure completely or emotionally detach entirely. The ideal state is to remain highly urgent without becoming insane. To separate emotion from logic, a leader should aggressively write down their thoughts, turning a psychological burden into an objective document that can be analyzed and solved.

When navigating near total disaster, the leader must focus on the road, not the wall. Staring at the thousand things that could sink the ship guarantees a crash, while focusing entirely on the narrow path forward allows the company to maneuver through the crisis. The greatest leaders are not defined by pristine strategic perfection, but by their absolute refusal to quit when the pain of the struggle becomes nearly unbearable.