Asher's Blog

As a company grows, the founder faces a difficult question: what should I continue to own personally, and what must I allow other people to lead?

It is tempting to answer with a simple rule. Some people say the founder should gradually remove himself from operations and become purely strategic. Others argue that great founders remain involved in every important detail. Both ideas can be right in one company and disastrous in another, because the correct answer depends on the nature of the business, its stage, its principal risks, the founder’s distinctive abilities and the quality of the leaders already in place.

The answer also changes over time. A founder may need to lead product intensely during one phase, spend the next phase building distribution, and later concentrate on capital allocation, senior leadership and external relationships. What deserves the founder’s direct attention today may become someone else’s responsibility in two years, while an area previously delegated may require the founder to return when standards decline or the company enters a new strategic chapter.

This is why the decision cannot be made by ego, fatigue or fashion. It requires judgment, experience and a clear understanding of where the founder’s involvement creates disproportionate value.

The objective is not to remain involved in everything. It is to remain deeply involved in the few things that determine whether the company becomes what it was created to become.

The founder’s role should change before it becomes a bottleneck

In the earliest stage of a company, the founder is usually involved in almost everything. The founder speaks with customers, shapes the product, recruits the first employees, sells, raises money, approves expenses, handles crises and often performs work that will eventually belong to several different departments. That breadth is not necessarily a management failure. It is one way the company learns.

The founder is gathering information that has not yet been organised: why customers buy, why they leave, which product promise matters most, where money leaks, who can be trusted and what kind of culture the company will require. Delegating too early can cause these lessons to be filtered through people who do not yet understand the business deeply enough.

As the organisation expands, however, the same behaviour can become a constraint. Every decision waits for the founder. Leaders stop exercising judgment because they expect to be overruled. Employees learn that the formal structure does not matter because the founder is the real owner of every function. The founder becomes exhausted, while the company appears busy but cannot move faster than one person’s attention.

Growth therefore requires a transition from doing the work to designing the system in which excellent work is done. The founder moves from personally resolving every issue to choosing leaders, clarifying standards, allocating capital, removing obstacles and ensuring that the most important decisions remain coherent with the company’s purpose.

This does not make the founder less operational in the sense of becoming detached from reality. It means becoming operational at a higher level of leverage.

Brian Chesky did not simply become Airbnb’s chief product officer

I remember listening to Brian Chesky discuss how he became deeply involved in product again at Airbnb. The lesson is important, although the precise description matters. Chesky did not formally stop being CEO and simply become the company’s chief product officer. During and after the disruption of the pandemic, he reorganised Airbnb around functions, reduced layers and centralised major product planning, becoming much more personally involved in the product and the quality of its execution.

In later conversations about what became known as “founder mode,” he explained that deep involvement should not be confused with the founder arrogantly doing everybody else’s job. In a detailed Decoder interview, Chesky described an organisation in which he collaborates closely with leaders on product and major decisions instead of hiring executives and then treating their functions as territories the CEO should never enter.

That distinction is useful. A founder can remain deeply involved in product direction without personally writing every product requirement, managing every designer or making every implementation decision. The founder may own the standard, customer promise, strategic sequence and final coherence of the experience, while an excellent product leader owns the organisation, discovery process, roadmap mechanics and daily execution.

In other words, being close to the work is not the same as refusing to build leadership beneath you.

For a product company, it may be rational for the founder to remain unusually close to product for many years, especially when the founder has distinctive product judgment and the product expresses the company’s core identity. Yet another company may be driven more by logistics, risk, operations, treasury or distribution. In that business, the founder’s highest-value attention may belong somewhere else.

Start with the nature of the business

The first question is not, “What do famous founders retain?” It is, “What determines success or failure in this particular company?”

In a software or consumer-technology business, product quality, speed of learning and user experience may be the central source of advantage. A founder with strong product intuition may need to remain close to customer research, product reviews, design principles and the sequence of major bets.

In a highly operational business, small inefficiencies may multiply into enormous waste as volume increases. Fraud, inventory loss, poor routing, weak procurement or uncontrolled staffing can destroy the economics. The founder may therefore need unusually strong visibility into operations and controls, even while an operating executive runs the function day to day.

In a financial business, treasury and risk can be existential. The company may appear profitable while mismatched maturities, weak reconciliation, concentration or careless treatment of customer funds creates a crisis underneath. In that situation, the founder may devote significant attention to liquidity, capital allocation, exposure and governance rather than to every product decision.

In a services business, leadership quality and delivery standards may matter more than proprietary technology. In a marketplace, the health of supply, demand and trust may dominate. In an enterprise company, distribution, implementation and senior customer relationships may deserve a disproportionate share of the founder’s time.

The founder should remain close to the constraint that most determines the company’s future, not to the function that is currently fashionable.

Retain what only the founder can credibly do

A useful way to decide is to ask which responsibilities are unusually difficult to delegate because they depend on the founder’s legitimacy, context or judgment.

The first is purpose and strategic direction. Leaders can shape strategy and should challenge it, but the founder carries a distinctive responsibility for ensuring that the company does not become successful at something that violates the reason it exists. The founder should be able to explain what the company is building, for whom, why it matters and which opportunities it will deliberately refuse.

The second is the standard for excellence in the company’s defining capability. If product is the heart of the business, the founder may need to guard the product standard. If trust and financial safety are central, the founder must make clear that growth will never justify risking customer funds. If operational reliability is the promise, the founder must insist that recurring failure is not normalised.

The third is the selection of senior leaders. Hiring an executive changes far more than a department. It changes which behaviours are rewarded, which information reaches the founder, who will be recruited next and how decisions will be made. The founder should remain deeply involved in choosing, assessing and, when necessary, replacing the people who carry major sections of the organisation.

The fourth is capital allocation. Budgets can be prepared by finance and investments analysed by teams, but deciding where the company places its scarce money, attention and risk is one of the CEO’s most important responsibilities. Capital allocation expresses strategy more honestly than a presentation does.

The fifth is organisational unity. As functions become stronger, each develops its own language and incentives. Sales wants commitments that help it close. Product protects the roadmap. Engineering protects reliability and capacity. Finance protects cash. Compliance protects the licence to operate. Each concern may be legitimate, but somebody must ensure that the company wins as one system rather than allowing departments to optimise themselves at one another’s expense.

The sixth is the external network surrounding the company. As the business grows, the founder’s network becomes an operating asset. Investors, regulators, senior customers, partners, advisers, potential executives, journalists and other founders can provide opportunities or solve problems that no internal process can manufacture quickly. The founder must not merely collect contacts; the founder must nourish trusted relationships before they are urgently needed.

These responsibilities may be supported by excellent people, but the founder cannot outsource accountability for them completely.

Let go of work that needs ownership, not your personal touch

Founders often remain involved in tasks because they can still perform them better than the current team. That is a poor long-term test. If the founder keeps every activity until someone can immediately do it better, the company will never develop independent capability.

A better question is whether the task genuinely requires the founder’s distinctive judgment or merely requires a competent owner, clear standards and enough time to learn.

Routine approvals should leave the founder’s desk. Departmental scheduling, ordinary hiring below senior levels, recurring reporting, standard customer issues, project tracking and reversible decisions should generally move to leaders and teams. The founder may define the principles and review outcomes, but should not remain the permanent traffic controller.

The founder must also release the need to be copied on everything. Information should be designed to flow through dashboards, operating reviews and escalation rules. If being copied on hundreds of messages is the only way the founder knows what is happening, the company has not built visibility; it has built dependence.

Letting go does not mean disappearing. It means changing the form of involvement. Instead of approving every marketing asset, the founder can establish positioning, voice and review standards, then examine a representative sample. Instead of attending every product meeting, the founder can join major product reviews and stay close to customers. Instead of personally resolving every complaint, the founder can review patterns, serious failures and the changes being made to prevent recurrence.

The goal is to preserve judgment while releasing throughput.

Use a founder-attention test

When deciding whether to remain personally involved in an area, I would ask several questions.

Does this function determine the company’s identity or primary competitive advantage? If yes, the founder probably needs continuing depth, although not necessarily daily control.

Could failure here threaten the survival, licence, reputation or financial stability of the company? Existential risks deserve founder visibility even when a capable executive owns them.

Do I possess rare context, relationships or judgment that the organisation has not yet developed? If so, the founder should remain involved while deliberately transferring that knowledge.

Is my involvement improving the quality and speed of decisions, or are people waiting for me unnecessarily? A founder who adds insight should stay close; a founder who creates a queue should redesign the role.

Can I define the desired outcome, appoint a capable owner and review the work through clear measures? If yes, daily execution should probably be delegated.

Is this a reversible decision? Reversible decisions should usually be pushed closer to the people with the freshest information. The founder’s attention should be saved for choices that are expensive, difficult to reverse or strategically defining.

Am I holding this because the company needs me, or because I enjoy being needed? That question can be uncomfortable, but it separates responsibility from ego.

The answers will change as leaders mature and the business evolves. The founder should revisit the attention map regularly rather than treating delegation as a permanent, one-time transfer.

Delegation is a transfer of context, authority and accountability

Many founders say they have delegated something when they have only assigned a task. True delegation requires more.

The leader needs context: why the work matters, which trade-offs have shaped previous decisions, what the company has promised and which risks cannot be tolerated. The leader needs authority: the ability to make decisions, spend within agreed limits, organise the team and say no. The leader needs accountability: clear outcomes, a review rhythm and consequences when commitments are repeatedly missed.

If any element is absent, delegation breaks. Responsibility without authority creates frustration. Authority without accountability creates drift. Accountability without context encourages people to hit a target while damaging the broader business.

The founder must also tolerate a reasonable difference in method. Delegation fails when the founder asks another person to own the outcome but requires every step to be performed exactly as the founder would have performed it. The standard should remain high, but ownership must include room for judgment.

There will be mistakes. Some will reveal that the leader needs coaching; others will reveal that the process or mandate was unclear; a few will reveal that the person is wrong for the role. The founder should not respond to every mistake by reclaiming the entire function. Otherwise the organisation learns that delegation lasts only until the first discomfort.

Great leaders need obstacles removed, not work constantly reclaimed

As the company becomes larger, one of the founder’s highest-leverage activities is helping strong leaders solve their most important problems. That does not mean solving the problems for them. It means removing barriers that only the founder or CEO can remove.

A leader may need a decision between two competing company priorities. Another may need cooperation from a peer whose incentives point elsewhere. A team may require capital, a senior hire, board support, a partner relationship or permission to stop work that no longer matters. The founder can unlock these constraints while leaving the leader responsible for the result.

This requires the founder to ask different questions. Instead of “What did you do this week?” ask, “What is the most important outcome you are trying to achieve? What is preventing it? Which decision do you need from me? Which dependency is at risk? What are you choosing not to do?”

Good leaders should leave a conversation with the founder clearer, stronger and more capable of acting, not with a longer list of instructions that turns them into assistants.

Leadership unity is now part of the founder’s job

One lesson I am increasingly learning is that a group of individually strong leaders does not automatically become a strong leadership team. Functions can perform well in isolation while the company fails between them.

Consider a product launch. Product may complete the roadmap, engineering may deliver the software, marketing may generate demand and sales may sign customers. Yet if customer success was not prepared, finance cannot bill correctly, compliance did not approve the workflow or operations cannot implement the service, the company has not succeeded. Each leader can present a respectable departmental score while the customer experiences one broken organisation.

This is why leadership cannot be evaluated entirely through isolated OKRs. Suppose one leader reports 95 per cent achievement, while another reaches only 70 per cent because a critical dependency from the first team was never delivered. The first score may conceal failure rather than excellence. If the company waits until the end of the quarter to discover that relationship, the operating system is too slow.

The founder should make dependencies explicit at the beginning of the planning period. Shared outcomes need shared measures. Leaders should see one another’s priorities, risks and progress, and cross-functional problems should be raised while there is still time to solve them.

I prefer important problems to be visible to the leadership team rather than isolated inside one function. This allows the leaders to interrogate the issue together, contribute information from different perspectives and understand how the solution affects the rest of the company. It also develops collective responsibility: a revenue problem is not automatically “sales’ problem,” a reliability problem is not merely “engineering’s problem,” and a retention problem may implicate product, service, pricing and customer selection at the same time.

Unity does not mean the absence of disagreement. A leadership team that never disagrees may be suppressing information. Healthy unity means leaders can debate strongly, share inconvenient facts, resolve the conflict and then execute one decision without undermining one another.

Creating that environment is one responsibility the founder should not delegate away.

Nourish the network before the company needs it

As the founder becomes less involved in routine execution, external relationships take on greater importance. The network is not a social ornament. It can influence capital, distribution, recruitment, regulation, reputation and access to knowledge.

Nourishing a network is different from attending every event. It means building relationships through trust, usefulness and consistency. It means staying in contact with people when you need nothing, making introductions, sharing insight, honouring commitments and allowing others to know what the company is trying to build.

The founder should still be selective. Events can consume enormous time while creating little value. The test is whether the relationship or forum can contribute to the company’s purpose, broaden the founder’s understanding or allow the founder to contribute meaningfully to others. Visibility without relevance is another form of distraction.

The founder’s internal and external roles must also be balanced. A CEO who spends all day inside the company may miss shifts in the market and fail to create opportunities. A CEO who is permanently at conferences may become a public representative of a business whose internal reality is deteriorating. The appropriate balance changes by stage, but neither world can be ignored.

Micromanagement and deep involvement are not the same

The conversation around founder involvement is often reduced to a choice between complete delegation and micromanagement. That is a false choice.

Micromanagement focuses excessively on controlling another person’s method, often because the founder does not trust the leader or has not defined the outcome clearly. Deep involvement focuses on understanding important work, improving the quality of decisions and protecting standards while leaving real ownership with capable people.

A deeply involved founder may ask difficult questions in a product review, spend time with customers, examine the economics of a strategic programme and challenge an executive’s assumptions. The same founder can still allow that executive to hire the team, manage the plan and make hundreds of daily decisions.

The difference is whether the founder makes leaders more effective or renders them ornamental.

Brian Chesky’s approach at Airbnb is useful as an example, not a universal template. A founder without product judgment can damage a product organisation by imitating his level of involvement. A founder running a different business may need to place attention elsewhere. “Founder mode” should not become a fashionable excuse for poor delegation, arbitrary interference or an inability to trust excellent people.

The point is to remain close enough to reality to lead the company, while building enough organisational capacity that reality does not depend entirely on you.

The founder’s job becomes leverage

As a company grows, the founder’s calendar should increasingly reflect leverage. Time should go toward choices and relationships that affect many people, large amounts of capital or the long-term direction of the business.

That normally includes strategy, capital allocation, leadership selection, culture, organisational design, major product or operating standards, important external relationships and the resolution of cross-functional constraints. The exact mixture will differ, but the pattern is consistent: the founder moves away from being the default owner of recurring tasks and toward shaping the conditions in which the organisation performs.

The transition can feel uncomfortable because execution provides immediate evidence of usefulness. You answer the customer, approve the campaign or correct the design, and something moves. Leadership at scale is less immediately satisfying. You may spend weeks recruiting one person, aligning two executives, building a relationship or clarifying a decision that will affect the company for years.

That work can look less productive while creating far more output.

Keep the standard; release the task

The founder should not ask only, “What can I delegate?” The better question is, “Where does my attention create unique leverage, and how can I build an organisation that carries everything else excellently?”

Remain involved in the company’s purpose, strategic direction, defining standard, senior leadership, capital allocation, major risks, organisational unity and the external relationships that only you can credibly build. Remain close to the function that determines the company’s advantage or survival, whether that is product, operations, treasury, distribution or something else.

Let go of routine execution, reversible decisions, recurring approvals and work that another capable person can own with the right context and authority. Do not delegate by disappearing, and do not stay involved by reducing leaders to spectators. Review outcomes, ask hard questions, remove obstacles and allow people to develop methods that are not identical to yours.

Most importantly, build a leadership team rather than a collection of departmental heads. Make dependencies visible, let leaders solve important problems together and judge success by the company’s outcome rather than isolated functional scores.

The founder’s job does not become smaller as the business grows. It becomes more concentrated.

You keep the purpose, the standard and the responsibility for the whole. You release the tasks, decisions and control that prevent other people from becoming real owners. When that balance is right, the company gains the benefit of the founder’s judgment without being limited by the founder’s capacity.