Harvey CEO Winston Weinberg's top interview question for leaders is to map their future organization at three, six, and twelve months. A candidate's ability to detail specific roles and profiles reveals their strategic thinking and capacity to build leverage, a key indicator of their potential to scale.
Harvey's early sales strategy was to find a target lawyer's public court filing, use its AI to find flaws in the arguments, and present the critique directly to them. This hyper-personalized "attack" immediately proved the product's value and grabbed the attention of busy, high-value prospects.
Contrary to conventional GTM strategy, Harvey intentionally targeted the largest law firms first. The rationale was that solving their complex needs and brutal compliance requirements would forge a product robust enough to serve the entire market, creating a powerful competitive moat from day one.
Harvey's COO doesn't own a single function like GTM. Instead, she tackles complex, cross-functional initiatives that the CEO would otherwise have to lead. She manages stakeholders and synthesizes options, effectively acting as a clone of the CEO for driving company-wide strategic projects and increasing his leverage.
Harvey CEO Winston Weinberg experiences a four-month cycle of accumulating pressure from unsolved problems. He argues the only release is a fundamental reinvention: making a new leadership hire, restructuring the company, or cutting a failing initiative. This cycle is necessary to unlock the next stage of scale.
Harvey CEO Winston Weinberg asserts that if you've never done a role, you will hire the wrong person 100% of the time. For first-time founders, spending even three months in a function provides the necessary context to understand the job's demands and successfully hire a leader for that position.
While efficient, focusing solely on fixing what's broken can be a major blind spot. Harvey's CEO realized that a part of the business doing "super well" could often be doing 10x better with more resources. The biggest growth lever might be amplifying a success, not just plugging a hole.
Harvey's CEO found his product decisions were worse when he isolated himself to work on strategy. He realized his best product insights come from being deeply involved in sales calls 24/7. The direct feedback loop from talking to customers is more valuable for roadmap planning than any internal brainstorming session.
Weinberg values speed over correctness. He'd rather an employee make a wrong decision and fix it in a week than spend three months paralyzed by analysis. In fast-moving markets, the cost of delay exceeds the cost of a correctable error, making inaction the true failure.
Instead of hiding the decision to layer a star employee, Harvey's CEO advises involving them directly in the hiring process for their new manager. While this risks them leaving, it's a calculated bet on trust. Success means they respect the decision, feel valued, and are primed to learn from their new leader.