Startup Systems

Unnecessary versus necessary chaos

In my 13 years working at startups, I’ve witnessed many examples of unnecessary chaos—here are a few.

A major release has been planned for months, but launch communications—new positioning, website copy, customer email, blog post—are reviewed at the last minute.

A manager reschedules 1:1s every week because of... See more

Product-market fit always starts with the customer. And Dan Olsen’s PMF framework starts from the bottom up.

Conventional hiring processes are designed to recruit the most skilled people to fill a specific role at the right price. The experience can feel dehumanizing — it’s laden with unwritten rules, negotiation, posturing, and indirect communication (if you’re lucky) through recruiters.

The process, at its core, is a transaction of resources. It’s not... See more

But here’s the key for an early-stage startup: "As we’re building our plans, we only focus on those first three months, that first chapter. So we break that down into monthly high-level goals, and that's what I hold the team accountable for,” he says. In other words, don’t try to get detailed for longer than a few weeks out. "At a startup, it’s... See more

We try to be as rigorous and data-driven as possible in quarterly planning. All objectives are measurable, either in terms of quantifiable thresholds or Boolean “was X completed or not.” Our objectives are very aggressive, and often at the end of the quarter we only end up completing 70% in one direction or another. The remaining 30% helps identify... See more

“Almost always, when I look at a team or project at a larger org trying to make a decision with differences in opinions, the root of those differences almost always starts with shared context,” Weiss says. “Or lack thereof.”

The first step to identifying if your team is lacking shared context is to ask yourself a series of questions, Weiss says.... See more