---
title: "Do You Know Which Positions to Hire First?"
section: "Team"
sectionId: "team"
date: "2026-05"
---

*Based on Jason Calacanis's startup checklist.*

## Priorities depend on what you're building

A deep AI or machine learning application may need different early hires than a fashion marketplace. Know the critical path for your specific product before defaulting to conventional wisdom.

## The generalist-to-specialist rule

| Stage | Hire |
|---|---|
| Fewer than 10 employees | Generalists |
| More than 10 employees | Specialists |

Early on, you can't afford people who only do one thing. You need people who figure things out, take on unglamorous tasks, and move fast. Specialists become valuable once the company is large enough to have repeatable functions worth optimising.

## Role sequencing

**Hire sooner:**
- Developer
- Product manager

**Can outsource early:**
- Finance / accounting — outsource until the complexity justifies a hire
- PR — not needed in the early days; outsource when the time comes

**Outsource first, hire later at scale:**
- HR — outsource initially; bring in-house around ~50 employees
- Legal — outsource throughout the early stages

## How to hire well: the Bar Raiser principle

Amazon's Bar Raiser concept sets a clear standard: every person hired should be better than 50% of those currently in similar roles. The Bar Raiser is an interviewer from *outside* the hiring team who acts as an objective third party — their job is to evaluate long-term potential against the company's principles, not just fit for the immediate role. The standard doesn't slip just because you need to fill a seat quickly.

See [The Amazon Bar Raiser Programme](/startup-wiki/team-amazon-bar-raiser) for a full breakdown of how it works and how to apply the principle at startup scale.

## Interview questions that work

You want questions that reveal how someone works and whether they'll fit your team — not just whether they're technically capable.

**What is a new skill you've learned in the last year?**
Signals curiosity and self-direction.

**Do you think it's more important to be talented or hardworking?**
Surfaces values and self-awareness. Neither answer is wrong — the reasoning matters more than the position.

**Teach me something in two minutes.**
Known as the Chamath question. Reveals passion, the ability to be concise, and the ability to convey information clearly. People who are great at this tend to be great at almost everything else.

**How do you handle having multiple assignments at once?**
Critical for early-stage hires who will always be juggling more than one thing.