How to Go From Executive Assistant to Chief of Staff: The Move Nobody Promotes You Into
Being a better EA won't make you a Chief of Staff. The move runs on a different kind of authority, and you can start earning it before the title changes.
How to Hire a COO: The Job Description Founders Write, and the One They Should
Most COO job descriptions describe a very senior project manager. Here's the one that describes an owner, and the five questions that find one.
Chief of Staff vs. Executive Assistant vs. Operations Manager: Three Jobs Founders Keep Hiring Into the Same Seat
Hire an EA and expect a Chief of Staff, and you'll be disappointed. Hire a Chief of Staff and use them as an EA, and they'll be gone in a year. The difference isn't seniority.
Chief of Staff vs. COO: Which One Does Your Company Actually Need?
Founders describe one role and name the other. The difference isn’t seniority or scope — it’s where the authority sits. Four questions that settle it.
You Don't Need an AI Policy. You Need Decision Rights.
When the AI rollout gets messy, the reflex is to write a policy. But a policy nobody acts on governs nothing. What works is decision rights — and that's org design, not paperwork.
Good Fences Make Good Neighbors: The Operational Case for Structure in a Flat Organization
There's a misconception that's been quietly costing growing companies for years. It usually surfaces around the time a startup hits 30–50 people. Leadership has worked hard to build a flat, collaborative culture, and they get nervous about anything that smells like “process” or “structure.” They worry that defining roles, building operating cadences, or writing things down will somehow undermine the culture they've built.
So they hold off. They keep doing what worked at 10 people. And then engagement starts slipping, execution gets sloppier, and the team that used to feel agile starts feeling chaotic. Leadership diagnoses it as culture drift and tries to solve it with more all-hands meetings, more values posters, or louder “we're a flat org” messaging.
The actual problem is upstream. The team doesn't need more flatness. They need clarity.