The First 90 Days: What a Great Chief of Staff Does in a Startup
How Chiefs of Staff drive value in their first 90 days—what to listen for, what to build, and how to earn trust fast.
Hiring a Chief of Staff is a major milestone for a startup. Done right, it’s like handing a trusted co-pilot the controls while the founder keeps their eyes on the horizon. The first 90 days can determine the success of the hire and the momentum of the leadership team. Here's what the best Chiefs of Staff do early on—and how they drive impact from day one.
1. Listen First, Act Later
- Conduct a listening tour with every department head and key team members to understand their priorities, bottlenecks, and perspectives.
- Sit in on leadership meetings, customer calls, and team standups to absorb context.
- Build a map of org priorities, informal decision-makers, and communication flows.
"Your first job isn’t to fix things—it’s to understand how decisions are made and where influence lies."
2. Build Systems, Not Just Solve Problems
- Identify recurring pain points and design simple, repeatable systems.
- Early wins often include founder calendar control, meeting cadences, OKR rollout, and board deck prep.
- Start documenting processes to build organizational memory.
3. Become the Founder’s Second Brain
- Filter noise, surface signals, and help the founder stay focused on the 2–3 things that truly matter.
- Take on special projects like a new product launch plan, investor updates, or hiring strategy.
- Serve as a bridge between vision and execution.
4. Set the Culture for Strategic Ops
- Model sharp written communication, speed without chaos, and thoughtful judgment.
- Codify how decisions get made—help leadership align around clarity and cadence.
- Elevate how the team works, not just what they work on.
5. Define the Role While Doing the Role
- Chiefs of Staff are often the first of their kind. That means writing the job description as they go.
- Meet weekly with the founder to calibrate priorities and scope.
- Leave behind a blueprint—so future Chiefs, or internal ops hires, can build on what’s working.
The first 90 days of a Chief of Staff should be about learning fast, earning trust, and quietly shaping the company’s most strategic work. Great Chiefs don't just plug gaps—they elevate how the org thinks, operates, and scales.