The management mistakes founders make right around employee number 10
The habits that carried a five-person team start breaking at ten. Here is what goes wrong first, and the specific fixes that keep a growing company from stalling.
The Leadership Desk
Editorial Staff
The Leadership Desk covers how companies are run: management, hiring, careers, workplace policy, boards and the founder's own time. Articles under this byline are published by Founder Insider and drafted with AI assistance under our AI policy.
Articles by The Leadership Desk
How to run a layoff legally and humanely, including the WARN Act rules
A practical walk-through of the notice rules, severance releases, final pay and benefits steps that decide whether a layoff is handled well or becomes a lawsuit.
How to build a startup board that actually helps you run the company
Most founders inherit a board one financing at a time. Here is how to shape its seats, its meetings and its paperwork so it adds judgment instead of friction.
How to set goals for a small team without building a bureaucracy
A lightweight quarterly goal system for startups between five and fifty people, with the exact documents, meetings and check-ins it needs and nothing more.
How to handle an underperformer before it turns into a firing
Most underperformance problems are left too long and handled too vaguely. A step-by-step approach to diagnosing the cause, setting clear expectations and deciding fairly.
Contractor or employee? The classification test that trips up startups
Calling someone a contractor does not make them one. How federal and state tests actually work, the red flags auditors look for and what misclassification costs.
What has to be in place before your first employee starts
The registrations, forms, insurance and agreements a founder needs before the first person joins payroll, and the order to tackle them in so nothing is missed.
What to check before you leave a big company for a startup
A due-diligence checklist for experienced operators weighing a startup offer, covering runway, founders, role scope and the questions that reveal what the pitch leaves out.
How to negotiate a startup offer when equity is half the package
The terms that decide what startup equity is really worth to you, from exercise windows to acceleration, and the levers worth pushing on beyond the number of shares.
The hidden paperwork of hiring a remote employee in another state
Hiring someone who works from a different state brings new tax accounts, insurance and employment rules. What changes, what to check and how to stay on top of it.
Write your startup's employee handbook before you actually need one
A startup handbook is where culture becomes specific and policy becomes enforceable. What belongs in the first version, what to leave out and the rules that catch founders off guard.
The quarterly calendar audit every founder should run
A founder's calendar shows what the company really prioritizes. A two-hour method for auditing where your time went, cutting meetings and protecting the work only you can do.
A decision-making system for founders who have become the bottleneck
When every decision waits for the founder, the company slows down. A practical system for sorting decisions, assigning owners and keeping a record that speeds everything up.