Leadership lessons from a unicorn startup's early employee

Executive overview

Early employees who rely on their seniority to direct others create resentment and stall growth. Genuine leadership means doing the hardest work yourself, removing blockers, and caring about your team's individual goals.

Employee happiness directly drives customer happiness — and the leader's job is to earn trust, not demand compliance.

Course-correcting fast

• Founders often know a mistake has been made but keep going anyway — the team already knows
• Delay compounds the damage; fix it as soon as it's visible
• Introverts or junior staff may hold the best solution but won't speak unless you create space for it
• A collaborative environment consistently outperforms a top-down one

Leading by doing the hardest tasks

• At Carta, promotion prompted "I feel sorry for you" — not congratulations
• A leader who only directs gets 100% effort; a startup needs 120%
• Taking the hardest, most uncomfortable tasks yourself earns team respect
• Handling difficult customer escalations directly signals that you protect your team

Genuine connection over authority

• Ask team members what they ultimately want to do — even if it's a different role or company
• Helping people reach their goals produces better performance now
• Listening and caring are not soft skills; they are the motivation multiplier
• Never assume you know everything — an intern can still teach you something

Coaching culture

• Carta ran like a sports team: managers as coaches, not commanders
• A coach's job is to surface what went wrong and help the team improve — not to set a path for their own sake
• Informal coaches (a kind manager, a mentor in their 70s) can be as valuable as paid ones
• Choose coaches based on genuineness, not status