Eight leadership lessons from running a $100M business

Executive overview

Most founders return to CEO after years away and assume they should lead from the front. The harder truth: effective leadership means serving, not directing. Attention, delegation, and documentation compound faster than any individual output.

The best CEOs do no work — they hire decision-makers and deal only with the unknown.

Serving, not leading

• Leaders don't have to be at the top — anyone in the company can lead
• Shepherd from the back: if you've hired excellent people, stay out of their way
• Set guidelines and direction; let the team execute in their excellence
• Challenging the team works best when you invite them to solve it, not solve it yourself

Paying attention

• Presence in meetings is rare — most leaders are mentally elsewhere
• You cannot be successful without genuine focus on what you're working on

You are not alone

• Default instinct as a founder: solve everything yourself with a genius idea
• Better approach: include your team in the problem, share what you like and don't like
• The why and direction is on the leader; the how and execution belongs to the team
• Leverage people inside and outside the company to make great things happen

Leaders hire decision-makers

• If a decision is easy or already solved, it shouldn't reach the CEO
• CEOs deal only with the unknown — novel situations that require real judgment
• Identify the desired outcome, then find who owns making it happen

Leading by example with focus

• A packed calendar signals to the whole team that meetings are mandatory and exhausting
• Intentionally design a sustainable calendar — it gives others permission to do the same
• Focus means saying no: if it's outside the core priority, decline it, even if it's fun
• Aligning company vectors — where everyone is pointing — is the strategic job of leadership

Documentation scales organizations

• Strong resistance to process is common; it feels like a cage for creative people
• Without documentation, nothing is repeatable and new hires can't ramp
• Even basic documentation (how we hire, how we market) creates a framework for decisions
• The framework becomes something you can refine, not a rule you're stuck with

Practical steps to become a better leader

• Study best practices first; reserve creativity for one area where you can truly excel
• Hire coaches — they've seen your problem before, and they reframe it fast
• When someone underperforms, ask: what decision makes the company and morale better?
• Dignifying the person and giving them a real chance often beats immediate action
• Seek advisors who complement your weaknesses, not mentors as a vague aspiration

Feedback as a growth tool

• Feedback is the greatest gift anyone can give you — ask for it explicitly
• Unsolicited feedback is noise; requested feedback is leverage
• No permission is needed to lead — it can happen at any level of an organisation