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Systems & Soul
(12) Hands Up Companion

Reading Habits of Great Leaders

July 24, 2026 5 min read

I do not read because leaders are supposed to have a tidy stack of books on the nightstand. I read because the world keeps changing and I refuse to lead from old information. That is the simplest definition of the reading habit that has served me: I read to update my judgment.

When I wrote Hands Up, I was not trying to create another business manual. I was trying to leave a letter about what it feels like to build through change. Reading is one of the ways I keep that letter honest. It keeps me curious, uncomfortable, and less impressed with what I already know.

What reading does for a leader

Reading gives language to things you have felt but not named yet. It gives you a second set of eyes on your own assumptions. It lets you borrow someone else's scar tissue before you pay full price for the lesson yourself.

For me, great reading is connected to curiosity in business. I am not looking for quotes to post. I am looking for better questions. What am I missing? What changed under my feet? Where did my confidence get ahead of the evidence? That is why I never stop learning.

When reading matters most

Reading matters most when you are successful enough to be dangerous. Early in business, humility is forced on you. Later, people start nodding. They laugh at your jokes. They repeat your language back to you. That is when a leader can confuse agreement with truth.

The 320-to-38 rebuild at CI Web Group required me to keep learning while everything I had built was being questioned. I had to read the market, read the technology, read the team, and read myself. The company did not need a founder defending her old thesis. It needed an operator willing to update.

What fails when leaders stop reading

They start recycling themselves. The keynote becomes a greatest-hits album. The strategy meeting becomes memory theater. The company keeps hearing about the year the leader was right, while the market quietly moves on.

Worse, leaders who stop reading usually stop listening. They treat curiosity as something junior people need and certainty as something senior people earn. That is backwards. The higher you sit, the more deliberately you have to expose yourself to ideas that do not flatter you.

The best leaders I know read like their relevance depends on it, because it does.

The proof in my own operating system

Reading helped me see that SOPs were not the highest form of operational maturity anymore. Systems had to become alive. People had to move from compliance to judgment. That idea shows up in SOPs Are Dead, in Systems, Not Heroes, and in the way we rebuilt CIWG around smaller teams with stronger infrastructure.

My proof is not a reading list. It is a company that changed because the leader kept changing first.

How to start

Do not make reading precious. Read one useful chapter. Mark one sentence that bothers you. Ask one better question in the next leadership meeting because of it. Then repeat. Pair reading with your daily habits, not with a fantasy version of your schedule.

Great leaders read to stay reachable by the future. That is the habit.