Seven Takeaways for Chiefs of Staff from Barry Diller’s Memoir

What do Chiefs of Staff and one of the most successful executives in media have in common? Everything.

Although not written about the Chief of Staff role, few books capture the reality of the position as clearly as Barry Diller’s memoir, Who Knew. His early career mirrors the path so many Chiefs of Staff find themselves on: learning in real time, operating without a clear playbook, and growing through proximity to leadership.

Barry started his career in the mailroom. No strategy background. No polished credentials. Just instinct, drive, and a willingness to dive in. He eventually became the CEO of Paramount Pictures, and today he’s the founder and chairman of IAC and Expedia Group.

Diller’s story is a masterclass in figuring it out. Not because he had the answers, but because he refused to stop learning. That mindset? It’s the essence of the Chief of Staff role.

You’re dropped into the deep end of a new business, with a new leader, a new team, and a job description that’s ambiguous. You learn fast. You lead with influence. And eventually, you look up and realize you’ve just earned the equivalent of an MBA, with a minor in humility.

7 Takeaways for Chiefs of Staff after reading Barry Diller’s Memoir

1. “I couldn’t add beyond basic math.”

Diller claimed he was financially illiterate while leading a company with $600M in debt. His strategy? Dive in and fake it until he figured it out.

→ Find resources & figure it out.

2. He talks about how managing top-down is nearly impossible if you haven’t managed from the bottom up.

He knew leadership isn’t about authority. It’s about understanding.

→ Ahem: influential leadership.

3. Instinct is what he prized — not experience, research, or data.

He called instinct, influence, and execution a kind of poetry.

→ Instinct > data is the hill he’ll die on.

4. He says that metrics applied to basic decisions waste time and money.

Staying naive and “under-expertised” helped him spot good ideas quickly.

→ Deep industry expertise is overrated.

5. “Muck around enough until the gears finally mesh.”

That was his creative process. Messy, hands-on, and full of trial and error.

→ Dive in & learn above all else.

6. “Well, I couldn’t do much, but I could tell a good story.”

That’s what he told bankers while trying to turn around a struggling company.

→ Storytelling is everything.

7. “Drop them in the deep end and see who survives. Promote the ones who do.”

His philosophy on hiring and leadership.

→ Totally agree.

The Chief of Staff path isn’t about having all the answers. It’s about becoming the kind of person who figures it out.

You lead with humility, high EQ, and strategic execution. And you do it without a roadmap; just instinct, trust, and the stamina to keep showing up. Eventually, you look back and realize you’ve leveled up in ways no job title can fully capture.

You’re not behind. You’re not under-qualified. You are becoming. And that messy middle? It’s where the magic happens.

P.S. This learning-through-action approach is foundational to how Nova supports Chiefs of Staff. Our Free Resource Library includes tools for operators navigating the messy middle, such as worksheets, templates, and a guide to pitching your promotion. Go check it out!