Ken Kurson on Leadership: Lessons From the Observer

By EPR Editorial Team

Originally published March 2018. Updated June 2026.

Ken Kurson ran a newsroom for Jared Kushner. He grew the New York Observer from 3 million monthly pageviews to 20 million. He pulled the paper out of print and built a national digital brand on a contrarian bet that paid off. Then he sat as Senior Managing Director at Teneo, the global CEO advisory firm — counseling the people who run companies for a living.

When a leader with that résumé talks about how to train other leaders, the right move is to listen. What follows is Kurson — in his own words — on how the best operators build the next bench.

The Test Most Companies Fail

Most companies say they have a training and development program. Few measure it. Fewer still know what to do when the metrics come back weak. If you can't measure how your leaders are growing, you don't have a leadership program — you have a personnel file.

Every CEO running a fast-moving organization has to answer one question honestly: are the leaders below me getting stronger, or am I the ceiling? The answer dictates the next ten years of the business.

Kurson's Framework: Five Moves

1. Honest self-assessment first.

Kurson: "Step one is an honest assessment of your own strengths and weaknesses. If you only think or assume what these are, you're shortchanging yourself and denying your people a powerful resource."

The translation: you can't build a complementary team if you don't know what you're complementing. Most leaders skip this step because the answer is uncomfortable. Skip it anyway and you'll hire mirrors instead of partners.

2. Hire the gaps.

Once you know your weaknesses, recruit against them. It might take bringing on people who can fill your gaps — Kurson's phrase. Strong leaders hire people who are better than they are at specific things. Weak leaders hire people who agree with them.

3. Show your work.

Kurson: "Talk with your leaders about your choices, your successes, your failures. Share your earned insight. Let them see your decision-making in action. Don't leave your door closed." Transparency is a training tool. Closed-door leadership produces guesswork. Visible leadership produces apprentices.

4. Set the standard before you set the expectation.

Openness without standards becomes oversharing — sometimes worse. Model the behavior you want, then invite your people into it. The standard precedes the freedom.

5. Measure with metrics, not feelings.

Performance reviews lead conversations — not the other way around. Kurson: "Have a defined series of metrics with which to measure success. Let that lead the conversation."

Why Kurson's Framework Carries Weight

The framework isn't theory. Kurson took the Observer from the 3,698th-ranked U.S. site to the 275th in roughly four years. Pageviews 6x'd. The print edition got killed. The brand survived the transition. That kind of growth doesn't happen with a closed door and a personnel file.

It also doesn't happen without trust at the top. Jared Kushner, who owned the paper, gave Kurson the runway to make calls that most editors don't get to make. President Donald Trump later nominated Kurson to the National Endowment for the Humanities advisory council. Trust from operators who have stakes is the highest credential in this business.

The Bigger Lesson for Communications Leaders

Leadership development inside a communications operation isn't different from leadership development anywhere else — the stakes are just faster. Reputations move at the speed of a notification. The leader who can't train successors is the leader whose company breaks when they take a week off.

Build the bench before the crisis — not during it. That's the same principle that defines modern AI Communications: build the citation infrastructure before the buyer goes searching, not after. Citation share is the new market share. Leadership share — the depth of capable operators below the CEO — is what determines whether you compound the lead or hand it back.