Darren Cahill’s Coaching Secret Is the Art of Listening

Adam's Favourites | 11 February 2026

A note to young leaders.

Australian tennis super-coach, Darren Cahill, has a remarkable claim to fame. He has now coached four players to world number one, across three decades:

  1. Lleyton Hewitt (at the time, the youngest ever);
  2. Andre Agassi (at the time, the oldest ever);
  3. Simona Halep; and
  4. Jannik Sinner.

What’s his secret?

First, Cahill believes anything is possible. He never caps his player’s expectations of what can be achieved. Hewitt and Agassi both broke records under his tutelage.

Second, Cahill doesn’t come in all guns blazing, assuming he has all the answers.

When he began working with Andre Agassi, Cahill spent the first six weeks simply asking Agassi questions and getting to know him – trying to understand how the legend saw the game.

Simona Halep praised his approach: “He didn’t come in and say, ‘I’m the boss, do it my way.’ He asked questions, he made me think, he made me grow personally, and that unlocked the next level for me.”

If you’ve been brought in to turn around a company’s fortunes, the temptation is to rush.

Do the exact opposite. For the first six weeks- only ask questions, ask lots of questions.