Why Leaders Need Someone Who Will Challenge Them

Gerald Ang
Gerald Ang
January 26, 2026
5 min read
The more senior you become, the more people agree with you, the less useful the conversations can get.

I just ended a meeting with another client and my phone rang.

In a calm steady voice, my client, a senior APAC leader in a global company, on the other end of the phone greeted me: "Hey Gerald, Happy New Year! Are you available tomorrow at 4pm?"

I replied in my usual casual chilled tone: "Happy New Year! What's up?"

"I need to bounce a few thoughts with you before I fly off to New York for a meeting with the global management team."

I replied: "I fly out tomorrow for another trip. How about today 4pm? I'll need to make a call to move an appointment around." (Thankfully I had a meeting with a friend who would understand!)

"Done. See you later."

This happened just last week. A senior APAC leader reached out before flying to New York for a critical meeting with their global leadership team.

We met at the client's office. We spent two hours in honest, robust conversation. We unpacked the proposal, the approach, the messaging, we spoke about the people in the room, the 'political' landscape and cultural dynamics.

Thankfully, I've ran a few leadership and Strengths workshops with the global team over the past 9 months and I knew the people on the leadership team and the overall business construct and progress.

I listened. We debated. We challenged each other to strengthen the thinking.

We challenged each other further. We disagreed with a smile.

Throughout the conversation, it was all positive energy.

By the end, the thinking was sharper, the choices clearer, and the intent more deliberate.

I walked away energised because I know how rare that space is.

At senior levels, there are very few places where you can be open and stretched. You’re expected to have answers, project certainty, and deliver, all while navigating increasing complexity.

This is why trusted advisors and executive leadership partners matter.

To help you see what you might be missing. To sharpen judgment before the moment matters.

Not to validate your thinking, but to challenge it.

Not to agree, but to help you see what you might be missing.

Not to rehearse slides, but to sharpen judgment before the moment matters.

I run leadership programs and workshops, and I love that work. But these one-to-one leadership conversations are just as meaningful to me.

Because this is where leadership really happens long before the meeting room.

If you’ve ever sat in that seat, you’ll know how valuable the right thinking partner truly is.

Every leader or manager needs a neutral, experienced, trusted thinking partner. That is what makes a difference every time you step into the boardroom.

If you don't have one, I would encourage you to find one.

No man and woman is an island.

Take our leadership quiz to discover your leadership style: https://www.wildnwise.co/leadership-strengths-quiz

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