Teachable moments #61 - The Vulnerable Leader

Ang Woon Jiun

12/15/20253 min read

black nikon dslr camera on white printer paper
black nikon dslr camera on white printer paper

We already know that sharing a little bit about yourself - what we call self-disclosure - is a superpower for leaders. It's how you show up as a human being, not just a job title. It's the secret sauce that builds trust, grants your team Permission to make mistakes, and models true resilience.

But let’s be real: Baring your soul every Monday morning is a fast track to awkwardness and oversharing. The real challenge for any leader isn't if they should be vulnerable, but how, when, and how much. It’s about being strategic without feeling manipulative.

Here’s the inner playbook for navigating this delicate balance:

1. Your 'Why': Check Your Heart Before You Speak

Before you share anything personal, stop and ask yourself the simplest, most crucial question: "Why am I telling this story right now?"

If your intent is clean, the impact will be positive. Think of your intention as the compass:

  • Is it to bridge a gap? A quick story about your struggle with public speaking can instantly connect you to a nervous team member. You're building Humanness.

  • Is it to teach a principle? Recounting a past professional fumble where your ego got in the way, and what you learned from it, is the best kind of Modelling. You're teaching a lesson, not just telling a story.

  • Is it to set a value? Explaining that you leave early on Fridays because you fiercely protect your family time gives your team Perspective on what matters to you and encourages them to do the same.


A Quick Gut Check: If the main reason you’re sharing is because you want your team to feel sorry for you, give you special treatment, or validate a tough decision, stop. Your disclosure will feel self-indulgent, not inspiring, and will actually chip away at the trust you're trying to build.

2. Your 'Where' and 'When': Context is Everything

Sharing the right thing at the wrong time or place can completely derail the message. You have to read the room and the calendar.

  • The Setting Matters: A heartfelt story about balancing work and a tough parenting moment is perfect for a relaxed one-on-one coaching session. It keeps the conversation intimate and focused. But sharing that same story during a massive, high-pressure project review? It will just sound like a distraction, or worse, an excuse.

  • Don't Vulnerability-Bomb a Crisis: When the office is in chaos, a huge deadline is looming or a major client just left, your team needs a steady hand. They need to see a leader who is calm, focused, and decisive. Save the stories about your sleepless nights and internal doubts for the reflection session after the storm has passed. Once the Closure is achieved, then you can share what you learned about handling pressure. Your stability during the crisis is what they will remember.


3. Your 'How': The Delivery Recipe

Vulnerability is a spice, not the main course. You need to use it sparingly and effectively.

  • Be the Editor of Your Own Story: Focus only on the part of the story that directly relates to the lesson. You don't need to give 45 minutes of backstory leading up to the mistake. Get straight to the point: What Happened --> How It Felt --> What I Learned. This keeps the disclosure professional and powerful.

  • Selective Transparency, Not Total Exposure: Remember, you are still the leader. You need to maintain healthy professional boundaries so you can make objective decisions. Sharing highly sensitive personal struggles (like deep medical or marital issues) pushes your colleagues into the role of therapist, which isn't fair to them and violates professional space. Use your disclosure to share a past struggle you've overcome, not a current trauma that requires their support.


The goal of this practice is to connect your human ego (which enables Humility) to your professional role. When you use self-disclosure with honesty and good intentions, you don't just build relationships; you build a team that trusts you enough to be human themselves.

Mastering the Art of Strategic
Self-Disclosure