If You Want to Grow, Seek Out the Toughest Direct Feedback—Even When It Hurts

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Maybe it’s a knot in your stomach before a meeting. Or a sinking feeling you’re not hearing the whole story when people politely nod. For Joe Gebbia, Airbnb’s cofounder, this discomfort came to a head as the company scaled and cracks started to show in his team. People weren’t telling him the full truth—mistakes, frustrations, or nascent problems were hidden away, only rising up when they became crises. During a 360-degree review, he learned the hard truth: his perfectionism and defensiveness made people scared to share problems, so they waited until it was too late. The news was bruising, but also a turning point.

He spent weeks wrestling with the realization, then began actively seeking “the bad news I need to hear.” At meetings, he opened by inviting critique, then sat with the discomfort, resisting the urge to fix or deflect. He thanked people for candor and made visible changes—like letting go of always having the perfect answer, or embracing faster, less-than-perfect decisions. Over time, this built trust, psychological safety, and unexpected strength in his teams. Research confirms that organizations where leaders regularly ask for and act on tough feedback are not only more innovative but also less likely to suffer from sudden, catastrophic failures. The hard part? Learning to ask—in detail, and with humility—and then actually listening.

Choose one area you want unvarnished feedback about—schoolwork, your project, or even how you show up with friends. Approach someone whose opinion matters, and ask them directly for what you could do better or where you’re missing something. When the answer makes you uncomfortable, resist arguing, and instead write down the points that surprise you. Take one piece of advice—however small—and do something with it this week. Then, report back to your helper, showing you value honesty over flattery. Notice how each uncomfortable moment can yield a concrete improvement.

What You'll Achieve

Develop deeper self-awareness, improve communication, and build a culture of trust within teams or relationships. Over time, this internal openness leads to increased learning, greater adaptability, and stronger collective performance.

Ask for the Bad News First, Then Act

1

Identify One Area Where You Want Truthful Input.

Pick something you want to improve—your leadership, project, or even personal habit.

2

Explicitly Request 'What Am I Missing or Messing Up?'.

Invite someone you trust to point out flaws, obstacles, or blind spots, emphasizing you want honesty over reassurance.

3

Practice Non-Defensive Listening.

When feedback comes, focus only on understanding (not arguing or explaining). Jot down surprising points and thank the person, even if it stings.

4

Act on One Piece of Feedback.

Commit to changing one behavior, process, or assumption—report back a week later to show progress and close the loop.

Reflection Questions

  • What kinds of feedback am I most afraid to hear?
  • How do I usually react when someone points out my mistakes?
  • Who in my life will give me honest, actionable feedback?
  • How will I know I’ve truly listened, not just defended myself?

Personalization Tips

  • For a group project, ask teammates: 'Where am I slowing things down?' Listen even if the answer feels tough.
  • In a friendship, request: 'Let me know honestly if I ever make you feel unheard.'
  • If you coach or lead, invite honest feedback on your meetings or communication style and visibly act on it.
The Airbnb Story: How Three Ordinary Guys Disrupted an Industry, Made Billions . . . and Created Plenty of Controversy
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The Airbnb Story: How Three Ordinary Guys Disrupted an Industry, Made Billions . . . and Created Plenty of Controversy

Leigh Gallagher
Insight 3 of 8

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