Enneagram at Work

253. Why We Question Things: What the Enneagram Reveals About Skepticism at Work

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Why do some coworkers question everything? And why can their questions sometimes feel like criticism, resistance, or a lack of trust?

Inspired by a recent conversation between Adam Grant and Brené Brown about the Enneagram, we're exploring skepticism through a different lens.

What if three people questioned the exact same idea, but for three completely different reasons?

In this episode of Enneagram at Work, we're looking at how Enneagram Types 1, 5, and 6 might approach skepticism, what's potentially motivating their questions, and how understanding those differences can help us communicate and collaborate more effectively.

We'll use a common workplace scenario (introducing a new process) to explore how questioning can be driven by a desire for improvement, a need for information, or a concern for trust and security.

And while any Enneagram type can be skeptical, these three examples give us a useful starting point for getting curious about what's underneath someone's pushback.

In this episode, we explore:

  • Type 1: Questioning to improve: Why a coworker's attention to errors, inconsistencies, or standards can sound like criticism when their intention may be to make something better.
  • Type 5: Questioning to understand: Why asking for more information, evidence, or processing time doesn't necessarily mean someone disagrees.
  • Type 6: Questioning to establish trust: How anticipating risks, questioning assumptions, and wanting contingency plans can strengthen a team's decisions.
  • Why we often mistake skepticism for negativity, resistance, or someone questioning our authority.
  • What each of these coworkers might need before feeling ready to move forward.
  • Three simple questions that can help you respond to skepticism with curiosity instead of defensiveness.

Three questions to try with your team:

  1. What about this doesn't feel right yet?
  2. What additional information would be helpful?
  3. What concerns do you have that we haven't addressed?

You don't have to know someone's Enneagram type to start asking better questions.

The takeaway: Skepticism isn't always resistance. Sometimes it's someone noticing something important that the rest of the team has overlooked.

The next time someone challenges an idea, try asking one question to better understand their concern before jumping in to defend your position.

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At Enneagram MBA, we help teams turn personality insights into practical conversations about communication, collaboration, and workplace relationships through facilitated workshops, leadership retreats, and team development programs.

Learn more at Enneagram MBA.


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