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I still haven't worked in a big company yet, so the phrase "comfortable with ambiguity" confuses me a little.

For awhile I was getting kind of frustrated with graphic design clients because I'd submit a draft and then find out they had requirements they just didn't mention to me, or they needed to see what they asked for to know that they didn't want it after all. Over time I was learning to ask better questions, and the UX bootcamp I took accelerated that improvement. Now I feel so much more confident that I can find out what I need to know to design the right thing right, but I need at least some cooperation from my clients or stakeholders to really make this happen.

Is "comfortable with ambiguity" talking about a need for a person who knows how to ask great questions and find some clear direction (both stakeholder interviews and user research), or a need for a person who's just comfortable with many rounds of guessing, because we don't have time up front but we have time for revisions and iteration?

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It should confuse you. It's confusing!

The intended meaning is, I think, quite like you suggested. When the answer isn't clear, think of good questions and proactively ask them. Don't throw your hands up in defeat. Don't park yourself on the sofa waiting around for the fog to lift. Save that for Saturday mornings in Los Angeles in January.

It's often used to describe what passes for a healthy attitude in an environment where nobody knows wtf is going on."We already know it's messed up, don't remind us" or "nobody knows for sure, maybe you can figure it out."

To answer your question, it's both! "Comfortable with ambiguity" is what people think they want when there are many rounds of wild-ass guessing go on.

What they really NEED is YOU -- someone unafraid to ask the tough questions directly, incessantly, and mercilessly -- until the ambiguity is vanquished by our hero's wand or sword.

Thanks for reading, Becky, it's great to have you here.

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