The Working Version - For the Career You Actually Have  /  Chapter 16

Chapter 16: What Someone Else Actually Sees

Non-Fiction

Last week you wrote a draft, then spent a week testing it against your own behavior. That gets you further than most people ever go. But there's a ceiling on self-observation, no matter how honest you are. You're the one person who can't see yourself from the outside in quite the same way everyone else does.

This week, you close that gap. You bring your draft to someone who's actually watched you work, and you ask them to tell you the truth.

This isn't a performance review, and it shouldn't feel like one. Pick someone specific. A peer you trust, someone who's worked closely with you for a while, or a mentor if you have one. Not your manager necessarily, unless your manager has also seen you in enough different situations to have a real opinion, not just a formal one shaped by reviews and metrics.

Bring your revised draft from last week, and bring the specific moments you wrote down, not just the label. If you walk in and just ask, "Do you think I'm more Directive or Coaching?" you'll get a guess, shaped by whatever they remember off the top of their head. Bring real examples instead, and the conversation becomes something else entirely, a genuine comparison between what you noticed about yourself and what they noticed about you.

A few actual questions worth asking, plainly, in your own words.

"When you think of a time I led something well, what comes to mind first?" Let them pick the moment, not you.

"Was there ever a time my approach didn't quite land, something that felt off to you, even if you didn't say anything at the time?" This one takes real trust to ask, and real trust to answer honestly. If the person hesitates, don't rush to fill the silence. Give them a moment to think. The useful answer sometimes takes longer to arrive than the easy one.

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