HeyJaredThe Art of Asking Questions
Behind every breakthrough lies a great question. I help curious-minded people ask questions that spark clarity, insight and action.
- Indexed issues, last 90 days
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- Sep 27, 2026
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- Aug 14, 2026
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You Read Your New Team Wrong (opens the original)
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A product lead runs the first week of onboarding calls with a newly assembled development team based in another continent. Every call ends with “any questions?” and gets silence in return.Our instinct is to explain this as a mix of shyness and language barriers, or maybe a team that understood everything already. Interestingly, all three explanations attribute the problem to the individuals on the call, without questioning whether the person running the meeting could have done anything different
Drop The Strength That Earned You The Promotion (opens the original)
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A promotion is evidence. Something about the way you work has produced results, and your organisation is telling you so. You have demonstrated a strength that your employer values, become known for it and been rewarded with greater responsibility.Then you arrive at the next level and discover something quite uncomfortable: the strength that got you there is not necessarily the strength that will make you successful now. In fact, you may need to stop leading with it. has spent seven years coachin
I Don't Want Them to Resent Me (opens the original)
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was recently speaking to a manager (let’s call her Gemma) who told her she was worried being assertive would make her sound like a jerk. Not incompetent. Just disliked. That was the fear underneath every difficult conversation she kept putting off.From previous interactions, Serena knows that Gemma is good at her job. Good with people too, the kind of manager others actually want to work for. But Gemma had noticed an unhelpful pattern in herself: when she needed to be direct, she’d soften her fe
Would They Still Choose You? (opens the original)
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You can usually feel when you matter to people. The calls come to you, and you consistently find yourself in the right meetings, where decisions get made. From where you’re standing, the message seems clear enough: you are valued, and the evidence is everywhere. But, in practice, two rather different states can produce that evidence:In one, people come to you because they trust you and would still come to you even with good alternatives in front of them. In the other, they come to you because th
Second-Hand Knowledge (opens the original)
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At some point you were probably sorted into one of two kinds of person. Left-brained, and therefore logical, analytical and at home with words and numbers; or right-brained, and therefore creative, intuitive and artistic. Perhaps you still reach for the labels to explain why you are hopeless at sums or no good at drawing. It is a tidy, memorable idea, and it is false. In anyone with a healthy brain the two hemispheres are connected and work together on more or less everything, and no one is run
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