• Matthew Lerner

Before I Call Someone out… I Ask This Question

Each year I give myself one personal development goal. In 2010, as a Director at PayPal, I challenged myself simply to “ask great questions.”


Last week I shared 3 of my best questions in my OKR Metrics post. (Really good if you haven’t read it!) Here’s one more question. Use it to really challenge your team when they ask a “what should I do" type question. Even if you think you know the answer, reply with “I don’t know, what do you think?”


It sounds like a copout, but... try it: you are guaranteed to learn something valuable like:

  • Maybe they're super switched-on and you’re totally aligned

  • Maybe they're missing a key piece of information / context that you can share

  • Maybe you are missing a key piece of information / context

  • Maybe they are utterly helpless (and that’s good to know sooner than later)

In any case, they should feel more empowered (and accountable) just from you asking.


Then, if you like their thinking, acknowledge that!


If you disagree… do not debate them (yet). Instead, say “Interesting, walk me through your thinking.” (Figure out what’s in their head — the root cause that led them to that conclusion). Aka, unpack their thinking and engage from there.


(Hint: I don’t literally ask “why” as it tends to make people defensive).


P.S. This question also works great with young children and VC investors. 😏

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