Deena Chadwick's Blog

You know the guy who asks for advice, nods along, says "totally, that makes sense"... and then does the exact opposite thing anyway?

That's an Ask-Hole.

So is the coworker who asks you and two other people the same question, hoping one of you gives the answer they wanted. So is the friend who asks "where should we eat?" and turns it into a 20-minute monologue before landing on the place you suggested at minute two. So is your boss who asks "just checking in — how's it going?" and means "why isn't this done yet."

(Curious if you're one of them? Take the quiz. Come back after — this gets better.)

Some Ask-Holes know exactly what they're doing — they're steering, extracting, or cornering you on purpose. Others are just bad at asking — wrong question, wrong time, wrong reason — and would be horrified to know the damage they've done. Both kinds cost you time, patience, and sanity. Only one of them meant to.

I wrote Don't Be An Ask-Hole — yes, that's really the title, no I'm not softening it — because after 20+ years in business analysis and project management, I've been on the receiving end of more bad questions than any human should have to survive. I started keeping a mental list. The list became 13 archetypes. The archetypes became a book.

Over the next few weeks, I'm breaking down each one right here — how to spot them, how to survive them, and (uncomfortable but necessary) how to check whether you're one yourself.

Next up: the one who asks for advice and never, ever takes it. You're already picturing him.

— Deena Chadwick