Listening through questions

As humans we have a tendency to make our questions reflect our own biases. This results in asking close ended questions, or open questions followed by leading examples that reflect our biases. And it is tempting.

The problem with such questions is they don’t make us keep an open mind, because we are expecting a specific answer. They also might trigger defensiveness in the other person, since the leading examples/closeness in those questions strongly show the bias.

Recently I am adopting those techniques in my questions. Try doing this for few weeks, it becomes natural after.

  • Make your questions open. Shut up. Don’t explain. You would be surprised by the answers you get. Also many times people misunderstand the question, still don’t explain, ask a different open ended one. This will make you get better.
  • Don’t ask “Why?”. I used to ask why so many times and I discovered it intimidates people specially in stressful situations. My “Why?” questions are all becoming “What makes you say/do so?” or “What are the reasons?”. People feel less threatened. Try it.
  • Smile.

What are you optimizing for?

Recently this is becoming one of my most favorite questions. Whether it is product or life, knowing what someone is optimizing for is key to making the right decision.

I start to feel wary when people give me multiple contradicting answers. Optimizing for multiple things in the opposite direction ends up with nothing, or at best with something mediocre.

Everything carries a risk, and our brains try to protect us by telling us not to let go of what we already have, which leads to “try to do everything” syndrome, or loss aversion at all costs.

Breakthroughs only happen by exploring new territories, and failures are data points for next steps.