Outstanding Question From An Outstanding Mentor

Guest Post by Alex Shalman

Liz and I go back to about mid-march of 2007. I had just launched a donation contest, and asked Liz to participate. Her initial reaction to the contest was that it was transparent link bait, and she was a bit annoyed. I immediately apologized for offending her, she saw past it, and the rest is history. I now consider Liz one of my best friends, and feel like I’ve known her forever.

As far as mentoring goes, we’ve had quite a few phone conversations, where Liz has been a great listener, as well as given me powerful injections of wisdom. I remember the exact moment when I first heard Liz use this question. It was during live open mic night of SOBCon. Yes, she’s even more amazing in person!

It’s simple:

“What do you do when you’re not doing this?”

I’ve used this very question to start countless conversations, and have been nothing but amazed each time at how people opened up. Whether talking to a new classmate, or even a random person I decided to talk to during my day. It never ceases to amaze me at how much people appreciate when you take an interest.

It also helps to practice the arts of proactive and empathetic listening to dig deeper into the conversation. It’s funny, but most people ask a question, listen to the response, and then go on about themselves.

Experience the outstanding response I’ve been getting with Liz’s magic question. Ask it of a stranger, really listen to what they say, and follow up at least 5 questions deep. You might be amazed just as I have been.

Btw, I would like to hear some other questions that you use to open up conversations with strangers. Let’s all share in the comment box below!

Alex Shalman

Thanks, Alex. The question seems to have served us both well. I’m smiling to think that we have met at the core of the matter where we both agree. . . . I consider you a friend, as well.

–ME “Liz” Strauss


  1. says

    My favorite opening question is:

    – “What makes your heart sing?”

    And somewhere later in the conversation:

    – “What’s important?”
    – “What question are you living with these days?”

  2. says

    My best way to start a conversation with a stranger ” Excuse me, do you know what time it is?” and I go from there ;-).

    It has worked so far

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