Be Prepared: 7 Questions to Ask at Your Next Lunch Meeting

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The Mind, The Mouth & Growth

G.K. Chesterton said, “The object of opening the mind, as of opening the mouth, is to close it again on something solid.”

If you feel you have nothing much left to learn, please don’t read the rest of this.  I don’t write that flippantly, I mean it.  This will be a complete waste of time if you’re not curious, humble, and passionate about bringing value to others and growing personally.  And time is a most valuable resource.  If, however, your mind is open and hungry for something solid-this is for you.


Scene 1: The Unexpected Dopamine High

You’re attending an event you didn’t really want to go to, and your friend asks, ‘have you ever met ___?  Come with me, you’ve got to meet ____.’  You roll your eyes a bit, take a breath and figure it’ll help pass the time. 
Shortly after the intros, you’re realizing that you just really hit it off with them.  Time flies and your mind is reeling with questions for this newfound sage.  They end up being the type of person you talk about the whole way home because of the incredible stories, leadership experiences and they were just so stinkin’ approachable. 

But there weren’t enough minutes.  You were just to the part where they explained how the leap happened from non-profit work in Bosnia to running an accounting firm in Indianapolis.   The good news is you both want to keep the conversation going so you exchange contact info before floating to your car.


Scene 2: Nailing the Why

It been about 10 days since the conversation and you finally have a date set to grab a coffee and pick up where you left off.  The excitement is beginning to shift though—what if you waste their time?  This situation is a lot different than the first, and what do you talk about?  Do you start right away with the leap from non-profit work, or do you bring stories of your own?

Then a question hits you: What’s my goal in meeting with them? 

Working through that question helps you realize your motive isn’t to gain a friend or to be wowed by a whimsical story.  Instead, you want wisdom, guidance, connection, and to have the time be of value to them as well.  But how do you do that? 


Scene 3: Genuine Questions, Honest Curiosity

Shortly after discovering your ‘why’ for the coffee date, you text your friend who made the introduction at the event.  “Hey, I’m meeting with ___ for coffee, thanks again for the intro!  I want to make the most of it, is it weird to bring a notebook?  What do you think I should do?”  *insert confused gif here* 

Your friend replies with a link to a blog that has several questions they’ve used and the words, “ask these and be yourself!  Asking thoughtful questions, listening, and respecting their time goes a long way.”  And like a good friend closes the text with--“Don’t screw it up.  kthxbai.”


The Questions:

Here are 7 questions to ask so you get the most out of the time together.  As with all things, use these as time allows and as it adds to the conversation. 

  1. Who or what has influenced your trajectory the most?
    1. Here is where you’re looking to gain wisdom
  2. What’s something you’ve learned recently?
    1. Taken straight from John Maxwell, this question is all about passion.  You’ll hear & feel the excitement, it’s contagious!
  3. How do you view failure?
    1. This is probably the most revealing of the questions
    2. Failure isn’t the opposite of success, it’s a compliment to success.  You can’t separate em, stop trying.
    3. Never met a successful leader who hasn’t had a failure—and most likely a bunch of em
  4. What does your morning routine look like?
    1. I love this question but I hate waking up early *Gulp*
  5. What are some resources I should check out?  (books, podcasts, movies, events...etc.)
    1. Listen for why it impacted them
  6. Who are some of the most surprising people you’ve met over the years?
    1. Stories will abound,
    2. You’ll gain insight into what makes an impression on an impression maker
  7. What can I do to bring value to you/serve you/reciprocate?
    1. Shouldn’t just be taking from them
    2. Use finesse, this question is powerful but also a bit robotic if you just read it.  Speak from the heart, communicate your gratitude

Bonus question: Can we do this again? 


Making it real:

Two things to keep in mind that I’ve messed up in the past:

  • Watch the time closely.

    • Just because you’re excited doesn’t mean they have an extra 47 minutes for you
  • If you discover that this person isn’t who you thought they were, don’t force it.
    • Have your lunch, thank them, and learn what you can

Take a risk, ask a few of these questions at your next lunch or coffee meeting and let us know how it goes!  Something I’ve discovered is that if you’re willing to learn and ask the meaningful questions, just about everyone has something to teach you. 


Need More?

Listen to episode #90, Interrogation vs Interview with Chad Stillman

Read Building Blocks of a Successful Company by Patrick Booth

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