What was the most interesting thing that happened today? What are you looking forward to tomorrow?

What things brought you joy last year? What are the smallest things that made a difference? (They could be little details, items that delight, virtual reconnections, accomplishments both minor and major, splurges, surprises, etc.)

Conversely, what things did you let go of this past year, willingly or otherwise? Why and how and when? What has that meant for 2023?

My brother-in-law’s agency (12 or so employees) established a recent tradition that I really like. Each Monday in their staff meeting, they go around the table to give responses to “The Monday Question.” 

The question is first revealed to everyone at the same time. Staff don’t have advanced knowledge, so the exercise serves as an impromptu storytelling opportunity and a chance to learn more about each other.

A few sample Monday Questions:

What’s the best advice you ever got?

Given the choice of anyone in the world, whom would you want as a dinner guest?

Are you superstitious? What are you superstitious about?

What would constitute a “perfect” day for you?

Tell us about one memorable day from your childhood. What happened?

Those are some terrific “icebreaker” questions and even though they’re asked in this case in a business meeting, they’re in a “lighter” vein.

The person who asks better questions, gets better answers. I’ve read the website of a local Austin guy who facilitates speed-networking meetings. He uses a form of icebreakers that are similar to the Monday questions. Here are few:

What was your first job?

Have you ever met anyone famous?

What are you reading right now?

What’s something you want to do in the next few years that you’ve never done?

With my own longtime buddies, I’m a big fan of periodic check-ins (email) with:

What are you currently reading/streaming/listening to?

That’s a great one, and (happily) self-serving, as it loads you up with new content/viewing ideas from your most trustworthy sources.

Because I interview executives for a living [more or less], I’m always looking for killer business questions. 

A communications guy like me gets put on the CEO’s agenda and usually only gets a precious few minutes of his or her time.

I’ll go in there needing information to write a case study or presentation and since I’ve got to adhere to a “Be Bold, Be Brief and Be Gone” gameplan, I love to walk in to the important human’s office (or appear on the Zoom) and lead off, if I’m already familiar with the person, with: 

What are you working on now that you are most excited about?

[This one works on everybody regardless of rank… Check it out!]

Voila, the energy shifts in the instant you give the other person permission to talk about himself. 

NOW we’re past the “ugh!” initial feelings of obligation to have to talk to the PR guy — he or she’s got a busy day ahead, and up until this moment you were regarded as a speed bump — and NOW the CEO is going to share with you his secret project, or some cool statistic she’s been waiting to use. 

…And will now be more receptive to these Qs:

• What surprised you most about the events in your industry over the past 12 months?
• What were some of the most notable difficulties your industry peers grappled with in the last year?
• What are some of the most exciting areas of progress, advancement and/or improvement you’ve seen over the last 12 months or so?
• What are 2-3 of the most formidable challenges your peers can expect to confront next year?

Bridging the personal/professional, one of my favorite questions is: What are you working on when time fades away?

Here are a couple fun ones — Peter Thiel’s contrarian, 2-question guide for startups, which also applies to life:

What important truth do very few people agree with you on? [careful with this one]

What valuable need is nobody out there filling?

Media consultant and interviewing coach/guru John Sawatsky urges open-ended questions. Rather than ask, “Did it hurt to get shot?” instead try, “What was it like to get shot?” The former is a Yes/No and the latter question could take you just about anywhere.

Ask a question and make an effort (it takes a little bit of practice) to get out of the way by using short, open-ended questions when you want elaboration.

A final thought: Ask fewer, but ask “better” questions… Less is more!

I had a colleague who would show up to customer interviews with a list of 25 scripted, specific questions. (Talk about daunting for the recipient.)

Soon we had the list down to five without losing substance.

Ask great questions! It’s all in the packaging. If there’s time to think about it, try to reduce the number of questions… in any and every situation.