The Five Principles That Drive Powerful Questions + Some of My Favourites and Where They Shine ✨

*This is a snippet of the most recent email sent to CommunityMade subscribers. To view the entire email (and get access to the full list of 79 conversation starter questions), visit: Communitymade.com

The quality of our lives... comes down to the quality of our relationships.

The quality of our relationships... comes down to the quality of our conversations.

The quality of our conversations... comes down to the quality of our questions.

The best questions catch people off guard (but not too much), get them to think differently/with curiosity, deepen connection and invite each person to discover something (new) about themselves.

Five Principles for Asking Powerful Questions

Principle #1 | Boring Questions Get Boring Answers.

Asking, “What are your goals?” is boring…

“What are you struggling with right now?” is uninspiring and will generally result in a shitty response.

Personally, I always thought asking “share an interesting fact about yourself that not many people would know” would garner something that was actually interesting, but literally testing it hundreds of times, it’s most often a dud.

The lesson?

Boring questions get boring answers.

This won’t be an area of concern should you decide to lean on the questions provided below, as they have proven their worth time and time again.

Principle #2 | There’s Power In Preparation.

Maybe it’s introversion, perhaps I’m a little socially awkward, but often in the first few minutes of an interaction, I’m not “present” because I’m afraid of how I’m being perceived, even if it’s someone I know well.

To combat this, I prepare a LOT.

”Preparation is—if not the key to genius—then at least the key to sounding like a genius. Spectacular achievement is always preceded by spectacular preparation.” —Robert H Schuller

In a sales setting I always tell the team: you don’t need prepared scripts, you need prepared questions.

I don’t remember this, but apparently, when I went on a first date with the woman who would later become my wife and love of my life, I confessed to having questions prepared in advance because I was fearful of an awkward moment or a lull in conversation somewhere in the evening.

To me, prepping questions in advance of a social interaction is super helpful. It’s finding the balance between conversations feeling rehearsed or recited and priming by brainstorming a bunch of questions. You can also do what Larry King did: focus your energy on the first question and let the conversation go where it goes (this requires presence, and it’s beautiful to see where conversations end up if you’re willing to stay connected).

As an important sidebar when it comes to the first two points, preparation and avoiding boring questions, ask yourself a question before you ask it of anyone else. There are many times when I’ve been excited about a question I’d planned, and when asked, the response was lacklustre. And when I would actually sit with the question a little longer/after the fact, it was easier to understand why that might have happened.

Alex Hormozi once said “People underestimate how much smarter you can seem with 20mins. of preparation.”

There’s huge power in preparation.

Principle #3 | Offer Colour & Thought Joggers.

The best questions are often primed with a story and are contextual. They give the question meaning and it serves as guardrails. Asking a question with context or colour can often result in a deeper, more connected response.

For example, Tim Urban does a really beautiful job with this in the “dinner table” questions on his blog. His website is also another great place that I scraped for questions for the master list 😉

”Thought Joggers” is a term I learned from my good friend Jon Bergoff and is something I’ve embraced as well when asking questions.

A very simple example could be a question like: What’s one of your happiest days? Why did this particular day stand out to you/what was meaningful about it?

Thought joggers, after the question has been posed, could sound like:

Perhaps it was a beautiful moment you shared with a friend….

Maybe it was on the backend of achieving a meaningful goal…

If you’re a parent, it could be a precious and unexpected interaction with your child…

It could be something a long time ago that sticks out… or something more recent… 

*Thought joggers aren’t leading, in fact, they often encourage folks to think beyond their initial response. And in doing so, you’re providing the person with primers to guide them and get their gears spinning.

Principle #4 | Set the Tone.

I often share the importance of leading by example.

It’s hard to expect folks to be vulnerable without leading with vulnerability. It’s hard to expect people to share openly and honestly without showing that it’s a space where they can feel safe (enough).

In the context of questions (especially in a group setting), I will often answer a question first to set a threshold for how deep people can go.

It’s worth mentioning that matching that vulnerability is an invitation. I always try to preface, especially if we are exploring a question that can really make them feel exposed, that they answer it at whatever level they feel most comfortable.

Also, instead of being the one to take the lead, there are times where I will lean on someone in the group (and even go so far as to prime them in advance about the question) to set the tone.

More times than I can count, I pose a question to a group, and responses are very “safe”. Midway through, someone courageously adds a layer of details that opens things up or answers with a new level of vulnerability, and this leads not only others to follow suit but those who already shared often want to revisit their initial response.

You can’t ask anyone for things you yourself don’t already give them.

So, be sure to set the tone.

Principle #5 | Relationships Move At the Speed Of Vulnerability (but don’t be too quick).

I believe this to be true; however, I’ve also learned that you can share too much, too quickly.

This can be problematic because if you overexpose yourself, you can’t run it back — you can’t put the genie back in the bottle.

Years ago, we bought out a restaurant in Toronto and hosted a dinner for about 80 entrepreneurs. I created a custom question set for their tables, and the cards were colour-coded by their level of vulnerability.

The moment I explained this in my opening remarks, every single hard-driving/type A personality entrepreneur in the room went for the most vulnerable questions in the deck.

Part of me definitely has an appreciation for those who choose to go all in, however maturity has taught me that the best approach is to ease into the pool.

A sampling of questions we’ve tested 100’s of times: x1 Q from each category

Personal Awareness (Jerry Colonna):

• “How have I been complicit in creating the conditions I say I don’t want?”

• “What am I not saying that needs to be said?”

• “What am I saying that’s not being heard?”

• “What’s being said that I’m not hearing?”

Order Questions: helps decide who goes first in a group setting

• Whoever’s been awake the longest (Fun/Quick)

• Whoever speaks the most languages (Fun/Quick/Connective)

• Whoever has the most siblings goes first (Fun/Quick/Connective)

Vulnerability: Light

• What do you, perhaps secretly, spend quite a lot of money on?

• If you could study with any expert in the world who would you work with and what would you study?

• What book has shaped you the most and share why it’s meaningful to you?

Vulnerability: Medium

• Complete the following statement: if you really knew me you'd know…

• What’s one of your proudest moments? Why?

• What did you have to overcome to become who you are today?

Vulnerability: Deep

• What makes it hard to be you? Why?

• Complete the following statement: what I don't want you to know about me is...

• What’s a conversation you've been avoiding? Why?

Get To Know You Questions:

• What’s one of your proudest moments? Why?

• Complete this statement: I lose track of time when...

• Talk about a devastating event in your life that turned out to be a ‘blessing.’

Reflection Questions:

• What’s become clear to you this year? Why and/or how?

• Looking back on your life what would you be proud to see in print? Why?

• What are you grateful you didn’t do this past year?

***To access the full question list that we sent out to our subscribers, visit CommunityMade.com.

What are others saying about this most recent newsletter?

In my next CommunityMade email, I’ll share how I designed my Outer Brain 🧠

A sneak peak 👀

In October, right after MMT Ojai (10th Anniversary!) I started to build my “Outer Brain.” A singular depository of quotes, principles and wisdom collected over the years that is easily searchable.

I now have a solid system for storing nuggets of wisdom from podcasts, books, and conversations with friends in a format that makes them retrievable when needed (in seconds). I'm looking forward to sharing it with you, as many of my friends have asked me to share the process and tools.

It's been a game-changer for me, and I think it may prove helpful for you as well.