Better Questions Build Friendships

Hello and welcome back to my newsletter! Last week I was writing about how most of the successful people I know don’t focus on being successful. Instead they focus on taking on projects that help them become a better version of themselves, which then leads to (sometimes surprising) successes.

Here’s my question this week: In this holiday season, how do we deepen and grow our relationships with friends and family? Because our relationships are among the most important parts of our lives. 

We tried a social experiment recently. My wife and I hosted a few friends for dinner. After people arrived and got situated and caught up with greetings and small talk, we introduced a conversation game.

In the days leading up to our gathering, my wife and I composed a stack of questions designed to help us learn more about one another. Keep in mind all of us have known each other for years — at least fifteen years or more. I had a bowl of cards with light and fun questions such as “Do you have an amusing or embarrassing Thanksgiving story?” and “If you could go back in time, what year would you like to visit?

We also had a deeper set of questions which asked things such as, “What is one of the biggest risks you have taken in life? How did it turn out?” And “What’s a memorable experience from childhood that you think shaped who you are today?

Everyone agreed the game was a success. We took turns asking each other questions we had never asked before, and as a result we had meaningful conversations, everyone had a balanced opportunity to contribute and listen, and we all learned something new about our friends.

I’ve been enjoying Kat Vellos’ book We Should Get Together: The Secret to Cultivating Better Friendships. She points out that there’s nothing wrong with small talk. Small talk is fine as an on-ramp to more meaningful conversations, but small talk alone doesn’t allow relationships to deepen and grow.

We often fall into conversational habits in which we ask the same questions, and provide the same answers. To build meaningful relationships and friendships, we can accelerate that by asking more powerful questions. Powerful questions are open ended and allow the person responding to choose the direction of the conversation. Powerful questions create possibilities and encourage discovery, understanding, and insight.

“The importance of friendship has been hiding in plain sight.”

Lydia Denworth, author of Friendship: The Evolution, Biology, and Extraordinary Power of Life’s Fundamental Bond

Friendship is as important as diet and exercise for our mental and physical health. We often think of friendship as enjoyable, nice, and comforting, but we don’t often think of friendship and social connection as being essential to our ability to thrive. We don’t think of our friendships as critical to boosting our immune system or staving off long-term mental ailments.

Chasing health and longevity, we puree kale smoothies, listen to meditation apps, read Brené Brown, and wake up for morning boot camp classes. But the secret sauce to long term mental and physical health might not just be the planks you do in your workout class, but the friends you see and spend time with.

According to author Lydia Denworth, the reason friendship and social connection has largely been ignored by scientists, until recently, is because it has been hard to define what friendship is. Scientists like to measure things they can define, and pin down. In her research, Denworth interviewed biologists and anthropologists, and found that their agreed definition of friendship is a relationship which is stable, positive and reciprocal.

Friends make time for each other consistently, leave others feeling buoyed and uplifted, and have their past interactions to build upon. In this way, the layers of a friendship are built over time such that with each repeated contact we get to reinforce past interactions, and then add new stories, ideas and values to edify one another.

For the holidays, ask the kinds of questions that bring us closer together. Looking for ideas? Try Vertellis. They have awesome questions you can try out. Happy New Year!


Our company Mindscaling, is busy building powerful online micro-learning experiences to drive the human change that propels your team. You can find our catalog of high-impact courses here. And if you want something more tailored, you can learn about our custom work here.

My book Small Acts of Leadership, is a Washington Post bestseller! You can grab a copy now.

And if you want to learn to apply some of these ideas and be an effective coach for your team, we wrote a course on that too. It’s called Coaching for Managers available over at UDEMY for Business.