Stop Asking Boring Questions
How to ask better questions and actually get to know your coworkers.
In my previous article, we discussed why it’s vital to get to know your coworkers on a deeper level. It helps you identify their core motivations, builds social capital you can draw on later, and reduces social friction during high-stakes team discussions.
Now, let’s talk about the practical application. This is the system I use to pivot from “office small talk” to meaningful connection.
Even though I previously discussed the need to move past small talk, these types of questions are where I start. No one likes to be jumped out of nowhere with a sudden, deep question. The difference is that I use the information revealed in the answer to pivot toward more insightful questions and more interesting topics.
Step 1: Start Surface Level
You’re likely capable of executing this step naturally. But if you need some inspiration to break the ice, here are a few questions to get you started:
What did you do this weekend?
What has been the highlight of your week so far?
Are you working on any personal projects or hobbies lately?
Tip: Avoid “yes or no” questions. A tired, rushed, or uncomfortable coworker will give you a binary answer rather than elaborating. For example, instead of asking “How was your weekend?” ask “What did you do this weekend?” or “Tell me about your weekend.”
Step 2: Generalize the Question
Next, ask a follow-up question based on the information they just shared. Your goal is to generalize the topic and uncover their broader preferences and values. For instance, if they mentioned hosting out of town family this weekend, ask about their philosophy on hosting guests. If they mentioned a specific meal, ask about their favorite cooking styles.
What is your favorite thing to do when [you have a visitor, you have a morning to yourself, you’ve had a long week, etc.]?
If you had all the time in the world, what/where would you [cook, visit, paint, etc.]?
When you’re looking to [relax/recharge/learn something new], what do you usually gravitate toward?
Step 3: Pivot Towards the Story
Ask questions about when these interests began. Exploring the origin of a hobby or preference often leads to the people associated with those memories—people who are frequently the very influential figures in their lives.
What was the first time you [cooked that meal, painted with a friend, went to that restaurant]?
Who taught you to [fill in the blank]?
What is your favorite memory of [hosting a dinner party, a shared experience with family, etc.]?
Was this something you grew up doing, or did you discover it later in life?
Step 4: The Follow-Up
In the weeks that follow, you can skip the surface-level fluff and jump straight to the specific topics your coworkers actually care about. This demonstrates active listening and genuine interest.
How is your friend Joe?
How is your mom’s new job going?
What was the most recent recipe or restaurant you tried?
Did you ever get a chance to finish that project we talked about?
Example in Action:
Surface: “What did you do this weekend?” Answer: “My parents were in town. We went to the botanical gardens.”
Generalize: “That sounds fun! What is your favorite thing to do when you have visitors?” Answer: “We love to open a bottle of wine and take our time cooking a fun meal—something we wouldn’t normally have time for on a weeknight.”
Pivot: “When was the first time you started hosting dinner parties like that?” Answer: “Well, actually, that goes all the way back to my first apartment out of college when...”
Asking better questions isn’t hard, but it does take intentionality. This week, pick one coworker and make it your goal to learn something new about them. Creating a team where people are known and love to come to work happens one person at a time.