One Way to Think About Onboarding Icebreaker Questions


Jason Bacaj | 4 min read

Some elements of effective onboarding are obvious. Some are more nuanced.

Obvious elements include managers greeting their new team members on their first day. The more nuanced pieces include structuring onboarding in a way that helps ease the process of digesting all the information the person needs to consume.

At least one element is simply underrated: the icebreaker question. Icebreaker questions might not be absolutely essential parts of onboarding—a certain degree of cheesiness is necessarily involved—but these questions can play a valuable role.

After all, the interview process focuses on the open job and the applicant’s work history. It’s hard for both the interviewer and interviewee to get more than a gut feeling about how they’ll fit with the company’s culture. This is where well-crafted icebreakers can help!

Wait, why focus on such a minor detail?

Icebreaker questions help people open up and build a sense of team. Collaboration and creativity are easier the more familiar and comfortable you are with those around you. Usually icebreakers are doled out a handful at a time.

Here at Wisetail we ask an array of icebreakers. We’ll go through each and talk about the rationale behind the questions. By the end you’ll have a list of questions you can use, and the background knowledge to tweak them to your own needs.


Icebreaker Questions

Do you have a nickname you prefer? The point of this one is fairly straightforward—we’d like to know how you like to be addressed in the office. Occasionally this leads to someone sharing an interesting anecdote about a formative moment.

What was your first username on AIM, MSN, or MySpace? My first handle on social media, jdawg2433, is a little embarrassing now. But risking a small amount of embarrassment helps others trust you more, research shows. Robb Willer, a social psychologist at University of California, Berkeley, says embarrassment is “part of the social glue that fosters trust and cooperation in everyday life.”

Do you have any hidden talents or random fun facts about yourself? You won’t know whether a coworker is related to the Wright brothers unless you ask.

What’s your favorite song to dance to? Or, what’s your favorite viral video? Almost everyone has something to say about music. And there are few better ways to start an entertaining conversation with coworkers than pulling up a favorite viral video.

If you could have any world-renowned skill, what would be your craft? Only once people are relaxed and have metaphorically let their hair down will a burly Wyoming native open up about his respect for those who can knit at a high level.

Half of all hourly workers quit within four months of starting a new job, research by the Society for Human Resource Management shows. Their research also found that half of senior outside hires fail within 18 months. And finding a replacement can cost upwards of three-fourths that person’s salary.

All that to say: onboarding is an essential, if somewhat procedural, part of any job. Getting it right the first time is super important. And to get it right you have to put the appropriate amount of effort into the small things, like icebreakers.