100+ Icebreaker Questions For Remote Employees (by Personality Type)


Start a new remote job? Want to get to know your remote coworkers better? Whatever your specific situation, there’s all kinds of scenarios that involve you being engaging with your coworkers that isn’t necessarily work-related. This can be difficult while remote though, so I’ve put together a list of icebreaker questions to help get that conversation snowball rolling.

Unlike other “icebreaker lists” out there, I’ve categorized these into the Big 5 personality types. This way, you will have a good chance at getting a better/longer answer out of your coworker!

Icebreakers for the “Openness” Personalities

The Openness personality type is often characterized by curiosity, creativity, and eagerness to explore new ideas and experiences. For your remote coworker, this will typically mean flexibility and adaptability, embracing change and innovation within the workplace. This coworker is likely to be an avid learner, continuously seeking to expand their knowledge and skills in various domains. They are not afraid to challenge conventional norms and take risks, which can result in novel solutions and unique perspectives that benefit the team. In discussions, they are receptive to the ideas of others, valuing diverse viewpoints and encouraging an open exchange of thoughts.

In a remote work setting, an individual with high Openness tends to excel at collaboration and communication. They often initiate brainstorming sessions and virtual meetups, fostering a sense of camaraderie and inclusion among team members. Their penchant for creative problem-solving and out-of-the-box thinking can be an asset in tackling complex projects or overcoming obstacles.

  • How do you stay organized and manage your time effectively while working remotely?
  • What’s the most rewarding project you’ve ever completed?
  • What’s your favorite productivity hack or tool?
  • How do you stay motivated when working on a challenging task?
  • Have you ever turned a failure or setback into a valuable learning experience? How?
  • What’s the most interesting thing you’ve learned recently?
  • What’s the best advice you’ve ever received?
  • What’s the most unique experience you’ve ever had?
  • What’s a place you’ve always wanted to visit, and why?
  • What’s a topic you’re passionate about, and why?
  • What’s your favorite “caught-on-Zoom” story?
  • What’s the most unconventional thing you’ve ever tried, and did you enjoy it?
  • What’s a cultural tradition or festival you’d like to experience, and why?
  • What’s the most thought-provoking book you’ve ever read?
  • If you could have dinner with any historical figure, who would it be and why?
  • What’s the most innovative product or service you’ve seen recently?
  • What’s a skill or talent you’ve always wanted to learn, and why haven’t you learned it yet?
  • What’s a futuristic technology or invention you’d like to see become a reality?
  • What’s the most inspiring TED talk or podcast episode you’ve listened to?
  • What’s a challenge you’ve faced that has changed your perspective on life?
  • If you could switch careers for a day, what job would you like to try and why?
  • What’s an alternative lifestyle or living arrangement that you find intriguing?
  • What’s the most unique or exotic food you’ve ever tried?
  • If you could choose a superpower, what would it be and how would you use it to make the world a better place?
  • What’s a quote or mantra that has helped you overcome a difficult situation or challenge?

Icebreakers for the “Agreeableness” Personalities

These are likely the coworkers that you would regard as the “yes men”. This personality type is often characterized by their warm, cooperative, and considerate nature. They are driven by the desire to maintain harmonious relationships and create a positive atmosphere within the team. Your coworker is likely empathetic and supportive, taking the time to understand the needs and concerns of colleagues, and offering assistance whenever possible. Their strong interpersonal skills and ability to put others at ease make them excellent at conflict resolution and fostering collaboration. They are typically good listeners, valuing the opinions and ideas of their teammates, and striving to make everyone feel heard and appreciated.

In a remote work setting, an Agreeable individual’s strong communication skills and amiable demeanor can be crucial in maintaining team morale and cohesion. They often go out of their way to check in on colleagues, offering encouragement and praise, while ensuring that everyone’s needs are met. This coworker is likely to be reliable, trustworthy, and committed to the team’s success, making them a valuable asset in any collaborative endeavor.

  • What’s the kindest thing someone has ever done for you?
  • What’s the nicest compliment you’ve ever received?
  • What’s something good that’s happened to you recently?
  • What’s your favorite way to show gratitude to someone?
  • What’s something that always makes you smile?
  • What’s the most thoughtful gift you’ve ever given or received?
  • If you could make one positive change in the world, what would it be?
  • What’s a random act of kindness someone has done for you that you’ll never forget?
  • What’s the best compliment you’ve ever given someone?
  • If you could thank one person for something they’ve done for you, who would it be and what would you say?
  • What’s something you’ve learned from a difficult or challenging situation?
  • What’s a cause or charity that you’re passionate about and why?
  • If you could have any job in the world, what would it be and why?
  • What’s your favorite way to spread positivity or happiness to others?
  • What’s the most inspiring story you’ve ever heard or read about?
  • If you could learn any language, which one would you choose and why?
  • What’s a life lesson you’ve learned from a family member or close friend?
  • What’s a personal achievement you’re proud of that you haven’t shared with many people?
  • What’s the most surprising or unexpected compliment you’ve ever received?
  • If you could choose one quality or trait to have, what would it be and why?
  • What’s a song or piece of music that always puts you in a good mood?
  • What’s something you admire about your coworkers or colleagues?
  • What’s a quote or saying that inspires you to be kind?
  • What’s something you’ve done to help someone else that made you feel good?
  • What’s a small gesture or act of kindness that can brighten someone’s day?

Icebreakers for the “Extraversion” Personalities

And who could forget: the social butterfly of the group. A coworker with the Extraversion personality type is just what you would think: outgoing, sociable, and having an energetic demeanor. They thrive on social interaction and enjoy engaging with others, both professionally and personally. This coworker is likely to be assertive and confident, eagerly taking on leadership roles and responsibilities within the team. They have a natural ability to motivate and inspire their colleagues, driving the group towards success and fostering a positive work environment. In discussions, they are comfortable expressing their opinions and sharing their ideas, contributing to a dynamic and stimulating exchange of thoughts. This is probably the easiest type as it relates to using icebreakers to open them up. In fact, they’ll probably enjoy answering the questions more than most!

  • What’s your go-to karaoke song, and why do you like it?
  • If you could travel anywhere in the world right now, where would you go and who would you bring with you?
  • What’s the best concert or live event you’ve ever attended?
  • If you could be a famous person for a day, who would you be and why?
  • What kind of social activities do you enjoy doing online, such as gaming or virtual meetups?
  • If you had to pick a theme song for your life, what would it be and why?
  • How would you describe your ideal weekend getaway?
  • What was the last movie or TV show that made you laugh out loud?
  • What’s the best party or celebration you’ve ever been to?
  • If you could have dinner with any fictional character, who would it be and why?
  • If you could be a contestant on any game show, which one would you choose and why?
  • Share a memorable experience from your favorite vacation.
  • Have you ever tried a new hobby or activity that pushed you out of your comfort zone? What was it?
  • What’s the best piece of advice you’ve ever received?
  • What’s your favorite way to stay active or exercise?
  • If you could create your own TV show, what would it be about and who would star in it?
  • If you were to plan the perfect group outing or team-building activity, what would it involve?
  • If you could attend any event in history, what would it be and why?
  • Do you have any hidden talents or party tricks that most people don’t know about?
  • If you could instantly become an expert in any subject or skill, what would you choose?
  • If you could have an unlimited supply of one thing for the rest of your life, what would it be?

Icebreakers for the “Conscientiousness” Personalities

The Conscientiousness personality type is identified by their strong sense of responsibility, diligence, and attention to detail. They are highly organized and disciplined, consistently setting and achieving goals, and following through on tasks and commitments. This coworker is likely to be reliable and dependable, with a strong work ethic and dedication to delivering high-quality results. They are excellent at time management and prioritizing tasks, ensuring that deadlines are met and projects are completed efficiently. Their careful planning and systematic approach to work contribute to a well-structured and smoothly functioning team environment.

  • What’s your morning routine like, and how does it help set the tone for the day?
  • What is one personal or professional goal you’ve set for yourself this year?
  • How do you stay focused when you’re working on a task that requires a high level of concentration?
  • Do you have any favorite books, podcasts, or resources related to personal development or productivity?
  • What’s one habit you’ve developed that has had a positive impact on your life or career?
  • How do you prioritize your to-do list when everything seems equally important?
  • What’s a challenge you’ve faced in your career, and how did you overcome it?
  • How do you handle distractions while working from home?
  • What’s the most rewarding project you’ve ever completed?
  • What’s your favorite productivity hack or tool?
  • How do you stay motivated when working on a challenging task?
  • Have you ever turned a failure or setback into a valuable learning experience? How?

Icebreakers for the “Neuroticism” Personalities

A remote coworker with the Neuroticism personality type is often characterized by their heightened sensitivity to stress, emotional volatility, and a tendency to experience negative emotions such as anxiety, worry, and frustration. They may be more prone to self-doubt and insecurity, which can affect their confidence and decision-making abilities. This coworker is likely to be highly conscientious of their performance and the opinions of others, potentially leading to increased pressure and self-scrutiny. In challenging situations, they might struggle to maintain composure, with the risk of their emotions impacting their work and relationships with colleagues. By nature, they may not be your most open audience when it comes to answering some of these questions, but if they do, you will probably learn loads of information that you never knew about them.

  • How do you manage stress or anxiety in your daily life?
  • What’s your favorite relaxation technique or self-care practice?
  • When you’re feeling overwhelmed, what helps you regain focus and balance?
  • How do you handle critical feedback or setbacks at work?
  • What’s a situation where you’ve had to step out of your comfort zone? How did you handle it?
  • What kind of support do you appreciate most from your coworkers or manager during difficult times?
  • Can you share a time when you had to navigate a difficult or challenging situation at work? How did you resolve it?
  • What’s a book, movie, or song that has helped you through a tough time?
  • How do you build resilience in the face of adversity?
  • When faced with a difficult decision, what strategies do you use to help you make the best choice?
  • How do you maintain a healthy work-life balance, especially when working remotely?
  • What is your favorite way to decompress after a stressful day?
  • How do you approach making mistakes or dealing with failure?
  • What’s a quote or mantra that helps you stay grounded or centered during tough times?

Take the First Step

No matter how you cut it, sometimes starting a conversation can be a bit intimidating and overwhelming. But like most things, sometimes starting is the hardest part. Hopefully these icebreakers will help you relate more with your coworker, even while working remotely.

Founder : Wherever I May Work | Website | Other Posts

Jared has worked remotely for 15 years in various marketing capacities, and has managed hundreds of marketing campaigns along the way. He has held freelance, agency, and in-house positions for companies large and small.

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