Finding it hard to spark lively conversations in your Virtual Assistant community? Would You Rather questions are a playful way to get members talking, sharing, and connecting. Use these ready-made prompts to invite fun debates and creative thinking.
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Would You Rather questions are powerful tools for community engagement because they lower the barrier to participation. Members only need to choose between two options, making it easy for everyone to jump in, even those who are usually quiet. The scenarios encourage imaginative thinking and allow members to reveal their preferences, which fosters connection and understanding.
In a Virtual Assistant community, these questions can highlight the unique challenges and joys of remote work, multitasking, and digital problem-solving. They also provide a non-intimidating way for members to express their personalities, compare experiences, and build camaraderie. By prompting members to explain their choices, you encourage deeper conversations and genuine engagement.
Would you rather automate all your email sorting or your calendar management?
💡 Example: "Would you rather automate all your email sorting or your calendar management?"
Would you rather work from a cozy mountain cabin or a sunny beach villa?
💡 Example: "Would you rather work from a cozy mountain cabin or a sunny beach villa? Tell us why!"
Would you rather handle 10 short tasks or one big project in a day?
💡 Example: "Would you rather handle 10 short tasks or one big project in a day?"
Would you rather use only keyboard shortcuts or only voice commands for a week?
💡 Example: "Would you rather use only keyboard shortcuts or only voice commands for a week?"
Would you rather work with clients in your timezone or across the globe?
💡 Example: "Would you rather work with clients in your timezone or across the globe?"
Would you rather never have a Monday meeting or always have Fridays off?
💡 Example: "Would you rather never have a Monday meeting or always have Fridays off? Share your pick!"
Would you rather use your favorite project management tool forever or try a new one every month?
💡 Example: "Would you rather use your favorite project management tool forever or try a new one every month?"
Would you rather specialize in one niche or be a jack-of-all-trades VA?
💡 Example: "Would you rather specialize in one niche or be a jack-of-all-trades VA?"
Would you rather attend a virtual networking event or an in-person one?
💡 Example: "Would you rather attend a virtual networking event or an in-person one?"
Would you rather work with a chatty client or a silent but efficient one?
💡 Example: "Would you rather work with a chatty client or a silent but efficient one?"
Would you rather master every productivity app or have an assistant of your own?
💡 Example: "Would you rather master every productivity app or have an assistant of your own? Tell us why!"
Would you rather always work with clear instructions or have full creative freedom?
💡 Example: "Would you rather always work with clear instructions or have full creative freedom?"
Would you rather manage social media or handle bookkeeping for a client?
💡 Example: "Would you rather manage social media or handle bookkeeping for a client?"
Would you rather work early mornings or late nights as a VA?
💡 Example: "Would you rather work early mornings or late nights as a VA?"
Would you rather have unlimited coffee or unlimited snacks during work?
💡 Example: "Would you rather have unlimited coffee or unlimited snacks during work? Vote below!"
Would you rather work in silence or with background music?
💡 Example: "Would you rather work in silence or with background music?"
Would you rather onboard three new clients in a week or take a month-long course?
💡 Example: "Would you rather onboard three new clients in a week or take a month-long course?"
Would you rather delegate your least favorite task or double your fastest one?
💡 Example: "Would you rather delegate your least favorite task or double your fastest one?"
Would you rather have the perfect home office or travel the world while working?
💡 Example: "Would you rather have the perfect home office or travel the world while working? Comment below!"
Would you rather get feedback instantly or receive a detailed report at the end?
💡 Example: "Would you rather get feedback instantly or receive a detailed report at the end?"
Would you rather become an expert in spreadsheets or graphic design?
💡 Example: "Would you rather become an expert in spreadsheets or graphic design?"
Would you rather work for startups or established companies?
💡 Example: "Would you rather work for startups or established companies?"
Would you rather use only one browser tab or unlimited tabs for a week?
💡 Example: "Would you rather use only one browser tab or unlimited tabs for a week? Share your struggle!"
Would you rather answer emails with templates or write fresh responses every time?
💡 Example: "Would you rather answer emails with templates or write fresh responses every time?"
Would you rather work with a team or solo as a VA?
💡 Example: "Would you rather work with a team or solo as a VA?"
Would you rather take on a challenging new skill or perfect a current one?
💡 Example: "Would you rather take on a challenging new skill or perfect a current one?"
Would you rather use only email or only chat to communicate with clients?
💡 Example: "Would you rather use only email or only chat to communicate with clients?"
Would you rather have every task come with a clear deadline or complete flexibility?
💡 Example: "Would you rather have every task come with a clear deadline or complete flexibility?"
Would you rather manage a full inbox or organize a messy digital workspace?
💡 Example: "Would you rather manage a full inbox or organize a messy digital workspace?"
Would you rather always have perfect wifi or never run out of battery?
💡 Example: "Would you rather always have perfect wifi or never run out of battery? Vote below!"
Would you rather create client reports or design marketing materials?
💡 Example: "Would you rather create client reports or design marketing materials?"
Would you rather get a surprise bonus or a heartfelt thank you note from a client?
💡 Example: "Would you rather get a surprise bonus or a heartfelt thank you note from a client? Share your pick!"
Would you rather have a four-day workweek or shorter daily hours?
💡 Example: "Would you rather have a four-day workweek or shorter daily hours?"
Would you rather work with high-maintenance clients for big pay or chill clients for less?
💡 Example: "Would you rather work with high-maintenance clients for big pay or chill clients for less?"
Would you rather only use cloud storage or only use local files for a month?
💡 Example: "Would you rather only use cloud storage or only use local files for a month?"
Would you rather train a new VA or learn a new tool yourself?
💡 Example: "Would you rather train a new VA or learn a new tool yourself?"
Would you rather batch all your tasks or switch between different tasks all day?
💡 Example: "Would you rather batch all your tasks or switch between different tasks all day?"
Would you rather plan your week in advance or go with the flow each day?
💡 Example: "Would you rather plan your week in advance or go with the flow each day?"
Would you rather have a standing desk or the ultimate ergonomic chair?
💡 Example: "Would you rather have a standing desk or the ultimate ergonomic chair? Pick your fave!"
Would you rather always meet deadlines but feel stressed or work stress-free but miss some deadlines?
💡 Example: "Would you rather always meet deadlines but feel stressed or work stress-free but miss some deadlines?"
Would you rather have instant access to all client info or unlimited free training?
💡 Example: "Would you rather have instant access to all client info or unlimited free training? Tell us why!"
To use these templates, simply copy and paste a question into your community platform and encourage members to reply with their choice and reasoning. Rotate them weekly or during slow periods to reignite discussions. You can also use them as icebreakers in live chats, virtual events, or team-building sessions for a quick boost in participation.
For all platforms, use clear formatting and add a call-to-action to encourage replies. Pin popular Would You Rather posts for new members to join in. Use images or emojis to make posts more eye-catching, but keep the focus on the question itself.
For maximum relevance and engagement, tailor your Would You Rather prompts to scenarios VAs encounter daily—like prioritizing between calendar management or inbox zero, client onboarding vs project tracking, or software choices like Asana vs Trello. This sparks meaningful discussion and knowledge sharing rooted in VA experience.
Pose Would You Rather questions highlighting real-world communication tool dilemmas, such as 'Would you rather manage all clients exclusively on Slack or stick to email only?' This helps VAs share preferences, tips, and frustrations, creating a supportive environment around a universal industry challenge.
Absolutely. Framing these challenges as Would You Rather questions—e.g., 'Would you rather handle a client with frequent scope creep or one who always pushes for tighter deadlines?'—encourages peer learning and empathy about high-pressure situations unique to the VA industry.
Yes, comparing industry-standard tools like Dubsado vs HoneyBook or Zoom vs Google Meet in your prompts will not only drive engagement but also facilitate resource-sharing and recommendations. VAs love discussing their tech stack, and these choices are central to their workflow.
Create prompts like 'Would you rather batch all your client calls into two days or spread them out for flexibility?' This gives VAs a platform to share time management strategies and discuss the unique work-life balance challenges faced in the VA field.
Yes—VAs often debate the pros and cons of different pricing models. A Would You Rather asking 'Would you prefer to charge hourly or offer retainer packages for all clients?' can kick off valuable conversations about income stability, client relationships, and sustainable business practices.
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