This or That Questions for Freelancing Communities (42+ Ideas)

Looking to spark more engagement and fun in your freelancing community? Quick This or That prompts are the perfect way to get members chatting and sharing their preferences. Use these playful templates to break the ice and keep conversations flowing, even on quiet days.

Freelancing 42 Templates

๐Ÿ“… Schedule a Week of Posts in 5 Minutes

Plan your content calendar and auto-post to Skool, Circle, or Mighty Networks

Try Free for 14 Days โ†’

Why This Works

This or That prompts work so well because they lower the barrier to participation. Members do not need to think too hard or worry about giving a 'right' answer. The simplicity and lighthearted nature of these questions make it easy for even the quietest members to join in.

Psychologically, quick-choice questions tap into our desire to share opinions and see how we compare to others. They create a sense of belonging and help members find common ground. In freelancing communities, where many work solo, these prompts foster connection and make the group feel more interactive and welcoming.

42 Ready-to-Use Templates

1

Morning hustle or late-night grind - which do you prefer when freelancing?

๐Ÿ’ก Example: "Morning hustle or late-night grind - which do you prefer when freelancing?"

๐Ÿ”ด High Engagement Barrier ๐Ÿ‘ค Average #routine #preferences
2

Work from coffee shop or work from home - what is your go-to spot?

๐Ÿ’ก Example: "Work from coffee shop or work from home - what is your go-to spot?"

๐ŸŸก Medium Engagement Barrier ๐Ÿ‘ค Irregular #workspace #lifestyle
3

Trello or Asana - which project tool do you swear by?

๐Ÿ’ก Example: "Trello or Asana - which project tool do you swear by?"

๐ŸŸก Medium Engagement Barrier ๐Ÿ‘ค Frequent #tools #workflow
4

Video calls or email updates - what is your preferred client communication?

๐Ÿ’ก Example: "Video calls or email updates - what is your preferred client communication?"

๐Ÿ”ด High Engagement Barrier ๐Ÿ‘ค Average #communication #client
5

Charge by the hour or by the project?

๐Ÿ’ก Example: "Charge by the hour or by the project?"

๐ŸŸก Medium Engagement Barrier ๐Ÿ‘ค Average #pricing #business
6

Work with international clients or local clients - which do you prefer?

๐Ÿ’ก Example: "Work with international clients or local clients - which do you prefer?"

๐ŸŸก Medium Engagement Barrier ๐Ÿ‘ค Frequent #clients #preferences
7

Early bird deadlines or last-minute rush - what is your usual style?

๐Ÿ’ก Example: "Early bird deadlines or last-minute rush - what is your usual style?"

๐Ÿ”ด High Engagement Barrier ๐Ÿ‘ค Average #deadlines #habits
8

Solo freelancing or collaborating with teams?

๐Ÿ’ก Example: "Solo freelancing or collaborating with teams?"

๐ŸŸก Medium Engagement Barrier ๐Ÿ‘ค Irregular #workstyle #collaboration
9

Monday start or weekend hustle?

๐Ÿ’ก Example: "Monday start or weekend hustle?"

๐ŸŸข Low Engagement Barrier ๐Ÿ‘ค Lurker #schedule #routine
10

Digital calendar or paper planner - which keeps you on track?

๐Ÿ’ก Example: "Digital calendar or paper planner - which keeps you on track?"

๐ŸŸก Medium Engagement Barrier ๐Ÿ‘ค Average #organization #tools
11

Take a midday break or power through till done?

๐Ÿ’ก Example: "Take a midday break or power through till done?"

๐ŸŸข Low Engagement Barrier ๐Ÿ‘ค Lurker #breaks #workday
12

Client calls with video on or off?

๐Ÿ’ก Example: "Client calls with video on or off?"

๐ŸŸข Low Engagement Barrier ๐Ÿ‘ค Lurker #client #meetings
13

Long-term contracts or short gigs?

๐Ÿ’ก Example: "Long-term contracts or short gigs?"

๐ŸŸก Medium Engagement Barrier ๐Ÿ‘ค Average #contracts #worktype
14

Work in silence or with music?

๐Ÿ’ก Example: "Work in silence or with music?"

๐ŸŸก Medium Engagement Barrier ๐Ÿ‘ค Frequent #environment #focus
15

Handle your own taxes or hire a pro?

๐Ÿ’ก Example: "Handle your own taxes or hire a pro?"

๐ŸŸก Medium Engagement Barrier ๐Ÿ‘ค Average #finance #admin
16

Fixed workspace or switch it up daily?

๐Ÿ’ก Example: "Fixed workspace or switch it up daily?"

๐ŸŸข Low Engagement Barrier ๐Ÿ‘ค Lurker #workspace #routine
17

Early invoice or wait till the deadline?

๐Ÿ’ก Example: "Early invoice or wait till the deadline?"

๐ŸŸก Medium Engagement Barrier ๐Ÿ‘ค Irregular #invoicing #finance
18

Learning new skills or perfecting your niche?

๐Ÿ’ก Example: "Learning new skills or perfecting your niche?"

๐Ÿ”ด High Engagement Barrier ๐Ÿ‘ค Frequent #skills #growth
19

One big client or many small clients?

๐Ÿ’ก Example: "One big client or many small clients?"

๐ŸŸก Medium Engagement Barrier ๐Ÿ‘ค Average #clients #business
20

Freelance full-time or as a side hustle?

๐Ÿ’ก Example: "Freelance full-time or as a side hustle?"

๐ŸŸก Medium Engagement Barrier ๐Ÿ‘ค Irregular #career #workstyle
21

Coffee or tea to fuel your work sessions?

๐Ÿ’ก Example: "Coffee or tea to fuel your work sessions?"

๐Ÿ”ด High Engagement Barrier ๐Ÿ‘ค Frequent #habits #energy
22

Morning check-ins or end-of-day wrap-ups?

๐Ÿ’ก Example: "Morning check-ins or end-of-day wrap-ups?"

๐ŸŸข Low Engagement Barrier ๐Ÿ‘ค Lurker #routine #communication
23

Use templates or start from scratch for new projects?

๐Ÿ’ก Example: "Use templates or start from scratch for new projects?"

๐ŸŸก Medium Engagement Barrier ๐Ÿ‘ค Average #workflow #tools
24

Work for agencies or direct with clients?

๐Ÿ’ก Example: "Work for agencies or direct with clients?"

๐ŸŸก Medium Engagement Barrier ๐Ÿ‘ค Irregular #clients #business
25

Batch tasks or tackle one at a time?

๐Ÿ’ก Example: "Batch tasks or tackle one at a time?"

๐ŸŸข Low Engagement Barrier ๐Ÿ‘ค Lurker #productivity #workstyle
26

Take Fridays off or work through the weekend?

๐Ÿ’ก Example: "Take Fridays off or work through the weekend?"

๐ŸŸก Medium Engagement Barrier ๐Ÿ‘ค Average #schedule #worklife
27

Strict work hours or flexible schedule?

๐Ÿ’ก Example: "Strict work hours or flexible schedule?"

๐ŸŸก Medium Engagement Barrier ๐Ÿ‘ค Average #worklife #routine
28

Get paid upfront or after delivery?

๐Ÿ’ก Example: "Get paid upfront or after delivery?"

๐Ÿ”ด High Engagement Barrier ๐Ÿ‘ค Frequent #payments #contracts
29

Reply to emails instantly or batch replies later?

๐Ÿ’ก Example: "Reply to emails instantly or batch replies later?"

๐ŸŸข Low Engagement Barrier ๐Ÿ‘ค Lurker #communication #habits
30

Use a standing desk or sit while working?

๐Ÿ’ก Example: "Use a standing desk or sit while working?"

๐ŸŸก Medium Engagement Barrier ๐Ÿ‘ค Irregular #workspace #health
31

Outsource admin tasks or DIY everything?

๐Ÿ’ก Example: "Outsource admin tasks or DIY everything?"

๐ŸŸก Medium Engagement Barrier ๐Ÿ‘ค Average #business #workflow
32

Join coworking spaces or work solo from home?

๐Ÿ’ก Example: "Join coworking spaces or work solo from home?"

๐ŸŸก Medium Engagement Barrier ๐Ÿ‘ค Irregular #workspace #community
33

Send proposals in the morning or at night?

๐Ÿ’ก Example: "Send proposals in the morning or at night?"

๐ŸŸข Low Engagement Barrier ๐Ÿ‘ค Lurker #workflow #pitching
34

Use Notion or Google Docs for your workflow?

๐Ÿ’ก Example: "Use Notion or Google Docs for your workflow?"

๐ŸŸก Medium Engagement Barrier ๐Ÿ‘ค Average #tools #productivity
35

Daily standup or weekly check-in with clients?

๐Ÿ’ก Example: "Daily standup or weekly check-in with clients?"

๐ŸŸก Medium Engagement Barrier ๐Ÿ‘ค Frequent #client #communication
36

Set strict boundaries or stay flexible for clients?

๐Ÿ’ก Example: "Set strict boundaries or stay flexible for clients?"

๐Ÿ”ด High Engagement Barrier ๐Ÿ‘ค Top #boundaries #clients
37

Quick calls or detailed emails for project updates?

๐Ÿ’ก Example: "Quick calls or detailed emails for project updates?"

๐ŸŸก Medium Engagement Barrier ๐Ÿ‘ค Average #communication #updates
38

Work in sprints or steady pace all week?

๐Ÿ’ก Example: "Work in sprints or steady pace all week?"

๐ŸŸข Low Engagement Barrier ๐Ÿ‘ค Lurker #workstyle #productivity
39

Save files in the cloud or on your device?

๐Ÿ’ก Example: "Save files in the cloud or on your device?"

๐ŸŸข Low Engagement Barrier ๐Ÿ‘ค Lurker #tools #security
40

Find clients through referrals or platforms?

๐Ÿ’ก Example: "Find clients through referrals or platforms?"

๐ŸŸก Medium Engagement Barrier ๐Ÿ‘ค Average #clients #growth
41

Prep for the next day at night or in the morning?

๐Ÿ’ก Example: "Prep for the next day at night or in the morning?"

๐ŸŸข Low Engagement Barrier ๐Ÿ‘ค Lurker #routine #productivity
42

Freelancer meetups or online networking events?

๐Ÿ’ก Example: "Freelancer meetups or online networking events?"

๐ŸŸก Medium Engagement Barrier ๐Ÿ‘ค Frequent #networking #community

How to Use These Templates

To use these templates, simply copy and paste a prompt into your community platform. Vary the timing and topics to keep things fresh, and encourage members to share their reasons if they like. Tag or mention a few members to kick off replies, and consider sharing your own answer to set the tone. Use them for daily check-ins, engagement boosts, or as fun breaks between more serious discussions.

Best Practices

  • Keep prompts light and non-controversial to encourage broad participation.
  • Rotate topics so members do not see the same style every week.
  • Reply to early answers to spark deeper conversation.
  • Encourage short explanations but keep it optional.
  • Schedule posts during peak community activity times.

All Platforms Tips

These templates work well on all platforms. For forums and Facebook groups, use bold or emojis to highlight the options. On chat platforms like Slack or Discord, post during active hours for maximum replies. On LinkedIn or Twitter, add a poll if the platform supports it.

Frequently Asked Questions

How can I use This or That questions to spark discussion about hourly vs. project-based freelancing rates?

You can create a This or That post asking 'Hourly rates or Project-based pricing?' and encourage members to share their experiences. This taps into a common freelancing dilemma and invites discussions on pros, cons, and negotiation strategies, fostering peer-to-peer advice.

What are examples of This or That questions that address freelancing client acquisition challenges?

Consider questions like 'Direct outreach vs. using freelancing platforms?' or 'Cold emailing vs. networking events?'. These scenarios reflect real choices freelancers face when seeking clients and will resonate strongly with your community.

Should I create This or That posts around popular freelancing tools, and how specific should I get?

Yes, tool-based questions are highly engaging. Use specific comparisons like 'Trello vs. Asana for project management?' or 'PayPal vs. Wise for international payments?'. These reflect actual decisions freelancers make daily, sparking relevant discussions.

How can I address the debate over niching down vs. being a generalist in a This or That format?

Create a post such as 'Specialize in one niche or offer multiple services?'. This question mirrors a major decision freelancers encounter and encourages members to share their strategies and outcomes.

What are some This or That questions that help freelancers discuss work-life balance challenges?

Try prompts like 'Strict office hours vs. flexible schedule?' or 'Dedicated home office vs. working from cafes?'. These highlight common freelancing struggles and invite members to share tips and preferences.

Can I use This or That questions to address late payment issues specific to freelancing?

Absolutely. Pose questions like 'Upfront deposits vs. payment on delivery?' or 'Chasing invoices yourself vs. using a payment service?'. These reflect industry pain points and can generate valuable advice from the community.

๐Ÿ“…
Schedule these posts to your community
Plan ahead & auto-post to Skool, Circle, or Mighty Networks
Try Free โ†’
✓ Copied to clipboard!