20 Conversation Starters for Connected Async Teams

Remote work has been the new norm for over five years, but asynchronous communication can still feel robotic and disconnected for some teams. Without the natural chit-chat of an office, teams risk losing engagement, morale, and productivity.

Is there a quick fix? Great conversation starters, for starters.

Thoughtful questions can break the monotony of status updates, spark creativity, and make async meetings more human and enjoyable to participate in.

In this guide, you’ll learn:

✔ Why conversation starters work for async teams that want to feel connected

✔ 20+ engaging prompts (categorized for any team)

✔ How to use them effectively in async meetings (and a few of our best practices)

Plus, we’ll show you how Team O’Clock’s async meeting templates make remote collaboration seamless and fun.

The Async Engagement Challenge

Remote teams often report struggling with:

• Disengaged meetings → Dry, robotic updates that drain energy and lack any engaging element.

• Low participation → "Ghost attendees" who never contribute or are more excited to find excuses not to show up.

• Misalignment → A lack of connection leads to misunderstandings, poor collaboration, and complex team dynamics.

Why does this matter? Because great async communication keeps teams motivated, aligned, and productive, without the fatigue of unnecessary live meetings.

How can you fix it? Structured, engaging async meeting check-ins with conversation starters that build connection.

Why Conversation Starters Work for Async Teams

1. Break the Monotony

Instead of another dull status update, such as "Working on Task X," fun questions like "What’s your go-to comfort movie after a long workday?" make meetings feel more human and interesting.

2. Build Psychological Safety

When team members share personal stories or opinions, they open up, feel heard, and valued. For example, use open-ended questions such as: "What’s one small win you had this week?"

3. Spark Creativity & Collaboration

Unexpected answers lead to innovative ideas and stronger bonds. Example: "If you could automate one part of your job, what would it be?"

4. Encourage Participation

Prevent silent "ghosting' of attendees by asking light, engaging questions that everyone can answer. Example: "Would you rather have a personal chef or a personal assistant?"

20+ Conversation Starters To Try in Your Next Async Meeting 

1. Personal & Hobbies (Lighthearted & Bonding)

✅ What’s one hobby you’ve picked up in the last year?

✅ If you could master any skill instantly, what would it be?

✅ What’s your go-to comfort movie/show after a long workday?

Why it works: Helps teams connect beyond work by sharing and potentially bonding over shared interests or activities. 

2. Work & Goals (Productivity-Focused)

✅ What’s one small win you had this week? ✅ What’s a professional skill you’re currently working on? ✅ What’s one thing that would make your workday 10% easier?

Why it works: Encourages reflection and shared learning through thought-provoking questions that allow all team members to share their ambitions.

3. Remote Work & Pet Peeves (Fun & Relatable)

✅ What’s your biggest remote work pet peeve?

✅ Do you have a ‘work from home’ hack that changed your life?

✅ What’s the weirdest place you’ve taken a work call from?

Why it works: It evokes laughter and creates shared experiences by encouraging team members to be genuine and humorous (in a way that is both funny and appropriate).

4. Travel & Future Plans (Aspirational & Engaging)

✅ Where’s the next place you’d love to travel, and why?

✅ If you could work from any country for a month, where would you go?

✅ What’s your dream ‘workation’ setup?

Why it works: Inspires future-focused, light-hearted discussions over a topic everyone loves talking about.

5. Tech & Tools (Great for Dev/Tech Teams)

✅ What’s one app you can’t work without?

✅ If you could automate one part of your job, what would it be?

✅ What’s your favorite keyboard shortcut?

Why it works: Sparks useful tool-sharing and efficiency tips that other members can benefit from to make their lives easier.

6. Fun & Random (Icebreakers to Spark Joy)

✅ Would you rather be able to time travel or read people’s minds?

✅ What’s the most useless talent you have?

✅ If you were a Slack emoji, which one would you be and why?

✅ What’s your favorite ‘dad joke’ that actually made you laugh?

✅ If your job had a theme song, what would it be?

Why it works: Pure fun times—nothing makes a team bond more quickly than funny or quirky icebreakers.

How to Use These in Async Meetings

Use Them With Team O’Clock’s Async Templates

Add these conversation starters at the beginning of your next meeting. For instance:

✔ Stand-ups → "What’s one small win this week?"

✔ Retrospectives → "What’s one thing that would make work 10% easier?"

✔ Weekly Check-ins → "What’s your dream work location setup?"

Your Async Team Now Connected with Team O’Clock

Small, thoughtful questions can turn async meetings from dull to dynamic. By fostering connection, creativity, and participation, you’ll boost morale, alignment, and productivity.

Looking for an easier way to run engaging async meetings? Try Team O’Clock’s async meeting templates—designed to automate engagement and make remote collaboration effortless.

Sign up for our free 15-day trial, explore our detailed async meeting templates, and try them with your team in your next meeting. 

Pro Tip: Start with just 1-2 conversation starters per meeting and watch more members look forward to participating in the conversation!

What’s your favorite conversation starter from this list? Drop it in your next async meeting and let us know what you think!