How 1 question a day can skyrocket your team's engagement

This is the story of how one simple Slack channel sparked countless amazing conversations and our team growing much tighter!

September 20, 2021

It’s December 18, 2019. A new Slack channel called #questionaday is created.

The description reads: Megan will ask a question a day and you get to answer. As our team grows, it'll be great to get to know each other better and find out our similar views, interests, quirky sides, hidden talents, and fun anecdotes. Let's go!

That’s me, Megan. And this is the story of how this one simple Slack channel sparked countless amazing conversations and our team growing much tighter—all in the time span of just a few weeks.

Oh and, keep reading all the way until the end… there will be a surprise! 👀


How the idea came about: The things you do for love

What’s love got to do (got to do) with it? Well, towards the end of 2019, I met a beautiful man. We connected in a very movie-scene-like way and had an instant mutual “you’re exactly what I’m looking for in a partner, and more” vibe. 

The only challenge? I was only in town for three more weeks. As our goodbye was approaching, I knew that I wanted us to keep connecting on a deeper level and really get to know each other while we were long-distance video calling.

I looked up conversation starter kits, but none of them were exactly what I wanted. So I went to the stationery shop, bought 30 business cards, a golden pen, and crafted my own. I wrote down 60 questions that would help us bond, learn, grow, and laugh.

Numerous question cards placed on the desk.

As I wrote down the last question, I felt so excited and thought: “Why not apply this idea to my work relationships?”

That’s how the Slack conversation starter idea came about. A day later, I introduced the channel #questionaday—of course, with “suitable for work” questions. 😉


The beginning: “Ah, so this is what people respond to”

When I began with the Slack question a day channel, I had just spent a winter in Bali—an island known for its healing powers. Stay there long enough and you’ll either become a certified yoga teacher, a Kombucha-loving vegan, or a chakra expert that wears colorful clothes and walks around barefoot.

I definitely (temporarily) turned into a crystal lady that got excited about ecstatic dancing on Sunday mornings.

Because of Bali, some of my first questions were on the more spiritual, “let’s all reflect” side. Questions like “What was your favorite memory of 2019?” and “What’s one thing you’d like to ask your team members?”

The responses? Only one and two replies. Conclusion: A little too deep too soon.

So I altered my questions to things like:

  • Q2. Did you dream anything last night? Do you normally dream and what type of dreams? (12 replies)

  • Q8. What was your first job? (18 replies)

  • Q12. Who would you love to see perform live? (16 replies)

Ha! So that’s the type of Slack conversation starters that get people to engage. Noted!

I also replied first to set the tone. Instead of answering briefly, I’d add a little story or anecdote. To my surprise, people often followed my example and wrote entire paragraphs of their own.

The more Slack questions we all answered, the longer the conversations became. The female-male ratio evened out as more guys from our development team joined in.

Their favorite Slack question a day?

“Would you rather not use Google or Social Media for the rest of your life?”

A question that started as a discussion on Internet privacy and then turned into a dialog about Facebook groups on manifesting and the Law of Attraction.

Screenshot of Megan's question in Slack about Google or Social Media preference with 36 replies.

Another team favorite turned out to be: “What is your best pizza combination?”—contributed by our Partnership Manager Jess.

Screenshot of the question by Jess for pizza lovers with 24 replies.

Project Manager Amanda answered: “If I’m in a spicy mood, chicken wing pizza. It’s diced breaded chicken, chicken wing sauce, loaded with mozzarella. Some may also add bleu cheese to this.” All non-vegans agreed on cheese, lots of it. And of course, the pineapple-debacle made an appearance too."


One month in: “Is it question time yet?!”

It's now January 15, 2020. We’re about one month in and the connectedness of our team has already significantly improved. People seem to love answering the Slack conversation starters!

Screenshot from the slack channel. Megan and the team love the Question of the day initiative.

And then came question 27, the most surprising one to date:

Screenshot of the Megan's question about dieting with 35 replies.

Now, I was expecting the women in our team to take the lead in this discussion. However, the men took initiative and shared most of the diet advice!

Content Writer Jonas replied: “Ok. I have done some weird ones. The 1-week potato diet is when you only eat potatoes for 5 days, but the trick is that the potatoes must be cooked and cooled overnight. No oils or butter but you can use salt and some non-calorie sauces like mustard or hot sauce. Apparently, when you cool potatoes overnight they transform into resistant starch so it doesn't affect your body like carbs, yet potatoes have most of the nutrients you need. The first 2 days were fine but by days 4 and 5 I hated potatoes. I lost almost 3kg that week though.“

Gif of Jimmy Butler's I can't believe what I hear reaction.

I bet you didn’t see that answer coming… (I definitely didn’t).

By the end of the Slack question a day thread, everyone gained knowledge about what different diet strategies worked for people personally—from potatoes to sleeping loads so you can’t eat. It was fabulous!

Le moment suprême: 63 replies (and this was the question)

It’s now the beginning of February 2020, we’re less than two months in and our #questionaday channel became part of almost everyone’s daily routine. We’re on a roll!

Here’s what team members shared:

“Question of the day is in my daily routine at the start of my shift. I really love the questions and getting to know the rest of us.”

“Thank you for letting us get to know each other in the most natural and comfortable way.”

“Great job with #questionaday and building the remote-team culture.”

“I LOVE the #questionaday channel. It's one of the things I look forward to reading and participating each day 🥰💪

On top of the group engagement, I’ve also had several 1:1 conversations to further discuss a Slack question. I’m talking deep, inspiring chats with team members that I’ve barely talked to before this initiative!

And as for the 63-reply question a day, it was this one:

Megan's question 'Tag 1 person you never talked to and ask them a question'.

Now, I knew my day ones wouldn’t let me down, but I was overwhelmed with the participation! People had so many great questions. 

Things like:

  • How was it like holding an owl? (our Deliverability Manager Gabija held one recently)

  • What is something you think everyone should do or try at least once? Anything from food to activities.

  • I love your name. Is there a story/meaning behind it?

  • What’s your favorite breakfast meal?

I watched this thread unfold with the biggest smile on my face!

After this question a day, over 80% of our team joined the channel and several colleagues asked if they could grab the mic to ask a question. We were only 30 questions in, but this simple idea has already flourished into a collective effort that has everyone in the team excited!

Is team bonding important for you when deciding on a new workplace?

Our team does not only connect over Slack questions, but we also regularly host virtual team meetups and workations around the world! Sounds good? See if there's a current opening that fits your skills!


Fast-forward to 2021: We’re more connected than ever

Since the creation of our Slack question a day channel until now, The Remote Company has grown immensely. Back then we had around 50 people, and now we're growing towards a team of 150 people! But how do we keep the connectedness of a small team as we grow big? That’s the challenge.

Our Slack #questionaday channel turned out to be a great start. It lets our team’s personalities shine, establishes new friendships, and reveals unexpected, fun stories. A must-try for every team—remote or not. So far, we've asked over 300 questions and people are still answering and engaging!

Oh, and how about my long-distance lover? We’re still going strong too, building a very solid foundation and carving out time to ask and answer our question cards.

Note: This article was originally published in March 2020 and has been updated with new learnings and bonus questions.


Bonus: 160+ example questions to ask!

Want to connect with your team too? We've collected over 160 questions we've personally asked. Copy, paste, and let the good times roll!

Leave your email below to get access. 👇

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We'd love your input! Comment below with your #questionaday to ask in our channel...

Megan

I’m Megan, Senior Content Writer at The Remote Company. Ever since I started working remotely, I pick my homes depending on the seasons: Europe during spring and summer, NYC for autumn, and winter escapes in Mexico.

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