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

This is the story of how 1 simple Slack channel sparked countless amazing conversations and our team growing much tighter!

March 13, 2020

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 1 simple Slack channel sparked countless amazing conversations and our team growing much tighter—all in the time span of just a few weeks.

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 3 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 channel #questionaday came about—of course, with “suitable for work” questions ;)

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

I’ve spent this winter in Bali—an island known for its healing powers. Stay here 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’ve definitely turned into a crystal lady that loves ecstatic dancing on Sunday mornings, though I still wear all-black and prefer to blast UK grime to calm down and be zen.

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 1 thing you’d like to ask your team members?”

The responses? Only 1 and 2 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 questions 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 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 question? “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.

Developer Lech’s favorite pizza was heavy on meat: “Olives, corn, onion, sausage, bacon, salami”. Project Manager Amanda said: “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. We’re about 1 month in and the connectedness of our team has already significantly improved. People seem to love answering the questions!

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 day 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 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 the beginning of February 2020, we’re less than 2 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 question. I’m talking deep, inspiring chats with team members that I’ve barely talked to before this initiative!

But anyway, back to the 63-reply question (I know you’re waiting!)…

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, over 80% of our team joined the channel and several colleagues asked if they could grab the mic to ask a question. We’re 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 questions, but we also regularly host virtual team meetups, workations around the world, and more! Sounds good? See if there's a current opening that fits your skills!

Summing up: We’re more connected than ever

The Remote Company has huge plans for 2020, and expanding our team is definitely one of them. But how do we keep the connectedness of a small team as we grow big? That’s the challenge.

The #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.

Oh, and how about my long-distance lover? We’re still going strong too, building a very solid foundation by answering a question every time we call ;)

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


I’m Megan, Content Writer at The Remote Company. You can find me in Berlin, NYC or somewhere escaping winter in Asia. I have helped many start-ups grow their online visibility. Blogging has always been my thing—from running artist fan pages as a teenager to now discovering upcoming talent on Sign This Kid.


We share our real experiences and actionable advice on how to work remotely and grow your remote business. Subscribe with your email.


2021 © The Remote Company