Ask these 3 quick questions to spark your team’s creativity…

When we fail to tap into our inner creatives, we engage less with our work (bad for us) and end up shipping less innovative solutions (bad for business). So, what can we do about it?

The creativity tunnel…kidding…just a cool neon-lit hallway in Atlassian’s Sydney offices (photo by Norman Ma)

As a content designer for many years and now as an Experience Design Manager for Trello at Atlassian, I’ve seen how our creative practices have evolved as we’ve grown. In conversations with our designers and leaders about this very topic, I noticed we kept coming back to three themes about the challenges our teams and our wider industry face when it comes to unleashing our inner creatives at work. We reframed these challenges as three questions any team can ask to cultivate a more creative and collaborative working environment:

1. The challenge: There’s pressure to be creative all the time.
   The question: Have we set enough context?
2. The challenge: Our perfectionist tendencies lead to isolated, slow work.
   The question: Have we collaborated early enough?
3. The challenge: We’re distracted and burdened by the wrong constraints.
   The question: Have we embraced the right constraints?

Let’s dive into each of these questions and tips for when to ask them.

Question 1: Have we set enough context?

One of the biggest challenges I’ve seen block the creativity of teams is the pressure we put on ourselves to be creative all the time.

Robert Dietz

, our Head of Experience Design for Products, termed this challenge “creativity on-demand” and it’s something that even our most experienced creative leaders struggle with.

When I started out as a content designer, I dreaded the moment someone would ask for a magically delightful error message or new feature name right then and there. My output in these situations was… not great and usually needed to be revisited or trashed before shipping.

A better recipe for creativity is one that provides collaborators with enough context to build a shared understanding. Then, you can iterate more confidently on creative solutions, error messages included.

✅ Tips for setting context

When planning a workshop or team discussion that requires a lot of creative thinking, make sure to share as much information about the agenda and goals beforehand. On the Trello team, we like doing this with short Loom videos that summarize the problem space, key customer insights, and perspectives needed in order to move the discussion forward.

A context-setting Loom video for one of our async project kick-offs

Setting context enables both on-demand creatives and more introspective thinkers to thrive. This results in more diversity of thought, a critical piece of the creativity puzzle.

Question 2: Are we collaborating early and often?

In Pixar co-founder Ed Catmull’s book Creativity, Inc., he shares the story of the company’s risky search for perfectionism. They created what they thought was the perfect team in the perfect environment to create a brilliant new movie idea. The team worked in a complete silo and, long story short, the entire project was scrapped (a costly lesson for the people involved and the business).

These perfectionist tendencies routinely get in the way of creativity. Even with a seemingly simple blog post. I wasted time and energy keeping this very post in draft mode because I was stuck thinking about the final published piece. I couldn’t face the messy draft in front of me. That’s perfectionism in action.

Early collaboration is the antithesis to perfectionism. It enables us to release assumptions and judgments we hold onto when we work alone. As uncomfortable as it can be to share messy work, that’s exactly what we should be doing more of.

✅ Tips for collaborating early

When planning an initiative, include milestones specifically around gathering and applying frequent feedback. Identify an “accountability buddy” and a review practice to keep you on track towards those milestones. I’ve found that our weekly design team meetings and review sessions have worked well for this. In a small group (6–8 people) where we’re all expected to share, we can more easily establish the trust needed to collaborate and give feedback.

Question 3: Have we embraced the right constraints?

We often encounter things that hinder our creativity, be it too many meetings, not enough deep work time, or tight project deadlines. But, it’s not the constraints themselves that block creativity. We’re just paying too much attention to the wrong ones. Embracing the right constraints is what enables creativity.

At Atlassian, the success of ShipIt Days is built around the 24-hour time constraint people have to work within. The size of teams in Point A, our new product framework, are kept as small as possible to constrain the scope of work to the strongest core idea. Constraints are part of life and they’re certainly part of work. And, I think we can do more to seek out the ones that help us tap into our inner creativity a little bit each day.

→ Strong caveat: This doesn’t mean you should accept having to attend a bunch of ineffective meetings. There’s a great ritual reset play you can use to tackle that!

✅ Tips for embracing constraints

Clearly define the constraints you and your team need to work within. Then, when you’re about to sit down for some real-life innovation time, add even more constraints to get those creative juices flowing. Try redesigning an entire onboarding flow in just 30 minutes. Rewrite the copy for that onboarding flow without the word “team”.

Our Disruptive Brainstorming board template with constraint cards in Trello

The point of these exercises is not to create something perfect. It’s about getting started and iterating from there.

Remember, everyone is creative

Asking these three questions (Have we set enough context? Are we collaborating early and often? Have we embraced the right constraints?) is just one action you can take to connect to your inner creative, reengage with your work, and revitalize your team’s innovation.

“Craft is what we are expected to know; art is the unexpected use of our craft.” -Ed Catmull

I love this quote because it reminds us that creativity is a skill we all have, regardless of our role, the team we’re on, or the thing we’re working on. Creativity can sometimes feel like this extra art form on top of our jobs. Really, it’s just finding the ways we can innovate more regularly with one another.

So, bring these three questions to your next meeting or async update and see what the answers look like for your team. And, don’t forget to share your learnings and keep the creativity conversation going!

Creativity resources:

• Creativity, Inc by Ed Catmull
• Disrupt brainstorming, from the Atlassian Playbook
• Are internal hackathons really good for business?, from Atlassian’s Work Check podcast
• Where does creativity hide? by Amy Tan
• 4 lessons in creativity by Julie Burstein

Thank you to

Clara Sherley-Appel

, Kirsten Shannon,

Liam Greig

,

Linette Voller

,

Roana Bilia

,

Robert Dietz

, and

Sam Irons

.