An “unreasonable” era: Mike Cannon-Brookes on leading, creating, and staying ambitious in the age of AI
This story is based on an interview with Harry Stebbings on the 20VC podcast. You can listen to the episode here.
Ever stare at your washing machine and wonder, “Why is this so complicated?” Mike Cannon-Brookes does. After more than two decades building Atlassian, he’s convinced that progress depends on being a little “unreasonable”: challenging the status quo, redesigning what doesn’t work, and empowering others to do the same.
The reasonable man adapts himself to the world: the unreasonable one persists in trying to adapt the world to himself. Therefore, all progress depends on the unreasonable man
George Bernard Shaw
In the AI era, where the rules are being rewritten faster than most companies can keep up with, this mindset makes the difference between a customer thinking, “Why is this so complicated?” and “I love this!”
Refuse default constraints. Redesign the system instead.
Mike calls his approach “constructive unreasonableness.” If something’s broken or needlessly complex, don’t just grumble. Fix it! “I get frustrated when things don’t work the way they should,” he says. “And then I try to change them.”
He wants that attitude to spread. He encourages people to treat every “this should work better” moment as a chance for rethinking.
But boldness needs backup. Teams need psychological safety to challenge conventions and experiment without fear. Atlassian’s culture is built on that balance: high standards, with plenty of room for smart risk-taking. The real danger? Getting too comfortable and missing opportunities to improve.
Making big bets – or “revisitable hunches” – during the AI explosion
To many people, the tech industry feels like it’s in the midst of a “Cambrian explosion” of creativity: a wild period where everything’s overvalued while real opportunities are hiding in plain sight. “Ten years from now, we’ll look back and say, ‘That era was crazy,’” Mike says.
His approach is to make a few big bets and pivot fast if the evidence says so. Mike calls these “revisitable hunches” that he and his teams test and re-evaluate every quarter. If something’s not working, they move on quickly without apologies or embarrassment. (Psychological safety in action!)
This isn’t about guessing the future – it’s about learning faster. Atlassian grounds decisions in customer outcomes: less friction, fewer clicks, faster value. Instead of chasing hype, the customer is the signal in the noise.
Insights from Mike on Atlassian’s AI strategy
Adopt, don’t invent
Atlassian doesn’t train its own foundation models. Instead, it integrates whichever model delivers the most customer value, fast. “We built [our AI systems] to be multi-model on purpose…Our job is adopting and delivering value quickly.”
Design is the moat
As coding gets cheaper, great design becomes the differentiator and the bridge between complex (sometimes messy) systems and real human needs.
Atlassian’s design teams are using AI to elevate the user experience by hiding complexity, anticipating what you want, and deliver instant clarity. “It’s really all about design…What differentiates is how it feels and works.”
The UI won’t just be chat
Mike doesn’t buy the idea that all software will become chatbots. He expects familiar interfaces but with smart layers that get you from intent to value faster. “It [interfaces] might look a lot more like today than we think, but it will be a lot smarter. It will do very different things, and there will be a lot lower click-to-value ratio.”
Constraints are creative fuel
Mike also believes longevity comes from creating through disruption, not clinging to the status quo.
If there’s something we have to protect, it’s our creativity…You can’t defend your way through it, you have to create.
In his mind, constraints are creative fuel, not roadblocks. They force sharper decisions and better priorities. At Atlassian, “killing” an idea is not only ok, but encouraged. Every feature retired or experiment ended frees up energy for what’s next.
Design is the thread running through it all. Atlassian’s teams keep their creativity alive with rituals: design critiques, customer showcases, and open post-mortems focused on learning, not blame. It’s this culture and mindset that Mike believes will help the company continue scaling and excelling through the chaotic AI era.
AI isn’t replacing engineers – it’s multiplying them
Believing in the power of design and creative problem solving means believing in the experts who do it. Despite the stereotypical storyline, Mike’s “spicy” take is that AI won’t take engineering jobs – actually, quite the opposite.
Five years from now, we’ll have more engineers working for our company than we do today.
As software gets cheaper to build, the roadmap gets longer. More engineers means more iteration and experimentation. But design keeps experiences coherent, not chaotic. As a result, scale fuels creativity instead of smothering it.
“Creativity isn’t scarcity – it’s capacity,” Mike says. The more people who can build, the more important design and culture become to make sure what they build actually matters and makes a positive impact on users’ lives.
Fighting ambition entropy
Ambition naturally fades. Even great companies can slip from hungry to ho-hum. Mike says his main role is to help his teams avoid that trap.
The founder’s job is to fight the entropy of ambition.
Managing both physical and mental fatigue requires knowing how to recharge so curiosity survives the grind. And he’s honest about the flip side of being “unreasonable”: “Almost always, your strengths are your weaknesses,” he says.
The same drive that fuels innovation can cause friction if unchecked. Self-awareness and open feedback keep that drive productive.
Ultimately, Mike’s leadership approach is simple: Question everything. Create freely. Stay self-aware. And take care of your energy.
Unreasonable, but far from unproductive
From Atlassian’s big AI bets to its philosophy and culture, everything is built on a foundation of pragmatic optimism. Pairing unreasonable ambition with evidence, design, and discipline can turn even the wildest era into a time of productive progress that transforms the customer – and employee – experience.
Or, as Mike might say, the real mistake is getting too reasonable.