For a long, long time, I was the ultimate rule-follower. Head down, no questions, never cut the line. “You are seriously such a kiss-ass,” my brother used to say. But I’d tell him it was actually just more efficient, that it was just faster to do what you’re told. Putting up a fight, questioning authority, asking “Wait, but, why?” felt like a waste of time. Or worse, would backfire on me. Because sometimes people just don’t want to hear it.

It would take me years to develop a practice of pushing back. It wasn’t that I didn’t have opinions. It was that I didn’t think it would be worth rocking the boat, and that it would just take longer to get anything done. Plus, there was the whole am I even senior enough to question this thing, despite how often my colleagues would point out how flawed that narrative is. They’d say, “You clearly think there’s a better way but you aren’t doing anything about it.” Oof.

Here’s what I learned: I wasn’t being true to myself, and was holding back when I had things to offer and needed to be voiced.

As an adult in the working world, this bad habit of not speaking up totally screwed me. The cycle was predictable. I’d obediently do what I was told, while silently thinking, This is really, really dumb. I’d deliver on-time and on-brief back to my boss, only to hear: “Should we really have done it this way? Should we have done this at all? Did you think about that?”

And then there I was with that drawing board, again and again. My efficiency hack (that is, just staying quiet) ended up being a terrible albatross and a productivity hindrance.

Here’s what I learned: Just staying quiet usually comes back to bite you in the end.

I’ll admit, a big part of this was me finding my voice. Gaining confidence. Developing a strong point-of-view. Demanding to be heard. I started optimizing for outcomes that I believed in, and not just faster output. It started with baby steps – I’d literally make myself ask at least one question in every meeting. Eventually, I graduated to prepping before meetings, and come with a pre-baked set of talking points. These were great habit-builders, but they lacked nuance – for example, certain questions or pushback is best delivered 1:1 or via email, as opposed to in a big room.

Here’s what I learned: New habits, like speaking up in meetings, take practice. I had to make myself try them out a little at a time, and adjust as I went along.

Separately, there was still the part of me that needed to get comfortable with just asking why. Turns out, it’s a really simple way to dismantle something dumb, or clarify something not dumb. I started asking why (why are we doing this, why does this matter, why is it being approached this way) not out of disrespect or laziness, but out of pure confusion. I’d often have people say to me after: Thank you for asking that question. Of course, they’d had the same one, but were afraid to ask. And how many times have you heard this, right? It’s a great reminder that we’re all just trying to figure it out.

Here’s what I learned: Don’t be afraid to ask the “dumb” question. There aren’t any. And when you do, you’ll become a hero for others who wanted to ask the same thing, too.

I’ve also learned, sometimes the hard way, that not all decisions come with a firm why, or were intended to be forever kind of things. A few years back, Mike (one of our co-CEOs) made this exact point in a meeting, after we defended a project outcome with the we-didn’t-think-we-could-question-a-decision-you-guys-had-made excuse. People assume the walls we built early on shouldn’t be knocked down. He was understandably frustrated. “I’m not asking you to question every decision we’ve ever made,” he said. “But I am asking that you seek first to understand why, and then propose something better, if it exists.”

He had a point, and while it’s hard to question things (especially when it’s senior leadership), it’s an important habit to cultivate. Asking about the rationale behind a decision isn’t disrespectful, it’s good hygiene.

Here’s what I learned: Brace yourself to learn the hard way. It’s not easy to question senior leadership, for example, and it’s even worse if you do it and they respond with exasperation. But you’ll see that in the end, it’s better for the entire organization to err on the side of openness and transparency.

Now, while asking why has led to better discussions, it doesn’t mean that it’s all roses. In fact, it’s still very annoying when it’s turned around on me. I’ve watched myself get defensive, impatient, and irritable after teammates question my decisions. It’s a good reminder that there’s a human on the other end of your questioning, and that the way you ask why, and the intent behind your why, is almost more important than the question itself.

Here’s what I learned: Ask why, but be thoughtful about it, and then actually listen.

At Atlassian, one of our most-cited yet unofficial values is “Seek first to understand,” a principle based on Stephen Covey’s book, The Seven Habits of Highly Effective People. The basic idea is to listen first and do so with empathy, get as good an understanding as you can, and then make your counterpoint known. If it still remains, that is. Remembering to seek first to understand is always helpful to me, especially when I’m questioning or being questioned.

Why you should ask why...