When is it okay to question authority? It’s a question that causes a lot of confusion in a business culture. There’s a core belief that’s hard to shake: the idea that you “have” to do whatever your boss tells you.

Any manager will say they’d love it if their employees took on more responsibility. Some managers understand that, for that to happen, they need to challenge people more. This means asking far more, and far deeper, questions to make sure employees understand what’s being asked. But very few managers ever put it all together. The question is why. It’s also the answer.

When the people on your team understand the “Why?” they can own the project or task better. They have context. They understand the logic. They know that other possible options were considered and why this one was chosen. They can apply that learning to other tasks. In other words, employees grow, and the company grows as a result when people understand the “Why?” of things.

But there are breakdowns. Managers get too busy. They find themselves in firefighting mode and don’t have time to train the right way. But the job still needs to get done. So, they resort to “telling.” Telling without explaining is how managers become supervisors, taskmasters instead of mentors. In the frustrated and overwhelmed reality of the supervisor, employees who ask “Why?” are an annoyance—they get annoyed looks or frustrated retorts. Those looks and responses are sometimes subtle. Sometimes they’re not. Either way, the cultural divide deepens.

I’ve never met a manager who set out with the intention to shut their people down. But, bit by bit, that’s what happens. And, it only has to happen a few times for the person on the team—even the “A player”—to give up trying. The team’s trust in their manager is a fragile thing. It’s fragile because the employee is reasonably concerned about going too far and getting fired. The power dynamic is weighted heavily against them; they have every reason to hide instead of push.

So, here’s where we are. On one hand, we have managers complaining that their employees don’t challenge them enough (without realizing they’re playing a major part in why that’s happening). On the other hand, employees complaining that their managers don’t listen (without realizing how they’ve given up trying, or never really did in the first place). Each side points to the other party as the cause.

Who will break the cycle? Will you?

If you and your manager have both read this article, that’s a good place to start. If you can have a conversation about this dynamic, you’ve taken the first step: defining the problem in as simple a way as possible.

For employees: Ask your manager if you challenge them enough. Ask for feedback about how respectful your “Why” questions are. You’ll likely be surprised at how not-challenged your managers feel by the questions you’ve asked up to this point.

For managers: Ask your employees if there are ways they don’t feel listened to. Listen between the lines—remember the power dynamic at play here—for what you suspect is true but they don’t feel comfortable telling you. You’ll likely be surprised at how difficult it is for them to be honest with you about things you both know are obvious elephants in the room.

For everyone:  Listen. Learn. Repeat as necessary.

The ideal company culture values a respectful questioning of authority. In that kind of culture, every manager has a responsibility to respond to any reasonable “Why?” question that an employee brings.

A manager who doesn’t take the time to explain the “Why?” behind a change, a directive, a task, etc. is treating employees like children who have no other choice but to do what they’re told (or quit). If you manage this way you’ll get exactly that—compliance at best, but no genuine ownership or personal responsibility. You’ll also lose some of your best people, who value their professional development too much to stick around.

An employee who doesn’t take on the responsibility to ask “Why?” when something isn’t clear plays their part in perpetuating the stuck dynamic. You break the dynamic by asking—in a respectful, non-combative way, and by being willing to consider that perhaps the answer has already been given, and you just don’t understand or don’t agree. Watch out for using the “Why?” as a weapon to avoid doing unpleasant work. Doing unpleasant work is a part of life. And, with the right attitude, you can find the joy in just about any task.

You’ll discover that the issue starts to resolve in the willingness to talk about it. The “Why?” questions ferret out things that don’t make sense. This can feel like a threat to a manager—it tugs on the insecurities we all have. If you’re a manager and feel threatened by a “Why?” question, or you don’t feel equipped to answer it, use it as an opportunity for growth. Instead of making the employee pay—by shutting them down for asking it—see it as an invitation to ask more “Why” questions of yourself. Use it as an opportunity to get some mentoring from your manager or someone else you trust. Maybe you want to have a mentor.

Ask yourself: “Why do I feel threatened by my employees owning their jobs more, and becoming more competent?” “Why am I not asking my manager the same question my people are asking me?”

The more people in your culture embrace the “Why?” question, the smarter and more skilled your team will get. Problems will get solved once, at the root.  If you let “Why?” be seen as insubordination, the root will remain untouched. The choice is there for everyone.