Pushing Back - A Villainous Act or a Path to Growth?

Have you ever found yourself hesitating to ask tough questions at work or in life? Maybe you feared coming off as rebellious, disrespectful, or even insubordinate. This hesitation is something I’ve grappled with throughout my career, and it raises a key question: Should pushing back and asking beautiful, thought-provoking questions be encouraged, especially in the workplace?

I believe the answer is a resounding yes—but with some nuance.

In my experience, encouraging thoughtful questioning and pushback can save organizations millions of dollars and countless hours. In fact, I can’t think of a situation where a project failed, a product flopped, or a relationship fell apart because someone asked too many meaningful questions. On the contrary, not asking enough questions—or simply going along with the flow—often leads to miscommunication, poor decisions, and missed opportunities. Yet, in many workplaces, questioning the status quo is seen as a problem. Why is that?

The Importance of Beautiful Questions

Asking beautiful questions—the kind that dig beneath the surface—can bring clarity, uncover hidden risks, and drive better decisions. However, there’s a delicate balance. Not all questioning is created equal. There’s a difference between asking because you genuinely want to learn and pushing back just for the sake of it.

I’ve learned that “compassionate curiosity” is the key. When you ask questions with empathy and a genuine desire to understand, you can avoid coming off as combative or annoying. This becomes especially important when you’re engaging with senior engineers, analysts, managers, or C-suite executives.

The goal should never be to challenge authority for the sake of it, but rather to prevent costly mistakes, misaligned expectations, or wasted effort. Done right, pushing back is not only a valiant act—it’s a vital skill for both personal and professional growth.

The Pushback Problem: Why It’s Misunderstood

In the professional world, pushing back often gets a bad rap. It’s seen as hesitation, stubbornness, or even rudeness. But in reality, pushback is an attempt to gain clarity and prevent potential pitfalls. So why do so many people feel uneasy when someone questions the plan?

The truth is, most organizational mistakes could be averted if pushback were encouraged and properly handled. Unfortunately, when employees push back too often, they can be labeled as not being “team players.” This creates a culture where questioning is discouraged, leading to more mistakes, dead-end projects, and missed opportunities for innovation.

Why Don’t We Encourage Questions?

Which brings me to a broader question: Why don’t we encourage asking questions in the workplace? Why do many organizations shy away from building a culture where employees feel empowered to question decisions and ask “why”? Whose responsibility is it to ensure this culture exists? Is it the manager, or is it embedded in the company’s culture itself?

I think we owe it to ourselves—and to our organizations—to take a step back and ask: Why are we doing what we are doing, and why is it being done this way? These are the questions that people who dare to dream and create real change always ask. But in many companies, this kind of inquiry is stifled. Perhaps it’s because questioning is seen as a challenge to authority or as a signal that the person asking is unsure of themselves or their work.

But this couldn’t be further from the truth. Encouraging employees to push back and ask meaningful questions can uncover inefficiencies, avoid costly mistakes, and lead to innovation. The key is creating an environment where curiosity is rewarded, not punished

Why “Why” Matters

From school to the workplace, we’ve often been trained to follow instructions rather than to question them. The result is that many people stop asking why things are done a certain way. But it’s those who keep asking “why” and pushing back thoughtfully who often rise to leadership roles—becoming entrepreneurs, executives, and senior managers. They know that innovation and progress come from challenging assumptions and uncovering blind spots.

But here’s the interesting part: while upper management and C-suite executives are celebrated for asking tough questions, it’s not always the same story for junior employees or individual contributors (ICs). Why is that? Why do questions seem to be welcomed at the top but frowned upon at the bottom?

The Tradeoff for Early-Career Professionals

For those early in their careers, especially junior, mid level ICs or interns, the tradeoff can be tricky. Is it their job to ask why, or is it their manager’s job to tell them why? Should they question decisions, or should they wait until they’ve gained more experience? This can be confusing territory to navigate.

One thing I’ve learned is that the distinction between junior and senior roles often comes down to the types of questions they ask. Juniors may focus on learning and understanding the “how,” while seniors, managers, and executives focus on the “why.” But here’s the catch: if you want to grow from junior to senior, you need to start asking the right “why” questions earlier. It’s this shift in mindset that sets you apart, propelling you forward in your career.

Final Thoughts: The Value of Pushback

Looking back on my career, and envisioning where I want to go, I’ve come to understand—thanks to a great coach—that pushing back with compassion and asking “why” in the pursuit of clarity is one of the most critical skills to develop. It’s not always easy, especially early in your career, when questioning can make you feel like you’re being difficult, disruptive, or not a team player. But the ability to ask meaningful questions with empathy and intention is what truly sets great professionals apart from the rest.

Whether you’re just starting as a junior IC or aiming for senior leadership, embrace the power of asking thoughtful questions. Push back when needed, but always with curiosity, compassion, and a focus on achieving better outcomes for everyone involved.