Let me cut to the chase: No, you probably don’t. Think about it: we can never know exactly how someone feels. What we can know is how we felt going through something similar. This is the only meaingful way our experiences can inform our response.
As leaders, experience is one of our greatest assets. We've faced challenges, had some amazing winds (and likely a few spills), navigated career paths, and learned lessons along the way. So when a team member struggles with something we’ve been through, it’s natural to think, I get it—I’ve been there – or – I know what they need to… [fix it, finish it, respond to it]. But what if that assumption is actually a blind spot?
The problem isn’t experience itself; it’s what we do with it. The danger is when we assume our experience mirrors our own. When that happens, we risk leading with assumptions rather than curiosity. And that is where the missteps can happen. You know – those moments when our good intentions don’t always lead to the outcome we had in mind. It is exactly in those moments when we may inadvertently dismiss, misinterpret, or oversimplify what they’re going through.
The Danger of Assuming You Understand
1. It Shuts Down Listening
When we believe we already know how someone feels, we stop listening actively. Instead of truly hearing their perspective, we filter it through our own past experiences. This can lead to responses like, Oh, I went through the same thing! You just need to…, which may not be helpful—or even accurate.
Consider a scenario where an employee is struggling and you read it as imposter syndrome. As a leader, you may recall your own experience of feeling out of place early in your career, but your emotional response and coping mechanisms were unique to you. Assuming their struggle is identical to yours can result in you offering solutions that don’t match their actual needs like a book to read or a 5-step strategy. When what they actually need is reassurance, space to reflect, or validation of their feelings, offering a prescriptive solution too soon can make them feel unheard or pressured to respond in a way that aligns with your experience rather than their own reality.
True listening means setting aside the impulse to compare and instead focusing on what the other person is actually saying. It involves paying attention to not just their words but their emotions, body language, and underlying concerns.
2. It Centers Your Perspective
The core of empathy isn’t about how you would feel in someone else’s position—it’s about how they feel. Our backgrounds, personalities, and emotional capacities shape how we respond to situations. Our past experience give us the ability to recognize what it feels like to struggle, to be uncertain or to face a similar challenge. But knowing what it feels like to go through something is not the same as knowing what it feels like to go through their experience. What was manageable for you might be overwhelming for someone else.
For example, an employee dealing with workplace conflict may feel intense anxiety about addressing the issue. You have always been naturally assertive, so you learned to approach conflict with confidence over time. If you assume they should “just speak up” because that’s what worked for you, you miss the opportunity to understand their hesitation. Maybe they have past experiences where speaking up led to negative consequences, or maybe they lack the necessary skills to navigate the situation effectively.
Instead of centering your own response, shift the focus back to the other person. Ask questions like, “What feels most challenging about this for you?” or “What support would help you feel more confident in addressing this?”
3. In Can make Others Feel Unseen
When leaders assume they get it, employees may feel overlooked or that their unique challenges aren’t being acknowledged. Instead of fostering connection, it can create emotional distance. As a result, they may hesitate to share more, sensing that their concerns are being minimized.
Imagine a team member expressing frustration about their workload. If you respond with, “I’ve been there, you just have to power through,” they might feel like you are just dismissing them. Their frustration might not just be about workload—it could be about unclear expectations, lack of resources, or feeling undervalued. You might even be part of the problem, but they can’t exactly tell you that in so many words. When leaders respond with quick fixes rather than deeper understanding it signals to employees that that their concerns, and the emotions they spark, aren’t worth discussing.
A simple shift in approach can make a world of difference. Instead of jumping to solutions, acknowledge their feelings: “That sounds like a lot to handle. What’s feeling most overwhelming right now?” This keeps the door open for honest conversation and meaningful support.
How to Lead with Curiosity Instead of Assumption
So, how can leaders break free from the assumption trap? The key lies in fostering curiosity, humility, and genuine engagement. Here are three ways to shift from assumption-based leadership to inquiry-driven leadership:
✅ Ask, Don’t Assume – Instead of jumping in with advice, start with curiosity. “Can you tell me more about how this is affecting you?” invites deeper conversation and understanding. When people feel heard, they are more likely to trust leadership and open up about their real needs.
✅ Validate, Then Support – People don’t always need a solution first—they need to feel heard. A simple “That sounds really challenging. I can see why that would be frustrating.” builds trust before moving into guidance. Sometimes, it can be as simple as a moment of shared silence or a simple knowing nod. Unspoken validation can be very powerful. By validating their emotions, you create a space where they feel safe to explore solutions rather than feeling pushed into a prescribed response.
✅ Recognize Experience as a Guide, Not a Rulebook – Your experiences provide valuable insight, but they don’t define others’ realities. Instead of saying, “I know exactly how you feel,” try, “I’ve had a similar challenge, but I’d love to understand what this is like for you.” This subtle shift signals that you respect their unique journey while offering your support.
The Power of Curiosity in Leadership
Leading with curiosity rather than assumption has profound effects. It strengthens relationships, fosters trust, and creates a culture where employees feel valued and understood. When leaders approach conversations with an open mind, they uncover insights that would have otherwise remained hidden.
Think about the impact of a leader who, instead of saying “I’ve been there”, asks:
What feels hardest about this for you?
How can I support you in navigating this?
What outcome would feel best for you in this situation?
These questions shift the dynamic from a leader assuming they have the answers to one who is actively engaged in learning from their team. This doesn’t just improve individual interactions—it builds a leadership style rooted in adaptability, empathy, and respect.
Final Thoughts
Leadership isn’t about having all the answers—it’s about creating space for people to be seen, heard, and valued. When we replace assumptions with curiosity, we build workplaces where people feel supported and empowered to show up as they are, in whatever capacity they can that day. Some days, they’ll be at their peak, delivering their best work with ease. Other days, their best might be showing up and pushing through at 50%—and that’s still their best in that moment.
The next time you catch yourself thinking, I’ve been there, pause. Instead of assuming you already understand, lean into curiosity. Ask one more question. Listen a little longer. You may realize that what they truly need is something different than what you expected—and that’s where real leadership begins.