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Home Leadership

The 1 question that’s quietly killing your leadership success 

October 17, 2025
in Leadership
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The 1 question that’s quietly killing your leadership success 
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Ever heard of “Sawubona”? It’s a Zulu greeting that means “I see you.” The idea is to recognize the value and dignity of each person you meet, accepting their humanity in its entirety and giving them your undivided attention. One response to this type of greeting is “Shiboka,” meaning “I exist for you.” Beautiful, right?

Now, take a minute to picture your everyday greeting with your team as a leader. In comparison, doesn’t yours feel rushed, unconscious and devoid of presence? But more importantly, does it lack empathy? Oh, and when I say empathy, I mean you showing your team that you are deeply interested in what they are emotionally invested in. Yet, every single day, that’s exactly why this one question is secretly leading to surface-level relationships, preventing you from earning intimacy, loyalty and trust with your team: how are you? Harmless? Maybe. Is there a better alternative? Certainly. Allow me to introduce you to my What, Feel, Who Method, which, when embodied, will help you ask an “Empathetic Question.”

Putting the 3 questions to work

Before we get into it, imagine this. You’re about to step into your initial 1:1 meeting with Mike, a new recruit on your team. To put your best foot forward, ask a series of meaningful questions during the conversation. “Mike, what are you working on outside of work that’s really important to you right now?” “How do you feel about it?” “Who in your life is this impacting the most?” These three simple, conscious questions (asked separately and intentionally) will unearth what is important to Mike in this season of his personal life, how he feels about it and who it is impacting. A meaningful conversation ensues, and a connection is formed. Now, the question is, what do you do with this information?

The key lies in following up on your initial series of questions, which shows that you care. This shows (not just tells) him that you are interested in the very thing he’s emotionally invested in. When used with integrity, not only will you build trust and loyalty, but you’ll become the type of leader others want to follow. 

Your series of questions was designed to uncover the What, Feel and Who. The key lies in asking an Empathetic Question in your next meeting, incorporating the very information you learned prior:

What is important to them?
How do they feel about it?
And who is this impacting

Fast forward two weeks, and there you are, walking into your follow-up meeting with Jamie. Instead of leading with an unintentional, “Hey Mike, how are you?”, you try something different. Instead, you say, “Hey Mike, the last time we spoke, you mentioned your wife was training for her first ever marathon [WHAT] and that you were feeling worried [FEEL] because she [WHO] recently had a knee operation. How are you both feeling ahead of the race?”

See the difference between this question and a throw-away “How are you?” Caring about what the person opposite you cares about, using their own language to describe how they feel, and displaying genuine interest in their life, is something that’s often missing when you’re too busy focused on your own challenges, desires and agenda.

Asking the Empathetic Question

By asking a question embodying this framework, you give people the chance to share what’s deeply important to them and spark intimacy, all while creating a layer of psychological safety in the relationship. This is how you go beyond the surface and build a meaningful relationship that matters. The outcome? You are showing them (not telling) that you truly listened to them and that you’re interested in what they are emotionally invested in. 

 Here are three tips to ensure you ask an Empathetic Question with impact:

Ensure the North Star of your question is nothing other than getting to the heart of their truth and understanding what’s personally important to them in this season of their life.
Use an upward inflection at the end of the sentence to convey curiosity.
If you didn’t uncover the What, Feel and Who in your prior conversation, you’ll struggle to ask a follow-up Empathetic Question in your current conversation.

Remember, the depth of your questions determines the depth of your relationships, both in business and in life. This type of question may unlock a connection, but actually listening to your conversation partner grows it. Your ability to truly connect with your team on a deeper level, understand who they are and uncover their core motivations is the difference between a good leader and an extraordinary one.

Opinions expressed by SmartBrief contributors are their own.

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