An 8-Word Question to Launch Any Conversation to the Next Level

When you meet someone,
treat them as if they were in serious trouble
and you will be right more than half the time.

HENRY B. EYRING

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Whether you're conducting a one-on-one, networking, chatting with a neighbor, or talking with your kids, there are certain questions and phrases that can take a conversation to the next level.  Here's one from the coaching perspective that I've been using lately in almost every single conversation with anyone I want to dive deeper into with or take to the next level:

What's your biggest challenge or obstacle, right now?

No matter how positive or happy people seem on the outside, almost all of us are dealing with some challenge or obstacle.  Like Eyring states in our opening quote, when we approach conversations as if the other person were in serious trouble, we'd be right more than half the time.  Some are facing small challenges and others are downright calamitous.  But we're all dealing with (or sometimes avoiding) something.  That's life.

It's amazing how even nearly complete strangers will open up and share.  Just recently, I've had people share challenges from needing to increase client acquisition or employee engagement to sharing how they're trying to deal with a toxic leader or childhood trauma.

Why do people open up and share?  When was the last time anyone asked you that question?  Yup.  Even though almost all—if not all—of us are facing some type of challenge, almost no one ever asks us what that is. 

Some places are even dealing with toxic positivity where people seem forced to wear a positivity mask all day and end up cloaking and suppressing their real emotions just to look good and stay in the good graces of the leader.

Leaders who genuinely understand their team members' challenges can create a more supportive, safe, and engaged work environment.  You may want to consider sharing your own challenges first.  This vulnerability fosters a culture of openness and trust.

When we ask a question about challenges or obstacles, we open the door for our true shared-humanity to connect us even deeper.  We open the door to deeper trust, to empathy, to more authentic compassion, and even to love.

Want to take it even deeper?
The importance of active listening after asking this type of question cannot be overemphasized.  You will gain valuable insights by truly understanding their needs and concerns.  As Covey has said, "Listen to understand, not to respond."  That also means paying attention to body language, tone, and other cues that might reveal more than words alone.

A great follow-up phrase when someone trusts you enough to share their biggest challenge or obstacle is, "Tell me more about that."  It gives them the wide open space to expand and explain the back story and context.  It opens up space to share feelings and perspectives.  It gives you space to ask clarifying questions so you can build even deeper understanding and empathy.  You might follow-up with, "How long has this been going on?" or "How do you know this is a problem?"

One of the most important things we can do during these conversations is to validate.  Validation in active or empathic listening is an oft-forgotten key element.  It is how others know that they are heard, cared for, and matter.  It might sound something like, "It makes sense that you're feeling frustrated when Mark doesn't acknowledge your contributions" or "I think anyone who had been ghosted like that would be feeling anxious."

Listening for why the issue is a challenge for them can reveal what a person truly values and how violating those values is and can impact them.

And the best part is, you don't have to fix it for them or offer advice.  That's probably a sure-fire way to shut the conversation down and turn them off.  Better, ask them what they've tried so far or what their plans are to remedy the situation.  You could ask, "Who is someone you trust that might help you?" or "What do you think will happen if you don't do anything?"

The overnight miracle
Another follow-up question to ask when you've gained clarity about their issue is, "If, when you went to sleep tonight, a miracle occurred overnight and this was completely resolved or achieved, what would have had to have changed?"  This helps them zero-in on key issues and actions that they need to take or ask of others.  Sometimes, it reveals to them that their issue is out of their sphere of control or influence and it might be time to let it go.

But none of those deeper questions and empathy can occur if I don't first ask, "What’s your biggest challenge or obstacle right now?"  When we approach key conversations with the perspective of curiosity about a shared common human condition—that we're all facing some sort of challenge, obstacle, or trouble—then we are leading with empathy, compassion, and love. 

Of course, this isn't the only question you can ask to take a conversation deeper or launch it to the next level, but it's a strong one to add to your toolbox.

Key take-aways

• Almost everyone is dealing with some type of challenge or obstacle
• Asking about that opens the door for deeper connection, learning, and understanding
• It can reveal what a person truly values
• It can help you understand your team members' challenges
• It can create a more supportive and engaged work environment
• It builds trust and more committed relationships
• You model leading with empathy, compassion, and even love
• You create an environment where people feel safe to come to you with future issues and challenges

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Have an amazing journey today!

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Alan Mikolaj is a coach and leadership development consultant with 15+ years of experience.  He is passionate about helping leaders transform their leadership, their teams, and their organizations.  Impactful, professional approach driven by a passion for meaning and purpose, a growth mindset, and a commitment to excellence and service in order to drive change and results.
Alan maintains the ethics and standards of behavior established by the International Coaching Federation (ICF), including the standards regarding confidentiality.  You can learn more about them on the ICF website.
Transformational change starts with a conversation!
Alan is on a mission to partner with like-minded leaders who want to make a positive difference in the world.
Schedule your free, one-hour session by clicking here: Discovery Conversation with Alan
Or call or email me: Contact Page

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