Ask this question to identify the real issue

Imagine a manager who notices her team missing deadlines.

She tackles the obvious issues—tight schedules, workload distribution—but progress stalls.

Frustrated, she sits down with a team member and asks, “What’s the real challenge here for you?”

The answer? A fear of admitting when they’re overwhelmed.

Suddenly, the problem isn’t logistics—it’s psychological safety.

This story illustrates why “What’s the real challenge here for you?” is a game-changer.

It’s not just a question; it’s a flashlight for the shadows where true obstacles hide.

Why the Word “Real” Changes Everything

The magic lies in the word “real.” It pushes us past symptoms to root causes.

• Surface-level challenge: “I’m overwhelmed with work.”
• Real challenge: “I struggle to delegate because I fear losing control.”

By focusing on what’s real, we shift from temporary fixes to lasting solutions.

Breaking Down the Question: A Tool for Depth

Each part of the question serves a purpose:

1. “What’s…” Opens the door to exploration.
2. “…the real…” Signals a hunt for the core issue.
3. “…challenge…” Acknowledges the struggle without judgment.
4. “…here…” Grounds the conversation in the present context.
5. “…for you?” Personalizes the inquiry, honoring individual experience.

Together, they create a scaffold for meaningful dialogue.

When to Ask This Question: 5 Transformative Scenarios

1. Coaching/Mentoring: A client says, “I can’t hit my sales targets.” Real challenge? Fear of rejection.
2. Team Problem-Solving: A project is delayed. Real challenge? Unclear ownership, not just timelines.
3. Personal Reflection: “Why am I procrastinating?” Real challenge? Perfectionism, not laziness.
4. Customer Service: A client complains about a tool. Real challenge? Lack of training, not the product.
5. Conflict Resolution: Colleagues clash. Real challenge? Misaligned priorities, not personality differences.

How to Ask It Right: Empathy Over Answers

To wield this question effectively:

• Tone matters: Ask with curiosity, not interrogation.
• Pause: Let silence do the heavy lifting—allow time to reflect.
• Listen deeply: Notice hesitations, emotions, and unspoken cues.
• Avoid fixing: Your role is to uncover, not solve.

Example: Instead of, “Just delegate more!” ask, “What makes delegation hard for you?”

The Ripple Effects of Uncovering the Real Challenge

1. Smarter Solutions: Fixing the root cause saves time and resources.
2. Stronger Trust: People feel heard, deepening relationships.
3. Empowerment: Teams gain clarity to tackle obstacles head-on.
4. Reduced Burnout: Addressing core issues prevents recurring stress.

Your Invitation to Dig Deeper
The next time you encounter a problem—yours or someone else’s—pause.

Skip the quick fix and ask, “What’s the real challenge here for you?”

You’ll uncover hidden barriers and open doors to growth.

Keep Crushing!
- Sales Guy