When the Same Issue Keeps Coming Up: What’s Really Going On


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Do you have an employee who keeps coming to you with the same concern—again and again—and you're wondering, "Didn’t we already resolve this?" If so, you’re not alone. Many leaders experience these recurring conversations and may find them perplexing, frustrating, or even exhausting.

But before jumping to conclusions like:

  • “Here we go again.”
  • “This person is so needy.”
  • “This person will never be satisfied.”

…pause. Take a breath. Let’s reframe what might be happening here.

The Story We Tell Ourselves

Sometimes, without realizing it, we start telling ourselves stories about a person or a pattern that make it harder to lead with empathy. Those internal narratives, while natural, can create hidden assumptions, such as:

  • “This is just their personality.”
  • “They aren’t listening.”
  • “They’re overreacting.”
  • “They obviously haven’t tried to resolve this themselves.”
  • “This is not my responsibility – they need to figure it out on their own.”

But what if those assumptions are limiting beliefs? In other words, what if you are the one holding you both back from finding a successful resolution? What if the employee is just as frustrated as you are—and they’re continuing to ask because their core need still isn’t being met?

Recurring requests are often a signal that something is unresolved beneath the surface. It’s not just about the problem at hand—it’s about being seen, heard, and supported in a meaningful way! Ignoring this pattern can lead to disengagement, burnout, conflict, and turnover.

The goal of this article is to help leaders explore how to approach these moments with curiosity instead of conclusion and shift the dynamic in a productive direction.

Step 1: Start With Self-Reflection

Before entering into another version of the same conversation, take a moment to check in with yourself. Ask yourself, or journal your responses to the following questions:

  • What story am I telling myself about this person or situation?
  • What evidence do I actually have—and what am I assuming?
  • Is this issue impacting performance or outcomes?
  • What solutions have I proposed so far?
  • Have I referred them to other support systems (e.g., HR, coaching, EAP)?
  • Have I discussed this recurring complaint with my support systems (e.g. HR, coaching, mentor, recent leadership program cohort, EAP)?
  • Am I labeling this as a “poor fit” without clear evidence?
  • What might I be missing about their experience?

Leading others skillfully starts with leading ourselves well. Self-reflection is not an optional leadership skill—it’s a vital one.

Step 2: Lead With Curiosity, Not Assumptions

Approach the next conversation with openness and a desire to understand. Resist the urge to “solve it and move on.” Instead, lean into the power of meaningful dialogue.

Set the Tone for the Conversation

Your tone, body language, and the clarity of your intention all help set the stage for the conversation. When you approach the discussion as a collaborative partner, it encourages the employee to engage as a problem-solver, rather than feeling like they’re just bringing a complaint.

Try one of these phrases:

  • “I want to understand what’s really going on here so we can figure it out together. Your success matters to me.”
  • “I want to work together to find a resolution to this problem.”
  • “I may not have all the answers, but I’m invested in helping you find the next right steps.”

This kind of messaging builds trust and emotional safety, two essential elements of productive dialogue.

Ask Thoughtful, Clarifying Questions

Resist the urge to ask, “Didn’t we talk about this already?” In fact, resist closed end questions that will result in a simple “yes” or “no” altogether during this brainstorming conversation because it will shut people down quickly and you will lose collaboration. Instead, try to find the next open-ended question that you can ask.

Try asking:

  • “What’s the biggest challenge for you in this situation?”
  • “What does meaningful support look like to you right now?”
  • “Can you paint a picture of what resolution would look or feel like?”
  • “If you were in my shoes, what would you try next?”
  • “Is there anything from your past experiences that’s making this feel more difficult?”

These questions shift the dynamic from repetition to insight and may uncover root causes that weren’t visible before. Another open-ended question you can use later in the conversation when you feel like they might have more to share is, “What else?”

The key here is to pause long enough after asking each question, for the employee to have a chance to answer thoughtfully. Practice active listening to illustrate that you genuinely care about the employee, are trying to understand the problem, and are thinking deeply about potential solutions.

Step 3: If the Pattern Persists

If you’ve had multiple conversations and the pattern remains unchanged, it may be time to escalate or redirect. Consider:

  • Consulting with HR or another resource to explore next steps.
  • Documenting the conversations in follow-up emails sent to the employee.

We’ll cover how to navigate persistent patterns in a future resource: “When There is No Solution.”

In Summary

When an employee keeps bringing the same issue to your door, it’s easy to feel stuck, or worse, to lose patience. But what feels like repetition might actually be a signal: a deeper need, an unresolved concern, or a breakdown in communication.

Your job as a leader isn’t to have all the answers; it’s to stay curious, challenge your own assumptions, and tune into the subtle cues that reveal what your team member truly need. It means asking thoughtful, open-ended questions and listening deeply. Your role isn’t to deliver your version of the solution, but to guide the employee in discovering their best next step and then support them in making it happen. You’re not a magical solutions fairy—you’re a trusted guide walking alongside them.


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