Ask Better Questions: The Leadership Skill That Transforms Performance Conversations

Venn diagram showing involvement, understanding, and clarity overlapping to illustrate how asking better questions leads to effective performance conversations.

As a leader, have you ever rushed to solve a problem, give an answer, or outline a plan of attack? If so, you’re not alone. HR professionals, compensation teams, and people leaders want to support others. They aim to guide, reassure, and advance the work. Yet this instinct often leads us to skip one critical step: understanding the root cause and genuine involvement — the foundation of effective performance conversations.

When we fail to involve the person the conversation is meant to serve, we miss context. We miss perspective. We misunderstand what is actually happening. And without understanding, we miss the real problem. This is why the ability to ask better questions is central to effective performance conversations for both HR and leaders.

In recent months, I’ve watched leaders, HR partners, and managers move fast. They jump in quickly, solve problems quickly, and provide advice quickly. And while their intentions are good, this speed creates avoidable blind spots. Those blind spots later show up as rework, confusion, and stalled progress — all barriers to effective performance conversations.

In the leadership programs I facilitate through CompAware™, I see one common pattern: leaders offer multiple-choice assumptions instead of questions. They say things like, “Did you miss this goal because your plate was too full? Was the direction unclear? Were you unsure where to begin?”

These guesses limit people. They push them to choose from our list instead of sharing what’s really on their mind. My guidance is always the same: ask a question and be patient with silence. Silence creates the space that makes effective performance conversations actually work.

If we want clarity and better decisions, we must slow down long enough to ask better questions and bring people into the process.


Why Effective Performance Conversations Depend on Involvement

Leaders don’t skip involvement because they lack care or skill. They skip it because they feel pressure. Meetings pile up. Emails surge. People want fast answers. So we jump in, ready to help.

However, every time we do, we increase the risk of solving the wrong issue — and effective performance conversations fall apart.

Here’s a real example. Recently, an HR professional online asked for advice on coaching a leader described as a “long processor.” Comments rushed in:

  • “Give them this script.”

  • “Tell them to summarize first.”

  • “Coach them on communication.”

But almost no one asked:

  • Does the leader know others see them this way?

  • What contributes to their style?

  • Do they see this as an issue?

  • Did something shift recently?

When we jump to solving, we remove the person from their own situation. That is the moment understanding ends — and effective performance conversations break down.

A question-first mindset does the opposite, involving the person, building ownership, and creating clarity. And it helps both HR and leaders address the real issue, not the assumed one.


Pay Conversations: A Critical Moment for Effective Performance Conversations

Pay discussions reveal this issue more than almost any other leadership activity. Managers deliver a merit increase and jump right into their talk track. They explain budgets, outline the range, and show where the employee sits.

Informative? Yes.
Gauging Understanding? No.

Without a doubt, these conversations lack interactive discussion that makes them effective performance conversations.

AI-generated talk tracks are improving, but many still miss the essential prompt component: ask the employee questions. Without question, the conversation becomes one-sided.

Consider stronger opening questions:

  • “What part of your work energized you most this year?”

  • “Where do you want more challenge?”

  • “What goals matter most right now?”

  • “What does growth look like to you next year?”

These questions turn performance discussions into effective performance conversations grounded in involvement, not assumption.

Here’s a recent example. A manager said to an employee:

“I don’t want to talk about the whole year. Next time, let’s only talk about the next six months.”

The employee felt dismissed, unheard, and undervalued. They left that organization soon after.

Skipping involvement doesn’t save time. It costs talent.


Why Asking Better Questions Strengthens Leadership at Every Level

At MorganHR, we see this in every organization. Leaders want to serve. HR teams want to support. Managers want to guide. But when involvement gets skipped, performance conversations lose meaning.

Real speed comes from effective performance conversations grounded in curiosity — not assumptions.

Asking better questions helps HR and leaders:

  • Reduce confusion

  • Avoid misdiagnosis

  • Strengthen coaching conversations

  • Understand expectations

  • Build shared understanding

Our WRAP™ and ENGAGE™ models teach leaders exactly how to ask better questions early and consistently — the core of effective performance conversations.


Four Universal Questions for Effective Performance Conversations

These questions work in compensation meetings, performance check-ins, coaching, and everyday leadership.

  1. “How do you see the situation?”
    Reveals perspective and reduces assumptions.

  2. “What have you tried so far?”
    Highlights patterns and barriers.

  3. “What else could you try that you haven’t tried yet?”
    Encourages exploration.

  4. “What does a good outcome look like to you?”
    Builds clarity and alignment — the heart of effective performance conversations.

When leaders use these consistently, stress decreases and clarity increases.


How SimplyMerit Supports Effective Performance Conversations

SimplyMerit strengthens performance discussions by removing administrative noise. When managers have pay history, range placement, performance data, and budgets in one place, they stop scrambling for data.

With clarity comes confidence. With confidence comes curiosity. Curiosity drives the questions that make performance conversations effective.

SimplyMerit helps managers:

  • Diagnose pay issues faster

  • Understand patterns

  • Prepare for conversations

  • Focus on development over spreadsheets

  • Create more effective performance conversations


How CompAware Helps Employees Join Effective Performance Conversations

CompAware™ is built on one belief: strong conversations create strong workplaces. CompAware teaches employees and leaders how to:

  • Ask better questions

  • Explore perspectives

  • Normalize two-way discussion

  • Reveal expectations

  • Build next steps

This is how effective performance conversations become part of everyday life — not just an annual cycle.


The Research: Questions Improve Performance Conversations

A 2024 Harvard Business Review article shows that follow-up questions increase empathy, clarity, and trust:
https://hbr.org/2024/02/the-art-of-follow-up-questions

Leaders who ask more questions run more effective performance conversations — and avoid costly misunderstandings.


Quick Implementation Checklist: How to Build Effective Performance Conversations

Small organizations (<250 employees):

  • Add three core question prompts to every HR intake.

  • Teach managers to ask before advising.

  • Use SimplyMerit to simplify preparation.

  • Use short, frequent check-ins.

Mid-size organizations:

  • Integrate question-first methods into merit cycles.

  • Use SimplyMerit to simplify preparation.

  • Provide talk tracks that support effective performance conversations.

Large enterprises:

  • Train leaders in WRAP™ and ENGAGE™.

  • Embed curiosity into competencies.

  • Use CompAware to normalize deeper conversations.

  • Use SimplyMerit to simplify preparation.


Key Takeaways

  • Effective performance conversations start with involvement.

  • Leaders skip involvement because solving feels faster.

  • Skipping involvement means skipping understanding.

  • SimplyMerit and CompAware strengthen conversations.

  • Asking better questions prevents blind spots.


FAQ: Effective Performance Conversations

1. Why do they matter?
They uncover expectations, reduce confusion, and build trust.

2. How does SimplyMerit support this?
It centralizes data so managers can focus on the conversation — not spreadsheets.

3. What if leaders feel too rushed?
Asking the right few questions reduces rework and misunderstanding.

4. How does CompAware help?
It teaches employees and leaders how to explore perspectives and build next steps.

5. What’s the biggest risk of skipping involvement?
Leaders solve the wrong problem and unintentionally damage trust.


Call to Action

If your organization is ready to build stronger, more effective performance conversations, MorganHR can help.

Let’s build a culture where curiosity drives clarity.

👉 Connect with Stacy: https://www.morganhr.com/contact

About the Author: Stacy Fenner

Stacy Fenner is a Senior Consultant and Program Director for MorganHR. Over the course of her 25 years of human resources experience she developed a passion for inspiring and coaching others to achieve results. Stacy’s multiple certifications—including InsideOut Coaching, Korn Ferry Leadership Architect, and many more—have given her a wealth of perspectives to draw from in designing effective customer solutions. Her expertise lies in the areas of HR Consulting, Employee Engagement, Culture, Coaching, and Leadership Development.