If your one-on-ones sound more like polite small talk than actual coaching… you’re not alone.

Supervisor: “How’s everything going?”

Agent: “Good.”

Supervisor: “Okay, keep it up!”

And just like that, another coaching opportunity disappears into the ether.

The truth is, most underperformance isn’t due to laziness or lack of willpower.

It’s often stress, confusion, burnout, or something the agent doesn’t quite know how to say out loud.

That’s where better questions come in.

The right open-ended question can unlock way more than data dashboards ever will. 

Below, we’ve pulled together 10 questions designed to get agents talking, thinking, and trusting that their coach is listening.

Why Better Questions Matter

Coaching isn’t just about fixing performance – it’s about understanding people. 

But too often, check-ins become box-checking exercises. 

Without trust or curiosity, agents default to surface-level answers, and real problems stay buried.

Open-ended questions give agents permission to share more and give you a clearer picture of what’s really going on.

10 Coaching Questions That Open People Up

Use these in one-on-ones or whenever you start seeing a dip in behavior or morale. 

They’re grouped to help you spot burnout, align on expectations, and build trust.

Burnout & Friction

1. “What part of the job is taking the most energy right now?”

A great way to surface early signs of burnout without forcing anyone to say, “I’m overwhelmed.” If the answer is “talking to customers,” that’s a red flag.

If it’s something like systems or note-taking, you’ve got a clearer fix.

2. “If I could wave a magic wand and fix one thing for you, what would it be?”

This opens the door to feedback without turning it into a complaint session.

It often uncovers lingering workflow issues or process frustrations that agents haven’t felt comfortable bringing up.

3. “Have you had a call lately that really rattled you?”

Performance slumps often follow emotional spillover from one bad call. This question helps you catch lingering stress before it festers.

Clarity & Expectations

4. “What’s something you wish we’d explained better during training?”

No matter how solid your onboarding is, something always slips through.

This question normalizes gaps and gives you insight into what might be causing confusion or hesitation.

5. “Do you feel like you have what you need to hit your goals?”

Sometimes the issue isn’t motivation, it’s a missing tool, system, or piece of knowledge.

This helps identify resource gaps that agents may be afraid to admit.

6. “Which part of the QA scorecard feels unclear or frustrating?”

This one flips the QA conversation from defensive to collaborative.

It gives you insight into whether expectations are aligned and shows agents that coaching is a two-way street.

Trust & Growth

7. “What kind of feedback motivates you most?”

Some people want praise. Others want blunt honesty.

Asking this helps you tailor your approach and makes coaching feel more personal.

8. “What’s something you’re proud of that I might not know about?”

Often, great work flies under the radar, especially from quieter team members.

This question gives them a chance to share wins and build confidence.

9. “What’s one thing I could do differently to support you better?”

It takes the spotlight off the agent and invites feedback on your leadership.

Even small responses can build mutual respect and improve your coaching style.

10. “If your future self were giving you advice right now, what would they say?”

A thought-provoking way to shift the conversation from “what’s wrong” to “what’s possible.”

This helps agents reflect and take more ownership of their growth.

Making These Questions Work

It’s not just about what you ask, it’s how you ask it.

Even the best coaching questions can fall flat if they’re rushed, robotic, or tossed into the middle of a chaotic workday. 

To make these questions land, you need the right timing, tone, and follow-through.

Here’s how to make your one-on-ones more than just routine check-ins:

Set the stage for honesty.

Before you dive into questions, create a space that feels low-pressure and judgment-free. 

Start with something casual, give them a heads-up that the conversation is about them, not performance metrics, and be genuinely present (aka close Slack and turn off notifications).

Leave space after you ask.

Don’t jump in to fill the silence. The first answer is often the safe one, but what comes after the pause is usually the truth.

Count to five in your head if you have to. 

Give them the room to think, process, and say what they really mean.

Don’t rush to solve.

It’s tempting to fix things on the spot, especially if the answer reveals a blocker. But resist the urge. 

Let the agent finish their thought, ask a few clarifying follow-ups, and then circle back with solutions later.

You’re building trust, not just to-do lists.

Follow up with curiosity.

Instead of moving to the next question, dig deeper. 

Ask:

• “Can you give me an example of that?”
• “How long have you felt that way?”
• “What do you think would make it better?”
  

These follow-ups show you’re engaged and that their answers actually shape what happens next.

Time your questions strategically.

Not every question belongs in week one. Save the more reflective or vulnerable prompts, like asking what rattled them, for when there’s some trust in place. 

Early on, stick to lighter questions about training clarity or the tools they need to succeed.

Take notes and act on what you hear.

This part’s critical. 

If an agent opens up and nothing changes, you’ve taught them not to bother next time. 

Whether it’s fixing a tool issue, clarifying a scorecard metric, or just checking in again next week, show that what they say matters.

Bottom line…

Good coaching isn’t reactive, it’s intentional. 

If you treat these questions like a script, they’ll feel flat. 

But if you treat them like doorways into real conversations, they’ll help you spot and solve problems that metrics never reveal.

Final Thought

Great coaches aren’t advice machines, they’re conversation catalysts. 

These 10 questions won’t solve everything, but will open the door to more honest, effective one-on-ones.

And that’s where real progress begins.