The Five Questions Every Leader Should Ask During Every One-on-One

By The Powers Forma

One of the biggest misconceptions about one-on-one meetings is that leaders need to have all the right answers.

I've learned the opposite.

The best one-on-one meetings aren't built on great advice.

They're built on great questions.

Questions create conversations.

Questions encourage reflection.

Questions uncover opportunities that might otherwise remain hidden.

Most importantly, questions communicate something every employee wants to know:

"I'm interested in what you think."

Throughout my leadership journey, I've asked hundreds of questions during one-on-one meetings.

Some sparked meaningful discussions.

Others fell flat.

Over time, I've found a handful of questions that consistently lead to thoughtful conversations, stronger relationships, and a better understanding of the people I lead.

They're simple.

But they often spark conversations that leave a lasting impact.

1. "What's been your biggest win since we last met?"

One-on-one meetings can easily start with problems.

Projects behind schedule.

Deadlines.

Challenges.

Concerns.

While those topics are important, I've found it's equally important to begin by recognizing progress.

This question shifts the conversation immediately.

It allows employees to celebrate something they're proud of.

Sometimes it's a completed project.

Sometimes it's helping a coworker.

Sometimes it's learning a new skill.

Sometimes it's simply making it through a particularly challenging week.

Celebrating wins builds confidence.

It also reminds both the leader and the employee that progress deserves attention—not just problems.

2. "What's getting in your way right now?"

Every employee encounters obstacles.

Sometimes they're obvious.

Sometimes they're invisible to everyone except the person experiencing them.

This question helps uncover barriers before they become bigger issues.

You might discover:

• A process that's slowing productivity.

• A resource they don't have.

• Conflicting priorities.

• Unclear expectations.

• A communication gap.

• A challenge outside their control.

As leaders, we can't remove every obstacle.

But we can often remove enough to help someone move forward with greater confidence.

Sometimes one conversation is all it takes.

3. "Where would you like to grow over the next few months?"

One-on-one meetings shouldn't only focus on today's responsibilities.

They should also create space to discuss tomorrow's opportunities.

Growth looks different for everyone.

One employee may want to strengthen presentation skills.

Another may want to lead a project.

Someone else may simply want greater confidence in their current role.

This question communicates something powerful.

"I'm invested in your future—not just your current performance."

People remember leaders who take an interest in their development.

Those conversations often become turning points in a person's career.

4. "How can I better support you?"

This may be one of the most important questions a leader can ask.

It's also one of the most humbling.

Leadership isn't about assuming we already know what people need.

Sometimes the support someone needs is encouragement.

Sometimes it's clearer communication.

Sometimes it's additional training.

Sometimes it's simply removing unnecessary obstacles.

Occasionally, you may hear something difficult.

That's okay.

One-on-one meetings should create space for honest feedback in both directions.

Great leaders aren't afraid to ask how they can improve.

5. "What should we make sure we talk about next time?"

I love ending one-on-one meetings with this question.

It shifts ownership of future conversations to both people.

It encourages employees to think ahead.

It also communicates that today's conversation isn't the end of the discussion.

It's part of an ongoing relationship.

Sometimes the answer is a project update.

Sometimes it's a development goal.

Sometimes it's a personal milestone.

Whatever the answer, you've already created momentum for your next conversation.

That's how trust grows.

One meeting at a time.

Great Questions Create Better Leaders

One thing leadership continues to teach me is that questions are far more powerful than they first appear.

The right question can build confidence.

Create clarity.

Strengthen relationships.

Reveal hidden opportunities.

Prevent misunderstandings.

Encourage ownership.

Sometimes one thoughtful question changes an employee's perspective more than an entire speech ever could.

That's why great leaders remain curious.

Make the Questions Your Own

These five questions aren't meant to become a rigid script.

Every employee is different.

Every conversation is different.

Every season is different.

Use these questions as a starting point.

Adapt them.

Build on them.

Ask follow-up questions.

Stay curious.

Most importantly, listen carefully to the answers.

The value isn't found in asking the question.

It's found in what happens after.

Final Thoughts

I've come to believe that the quality of our leadership is often reflected in the quality of our conversations.

And the quality of our conversations is often determined by the quality of our questions.

You don't have to ask dozens of questions during every one-on-one.

Sometimes one thoughtful question is enough to uncover an opportunity, strengthen a relationship, or encourage someone who simply needed to know their leader cared.

Never underestimate the power of asking—and then truly listening.

Because the best one-on-one meetings don't happen by accident.

They begin with curiosity.

Connection Check

Before your next one-on-one meeting, consider these questions for yourself:

• Which of these five questions would create the most meaningful conversation with this employee?

• Am I asking questions to gather information—or to understand the person?

• Which employee hasn't had an opportunity to talk about their future recently?

• Have I created enough space for honest feedback?

• What follow-up question could deepen the conversation?

Great leaders don't ask great questions to sound impressive.

They ask them because they're genuinely interested in the people they lead.

Continue Building Your Leadership Toolkit

Meaningful one-on-one meetings begin with meaningful questions.

That's why I created the One-on-One Conversation Guide from The Powers Forma. It includes practical conversation prompts, meeting frameworks, development questions, and follow-up tools that help leaders create one-on-one meetings that build trust, encourage growth, and strengthen communication. One thoughtful question can often have a greater impact than a dozen quick updates.