How to Lead a Developmental One-on-One Meeting With Your Direct Reports

 
“Each individual person is on their own growth trajectory.”
— KIM SCOTT

Think about your last three one-on-one meetings with your direct reports.

What did you discuss?

Chances are, you reviewed project updates, clarified priorities, worked through an obstacle, or checked in on an upcoming deadline. Perhaps you addressed a performance concern or provided feedback on a recent assignment.

Which are all important conversations, of course.

But here's a different question:

How much of that time was devoted to your employees' growth and development?

For many managers, employee development is something they genuinely care about but struggle to prioritize. The daily demands of managing projects, solving problems, and keeping work moving forward tend to consume whatever time is available.

And when development does come up, it's often squeezed into the final few minutes of a meeting or reserved for the annual performance review.

The result? Employees may receive plenty of direction about their current responsibilities without having much opportunity to reflect on where they're growing, what they're learning, or what they might want to pursue next.

The good news is that meaningful development conversations don't necessarily require another meeting on your calendar.

With a little intentionality, your regular one-on-ones can become valuable opportunities to support employees' professional growth.



What Makes a One-on-One Meeting Developmental?

A developmental one-on-one is a manager-employee conversation that makes space for learning, professional growth, and future development alongside immediate work priorities.

Rather than focusing exclusively on what's happening this week, it also explores broader questions:

  • What is this person learning about themselves and their work?

  • Where are their strengths being fully utilized?

  • What skills or experiences would support their development?

  • What opportunities could help them grow?

In its guide to manager development, Gallup describes several types of coaching conversations, from quick connections and regular check-ins to developmental coaching and progress reviews.

The distinction is useful because effective managers need to address both immediate performance needs and longer-term employee development.

That doesn't mean every one-on-one must cover everything.

Rather, managers can intentionally incorporate development into their regular conversations, occasionally setting aside additional time for deeper discussions about career aspirations or growth priorities.

Development Is Broader Than Promotion

One common limitation of employee development conversations is assuming that growth must involve moving into a higher-level position.

Certainly, advancement may be important to some employees. Others may be more interested in deepening expertise, expanding their influence, gaining autonomy, or finding work that better fits their strengths.

In their approach to career conversations, Kim Scott and the Radical Candor team encourage managers to understand employees' motivations and aspirations before creating development plans.

One employee may want to lead a team someday. Another may want to become a respected technical expert without supervising anyone. And another may have advanced leadership promotion targets in mind.

Effective development conversations begin by understanding what growth actually means to the individual.


How to Lead a Developmental One-on-One Meeting With Your Direct Reports

How to Prepare for a Developmental One-on-One

A productive one-on-one begins before the meeting itself.

When you have just 30 minutes together, it's easy for the most immediate issues to dominate the conversation. An unexpected challenge, a project that needs attention, or a pressing question can quickly consume the time you've set aside.

Before you know it, the meeting is over, and the developmental topics you hoped to explore have been pushed to another day.

A little preparation can help you and your direct report approach the conversation with greater intentionality. It also creates an opportunity for both of you to reflect on the employee's growth before getting caught up in the demands of the day.

Here are three ways to prepare:

1. Make development part of the agenda.

Let your direct report know that you'd like to spend some time discussing what they're learning, enjoying, or hoping to develop. Sharing the purpose ahead of time gives them an opportunity to reflect.

You might say:

"Along with our usual check-in, I'd love to spend a little time talking about your professional development—what you've been learning, where you'd like to grow, and opportunities I might be able to help you explore."

2. Invite the employee to contribute.

Encourage them to bring questions, concerns, and topics they'd like to discuss. A shared agenda gives both of you an opportunity to shape a conversation that feels relevant and worthwhile.

3. Bring your observations, but hold them lightly.

As a manager, you have valuable insights into your employee's strengths and potential and it’s a valuable gift to share your perspective with them — at relevant times when they are open to hearing your thoughts. Consider recent accomplishments, emerging capabilities, or opportunities you might suggest.

Your observations can help employees recognize possibilities while leaving room for them to explore their own interests and aspirations.


How to Lead a Developmental One-on-One Meeting With Your Direct Reports

A 30-Minute One-on-One Meeting Agenda That Includes Development

A focused 30-minute conversation can create meaningful opportunities for employee growth.

Here's a practical structure that balances immediate work needs with coaching and development.

Step 1: Connect and Check In (5 Minutes)

Begin by checking in on how your direct report is doing.

Invite them to reflect on their recent experiences and identify what's most important today.

You might ask:

  • "What's been going particularly well this week?"

  • "What's taking up the most mental energy right now?"

  • "Is there anything you'd especially like to discuss today?"

These questions provide a starting point for understanding both the employee's experience and their immediate needs.

Step 2: Discuss Priorities and Challenges (10 Minutes)

Next, address the work-related issues that need attention.

This might include clarifying priorities, providing feedback, discussing a challenging situation, or helping an employee work through an obstacle.

Consider using written updates or project management tools to share routine information, preserving your one-on-one time for topics that benefit from conversation.

This is also an opportunity to practice coaching and help employees strengthen their problem-solving skills.

For example, if an employee is struggling to manage competing priorities, you might ask:

"What's making it difficult to decide where to focus your attention?"

Or:

"What options have you considered for approaching this differently?"

These questions encourage employees to strengthen their judgment while giving you insight into where they need support.

Step 3: Explore Growth and Development (10 Minutes)

Now, intentionally shift the conversation toward development.

You might explore something the employee has learned, a strength they've been using, or an opportunity they'd like to pursue.

Consider questions such as:

  • "What's something you've become better at recently?"

  • "Which part of your work has been especially energizing?"

  • "What capability would you be excited to develop over the next few months?"

  • "What's one responsibility or experience you'd like to explore?"

Pay attention to patterns in their interests, strengths, and emerging capabilities.

For example, an employee who particularly enjoys facilitating challenging meetings may be discovering an interest in leadership or collaboration that could be developed further.

Employees may have varying degrees of clarity about their long-term career goals. Exploring their curiosity and recent experiences can help them recognize potential directions.

For additional inspiration, BetterUp's collection of career development questions offers practical prompts managers can adapt.

Step 4: Agree on Next Steps and Follow-Up (5 Minutes)

Before ending the conversation, identify any next steps related to immediate priorities and longer-term development.

When a growth opportunity emerges, help your employee translate it into something tangible.

For example, imagine a direct report who wants to become more confident presenting ideas to senior leaders.

You might recommend a public speaking course, identify an opportunity to present recommendations at an upcoming leadership meeting, or suggest observing a skilled colleague.

These experiences help employees develop capabilities while contributing to meaningful organizational work.

You might conclude:

"I'll introduce you to the project lead, and you'll explore whether there's an opportunity to facilitate the next planning session. Let's reconnect afterward to discuss what you learned."

Even one meaningful development opportunity, supported by a clear next step, can create valuable momentum.


How to Lead a Developmental One-on-One Meeting With Your Direct Reports

What Developmental Coaching Looks Like in Practice

Consider a hypothetical example.

A manager meets regularly with an experienced employee who consistently delivers excellent work but has recently expressed feeling somewhat stagnant.

During a one-on-one, the manager raises the topic. The employee is capable, dependable, and well respected, and the manager sees potential for expanded responsibilities.

Curious about the employee's interests, the manager asks:

"What kind of work would you find most interesting if you had more freedom to shape your role?"

The employee describes enjoying complicated problems and improving inefficient processes. They express an interest in becoming more involved in organizational strategy.

That insight opens up a new direction for the conversation.

Together, they identify an upcoming cross-functional initiative where the employee could contribute their expertise while developing analytical and influencing skills.

The manager gains a deeper understanding of the employee's aspirations, and the employee identifies an opportunity that genuinely interests them.

A thoughtful question, followed by genuine curiosity and attentive listening, helped reveal a developmental direction worth pursuing.


The Coaching Mindset That Makes These Conversations Effective

A good agenda provides structure, but the quality of the conversation ultimately depends on how you show up as a manager.

It's easy to slip into advice-giving when someone expresses uncertainty or describes a challenge. You may already recognize an opportunity or have valuable experience to share.

Your experience can be a valuable resource. So can your ability to ask a thoughtful question, listen carefully, and help an employee explore their own ideas.

Developmental conversations provide opportunities to strengthen employees' awareness, judgment, and decision-making.

In my article on how to cultivate a coaching mindset, I explore how curiosity, listening, and intentional questions help leaders create space for others to think more deeply.

Three practices are particularly important:

  • Listen for what matters beneath the employee's words. Someone who wants a promotion may be seeking greater autonomy, recognition, or challenge. Exploring their underlying motivations can reveal additional opportunities for development.

  • Give employees space to explore. Invite them to consider different possibilities, weigh their options, and determine what feels most compelling.

  • Share your perspective thoughtfully. Offer observations, identify possibilities, and discuss practical constraints while keeping the employee involved in shaping their development.

  • These skills are equally valuable during everyday leadership interactions.

For more guidance, explore how to maximize a coachable moment.


Keep Development on the Agenda

The balance of topics in your one-on-ones will naturally shift from week to week.

Some conversations will require more attention to urgent challenges or sensitive employee concerns. Others may provide more space to explore longer-term goals.

Maintaining a developmental focus over time helps ensure employees have regular opportunities to reflect on their growth.

Consider including a recurring development prompt in your shared agenda or dedicating one meeting each month or quarter to a deeper conversation.

You might ask:

  • "What have you learned since we last discussed your development?"

  • "What's becoming clearer about the direction you'd like to pursue?"

  • "What support would make the next step easier?"

These follow-ups help maintain momentum and reinforce an important message: your direct report’s growth deserves nurturing throughout the year.


How to Lead a Developmental One-on-One Meeting With Your Direct Reports

Frequently Asked Questions

Make Development a Regular Part of Your Leadership

Think about the people you lead.

You probably have a clear understanding of what they're responsible for, how they're performing, and what you need from them over the coming weeks.

But how much do you know about what they're hoping to learn, the capabilities they want to develop, or the kinds of work that would help them feel more engaged and challenged?

Your regular one-on-one meetings offer a valuable opportunity to explore these questions.

Thoughtful development conversations can help employees recognize their strengths, discover new possibilities, and take meaningful steps toward their professional goals.

And as a manager, you have the opportunity to support that growth through your curiosity, encouragement, and willingness to create space for their thinking.

Strengthen Your Coaching Approach to Leadership

Helping others grow calls for curiosity, thoughtful listening, constructive feedback, and the ability to recognize when to guide, challenge, or create space for someone else's thinking.

At The Leadership Coaching Lab, I work with leaders who want to strengthen these capabilities and become more intentional about how they support their teams.

Through individualized Executive & Leadership Coaching, we can explore your leadership challenges, develop practical coaching skills, and identify strategies you can apply directly in your everyday conversations.

Explore Leadership Coaching to learn more.

Or schedule a free consultation and tell me a little about your leadership development needs. We can talk through what's happening, what you'd like to accomplish, and which approach might be the best fit.

 
 

Dr. Bethany Peters is a Professional Certified Coach (PCC) and leadership expert who helps individuals, teams, and organizations grow through leadership coaching, executive development, team facilitation, and evidence-based assessments. Whether she's coaching one-on-one or leading a workshop, Bethany creates practical, engaging experiences that help people communicate better, lead with confidence, and create lasting change.

Dr. Bethany Peters

With over 20 years of experience in leadership development and a Ph.D. in Organizational Leadership, I take a coach approach to help leaders and teams thrive. As an expert thought partner, I facilitate clarity, inspire creative thinking, and help growth-minded professionals overcome barriers to make meaningful progress.

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