How to Hold a Coaching Conversation (Tips & Templates)

Coaching conversations can be one of the most powerful tools in leadership, but they often don’t go as planned. Have you ever left a coaching session feeling like you didn’t make the impact you intended or that the conversation didn’t achieve its goals? 

You’re not alone. Many coaches struggle with the same issue, and a glance at a Reddit thread reveals how common this problem is.

Source

From unclear objectives to clients feeling disengaged, there are numerous challenges that can undermine the effectiveness of coaching conversations. 

In this guide, we’ll dive into these challenges and explore how to hold coaching conversations that truly drive growth, engagement, and results. But before we dive deeper, let’s first look at the basic understanding of a coaching conversation.

How Coaching Conversations Build a Strong Coaching Culture 

Coaching conversations are meaningful exchanges where you, as the coach, guide the person you’re coaching to explore their potential, set goals, and overcome obstacles. Instead of telling them what to do, you help them find their own answers and paths forward. These conversations are rooted in self-reflection and goal setting, empowering your client to take charge of their growth, both personally and professionally. 

Podcasts like “Evolving Client Expectations in Digital Coaching – How Coaches Can Stay Ahead” from Growth Dialogues by Simply.Coach offers practical insights on adapting your coaching approach to meet shifting client needs.

Ultimately, effective coaching not only boosts engagement but also helps your client achieve their goals, contributing to their success and that of the entire organisation. 

As you consider the importance of adapting to client needs, let’s now explore the key principles that make coaching conversations truly effective.

Key Principles of Effective Coaching Conversations

Coaching conversations are driven by key principles that help your client grow and reach their goals. Here are the essentials:

• Active listening: Focus fully on your client’s words, tone, and emotions. This helps you identify their true challenges and needs, enabling more effective guidance. 
• Answer thoughtfully: When offering guidance, be deliberate and thoughtful in your responses. Providing clear, considerate answers helps ensure your client feels supported and understood.
• Powerful questions: Ask questions that encourage self-reflection and clarity, such as “What’s the real challenge here?” or “What would success look like to you?” This helps your client think critically and find their own solutions.
• Building trust: Create a safe, open space where your client feels comfortable sharing personal information openly. Trust is essential for deep, meaningful conversations that drive growth.
• Empathy: Understand and connect with your client’s emotions. Empathy fosters a supportive environment where your client feels heard and motivated to address both their strengths and weaknesses.
• Reinforcing strengths and addressing weaknesses: Focus on both reinforcing your client’s strengths and identifying areas for improvement. This balanced approach boosts confidence and guides development.
• Avoid imposing your own solution: Allow your client the space to discover their own paths rather than pushing your own suggestions. This fosters a sense of ownership and builds their confidence in making decisions.
• Encouraging independent thinking and collaboration: Support your client in making decisions and finding solutions on their own. Encourage collaborative problem-solving, allowing both of you to brainstorm ideas and share insights.

Explore Adaptive Communication in Coaching Relationships for more accurate and impactful coaching strategies. By following these principles, you create a coaching environment that promotes growth, self-awareness, and long-term success. Now, let’s discuss how to conduct an effective coaching session, complete with a few examples to help you chart the right path. 

How to Conduct an Effective Coaching Session (Sample Questions)

An effective coaching session goes beyond the basics—it’s about creating an environment where your client can truly reflect, grow, and take ownership of their development. Here’s how you can make each step impactful:

1. Start the conversation with a connection

Before diving into the core issues, it’s important to create a comfortable, open environment where the client feels heard and respected. Start the coaching conversation by connecting on a human level. This could involve some casual conversation or simply acknowledging how they are feeling at the moment. Establishing rapport is key to making the client feel safe and open to sharing.

• Set the tone: Begin by letting them know that this is a judgment-free space. For example, “I’m here to support you and explore whatever is on your mind today.”
• Create a comfortable environment: Ask open-ended, welcoming questions like, “How have things been going lately?” or “What’s been on your mind recently?”

Example: If a client enters the session looking stressed, you might begin with, “It seems like you have a lot on your mind today. Let’s take a moment to talk about what’s been going on. What’s been on your plate lately?”

2. Listen intently, beyond active listening

Now that you’ve established a connection, don’t just actively listen to the client’s words but also focus intently on the underlying meaning. This isn’t just about hearing the content but tuning into the emotions behind the words.

• Look for non-verbal cues: Observe their body language, tone of voice, and facial expressions to understand what might not be said directly. For example, a client who avoids eye contact or seems tense might be holding back emotions.
• Interpret emotional cues: If a client says, “I’m fine,” but their body language suggests otherwise, it’s an opportunity to gently explore those feelings. Ask, “I noticed you said you’re fine, but it seems like there’s something more. Can we talk about it?”

Example: If a client downplays a recent setback and says, “I’m fine,” but you notice they’re looking down and seem tense, you could respond with, “It seems like there’s more to this. What’s really going on under the surface?” This invites them to explore deeper feelings they may be hesitant to share.

3. Respond thoughtfully with non-directive questions

Once you’ve listened and understood the client’s situation, the next step is to help them reflect and gain clarity through questions that promote self-discovery.

• Ask open-ended questions: Instead of directing them toward specific answers, ask questions like, “What do you think might work here?” or “What’s your gut telling you about this situation?” This gives them space to think critically and find their own solutions.
• Encourage exploration: Use questions to challenge assumptions and expand their thinking. For example, “What would you do if you weren’t afraid of failure?” or “How might you approach this if you had unlimited resources?”

Example: If a client is unsure about taking on a new role, you could ask, “What excites you about this opportunity?” or “How does this align with your long-term goals?” These types of questions help them focus on motivations and values, which can help in making a clearer decision.

4. Avoid imposing solutions to foster empowerment and trust

As a coach, your role is not to provide solutions but to empower the client to discover their own path forward, independently. By resisting the urge to fix the problem, you help them take ownership of their growth.

• Give space for self-discovery: Instead of jumping in with advice, encourage the client to come up with their own solutions. Ask, “What have you thought about doing so far?” or “How do you think you could approach this differently?”
• Build accountability: Once they come up with an idea or solution, help them break it down into actionable steps. For example, “What’s the first step you’ll take to move forward?” or “How will you know when you’ve made progress?”

Example: If a client is facing a challenge with delegation at work, instead of giving them a solution, ask, “What do you think would make it easier for you to delegate tasks effectively?” By asking, you empower them to reflect and come up with solutions, making them feel more in control.

5. Plan for follow-up and accountability

In many coaching situations, the client may ask, “Can we check back on this later?” or “Let’s follow up next time.” It’s important to set a clear timeline for follow-up to ensure accountability and progress.

• Agree on follow-up: At the end of the session, agree on when the next check-in will happen. For example, “Let’s touch base in two weeks to see how you’ve made progress on your action plan.” This gives your client a concrete time frame to work toward.
• Clarify expectations: Make sure you both understand what will be checked upon  during the follow-up. This could be progress on a specific action item, or reflection on challenges faced. For example, “When we check in, I’d love to hear how your new strategy has worked for you. If you run into any roadblocks, we’ll address them together.”
• Reaffirm accountability: Before the next session, encourage the client to stay on track with their goals. A simple reminder like, “I’ll be looking forward to hearing how things have been going,” helps reinforce their responsibility.

Example: If a client has committed to improving time management, end the session by saying, “Let’s review in a week how your new schedule has worked. If you’ve faced any challenges, we’ll adjust together in our next session.

Example in Action: A Coaching Conversation on Work-Life Balance

Background:
Alex, a mid-level manager, is struggling to maintain a work-life balance and feels overwhelmed by a growing workload. He’s uncertain how to regain control and manage his responsibilities effectively.

Sample Coaching Conversation

Coach: Alex, thanks for taking the time to meet today. What’s been going on lately that’s making you feel so overwhelmed?

Alex: It’s just the sheer volume of work. New projects keep coming in, and I’m trying to manage my team’s performance while also handling my own deliverables. I’m constantly working late, and even at home, I’m still answering emails.

Coach: That sounds really tough. As you think about your current situation, what would you say is the biggest challenge you’re facing right now?

Alex: I’d say it’s prioritizing. There’s so much coming at me that I don’t even know where to start. I end up working on whatever seems most urgent at the moment, but that just leaves me feeling more stressed.

Coach: I see. What would a successful outcome look like for you? If you could make one significant change, what would that be?

Alex: I’d love to feel like I’m on top of things again—like I have a clear plan, I know what needs to be done, and I have time to actually recharge after work.

Coach: That makes sense. What steps have you tried so far to address this?

Alex: I’ve tried making to-do lists and blocking time on my calendar, but something urgent always seems to derail those plans.

Coach: That’s a common experience. When you think about the times you’ve felt most in control, what was different then?

Alex: I guess when I had fewer projects, I would check in with my team more regularly and delegate tasks. I felt more confident about what everyone was working on, and I wasn’t trying to do so much myself.

Coach: That’s a really valuable insight. What do you think it would look like to reintroduce some of those habits now?

Alex: I could start by having a quick daily check-in with my team to see where they need help and what I can delegate. I also think I need to set clearer boundaries for my own workload, like not responding to emails after a certain time.

Coach: That sounds like a great approach. By when would you like to start implementing those daily check-ins and setting those boundaries?

Alex: I’ll start with the daily check-ins tomorrow and aim to have my new email boundaries in place by the end of this week.

Coach: Perfect. Let’s check back in next week to see how these changes are working for you and what adjustments might be needed. Sounds good?

Alex: Absolutely. Thanks for helping me clarify the next steps. I feel more confident already.

In this coaching conversation, Alex, a manager overwhelmed by the workload, identifies prioritisation as the main challenge. Guided reflection reveals that delegation and setting boundaries can help improve balance and control. 

By following these steps, coaches like you can encourage self-discovery and trust, helping your clients build skills and address future challenges on their own.

Tips for Enhancing Coaching Conversations

To further enrich your coaching sessions, here are practical strategies designed to deepen the impact of your coaching:

• Encourage ownership: Guide clients to lead the discussion by asking questions like, “What would you like to focus on today?” This empowers them to take charge of their own growth.
• Incorporate reflection: Prompt clients to reflect on past successes—”What worked well last time?”—and use those insights to build actionable steps.
• Focus on the future: Help clients envision their future with questions such as, “Where do you see yourself in three months if you apply this strategy?”
• Use metaphors: Frame complex issues with creative analogies—“If this situation were a road, what would it look like?”—to inspire fresh thinking.
• Celebrate wins: Acknowledge every step forward, no matter how small, to reinforce positive behaviours and build confidence.
• Create a comfortable setting: Choose a quiet, distraction-free environment and be fully present, actively listening, and patient.
• Use a framework: Consider the GROW or CLEAR model to guide discussions, maintain focus, and create actionable outcomes. 
• Model vulnerability: Share relatable challenges you’ve faced to foster an open dialogue and build rapport.
• Balance challenge and support: Offer both challenging questions and supportive encouragement to help clients overcome obstacles.

Also read: 8 Language and Communication Coaches to Follow Online for additional insights.

Best Practices for Sustaining Coaching Engagement

To ensure that coaching sessions remain effective and drive long-term growth, it’s important to implement best practices that keep the process engaging and impactful. Here are key practices to maintain coaching momentum:

1. Scheduled follow-ups for accountability and progress tracking

Coaching shouldn’t be a one-time event. Regular follow-ups keep clients on track and using a tool like Simply.Coach makes this process seamless with its streamlined client management features.

To see how this approach can enhance your coaching practice, watch the video “Capture & Track Progress on Client Goals | Simply.Coach. It provides a step-by-step overview of how you can use Simply.Coach to manage client goals, track their progress over time, and ensure ongoing accountability.

2. Allowing adequate thinking time between sessions

Don’t rush into the next session without giving your client time to reflect. After every conversation, leave room for them to process what was discussed. Reflection allows them to internalize the coaching and form their own conclusions. Time between sessions allows your client to digest and apply the insights from your conversation. This is where the real growth happens. 

3. Implementing the 90/10 listening rule for more impactful conversations

The most impactful coaching conversations are the ones where you listen far more than you speak. Aim for the 90/10 rule—90% listening, 10% speaking. When you allow your client to do the majority of the talking, they gain more clarity, discover their own solutions, and take greater ownership of the process. 

Recommended Listen: For more on creating meaningful dialogues, check out Growth Dialogue’s podcast, “Inside the Mind of an OKR Coach, with Sara Lobkovich,“ which discusses the power of active listening in setting clear objectives and tracking progress.

4. Sustaining long-term coaching relationships

Coaching isn’t about checking a box and moving on. It’s about building a long-term relationship that supports continuous development. Even after your client reaches their goals, keep the connection strong. Coaching is about fostering a growth mindset, so continuously revisit and evolve goals as they achieve milestones.

If you’re looking to deepen your expertise in grief coaching, consider exploring Becoming a Successful Grief Coach: Online Certification Programs to enhance your professional development.

Conclusion

Effective coaching is more than just following a set of steps; it’s about creating a space where your client feels supported and engaged, enabling them to grow. It starts with building trust and ensuring a safe environment where they can express themselves openly. Through active listening and powerful questioning, you help guide them to uncover their insights and solutions. Instead of providing immediate answers, the focus is on encouraging self-reflection, empowering them to take meaningful action on their terms. Regular follow-ups are essential to track progress, ensure accountability, and provide continued support.

To continuously improve and adapt your coaching, Simply.Coach provides tools to implement best practices, track progress, and maintain long-term engagement. Features like goal setting, progress tracking, and session management help keep coaching structured, scalable, and effective for both one-on-one and team coaching.

Schedule a demo with Simply.Coach or sign up for the free 14-day trial today and see how it can enhance your coaching practice.