Coaching Conversation Examples

When planning your annual family vacation, you can already visualize the route you will take.

You see the road ahead and the pit stops, and you see yourself arriving at your destination.

The kids pile out of the car, racing to be the first to splash into the sea. It comes naturally since you have taken this trip many times before.

As professionals, we may not always consider our way of preparing for sessions as planning since it is something that we naturally do.

Yet planning and having a rough outline of the conversation you will have with your coachee are essential pieces of guiding them to achieve their goals.

This article will provide you with several ideas on how to structure your coaching sessions, useful tips for planning your sessions, and specific examples of successful coaching conversations.

How to Structure Your Coaching Session

Structuring coaching sessions is beneficial for clients and provides the coach with a clear outline to keep them organized and focused on achieving the client’s objectives.

One of the most widely known models used in various types of coaching is the GROW model (Whitmore, 1988). Our GROW Coaching Model article provides an outline of this popular model, as well as a selection of tools and coaching techniques to integrate into your practice.

While having structure is important, it is also essential to understand how the coaching structure benefits both yourself and your client. One of the most effective ways to do this is through questioning.

Asking good coaching questions is at the heart of effective coaching, regardless of the model that the coach uses. All coaching approaches use questioning in various forms to help uncover individual thought processes (McMahon, 2021).

The coach can stimulate thinking and turn ideas into actions by using five key questions (Barlow, 2005). The five questions can be asked in order, based on the difficulties and topics the coachee wants to discuss, as the ultimate goal is to get them where they need to go.

1. Where have you been?

Ask the client about their histories, such as education, previous work experience, or even their personal experiences that have led them to this point. It builds rapport and creates space for the coachee to feel comfortable. By establishing a history, they can pinpoint where they want to go in the future.

2. Where are you now?

Exploring the present situation is key to understanding why and how the coachee wants to engage in self-improvement. This can also be done by asking your client about their general state of mind (i.e., what they are thinking and feeling; Nawalka, 2020).

By understanding their trajectory and where they are coming from, the coach is better able to meet the client’s needs.

3. Where do you want to get to?

Once the present situation has been explored, this question can help the coachee visualize what they want to achieve. We also consider this the breakthrough point of the session, where the coach should be at their most present, engaging the client in questions that force them out of their comfort zone and create the internal shift they need to move forward (Nawalka, 2020).

Powerful questions are open-ended and cannot be answered with a simple “yes” or “no.” A way to ask open-ended questions is to start with one of the following statements (Evercoach, 2020):

  • Why?
  • How?
  • What do you think about…?
  • Tell me more about…

Asking open-ended questions guides coachees to come to realizations on their own, rather than toward the answer you think they should pursue.

A lot can happen in the silence between the questions you (the coach) are asking and the coachee’s responses, as they are processing what you are asking them and making connections within their subconscious (Evercoach, 2020).

4. How will you get there?

After identifying where they want to be, the coachee may have trouble figuring out how they want to get there. This is often when the learner wants advice from the coach but can be assisted to think through the alternatives and options that they might use.

Going through each option or playing through the plausible scenarios helps them select the counseling approach they are most comfortable with (Barlow, 2005). Alternatively, the coachee may choose to play through the riskiest option first as rehearsal with their coach so they can develop the courage to go outside their comfort zone and achieve their goals using a method they may not have considered before.

5. How will you know you have arrived?

This last step asks for the learner to examine how they would measure their learning and decide if they have achieved the learning goals they set for themselves. It can also help clarify what actions to take and the method they will use (Barlow, 2005).

This final section is also referred to as the “takeaway,” where the coachee can reflect on what they need to do next and whether they learned or discovered anything new during the session (Evercoach, 2020).

If the coachee is having trouble identifying anything concrete, they can also reflect on how they are feeling after the session, as this will still help move them forward.

Coaching Conversations Can Build a Coaching Culture — Here’s Why

As more and more people in your organization develop their coaching and conversational skills, you build skills at holding coaching conversations and start to instill a coaching culture, which increases:

  • Employee engagement
  • Job satisfaction and morale
  • Collaboration
  • Teamwork
  • Bench strength

Coaching conversations aren’t just for specialized professionals. Nearly anyone can conduct a coaching conversation. Coaches can help people who are ready to identify problems and find solutions. And developing people — coaching others — is an important part of leadership.

Some of the most powerful coaching conversation experiences are informal exchanges in hallways, cafeterias, workspaces, virtual chats, and video calls in the course of everyday work.

When enough people at an organization begin coaching one another, the organizational culture can shift. As a critical mass is reached, with people having candid coaching conversations with one another across the entire company, something powerful begins to happen. Team relationships strengthen, employee engagement increases, and business performance improves.

In short, interactions across the entire organization, whether in-person or virtually, become more honest and more effective, and together, all these coaching conversations start to create a better culture at the organization.

Holding a Coaching Conversation

Recognize When to Hold a Coaching Conversation

First, identify when there’s an opportunity for a coaching conversation. Not all conversations lend themselves well to coaching. Make sure you know whether it’s the right time and you’re ready to try and coach your people. To recognize when someone is open to having a coaching conversation, pay attention to their cues. Listen for phrases like:

  • “Can you help me think things through?”
  • “I’d like to bounce some ideas off of you.”
  • “Could you give me a reality check?”
  • “I need some help.”

In these moments, you can turn a typical conversation into an opportunity for a coaching conversation.

3 Steps to Follow for Coaching Conversations

At that point, remember these 3 guidelines to hold a coaching conversation:

  1. Listen carefully.
  2. Respond thoughtfully.
  3. Resist imposing your solution.

1. Listen carefully.

Don’t assume what the conversation is about or what path it should take. Truly listen, allowing space for others to think, reflect, and express themselves. Start with building your active listening skillset, but know that truly listening goes beyond active listening, to listening to understand.

Listening to understand focuses on the idea that there are multiple levels of information we must tune into during conversations. One level, of course, is the factual information being presented — most of us tend to pay attention primarily to that. But listening to the values behind the topic at hand and the emotions that people bring to an issue is an important part of a better conversation.

That’s where we often find unstated objections, sensible reservations, and concealed barriers that might torpedo new initiatives. More robust solutions to business challenges emerge when people are listening to understand one another.

2. Respond thoughtfully.

Coaching isn’t about the quick fix or first solution. It’s about uncovering answers through inquiry, openness, and exploration. Start by asking powerful questions that draw out more information or stretch the other person’s thinking, such as:

  • What else could you do?
  • What else occurs to you?
  • Who else have you talked to about this?
  • Who else is affected in this situation?

Beyond creating mutual understanding about facts, when leaders ask good questions, it can help to uncover insights that wouldn’t have come to light otherwise.

A non-directive prompting question like “How do you want your team to feel when you announce the new initiative?” is likely to spark more reflection and lead to greater insights than asking “When are you announcing the new initiative?” While the latter question might help get the person inquiring up to speed, it isn’t particularly powerful and isn’t likely to add any real value for the person answering, as they simply repeat a straightforward fact they already know.

Be sure you set a comfortable tone, maintain eye contact, and give plenty of time for them to think and respond to your questions. Encourage them to express themselves — without you agreeing or disagreeing.

3. Resist imposing your solution.

Shift away from the common and natural tendency to want to problem-solve or give advice. There are times to direct or give answers, but coaching conversations are about the other person’s learning — not about your opinion or expertise.

Informed by neuroscience, the real art of conversation is balancing an appropriate mix of challenge and support. Providing support includes assuring people that they’ve been heard and, especially, that their feelings and values are understood. It provides an important sense of creating psychological safety at work, building trust, and encouraging greater honesty and transparency.

When that ratio is right — and practiced in an authentic rather than formulaic way — the challenge is received and fosters more constructive dialogue, rather than triggering defensiveness.

When you’re able to listen carefully, respond thoughtfully, and resist imposing your solution, you have the basis of a coaching conversation.

So whether that conversation was a planned coaching session or an impromptu moment, you’ve opened the door to new thinking, new action, and valuable learning. And when coaching conversations start to happen all across your organization, you have the foundation for a strong organization-wide coaching culture.

Planning Your Sessions

When planning your sessions, it is important to first understand the coachee’s needs.

To achieve this, the coach should structure the first session around developing a connection with their coachee.

While it is important to prioritize the coachee’s goals, it is difficult to understand their objectives without making them feel emotionally comfortable.

The “where have you been?” and “where are you now?” questions from Barlow’s (2005) model are good questions to establish a baseline.

One strategy coaches can use to help clarify their client’s goals is to invite them to complete a short, standardized questionnaire before their first coaching session.

This can give clients the space to carefully consider their coaching goals without the fear of being judged or the distraction of any anxieties or nerves about their first session.

Cuenca (pictured here) is a great tool for the job. It features a simple drag-and-drop activity builder that allows coaches to design a range of questionnaires and activities that clients can complete on their handheld devices.

Using the tool, coaches may also design the check-in surveys for completion throughout the coaching relationship. These can allow clients to express how they feel they are progressing toward their goals, provide feedback, or indicate what they’d like to discuss in their upcoming sessions.

After establishing an understanding of the coachee’s motivations, it is time to understand each goal and work through how the coachee will go about achieving them.

Goals provide a basis for planning, guidelines for decision-making, and justification for actions taken. It is worth stressing that the realization of the coachee’s goal often consists of particular actions that require particular behaviors (Dolot, 2017).

Goals can be set using a variety of different theories and goal-setting methodologies, depending on what your coachee wants to work toward. Our article on goal setting has 20 templates you can explore and use when helping the coachee identify and break down their objectives.

2 Useful Templates for Your First Session

These two templates can help you in the initial stages of getting to know your coachee and helping them discover more about why they are pursuing their goals or objectives.

  • Is Coaching Right for Me? — A few questions for coachees to consider before pursuing coaching to achieve their goals.
  • SMART Goals Worksheet — A worksheet that takes the coachee through the SMART goal-setting process, which is useful when figuring out if the objectives they are striving for are measurable and realistic.

Tips for a Successful Coaching Conversation

Knowing how to engage the coachee in conversation during a session is one of the most important aspects of coaching.

Here are three guidelines that can help facilitate a meaningful coaching conversation.

1. Listening

True listening goes even further than active listening and aims to listen to understand. Listening to understand is recognizing that there are multiple levels of information during a conversation to consider.

While engaging in coaching, it is important to listen for emotions by not assuming what the conversation is about and, rather, allowing space for the coachee to express their ideas and the underlying emotions that drive them.

One method of doing this is expanded on in the next section and focuses on asking questions in your response to the coachee.

2. Further questioning instead of expanding or directing

This is a strategy that is used in coaching and other helping professions such as teaching and counseling. When the coachee discusses or states a goal they want to achieve, it is important not to give too much direction on how they will get there, but instead, get the coachee to explore or answer that question on their own.

A few leading questions (adapted from the Center for Creative Leadership, 2021) that can prompt the coachee to reflect instead of request direction include:

  • What else can you do to set this initiative in place?
  • Is there anything else that occurs to you?
  • Have you discussed this with anyone else? What were their initial thoughts or reactions?
  • Who else may be affected by this? How do you think you can address this?

3. Leaving room for discovery

Instead of immediately problem solving or giving the coachee the answer based on your experience, give them the space to figure it out. Strive to provide a balance of challenge (through questioning) and support during coaching sessions.

Providing support is done by giving assurance that you hear your coachee and understand where they are coming from (Center for Creative Leadership, 2021). Giving this balance will ensure that your clients are receiving the support they need and challenging the assumptions that may hold them back from achieving their goals.

Examples of a Coaching Session and Conversation

When structuring or timing a coaching session, it is important to ensure that you leave enough time for the coachee to get situated, engage in meaningful work, and then wrap up the session while still keeping what they have learned fresh in their mind. This begs the question, how long should your coaching sessions be?

The answer is that timing is variable, depending on your coachee’s goals and how they work best. While a few individuals might work best under pressure and thrive in a 10- to 20-minute session, others might need 60–90 minutes to dig deeper into their answers.

Regardless of how long your coaching session is, the bulk of the session should be focused on exploring how your coachee will achieve the objectives they have identified.

Below is a sample of how a coaching conversation may materialize, using coaching techniques that have been outlined in this article.

Sample of a session warm-up

Coach: Hello ____. How are you doing today?

Coachee: Hi. I’m doing well, thanks, and you?

Coach: I’m doing well. How has your week been going?

Coachee responds. 2–3 minutes of neutral conversation.

Coach: Great. I’d like you to start today’s session by thinking about where you have been. Think back to the conversation you just had with me about this week to get started. Give a minute for the client to reflect.

Coachee: Wait… how does thinking about where I’ve been this week relate to goal setting?

Coach: How do you think it might relate? Give the client a minute to respond. Now, I’d like you to identify something that could have been improved upon this week. Think about what could have been improved and how you would have liked to see it materialize. Let the client respond.

Coach: Great. This exercise was meant to help you use an event that was recent in your memory to help you go through the process of identifying the event and what you would have liked to see improve. Now, let’s apply this same exercise to a broader area where you would like to see improvement. Start by identifying the area where you would like to see improvement and what you would like to see change.

After this introductory activity, the coach can continue to discuss the goals or objectives with the coachee. The bulk of the session should be focused on breaking down each goal and guiding rather than directing the coachee toward a solution.

An example of how to engage the coachee in this type of dialogue is included below.

How to guide your coachee

Coachee: One of my goals is to get a promotion within this calendar year. Do you have any tips or advice about how to do that more quickly?

Coach: Okay… so let’s break that down. You want to get a promotion the next year. That sounds like a pretty significant goal.

Coachee: Yes, but it’s really hard to get a promotion in my department.

Coach: Do you think it would be more helpful to break down this objective into smaller, more manageable goals?

Coachee: Why would I do that?

Coach: Sometimes, larger goals like the one you mentioned might be intimidating. Breaking down this promotion into a step-by-step process may help you better plan what you need to do to achieve this goal.

Coachee: Okay… well, I guess I need to start by having a conversation with my boss.

Coach: Okay. How do you think that conversation should look?

The coach would then guide the coachee through this goal, using leading questions such as “how do you think… ?” or “do you think it would be more helpful to… ?” This forces the coachee to examine how they would approach a situation.

While suggesting the coachee break things down into smaller parts might be interpreted as being directive, setting specific goals leads to more effective coaching (Coaching Research Institute, 2013). Therefore, this is considered an important part of coaching, as it allows for the process to take effect.

Questions to Ask Your Clients

When asking questions in a coaching session, it is not about what question you ask, but how you ask it.

Powerful questions are open-ended and asked with true intention.

One of the most effective ways to understand the coachee’s intentions is by asking how and why framing the questions around the intent or purpose that they are chasing.

By keeping the questions open-ended, you are allowing your coachee to think more about the significance of their objectives and understand the steps they need to take to achieve them, which is fundamental in understanding the process of self-improvement.

For more specific coaching questions, this article lists powerful life-coaching questions that will help your clients achieve their goals.

Understand the Current Reality:

It’s hard to solve the problem without looking at the starting point. The solution may start to arise as the employee describes their situation.

Questions to ask:

  • How would you describe the situation?
  • What advice would you give someone in your shoes?
  • What have you tried already?

Discuss Options:

Determine all the possible options for achieving the goal. Employees should start by sharing their possible solutions followed by any ideas the manager may have.

Questions to ask:

  • What else could you do?
  • What if this or that constraint were removed? Would it change things?
  • What are the advantages and disadvantages of these options?
  • What obstacles stand in the way?
  • What do you think is the strongest solution?

Commit to a Way Forward:

You have now explored the potential solutions. Now it’s time to lock one in. Help the employee establish their way forward.

Questions to ask:

  • What steps can you take today/this week to resolve the problem?
  • What obstacles might you come across?
  • How can we eliminate them?
  • Who else on the team could help you?
  • How can I help you?

Coaching Conversation Sample

Since all coaching conversations are different, we don’t know how the employee is going to respond to the manager’s questions. But we’ve put together this sample coaching conversation to give managers a general idea of how to ask questions in response instead of telling employees what to do.

Sam (Employee): Thanks for making time to meet with me, I wanted to talk to you about my struggle with managing my time well.

Kristin (Manager): Not a problem, this is what I’m here for. How did you conclude this is a problem?

Sam: I have lots of different projects going on simultaneously. I feel like if I don’t jump around to each project often, then they get put off and I don’t get them done. I know I have to get it all done, but I’m struggling with prioritization as there just aren’t enough hours in the day.

Kristin: I understand your struggle. What would you consider success in solving this problem?

Sam: Being able to get everything assigned to me done in a timely fashion.

Kristin: What steps have you taken already to solve this issue?

Sam: I have made a list of everything I need to accomplish. When I got done writing the list it just looked daunting.

Kristin: Okay, what do you think your options are to solve this problem?

Sam: Ask for less workload, ask for help, work more hours to get it done, set boundaries, or make a schedule.

Kristin: Those are mostly all plausible solutions, Sam. Which do you think would be the best solution for you?

Sam: Asking you and my team members for help.

Kristin: That sounds like a great idea! I think we could add more hands to help you accomplish tasks. Who would you like to help you?

Sam: I think Hunter would be a great help on the project for Sales and Savannah could help with copyediting.

Kristin: I think that sounds like a good idea, what is your next step?

Sam: I can send them a message this afternoon asking if we could set up a time to chat to see if they’d be willing to help.

Kristin: That sounds like a great solution. Let’s set up a time next week to follow up and see how you’re feeling then.

Sam: Thank you.

Coaching Levels

Level 0: You in danger, girl (or guy)!  

You’re letting someone know some aspect of their performance is completely unacceptable.

Level 1:  How are you doing?

Getting basic information about work performed/ project status/ next steps and/ or providing content needed to do the job.

Level 2: Let’s get it crackin’

Providing refinement feedback/ maximizing strengths/ preparing for work not yet started.  Receiving ideas/ suggestions/ creating processes jointly.

Level 3: Boss up

Digging deeper beyond the work at hand to the set of behaviors/ attributes/ characteristics that are going to get the employee to the next level/ company to the next phase.  Moving from doing to leading

Level 4: Relationship goals

Working with the employee to help them effectively integrate work they are leading into the organization cross-functionally and at different levels.

Level 5: Alchemy

Helping effective leaders unlock treasures within themselves for powerful transformations.

Employee Levels:

Level 0: Poor or unacceptable performance in 1 or more areas.

Level 1: Doing job basics at a level good enough to keep the job

Level 2: Bringing ideas to the table, starting independent execution, may need help exercising good judgment

Level 3: Clear leadership, strong energy, independent initiative, can see what needs to be done or what is lagging and has ideas and plans to change it and when approved is getting these things done.  Has self-awareness.

Level 4: Working to expand the scope and integrate others in the right way; functioning as a leader inside the business unit, is developing even stronger and more predictive levels of self-awareness.

Level 5: Works super effectively cross-functionally, is a leader of people and processes and is on a continuous quest to improve self/ results/ the business as a whole

As I explained to the manager in my organization, it may start to feel uncomfortable when you do an annual review for some of your employees, because an annual review is by definition a level 3 (and occasionally a level 0) conversation. So you might be setting up a level 3 conversation with an employee whom you’ve been coaching at a level 1 or 2 all year. Does this make you a bad coach? No — you cannot have a coaching conversation that works too far past where the employee is.

What you can do is consider turning at least 1 one-on-one per quarter into a session where you coach “at the next level” for that employee. So if it’s a level 2 employee, you coach them at 3 and so on AND you clearly explain to them how they move to this next level in coaching more often by leveling up their behaviors and what they’re bringing to the table during the coaching conversation.

7 steps to ending a coaching conversation

However, ending a coaching conversation is not as easy as the final bars of a song. When a song is over, it’s over. Maybe the audience wants an encore, but no one wants the continuation of the song. This is different from coaching conversations. Sometimes the client would like a few extra minutes, sometimes you can give them, sometimes you have another client waiting…. I think everyone knows the problem. So, how can we end coaching sessions in ways that work for the coach and the client?

Start “ending” early enough

I think the most standard international coaching format is one hour, so I am going to use that as an example. If your timings are different, maybe you need to adjust. I usually think about ending the coaching session around 20 minutes before the actual end. Around that time, I will be looking for a good place to start winding down the conversation.

Partner with your client

When the client has finished a line of thought around that time, I ask them: “Would this be a good time to summarize what has emerged for you so far, or is there another thought that you would like to bring into the session here?” Usually, the client is fine and if not, they will let me know. Summarizing the learnings, and insights up to now sets the stage for the close of the session.

Invite description of signs of progress

After the client has summarized the learnings and insights, it is quite easy to invite a description of these learnings and insights playing out in the future. You might ask something like: “Suppose, you take these learnings and insights into the future, how will you know that you are making progress?” You can get an experience-near, rich description of the changes that may be happening. What will be different, how will people respond, and how will the client respond to those responses?

Collect learnings about “what”, “who”, and “how”?

Ask about “what will be different”, but don’t forget to invite the client to reflect on what they have learned about themself. If the learning process in the session was interesting or new, you could also explore together how the session’s process went and whether this is a process the client may want to use again in the future.

Ask about the client’s way of implementing

Don’t assume everyone needs support to hold themselves accountable or that everyone needs a plan with dates and deliverables! Simply ask your client whether they need any support or what they know about what they need to successfully implement a change. It may be very different from what you think!

Create a topic-parking

If the client brings in different and interesting topics near the end of the session, offer the client the choice: do they want to dive into the new one quickly and forgo the collection of learnings from this session, or do they want to use a separate session for the new topic? If the client is very creative when it comes to discovering new topics during a session, you can also create a “topic parking lot”, a piece of paper or file in which you note down all the topics for later consideration.

Be mindful of “openness hangover”

Many clients don’t have anyone who listens to them intently. When they experience coaching, maybe for the first time they have someone they can share their thoughts and feelings with. Clients find themselves speaking about things that they have not shared before. Near the end of the session, they reflect on what they have shared, and sometimes they experience a moment of fright: “O no, what have I done – I have shared too much.” Something like an “openness hangover”. I think this is completely normal. As coaches, we can help by also “normalizing” this, when it happens. Being appreciative of the client’s openness, their willingness to learn, and honoring the shared experience that way is a really good way to close.

So as I am closing this piece of writing:

  • what stood out to you?
  • in your next coaching session — what will you notice yourself experimenting with?
  • what will your client notice?
  • how will they respond?
  • how will you respond?
  • what might that say about you as a coach?
  • and what are you learning about how you learn when reading stuff?

A Take-Home Message

Although planning a conversation may sound like a redundant process, it is an essential skill to develop as a coach. It maximizes your client’s time and provides them with more targeted conversations that will help them achieve their goals.

Since coaching is about learning and not teaching, allotting as much time as possible to encourage a client to enhance awareness of their potential through conversations is key to achieving your client’s objectives.

We hope this article provided you with practical examples to integrate into sessions with your clients and gave you ideas to initiate meaningful conversations in your practice.

REFERENCES

  • Barlow, L. (2005). Effective structure of coaching: Using five questions. Development and Learning in Organizations19(6), 11–12.
  • Coaching Research Institute (2013). Behaviors and structures for coaching to maximize effects on coaching. Retrieved February 10, 2021, from https://www.semanticscholar.org/paper/Behaviors-and-Structures-for-Coaches-to-Maximize-on-Bansho/1242bd92d1077275ae6e3705912d5f061ec807ef
  • Center for Creative Leadership. (2021). How to have a coaching conversation. Retrieved February 7, 2021, from https://www.ccl.org/articles/leading-effectively-articles/how-to-have-a-coaching-conversation/
  • Dolot, A. (2017). Coaching process and its influence on employee’s competencies in the hospitality sector: Case study. International Journal of Contemporary Management16(2), 75–98.
  • Evercoach. (2020). Chapter 2: The three-step coaching structure. Retrieved February 6, 2021, from https://www.evercoach.com/ultimate-guide-to-transformational-coaching-sessions/coaching-session-structure
  • McMahon, G. (2021). The purpose of coaching questions. Cognitive Behavioural Coaching. Retrieved February 6, 2021, from http://www.cognitivebehaviouralcoachingworks.com/the-purpose-of-coaching-questions/
  • Nawalka, A. (2020). What makes a great coaching session? International Coaching Federation. Retrieved February 6, 2021, from https://coachingfederation.org/blog/what-makes-a-great-coaching-session.
  • Whitmore, J. (1988). Coaching for performance. Nicholas Brealey Publishing.

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