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How to Effectively Conduct One-on-One Coaching Sessions

Group coaching | March 17th, 2021

How to Effectively Conduct One-on-One Coaching Sessions

There are at least 18,000 personal coaches in the United States alone. And that’s a conservative estimate, which means that the number is probably much higher.

And with more people looking for ways to better themselves and propel their career forward, coaching is set to become even more important and popular in the future.

But if you want to succeed as a coach, you must have a deep understanding of how to organize and execute effective one-on-one coaching sessions. 

You need to be able to make the most of the time that’s available and provide value on multiple levels, which is why a structured approach to one-on-one coaching is essential.

But what is one-on-one coaching? And how can you make your practices more effective?

Let’s answer these questions below. 

What is One-on-One Coaching? 

One-on-One Coaching

One-on-one coaching is the process of one person helping another overcome an issue or improve performance. It revolves around sharing experiences and knowledge around specific topics or areas, showing how to best approach different situations, and laying out the steps that should be used when executing the task.

The main difference between group coaching and one-on-one coaching is the personal attention that the coach can give their client. Unlike when working in groups, individual coaching means that they can take the time to understand the unique challenges that the client is facing and show them the most effective way to move forward.

One-on-one coaching can take many shapes and cover almost any topic, as long as it helps a person move forward and improve themselves. Experienced thought leaders can act as guides that provide a roadmap through obstacles and prevent the person from having to figure everything out on their own.

It might also involve helping someone improve their current skills or learn new skills required as they progress within their career.

There are thousands of coaches all around the world that help their clients overcome various challenges and become better. And one-on-one coaching is an integral part of the process.

The Six-Question Process for Better Coaching

Whether you’re a professional coach or someone who wants to learn more about becoming one, the good news is that there are a few essential coaching questions that, when answered, will provide you with a reliable process for approaching any one-on-one coaching. 

The Six Question process was first developed by Marshall Goldsmith, a best-selling author with many excellent books on leadership and success. It’s incredibly useful for making one-on-one coaching sessions more productive and engaging for the coachee.

Although these questions are primarily aimed at executives who do quarterly one-on-one sessions with their direct reports, they can be equally powerful in almost any personal coaching session because of the way that they frame any situation and allow finding the best path for moving forward.

Let’s explore them in more depth below.

Where Are We Going? 

The first question is the one that sets the stage for everything that follows. It deals with the “big picture” stuff and provides a bird’s eye view of the situation, which shapes the entire session and gives it more context. 

In an organizational setting, a coach might talk about their own direction and vision. This is incredibly helpful for mentees who often lack an understanding of why their work matters and how the bigger picture might look for them.

At the same time, the coach should allow the person they’re coaching to provide their input on the situation and even make suggestions about what the big picture goals should be. 

This part of the process should focus on talking about the broader context of the industry, field, or aspirations that are relevant to the situation, so that the person being coached can feel more confident about the direction they are heading in.

Where Are You Going? 

After a broader view of the situation, it’s essential to look at the personal level, asking the person how they are doing in terms of the challenges, goals, and concerns related to what they’re trying to achieve.

The coach should encourage the person they are working with to open up about their situation, how they feel about what they are doing as part of their bigger goals, and what they think could be improved. 

The coach or executive should also evaluate and talk about how the personal goals and challenges of the person being mentored aligned with what is happening in the industry and with what the coach believes should be the best way to move forward right now. 

This second question helps ensure that the mentee doesn’t get sidetracked with things that aren’t essential to their success right now, as that’s crucial when the person has to make decisions about how to focus on their calling as they go through their work. 

What is Going Well? 

If a coach is not careful, coaching sessions can take a negative turn pretty quickly. That’s because, as a coach, your instinct is to work on the weakest areas or biggest issues, and that can quickly make the person you’re working with feel discouraged or even demotivated. 

That’s why it’s important to take the time to recognize the positives and allow the person you’re coaching to share their wins as they see them. This is also very useful because it will provide you with insights about how the person you’re working with sees their own progress and what they feel are the most important success measures.

Sometimes, you may even discover that the person has achieved outstanding results in their work that you might have missed. As a coach, you must help the person you’re coaching realize that they are actually moving forward and achieving great results if you want them to stay motivated and not get discouraged. 

This question can also set up further conversations about priorities or things to work on and monitor. If you know something is going well, the person you’re coaching might need less guidance in these areas in the future, which means you might be able to spend more time on other areas and accelerate the progression your mentee is making.

What Are the Key Suggestions for Improvement? 

At this point, it’s time to look at the performance of the person you’re coaching and provide helpful suggestions for how they could improve. You should have a lot more information than at the beginning of the session, which should give you enough context to give useful insights the person can use.

However, the way that you convey this information matters a lot, at least if you want it to actually stick and make an impact. If you’re making suggestions, try to make them constructive and helpful instead of judgemental. 

Real learning occurs when people aren’t afraid to share their shortcomings, and that can only happen if the person providing coaching instills confidence and turns mistakes into learning opportunities. 

Finally, Marshall Goldsmith recommends asking the person you’re working with what suggestions would they give themselves if they were their own coach. This might give you new perspectives on what they should focus on and might even force you to adjust the advice you provided earlier, which is always a good thing for the coaching session’s quality.

How Can I Help? 

Listening is the only way to ensure that your coaching is effective. A big part of one-on-one coaching is providing personalized assistance and suggestions, and that’s only possible if you listen to what the person you’re coaching has to say and adjust your advice accordingly.

After you make suggestions for what should be improved, it’s important to back up those suggestions with support and actual implementation tips so that they have at least a general roadmap of how to move forward.

The best way to do that is to ask how you can help implement the suggestions and listen to what the person has to say.

Sometimes, that might mean more coaching sessions, while other times, it might be resources or tools that help tackle the tasks more effectively. Whatever it might be, listen to the needs of each individual if you want to truly help them move forward.

What Suggestions Do You Have for Me?

In coaching, feedback should be a two-way street. And so, as a coach, you should take the sessions as a learning experience that can help you improve as a leader.

Don’t be afraid to ask your clients for a feedback. You might be surprised to discover that some areas of your coaching need work, which can help you become more effective in the future. 

Everyone benefits from good coaching practices, so striving to improve your coaching to help others is definitely worth your time and effort, especially when all it takes to improve is asking for feedback yourself. 

How to Structure Effective One-on-One Coaching Sessions

Structure Effective One-on-One Coaching Sessions

When planning one-on-one coaching, you need to think not just about the sessions themselves but about how they fit into the bigger picture of the goals you are trying to achieve.

And there are a few key aspects of structuring effective coaching sessions that deliver results and put the person being coached in a position to succeed.

First, you should consider how frequently the sessions should take place.

Many coaches think weekly sessions are necessary. However, others work on a bi-weekly or even monthly schedule in situations where weekly sessions might not allow the person being coached enough time to progress.

If availability and time are limited, you could opt for shorter but more frequent sessions that allow you to stay in the loop about the progress the person you’re coaching is making.

To make the sessions more efficient, you should also think ahead about the primary goals of each time you meet. By establishing the goals in advance and structuring the session accordingly, you’ll be able to get more out of the available time and provide as much value as possible. 

We already talked about the most important questions you should ask during one-on-one coaching sessions. Still, as your relationship with the person you’re coaching evolves, you can tweak your approach and implement new questions or processes to improve the results you can achieve. 

Bottom line

One-on-one coaching benefits are hard to ignore, and it can have a transformative effect on the person being coached, helping them overcome obstacles and discover new ways to solve problems from someone who has more experience in the field.

But in order to provide more value, it’s crucial to structure your sessions accordingly, which is why the six-question approach is so beneficial. 

If you take the time to ask the right questions, develop a consistent structure, and listen to feedback, you can become an excellent coach even if you have little coaching experience. 

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I’m CEO of UpCoach and a serial entrepreneur. I’m passionate about helping entrepreneurs and executives to find success and harmony in business and in life.