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What to Ask at Your First Coaching Session

EZRA
Apr 27 2021 | Insights

Get the most out of your first coaching session with this guide to the key questions to ask, and learn how to prepare to get the maximum benefits from your coach from day one of your interactions.


It’s ironic that the hardest lesson people have to learn is that it is never too late to learn anything. This is especially true in our professional lives as well – even people who would regard themselves as mature in their careers can always learn something new and useful.

Coaching is one way you can further hone your skill set, drive your career, and find new ways to tackle familiar tasks. Others may take it as an opportunity to go back to basics, helping to relearn a skill that they may have picked up bad habits in doing or to keep afresh of new developments and techniques.

Preparing for your first coaching session

The first coaching session can be a little daunting, especially for those who’ve never received it before. But remember that the process is for your benefit, so always make sure you get the most out of the experience by asking the right questions. The right frame of mind is always a bonus as well.

Know your goal

Any kind of leadership coaching is for the purpose of self-improvement, so the first place to start is to ask yourself where you’d like to improve. Keep in mind that this doesn’t have to be a skill you struggle with – it could equally be a new skill you wish to acquire, whether a hard skill like a language or a soft skill like time management.

Make sure your end goal is identifiable and quantifiable, so you can keep a track of success more easily. You can also have several sub-goals running alongside the main length of the coaching program.

Once again, the coaching exists for you. The time spent with a coach is your time and you are very much in charge of how it is used.

Avoid binary thinking

Viewing coaching as some sort of test with a binary pass/fail outcome is not only stressful, but unhelpful in hitting your target. Coaching is not a sink or swim scenario. It’s a chance to gain new outlooks and experiences that can be used constructively in the future. Say you don’t perfectly grasp your desired skill at the end of your coaching course. Even so, you’ve already built a strong base to be able to train and condition your skill down the road. 

Remember that the coach and the time spent with them is an asset for your benefit. You don’t need to impress them – you can use their expertise however you wish.

Ask questions

The only bad question is one left unasked. The more you ask, the more you’ll know. Communicating with your coach will give them a better idea of how to help you and you’ll have a more rewarding experience.

Asking questions can give you those lightbulb moments you’re looking for. It’s a shot at uncovering new insights, old blocks, bad habits or unseen shortcomings. A fresh perspective may inspire you to approach routine tasks in exciting and revolutionary ways.

Get the answers by knowing the questions

So, with this in mind, what sort of questions should you ask in a coaching session, specifically your first? What should you ask your coach and where do you need to look deeper and question yourself? 

“Do my goals seem realistic?”

Know yourself and the tasks ahead, and you will know success.

Our knowledge of ourselves can be clouded by idealised images and expectations. We imagine we can take on far more than we really can. Other times, we inflate the seriousness of the issue by setting ourselves impossible standards we’re doomed to fall short of.

Ask your  coach whether your goals seem reasonable and achievable. Set goals that motivate you, not discourage you.

This can follow on to collaboration with them on how to make those goals realistic. Maybe you need to give yourself more time. Perhaps the best course is to approach the challenge from a different direction. What’s the real goal here?

“How should I be challenged?”

In order to get the most out of coaching, you need to be challenged.

After long periods in the same job, there’s a tendency to get comfortable. In that comfort, bad habits start to form. Corners are cut. Little mistakes creep in that become learnt behaviour. Our work routines become muscle memory, which is not always a good thing. 

An important question to ask yourself is how to break out of those comfortable downswings. How do you challenge yourself enough in order to force your behaviour down a more positive and constructive course? This is a good topic to discuss with your coach, who may have a series of techniques intended to bust through those stubborn behavioural blocks we always develop.

“Am I being honest?”

We really do have the capacity to see ourselves through a less than honest lens! So be upfront with your coach as much as possible, giving them all the gory details of your work habits and practices. The more you communicate with them the more you’ll get out of your course.

Likewise, keep an open mind and be ready to receive new experiences and insights. When you are open to the greatest change, you can grasp the greatest opportunities.

“How much time should I set aside for this?”

Your course should fit around you and your requirements, not the other way around. It’s also more practical to make sure coaching doesn’t interfere with your working life; when it becomes just another chore added to a long to-do list, the temptation to put it off increases.

Chat with your coach to work out how much time you need to get the most benefit from the exercise. Then work together to ensure it fits in neatly with your daily and weekly schedule.

Ultimately, you’ll get as much out of any developmental engagement as you’re willing to put into it. So put the effort of time and thought in to really make the most of every coaching session, and you’ll be well on the way to achieving much more than someone who just rocks up to their meeting with no idea what they really want out of it.

Get a taste of how easy coaching can be with Ezra’s world-class employee coaching, built to fit into today’s working life. We’ve redesigned leadership coaching for the modern age to help transform people through affordable, scalable and high-impact solutions, with equitable access through our world-class coaching app. Find out today how digital coaching could make a big difference to your organization.

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