What to Ask at Your First Coaching Session

  • Ezra
  • April 27th, 2021

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.

What To Ask At Your First Coaching Session

It can be 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 of many ways people can further refine themselves, further their careers, and find different 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 what you want to achieve. Any kind of leadership coaching is for the purposes 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.

Ensure that the end goal is identifiable and quantifiable, so as to 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.

Viewing the coaching as some sort of test with a binary succeed/failure outcome can be unhelpful and add unnecessary stress. The purpose is neither to sink nor to swim, but instead to provide new outlooks and experiences that can be used constructively in the future. Even if a skill is not immediately grasped at the end of the course, you can still be given the germination of that skill for you to grow and nurture in your own time afterwards.

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 utilise their expertise however you wish.

Ask questions. Like anything else, questions are encouraged. To reuse the old adage: the only bad question is one left unasked. The more you communicate with your coach, the better idea they’ll be given to help you and the more rewarding you’ll find the experience.

Often by asking questions new insights into old blocks, bad habits or unseen shortcomings can be uncovered. Likewise, the chance to hear a fresh perspective may inspire you to approach routine tasks in exciting and revolutionary ways.

Get the answers by knowing the questions

So, with all that being said, just what sort of questions might one ask during a coaching session? In particular, their first coaching session? Some can be asked of the coach. Others are more introspective questions you should ask yourself.

“Do my goals seem realistic?”

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

Sometimes, however, our knowledge of ourselves is 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.

One of the most valuable questions you can ever ask a coach is whether they think 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 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, settling to our routines like barnacles to the hull of a boat.

An important question to ask yourself is how to break out of those comfortable downwards cycles. 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 from the 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 ensure that the lessons and work don’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 is needed 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 opens up their coaching app with no idea what they really want out of it.

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