How To Choose An Executive Coach

By Jaci Reed

You know that old adage “It’s lonely at the top”?

Unfortunately, in many cases, once you reach an executive level position this can end up being too true. You can find yourself in a position where you no longer have someone to guide you, or to give you feedback and appraisals on how you’re doing at your job. Many times you may not even have peers you can use as a sounding board for your ideas.

At Transcend, we know that being an executive can sometimes be an isolating and challenging experience. But that doesn’t have to be true.

It’s a fallacy to think that once you’ve arrived in an executive level position you no longer need guidance or feedback. Without an external resource that will help you to look at your leadership skills and your vision through different lenses, you can get stuck in a rut. This can potentially lead to repeating ineffective leadership practices, or engaging in mindsets that can be damaging for you and your organization.

That’s where executive coaching comes in.

What Will An Executive Coach Do For You?

In short, an executive coach is an individual who is there to fill the support gaps for executives and business leaders who feel alone on their island. They have the gift of helping you discover new things about yourself and your team, and allow you to unlock your own potential and greatness.

They do this by uncovering the limiting behaviors that get in the way of allowing you to be the best leader you can be. They then attack and challenge those behaviors and provide alternative perspectives that you may not have previously considered. But perhaps most importantly, an executive leadership coach will allow you to uncover strengths you didn’t know you had, as well as foster those you did through a process of guided self-discovery.

Some of the key traits an executive coach will focus on during your time together:

  • Strengthening your executive competencies
  • Providing insight into how you lead your team and assessing whether you actively inspire them the way you desire to
  • Developing and/or clarifying your own personal and professional mission, vision, and values
  • Discovering what executive-level tasks you should focus on versus where your time is spent currently 
  • Imparting you with the ability to strengthen your organizational dynamics by fostering executive leadership skills in others
  • Giving you the assessment tools to not only evaluate yourself but your team as well

Selecting The Right Coach

Now that you have an understanding of what executive coaching is, of course the next question is how do you go about choosing a coach that is right for you and your organization?

If you’re not sure what to look for in a good coach, that’s okay. Most executives seeking out a coach for the first time don’t know what they should be looking for or what questions they should be asking. Which is why we’re here to provide you with some key characteristics to look for when choosing an executive coach.

Uncovering the answers to these questions will take more than just a glance at their resume or LinkedIn profile. You should always take the time to have an in-depth conversation with a coach before committing to them. Ask your prospective coach if you can have a practice session where they help with something you are stuck on. Any good coach will have no problem providing an exploratory session on the house.


An executive coach should already know what it’s like to be an executive leader themselves or have helped countless executives transform their performance and their teams’ performance. They should not only have the expertise to understand the ins and outs of your position, but more importantly, they should be able to understand what it’s like to be in your shoes. 


Is the coach not only able to hear what you’re saying but know what you’re not saying as well? Some of the executive coaching discovery process is done through the things that are not said, rather than the things that are. Most people have a hard time recognizing their own limiting behaviors, and those things can only be drawn out by a person who has the ability to truly listen, understand, and at times challenge in an empathetic and non-judgmental way.


Is the coach someone who will appropriately challenge you but do so while maintaining your dignity? A large part of successful coaching is having the courage to ask difficult questions that may be uncomfortable at times. However, they should also be able to challenge you in a way that is productive and insightful, rather than demeaning.


A good coach will ask questions in a way that allows you the space to look at things through a different lens, often deepening your understanding and strengthening your resolve going forward. The goal is to understand your process and mindset, and uncover both your strengths and potential blind spots or opportunities for growth.


Finally, having a feeling of close connection with your coach is important. Assessing if your personality clicks with that of the coach is often more important than the coach’s style. Your coach will learn things about you that most people won’t know so having a strong bond of trust, confidentiality, and connection is critical. Only if you feel like you can truly open up to your coach will the process work.

In turn, a quality prospective coach will have some pointed questions to ask you before beginning your coaching engagement.

First off they’ll ask you whether you are truly serious about and ready for the executive coaching experience.

Executive coaching does take time and effort, and in order to make it work you need to be all in, for the long term. You’ll need to be prepared to invest the time in 4 coaching sessions a month, plus some discovery work each week. Our coaches are super-competitive. They want to see you become the best executive you can be, so they’ll want to ensure that you are “all-in” on the process before moving forward.

The second thing they’ll want to know is if you are in a good space where you’re ready to be challenged and pushed out of your comfort zone. 

A successful coach will be asking you some very tough questions during your time together. They will be challenging your notions of what it means to be a good leader, providing you with an honest look at your potential blind spots. However, they will also be there to provide support and guidance as well. These hard questions can help you foster your existing leadership competencies and uncover strengths in yourself that you never knew you had.

A good coach asks these questions because they want you to be the best that you can be. They are competitive and want to win, and winning means that you are going to be a better leader in the long run.

What Do You Stand For?

Bottom line, in order to be a great leader an executive must truly know what they stand for. They must not only be clear on their personal mission and vision, but the mission and vision of the organization as well. They must have the competencies and tools to successfully lead and inspire that vision in others.

Choosing the right executive coach to support you in this process of discovery and growth could very well be one of the best investments you ever make. By taking the time to define what you stand for, and allowing yourself to realize your strengths and rethink your limiting beliefs, you can win back freedom and time, and help your organization achieve its goals in the end.

Remember, it doesn’t have to be lonely at the top. Transcend executive coaches are here to provide you with the support and guidance you need, and provide you with the tools to uncover your true greatness.

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Jaci Reed's profile picture.

Jaci Reed

Senior Executive Coach and Strategist

Jaci holds master’s degrees in behavioral psychology and organizational development. She is a senior HR-certified professional (SHRM-SCP), certified Prosci change management practitioner, certified ATD consultant, and certified employee engagement specialist.

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