Valuable Questions to Ask A New Career Coach

Valuable Questions to Ask A New Career Coach.jpg

Finding the right coach for you is a very important decision. 

You’re looking for someone who understands you and with whom you can connect in a unique way.  Your coach will be your partner, and it will important for you to understand and relate to each other. You’re hiring them to do a job for you, so you’ll want to be intentional during your discovery conversations.

Of course, there are some obvious things you’ll want to know such as pricing structure, meeting frequency, how success will be measured and what happens between meetings. It’s also important to ask some unexpected questions so you can gauge how you and your coach will relate to each other.

Here are some valuable questions you can ask a prospective coach or a current one. Pay attention to their answers and also, their reaction when you ask.


1. What enneagram number are you? 

Enneagram is a great tool that defines various personality types. There are free or inexpensive tools online where you can answer a few questions to determine your personality type.  It’s a powerful way to learn about yourself. 

The real power, however, comes when you know Enneagram numbers for those with whom you interact. 

There are a number of resources available to help you learn about each number and the associated personality traits.  The Road Back to You: An Enneagram Journey to Self-Discovery is highly recommended as a great resource to immerse yourself in this body of work.

Most coaches are trained on this topic, so your question should be well-received.  And, once you know their number, you can do your own research to determine if you’d be a good match.


2. What do you wish you had known before you started your career that you know now? 

This question will give you some insight on how your prospective coach thinks. 

You’ll learn a little about their story and perhaps even how they managed a mistake along their journey. 

Their answer will likely spark some ideas in your mind of things you want to do, or avoid as you move forward in your career, so be sure to take notes.  Also, how they answer this question will give you a glimpse into how vulnerable your coach might be with you.


 3. Who else should I talk to?  

This question will accomplish two goals as you’re selecting your coach.  

First, it will allow you to see how well your coach has listened to your story.  The answer should be something specifically related to what you shared with them about your personal career journey.  Or, they may answer with some follow-up questions, which will also show their genuine interest in you.

Second, it will allow you to experience the format and approach your prospective coaches uses to give advice.  This is important to know on the front end as you will likely have many crucial conversations going forward. 

You want a relationship where advice and feedback is easy to receive. 


 4. What’s your personal mailing address? 

Let your coach know that you like to stay in touch on holidays, birthdays and other occasions.

As we discussed in Ways to Nurture Your Professional Network, writing cards and letters of encouragement needs to become a habit. Your coach is a vital part of your growing “professional connections,” so keep her on your list.

Put Me In, Coach!

Finding the right coach is can be a big commitment of time and money, so you’ll want to find an excellent match. 

Like building your network, it’s best to start a relationship with a coach before you need one.  This will give you both the opportunity to get to know each other, so that when you have a major event in your life or career, you’ve already laid the groundwork necessary to hit the ground running.



Chapter You Coaches