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What to Ask When Hiring a Coach

There are two kinds of coaching. The cheerleader coach is just that, they cheer you on, remind you who you are, and tell you it’s going to be okay… to keep going. They help you immediately see the positive side of a situation and give you hope that everything will work out. Your views are validated and your conviction strengthened. While the cheerleader makes us feel good in the moment, if coaching stays at this level, the same patterns repeat and the coaching can actually stunt personal growth. The champion coach, on the other hand, waits for a trigger or wound to show up, and then actively champions its exploration, facing it dead on with courage, vulnerability and openness. Being coached by a champion coach often feels emotional, brings up resistance, and challenges your beliefs and views of a situation and the world. It can encourage you to embrace personal responsibility and a new level of humility.

It’s said that a coach cannot take you anywhere they have not been themselves. Regardless of their coaching certification or training, coaches who have done the work themselves… for years… are coaches who can take you farther faster, not by pushing or driving, but by opening the space for you to peer deeply inside yourself.

When hiring a coach, ask them these questions:

  • What has been the most profound experience in your own development journey?

  • Who are you working with now and what are they exploring with you?

  • Where do you get triggered in life and struggle to transform patterns yourself?

  • What topics or areas of life make you uncomfortable or triggered when coaching?

From their answers, you’ll understand their capacity of support and whether your investment will create lasting, transformational change or simply be an experience in mood-boosting self-confidence building that will help you take the next step. A good coach knows how and when to do both.

At Collective Gain we have created a team of coaches based not just on their certificates and training, but more importantly, by their own engagement in the work. Our coaches are constant explorers and heart-centered people who play in the invisible as much as the visible and who have committed their life’s work to fostering transformation.

Click here to be matched with a coach for a discovery call and experience the Collective Gain difference.



I started Collective Gain out of a desire make work better, where being on a magic team was the norm vs. a rare chance occurrence. Through coaching, I discovered deep self-awareness, new perspectives and ways of working that I am passionate about bringing to you.

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