“Is It Working?” How To Evaluate Your Progress and Get the Most Out of Coaching

“But I guess what I really am worried about is… Is it working?”

David had come into the session agitated. A high-achieving ex-marine, business owner, and father of three, David (name changed to protect his privacy) lived a very busy life and had very big goals for himself. We had been working together for six months, during which time I had seen him exhausted, agitated, and panicked that he wouldn’t be able to fulfill his promises to his clients and to his wife.

But there was something different that day because it was very clear - by most objective measures - that coaching was working for him. David was killing it. He’d tripled his business in less than a year, his relationship with his wife was better than it had ever been, and he was spending more time with his kids than he had thought possible. He was, by most measures, creating extraordinary results. 

So what was creating the cognitive dissonance? Why was David’s experience, his fear that coaching wasn’t working, so at odds with the measurable reality of his life?

I reflected this dissonance to him, and he got quiet. Very quiet. We entered a space that I treasure as a coach – a space of deep befuddlement. For the first time in his life, David started to register the deep disconnect between his perception and reality. That day, David was able to see the automatic pressure he put on himself to perform. The child of an alcoholic and dysfunctional family, achievement had become his way to quiet his own fear as a child and placate a deeply critical father. He was driven to achieve in order to dampen the near constant fear that he wasn’t good enough. He had uncovered some of that history in therapy; that day, in coaching, he was finally able to see how he was continuously living inside of that history in his present. He was living his life inside of an unanswerable, black hole of a question: “Is it working?” was actually code for “Am I good enough yet?” 

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The possibility of coaching is that it can help us create the future that we desire; however, with this possibility comes questions. Do we have the vulnerability and the courage to imagine and create a vision of our future? Can we honestly look at our present ways of being and acting, and acknowledge what is out of alignment with that future? And finally, do we have the grit and humility to do things differently in service of an imagined future that doesn’t yet exist?

It’s no surprise that we have a tendency to freak out in the face of all this possibility. Our humanity will come up, our fear will get activated, we will lose sight of the bigger picture, and we will want to fight, run, or give up. So, what are we to do when this normal human reaction arises, either in ourselves or in others? I want to use my story about David to highlight a foundational tool that I use with clients: feedback systems.

Feedback Systems

There are many different types of feedback systems. The only requirement for a feedback system is that it is some process by which to obtain corrective or affirmative information about how a project is going.

Milestones

Measurable milestones give us a footing in reality. If, for example, you’re asking if coaching is working, then you must simply look at the facts! It felt to David that it wasn’t working, and in that moment his feelings were not an accurate measurement of reality, but rather a reflection of the disempowering story that ran his life. 

Milestones are also opportunities to celebrate our progress and be acknowledged. Like a mile marker on a long run, they can give us the momentum we need to keep going.

A Vision

A vision adds texture and nuance to our declared results. It’s an opportunity to measure not just the results, but also the experience you want to create. David was creating results, but when we went back to his vision, it became very clear that what was missing was his desired experience of peace and joy. Again, this was a reality check; it gave us the opportunity to course correct, to look at what needed to shift for him to create financial results and joy in his life.  

Your Inner Compass

You were born with a built-in feedback system, perhaps better known as your heart, your gut, and your intuition. Unlike much of the world which is conditioned to offer advice, direct, or manipulate, coaches are trained to listen deeply for your inner wisdom. They help you bypass the distractions of the ego and facilitate a more direct conversation with your inner guidance. This process becomes one of the most effective feedback systems, as coaching sessions allow you to connect deeply with yourself.

From this transformative work, you develop a deeper attunement to yourself, to others, and to the world around you. Much like a high-level athlete, you begin to assess and respond at a subconscious level. Your internal resources communicate with you by signaling when something feels "off," enabling you to navigate with greater insight, responsiveness, and integrity. 

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David had a strong internal feedback system in the form of a young, panicked, internal voice that was starting to scream for his attention. As we shifted the focus of our coaching, we learned to slow down together and listen to that voice with respect. Like a child who felt abandoned, it was a part of him that was calling out for his attention and love. 

We adopted a slower pace in our sessions and listened to his unmet needs. As David learned to respond to and meet these needs, he began to create the experience he was craving. He continued to grow his business and keep his promises to his family, while also growing his skills in self-love and compassion. 

You can probably imagine the difference that this made in his leadership, his relationship with his wife, and most movingly, in his relationship with his young son. David had created a future that once seemed impossible, one in which he was able to pursue excellence while experiencing peace, fun, grace, and forgiveness. His son gets to grow up with a father who is present, loving, and generous. 

So, as you work with your coach, I encourage you to ask, “Is it working? Am I creating the experience I desire? Am I being the leader, spouse, friend, and parent I envision for myself?” Begin to build and cultivate your external and internal feedback systems so that you can continue to refine your experience of your life and of your work. You might one day discover that you have created the life you were once brave enough to imagine.