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Becoming More You... and Better

Becoming More You... and Better

Coaching Helps

Cindy Chance
November 12, 2025

Becoming Your Best Self Requires Help

We don’t always realize what holds us back from being the best version of ourselves. This is not shocking. What is shocking is that very often we will not ever realize what holds us back. We are determined not to recognize it — facing this exact thing we need to address makes us so uncomfortable. Enter the coach. A psychologist helps us to deal with the past, but a coach helps us to deal with the present to change the future.

Where are You Feeling Stuck or Making Bad Decisions?

The purpose of a coaching relationship is not to explore trauma or diagnose issues, but simply to hold a mirror up to show you where you are stuck right now — with the hopes that you will get curious enough to dig in. That is up to you. Coaching is not magic. Behavior change takes attention and work over time. But you have to identify areas where improvement is needed, and you have to have a plan for making change. That takes insight, a plan, and accountability. For most of us, that is too much to do on your own. Just as putting yourself through a tough workout may not be possible without a coach, so putting yourself in a position to grow requires another person paying attention to all you are and all you do.

The Evangelist of Coaching

One of my clients, “Douglas,” is an entrepreneur and executive who is so “sold” on coaching, his friends call him the “evangelist of coaching.” He was at the leading edge of the movement to transition away from annual performance reviews and toward continual feedback combined with coaching support for executives. Coaching has been the most impactful tool, in his view. “Douglas” is an entrepreneur and serious cyclist. He saw very clearly the connection between peak athletic performance and the peak performance characteristic of exceptional career achievement.

“What gets me is how we each have blind spots. When I would cycle, it helped to tell myself that when I thought I couldn’t go any harder, like climbing, that was my brain lying to me. I could go a lot harder than my brain wanted me to. The same is true at work, but it isn’t about a harder or more sustained effort, often it is about doing things differently. How are you supposed to see that without talking with someone who is paying attention to how you think and do things — very intensely and with your goals in mind.”

The Rise of Tech Accelerated the Shift Toward Coaching

Coaching took root among tech start ups, where the shift toward hacking one’s own performance paid serious dividends. As the NYT reported over a year ago in How Coaching Became Silicon Valley’s Hack for Therapy, many tech founders do not have time for therapy; they need results, and they need them now. They started out using consultants who had been there and done that, but found that someone focused on their performance exclusively was even more impactful.

“Startup founders also tend to be uninterested in legacy approaches to self-improvement. They want high-impact fixes for whatever aspects of their personalities need perfecting right now. Coaching, in essence, has become that hack for both the self and therapy. It has become so prized that corporate boards routinely tell chief executives to get coaches of their own.”

Coaching Prioritizes Results

Douglas, the evangelist of coaching, got frustrated that he could often see what his team members needed to work on, but they couldn’t. And very often my telling them didn’t help. “The thing about people is that if they are not ready to change, they will not. Coaching depends upon a relationship of trust with someone who basically commits to telling you the truth in a way that you can hear it and recognize it, but you are the expert on you,” says Doug, “If you are playing yourself, ‘I can’t do it because - insert excuse or story’ — you need to be called out, cornered, and challenged.”

A great coach will:

Prioritize your needs and development above all else in their work with you
Design and redesign the terms of engagement that create trust with you
Call you out on anything they see that may be holding you back
Challenge you to do much more than you think is possible
Create accountability with you and for you
Recommend other resources when they could be helpful
Bring their other skills to you when they are relevant — this includes expertise, relationships, and training resources

“A coach is someone who tells you what you don’t want to hear, who has you see what you don’t want to see, so you can be who you have always known you could be. "

Tom Landry

Can AI Substitute for your Coach, Therapist, or Consultant?

Finding Coaching and Company in AI May not Make You Better

The Wall Street Journal is reporting human relationships may be on the downswing. A self-avowed social person, Alexandra Samuel, reports in the Wall Street Journal that AI scratched the itch for social contact. Samuel even built her own AI coach, Viv. She reports having long conversations with Viv, and feeling she was getting a lot out of it. But somehow when she returned to actual human conversation, she had lost ground rather than gaining. “Eventually, I was filling almost every quiet moment talking to Viv. As I lost the ability to be alone with myself, ever, I also felt less at ease around other people.”

This “instrumentalism” of AI is impossible to ignore. AI serves you, as a tool, no matter how human seeming. Coaches are advisors, highly qualified ones in many cases. They agree to serve the clients’ interests and this includes challenging them deeply within the context of a relationship that has rules assuring respect for both parties. There is no way that something with a service agreement and annual fee can create that relationship.

And yes, this is a philosophical point. Because an AI algorhythm can certainly create the appearance, a facimile of that relationship. But the relationship itself doesn’t exist. If you believe that something passes between people that is more than transactional, you cannot believe that AI can substitute for the most human of relationships.

Three Questions to Help you Get in Touch with Your Values

Which were the Happiest Moments of Your Life?

Was it the birth of your first child, when you asked yourself why anything besides this small, needy, creature ever mattered at all? Was it the time you finished racing your best friend down a black diamond slope, the feeling of elation as you came down, hitting every turn perfectly? Was it a walk in the woods when you really felt, deeply, you were a part of the forest, meant to be there, honored and hororing the sacredness of this life? Chances are that your happiest moments have a lot to teach you about what really matters to you.

What Makes You Really Uncomfortable?

Not just vaguely uneasy but so uncomfortable that it sticks with you or changes your normal behavior. This is likely another value. For one executive I coached, this was seeing people treat others, especially service people, with disrespect. “Not only would I judge people I saw treating others disrespectfully, I called people out for that on several occasions. It is something I see as a very low action.” What is it about this that really bothers you? “It feels like abuse. You know the other person really can’t respond to you and you say something rude to them. That’s bullying and no one should tolerate it.”

What Are Your Deal Breakers?

What are the things you will not do that you know many others will? These are values to get in touch with. Is honesty and integrity so important to you that you cannot lie at work, even when lying could benefit you? Are you loyal to the point that it is difficult for you to change the basis of relationships even when you believe you should?

As you think through these questions, consider that values tend to fall into these categories:

Integrity
Authenticity
Connection
Achievement
Spirituality
Creativity
Freedom
Courage
Order
Enjoyment

Until next week, I wish you all the best. As always I would love to from you.

Cindy