How To Coach Clients Who Are More Successful Than You


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Do you ever get afraid of losing a potential client? Do you ever get afraid of being embarrassed in front of a client? Do you ever feel inferior? How to coach successful clients?

Do you ever think “I couldn’t coach ‘that’ person”

According to Patrick Lencioni in his wonderful book, Getting Naked, there are three fears that sabotage the creation of great clients.

Immersed in these fears, coaches censor their feedback. And to avoid difficult issues, they hold back their ideas, hide their mistakes and edit themselves to save face. They’re trying to look good in front of their client at all costs.

They do this because of a fundamental misunderstanding that clients don’t want to be challenged or face their fears. They do this because they’ve fallen into the myth of the ‘expert’—so they want to appear to be one. And they do this because they are afraid to step into their power as a leader.



What most people don’t realize about success is that the biggest challenge success brings is success itself.

You see, everything that got you to the level of success you’re at today is precisely what will hold you back from your ‘next’ level of success.

Or as Marshall Goldsmith put it quite succinctly, what got you here won’t get you there.

Anyone who has worked in the corporate or start-up world is familiar with this concept. A great reporter becomes an editor, a great accountant becomes a manager, a Vice President becomes the CEO, a great teacher becomes a principal and you have a world of struggling leaders and managers.

A start-up becomes successful and its biggest liability—once it’s biggest asset—is often its founder. What it takes to lead a start-up is very different to running a thriving business or a business with investors and shareholders.

Ever worked for a boss who was working beyond his or her ability level?

There’s a name for this concept. It’s known as The Peter Principle—you rise to your level of incompetence.

The Peter Principle is cemented in, in most fields, where the easiest way—often the only way—to earn financial reward is by rising up the ‘career ladder’. It’s rare that mastery of the skills that you love in the first place will lead to the same kind of financial success.

So we live in a world where highly intelligent, creative and thoughtful people are far too often working beyond the level of their current abilities. A world where leaders are rarely trained to turn their intelligence, creativity and thought to mastering their ‘next’ level of success. A world where editors, managers, principals, CEOs and leaders are struggling to understand why doing MORE of what made them successful in the first place just isn’t working.

As Tracy Goss explains in The Last Word On Power: Re-Invention for Leaders and Anyone Who Must Make the Impossible Happen, it is the very power that brought you to your current position of success as a leader that is holding you back from achieving ‘impossible’ goals in your life and in your work.

When you live life based on the power that has been the source of your success in the past, you hold yourself back from a more creative future.

So, how to coach clients who are more successful than you?

You help them see the things they simply cannot see in their own world. You support them in a mission to build a new kind of power—the power to consistently make the ‘impossible’ happen. You help them access the source of their new power by completely re-inventing themselves, again and again.

It’s the scariest thing in the world—especially for highly successful people. You help them put at risk the success they’ve BECOME to create the success they DESIRE, to create what looks impossible—to them, but not to you.



“Experts are good at working on problems that require known skills. But innovation requires that you make new mistakes, which is something that experts don’t do. Also, experts supposedly have all the answers, but innovation requires that we ask new questions; experts don’t do this.” – Joe Calloway

If intelligence was all it took to live an extraordinary life, create an extraordinary business or have an extraordinary relationship, high performers would have no need for a coach. 

Yet, the title of this book says it all: The Smartest Guys in the Room: The Amazing Rise and Scandalous Fall of Enron.

Before its bankruptcy in 2001, Enron employed around 20,000 staff with claimed revenues of nearly $111 billion. It was named “America’s Most Innovative Company” for six consecutive years by Fortune magazine. But by the end of 2001, it was engulfed by the Enron scandal before it closed its doors forever.

Lehman Brothers, Washington Mutual, Delta Air Lines were all billion dollar companies that went bankrupt. Arthur Andersen, formerly one of the “Big Five” accounting firms, ended business after being found guilty of criminal charges. The UK-based retail site spent $185 million before it shut down and was sold for less than $2 million, less than two years later. It is now hailed as one of the greatest dot-com busts in history.

And Harvard Business School is now citing research that three-quarters of venture-backed firms in the U.S. don’t return investors’ capital. That’s 3 out of 4 start-ups that received venture funding of at least $1 million, went on to fail.

In his research into why smart people do stupid things, Rajesh Setty notes that smart people test boundaries by breaching them a little beyond normal limits. They then give repeated deviations a positive twist and start believing their own story.

As he says, “The problem with repeated deviations is that they become “normal” routine in your mind. The world notices the deviations but won’t speak much and in your early stages of fast-growth career, these things won’t matter much.

In How Will You Measure Your Life? by Clayton M. Christensen, he notes that we often employ the marginal cost doctrine in our personal lives when choosing between right and wrong:

“A voice in our head says, “Look, I know that as a general rule, most people shouldn’t do this. But in this particular extenuating circumstance, just this once, it’s OK.”

The marginal cost of doing something wrong “just this once” always seems alluringly low. It suckers you in, and you don’t ever look at where that path ultimately is headed and at the full costs that the choice entails. Justification for infidelity and dishonesty in all their manifestations lies in the marginal cost economics of “just this once.”

The challenge that most businesses and leaders face is that they are biased to leverage what worked well in the past, instead of building the capabilities they will need in the future.

Since the future is almost always different to what came before it, this is almost always the wrong thing to do.

So, how to coach clients who are more intelligent than you? 

Explain that their very intelligence is their biggest challenge and demonstrate that your naivety is your biggest asset. You’re a coach, not a consultant. You don’t need to know more about their job or their industry than they do. And if they are a real high-performer, how could you?

Instead, tell them that you are there to ask potentially dumb questions and make potentially dumb suggestions. You are there to support them—not to look good.

Demonstrate your vulnerability and take risks even before you begin coaching together.

Admit your weaknesses and celebrate your mistakes. And serve them as powerfully as if they were your highest paying client—even before they’ve paid you a single penny.

Serve them so powerfully, that even if they never become a client, they’ll never forget your conversations for the rest of their life. 



Several years ago—my coach at the time—Michael Neill, invited me to join him at his seminar in Sweden called The Happy Millionaire.

I met a woman who was a multi-millionaire. She told me that if she stopped working today and didn’t change her lifestyle one iota, she could go for another 37 before she’d have to earn more any money.

Then why are you here? I asked rather incredulously (and naively).

She told me that she’s constantly worried about the money running out, someone stealing it from her, or how her investments are doing.

Later that day, I asked a financial expert about her situation. And he told me that based on interest earned, alone, she’d never need to work another day in her life.

A few years later—I’ve now coached several millionaires and ultra-high net worth clients—and it’s clear to me that you can never have enough of what you don’t really need.  

A client of mine with a twenty million dollar net worth once called me, full of frustration with her husband. He’d been really upset with her when she paid for dinner for a group of their friends at an upscale restaurant in New York. And she couldn’t understand it because the amount of money she’d spent had been tiny compared to their wealth.

She loves to be generous—generosity is one of her highest values. But her husband has this deep underlying fear that one day all the money will run out. Security is one of his highest values.

I helped her see that their issue was never going to be resolved on the surface question of whether or not to pay for dinner for friends. We had to dive much deeper.

Another client, who managed billions of dollars of assets and was amongst the top 0.1% of income earners was secretly driven by a deep personal shame of being an immigrant. An Ivy League school education, millions of dollars in his bank account and homes in several countries would never be enough to counter his deepest, underlying fear that he wouldn’t ever truly be accepted.

You can never have enough of what you don’t really need. And money can never solve issues that are not related to money.

So, how to coach clients who are wealthier than you? 

Dig deeper than anyone has ever gone with them. Explore their secret doubts and their deepest fears. Then remind them of their own mortality—because there are only two real truths in this world:

One, we’re all going to die. And two, we don’t know when it’s going to happen.

Remind them that they can’t take their money with them when they’re gone and dive deep into the impact they want to make and the legacy they want to leave.

Don’t be afraid of speaking the truth. Wealthy people have few people in their lives who are willing to tell them what they most need to hear

Care so much that you don’t care. Tell your client that you care so much for them you are with that you are willing to hide nothing and hold nothing back. Tell them you’re not looking for another friend or to be liked or to get hired. Tell them you are here to SERVE them and not to PLEASE them.

These things aren’t easy to say. And they aren’t easy to hear.

But if you show up powerfully in this way, your ‘right’ clients will, too.

One day, I was in a session with my own coach at the time, Steve Hardison. I’d been sharing my own doubts and dreams, my own deepest fears and deepest desires when Steve looked at me with his piercing eyes.

He was silent for a moment.

Then he said these words: I’ve got nothing on you, Rich. I’ve got NOTHING on you.

And it was one of those INSIGHT moments for me. I got it in an instant.

This powerful man—this powerful coach—was telling me that he had ‘nothing’ on me.

The deepest work we do as coaches is to let go of our own stories, to make visible our own blind spots, to speak loud our secrets, fears and desires. 


Great coaches ARE great leaders.

Great coaches COACH great leaders.

This post has been extracted from a private coaches tribe led by Rich Litvin at Evercoach.

About The Author

Rich Litvin

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Rich runs a leadership consultancy for world leaders, based in Los Angeles and London. The methodology is deep coaching. Bespoke. Not time-based. He is the author of a best-selling book on coaching and he runs a program for 40 of the world’s most successful consultants and coaches.

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