What's the Best Coaching Question in the World?

Michael is the Senior Partner at Box of Crayons, a company that helps organizations do less Good Work and more Great Work. He’s also the author of several books, including The Coaching Habit and Do More Great Work. Michael has written for or been featured in numerous publications including Business Insider, Fast Company, Forbes, The Globe & Mail and The Huffington Post.

Favorite Success Quote

“If you’re going to try, go all the way. Otherwise, don’t even start.” ~Charles Bukowski

Key Points

1. Forget All About Doing Good Work and Focus on Great Work 

There are only three kinds of work.

Bad work, good work, and great work.

Ironically, the type of work that is most deadly to your dreams and ambitions is not bad work.

Because bad work is obvious.

It’s the kind of work that creates a visceral reaction each time you are forced to engage in it.

You know what I am talking about. That work you try and outsource as soon as you receive it. That work that leaves you anxious and exhausted each time it pops up in your inbox. That work that requires no talent, skill, or ability, simply an ability to switch off your brain and put your nose to the grindstone.

And most importantly, that work that does nothing to push you closer to your ultimate vision.

You know bad work when you see it, which is why it’s not truly a danger to your dreams.

Good work, on the other hand, is an innocuous killer of greatness.

Because good work (again, as the name implies) is good. 

You enjoy good work, you can profit from good work, and good work leaves you with a feeling of satisfaction and fulfillment.

But there’s a disconnect.

Good work is often what we use to fill our time and distract ourselves from great work we know we should be doing.

Good work is that high-paying freelance project that distracts your focus from your new startup. Or that client you keep on retainer who doesn’t push your abilities or stretch you. Good work can even be a relationship, a friendship, or a career that is blowing you off course from your life’s mission.

Good work will not steal your soul and crush you underfoot like bad work will. Instead, it will ensnare you and keep you playing the game of life at a small level.

So it’s time for you to decide. Do you want to do good work that will make you a living? Or do you want to do great work that will make you a legend?

2. Learn to Understand the True Problem 

Men are problem solvers.

This isn’t some sort of gender-based stereotype, it’s simply how we are biologically hard-wired.

But the unique problem with being a problem solver is that it can often lead to impatience and unnecessary haste.

Which, especially when it pertains to leadership and management, can be fatal to your efficiency.

After all, how can you effectively solve a problem if you haven’t fully defined the problem you are trying to solve?

For example, let’s say that you receive a call from a long-time client who is responsible for more than 25% of your bottom line.

As soon as you pick up the phone, the client regretfully informs you that your contract is being terminated and when you inquire as to why he simply responds by saying “We no longer need your services.”

At this point, you could make assumptions about the problem, politely hang up, and face the consequences of losing such a big contract.

Or, you could ask a simple question, “What’s the real challenge here?”

By diving deeper instead of simply assuming that the client is lost, you might find out that they recently underwent significant budget cuts and don’t feel that they can afford your retainer.

And while you may or may not be able to renegotiate an agreement, you have stepped further into understanding what the real challenge is.

The next time that you are presented with a challenging situation, even an internal one, I challenge you to pause, take a step back, and ask “What’s the real challenge here?”

If you are feeling unfulfilled in your work and you’re thinking about quitting your job, stop and ask “What’s the real challenge”? Are you bored and unchallenged? Do you feel stuck? Do you feel underpaid? Talk to your manager and see if you can take on more challenging projects, move into a different division, or negotiate a raise.

However, if you feel like your talents and abilities genuinely need to be applied to a different endeavor, then follow through and quit with a full understanding of the challenge you need to surmount.

If your marriage is on the verge of collapse, pause and ask yourself, “What’s the real challenge here?”. Are you and your partner simply struggling to connect? Do you feel the need for more time alone and with friends? Do you feel that you have lost touch with what made you fall in love with one another? These issues (although difficult) are all fixable.

But maybe the real struggle is that you were married too young and your goals are no longer in alignment. Maybe the solution is to part amicably and move towards your own individual purposes.

Whatever problems you are facing in your life, take a step back and figure out what the real challenge is.

Sometimes, your assumptions will be correct. But more often than not, you will find that the real challenge is much deeper and much more nuanced than you originally thought.

3. Knowledge is Never the Issue 

I want you to imagine that you are walking through a dark alleyway late at night in your hometown.

You feel a tingle at the base of your spine, and when you turn around, there is a man with a gun pointed at your head.

He doesn’t want your money, he doesn’t want your watch, in fact… He doesn’t give a damn about any of your valuables.

All he wants is the answer to four questions.

“What can I do to become healthier? What can I do to make and save more money? What can I do to attract more women and love into my life? And what can I do to become a stronger grounded man?”

Would you be able to respond?

If you have been listening to this show for any appreciable amount of time, then I can guarantee that you could.

“Lift heavy weights for 5 hours a week and only eat real food. Start a side hustle, save away every extra penny, and then invest in some sort of asset like a real estate deal. Talk to five new women every day, be genuinely interested, and be authentic with them. Start journaling, meditating, and pushing yourself to embrace adversity.”

Boom! He puts the gun down and you are free to go.

Now, I know that the above scenario is implausible, to say the least, but my point in sharing this is that you know what you need to do.

I doubt that the above responses were new to most of you. You already knew how to become healthier, wealthier, attract better relationships, and become more grounded.

And if you don’t, then a short glance through the Knowledge for Men archives will solve that problem once and for all.

For 99% of you reading this, however, knowledge is not your problem.

You know everything that you need to do.

So why aren’t you doing it?

Why aren’t you taking action?

Why aren’t you moving forward?

Before you get upset and start casting blame and recoiling in defense, pause… And ask yourself, “What’s the real challenge here?”

What is it in your life that is stopping you from moving forwards? Why aren’t you taking action? Why aren’t you doing what you need to do?

Instead of judging yourself and trapping yourself in a vicious cycle of frustration, shame, and inaction, take a step back and analyze your inaction.

If lack of knowledge isn’t your problem… What is?

4. What Do You Want?

Seriously… What do you want?

What do you want?

Not “What do mommy and daddy want?” Not “What does society want?” Not “What people tell you that you should want?”

What do you want?

It’s funny to me how few men will actually take the time to uncover the answer to this question.

To our knowledge, we only get one shot at this thing called life.

We only have one chance to live the lives that we want.

So why the hell do we go about living our lives based on other people’s values and desires?

If you only have one chance to live your life and achieve your dreams, then why would you pursue a career that makes you miserable? Why would you marry someone you don’t truly love? Why would you live one second of your life out of alignment with your deeper calling and purpose?

Ask yourself every single week, month, and year, “What do I want?”

Don’t filter what comes up, don’t judge it, just embrace it.

Once you know what you truly want… Go out and get it.