#130 How Do You Win: I Was Asking The Wrong Question

I used to make a point of asking employees this question…

“How do you win?”

The idea being that if I knew their desires then I, and the organization as a whole, could help them achieve them.

My “win” question tended to get response like these…

I want to close this huge new piece of business.
I want to be promoted to manager, director, VP.
I want to be the top salesperson in the company.
I want to be the youngest VP in the history of the company.
I want to make $100,000 dollars a year, or more, so I can afford the house, the car, the vacations, the kids colleges that we want.

Notice what all these answers have in common- they’re all about wanting our peers, managers, and others to see and reward our contributions. Getting psychological, they’re all about the common human desire to be differentiated, appreciated, externally validated.

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Pretty typical stuff, but let’s dive a little deeper. Let's think for a minute about who hands out those rewards, those pay raises, promotions, bonuses, corner offices, attaboys, attagirls, and contracts. Whether it’s a committee or a single individual, the one thing we know for sure is that the “choosers” are imperfect human beings just like us. Their priorities aren't always clear. They have biases they aren't aware of. They make good and bad decisions every single day.

So if we’re attaching our emotional well-being to being chosen by imperfect people using imperfect information and imperfect processes, then we're setting ourselves up for eventual disappointment.

And imperfections aside, what if you’re running with the big dogs?

What if you work with amazing people where excellence is the norm - no promotions or awards coming your way - but you’re an important part of an accomplished, cohesive, motivated team? Isn’t that way better than slumming around the minor leagues - way better than being the top dog amongst a team of unmotivated, self-focused, status-quo knuckleheads?


Looking back it’s clear that my “how do you win” question was a trigger for the kind of answers I received. Answers that were all about being chosen and externally validated.

A much better question would have been “how do you want to grow - where and how do you want to increase your skills, insights, maturity?”

And I’m not being naive here, I get that it’s probably our nature to always have one eye on differentiating ourselves vis a vis our peers, the market, the world. But, if we’re really interested in tapping our potential, we better make damn sure our other eye is locked on our internal intrinsic growth needs.

This path - de-emphasizing winning and be chosen and instead locking in on intrinsic growth - is, ironically, the most direct path I know to winning and being chosen.

#126 Immense Pleasure: It Lives Where We Least Expect It

Alan Watts was a British philosopher that acted as somewhat of a bridge between Eastern and Western philosophies. And a topic he probed that caught my eye was the relationship between skills and pleasure. Here’s a quote of his…

“There is immense pleasure in learning how to do anything skillfully”.

And he seems to have considered us Americans especially dense when it came to this point…

“Whatever you do, you require a skill. And it’s enormously important, especially for American people, to understand that there is absolutely no possibility of having any pleasure in life at all, without skill.”

During my employed years I don’t think I ever thought to relate skills to pleasure. Maybe skills and winning. Or skills and promotions. Or skills and more income.

Or maybe I did tie skills to pleasure in the sense of the pleasure derived from showing off an acquired skill. But if you read that first quote carefully - “there is immense pleasure in learning how to do anything skillfully” - I think he’s talking about more than just finding pleasure in the end result.

Isn’t Watts also suggesting that we can find pleasure in the “learning how” part of the process? After all, that’s where we spend most of our time. Locked in the struggle. Stretching to figure something out. Hitting roadblocks. Restarting. Iterating. Grinding.

Can this “drudgery” be pleasurable?


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I spent a good bit of my career in sales. Managing teams with rapidly growing numbers hanging over our heads. And I recall spending the bulk of my mental time focused on the hassles of budgets and managing and those damn customers. And too little time appreciating the raw pleasure of the skill-building process.

For instance, I loved presenting our story to audiences. I found pleasure watching them nod their heads in agreement as my points hit home. But I too often overlooked another source of pleasure that was right in front of my face. The pleasure I could have experienced during my endless hours of preparation.

Let me give you a current example of what I'm talking about.

I’ve recently started doing public speaking again. And yes, I still find great pleasure in seeing those nodding heads when I get my points across. But this time I'm also way more conscious of mining the pleasure that’s hidden in the "drudgery" of the countless hours I spend preparing.

Finding the perfect image, the perfect font, the perfect phrase to make my point. These small victories, so long as I pay attention to my emotions, offer me constant sips of pleasure. Tiny rewards that keep me moving forward hour after hour. Day after day. Week after week. Turning drudgery into non-drudgery, and maybe even fun.

I’m not much of a philosopher, and I don’t know a whole lot about this Watt’s guy. But I thank him for pointing out that hard work can be a wonderful source of pleasure.