The CEO Paradox: Getting Out Of Your Own Way

Jim Blasingame

Paradox: when two associated things – words, traits, situations, etc. – seem illogical and/or contradictory, but may, in fact, be true, compatible, or justified. Examples: “You have to spend money to make money” or “less is more.” Here’s a digital transformation example: “Using artificial intelligence to get closer to customers.”

Contemplating the paradox is fascinating, but never more so than how paradoxical humans are. Consider these human paradoxes:

  • Your intense personality can seem aggressive, but the other side of your paradox is an outgoing nature with a handy sense of urgency.
  • You’ve been called a workaholic, but the rest of the story is that others benefit from the fruits of your labor.
  • You may seem unorganized, but your creative paradox sees order in clutter.

We, humans, are at once a sweet and sour but always spicy Brunswick stew of paradoxes. But most of us don’t spend a lot of time thinking about it because paradox sounds negative and we don’t like dwelling on our negatives – just the good stuff. And there’s the rub.

My friend and paradox expert, Kelle Olwyler, says that trying to eliminate the half of a personal paradox we don’t like can create problems because that part is as essential to who we are as the cool part. Thus, the paradox. 

Olwyler says, “Eliminating our negatives is like trying to eliminate one side of a pendulum swing,” and urges us to use “paradoxical thinking.” This is consciously acknowledging, accepting, and valuing the power of our paradoxes, while taking into account those of the people around us. Paradoxical thinking helps you perform more successfully by harmonizing both sides of your pendulum.

Paradoxical thinking gives us permission to not deny our so-called negatives, which is counter-productive at best and destructive at worst. And it allows us to effectively manage both sides of our paradoxical pendulums that make up who we are. Now apply paradoxical thinking to the previous examples:

  • By recognizing that your intense nature creates both opportunities and challenges, you can manage this paradox more successfully in professional and personal relationships. 
  • By accepting that you like working, you can identify ways to accomplish professional goals in concert with those of the family, without feeling guilty about doing what you love.
  • Accept that just as water seeks its own level, your creative paradox seeks its own clutter/organization balance. 

Another aspect of paradoxical thinking is associated with a human trait I call “The CEO Paradox,” with the inextricable sides of that coin being control and delegation:

  • Heads: In the early stage of any venture, control is essential, which by definition is a stingy delegator.
  • Tails: Long-term success requires every CEO to become an effective delegator.

In classic paradox form, the CEO’s is at once simple and complicated: control is simple while delegating is complicated. And there’s the challenge.

It’s an article of faith that a small business is more like a benevolent dictatorship than a democracy, with many decisions being made at different impact levels. And everybody knows that in a small business there are too many hats and not enough heads.

Consequently, throughout their career, Main Street CEOs are required to flip from heads (controlling decisions) to tails (delegating decisions) almost at a moment’s notice. And perennially successful CEOs use paradoxical thinking to become wise leaders, calling the correct side of the coin more times than not. Let me restate that: Your CEO Paradox will be balanced best when you know when to get out of your own way.

One of my mentors gave me the best advice for managing the control side of my CEO Paradox. Once, when I was stuck, he said, “Check your position.” That means look around at the wake from your efforts, and if what you see looks like success, then full steam ahead. But if what you see looks like sinking performance goals, a team awash in attrition, or (your missed opportunity here), then you’ve got a CEO Paradox problem. It’s time to recalibrate your control/delegate pendulum.

The recalibrating of your CEO Paradox requires taking these steps – in this order:

  • From the CEO orbit, regularly check your position for opportunities to lead more and manage less.
  • Fire yourself from jobs you’re still doing that someone else can do.
  • Promote yourself to new jobs only the CEO can do.
  • Seek excellence, not perfection. This means admitting that the way you did that job was perfect only in your eyes, not in reality. You can win with excellence – perfection will take you down.
  • “What did we learn?” Redemption is the most powerful of all recalibration tools and doubles as the most powerful four words in leadership. When someone messes up while seeking excellence, redeem them, and recalibrate your CEO Paradox with that question. Do it early and often.

When you release control and delegate a job to someone, prepare to be surprised when their excellence produces a better result than your perfection. And that’s the moment you realize that you just might be able to take a day off or maybe even an entire week of vacation. (Don’t worry – you can still call in.)

The CEO Paradox: Your business cannot sustain successful growth, with happy stakeholders, without the Founder’s control being balanced by the CEO as delegator. In other words, get out of your own way.

Write this on a rock ... Humans are made up of dimples and warts all rolled into the cutest bundles of annoyingly endearing paradoxes. But remember – without warts, dimples wouldn’t be so cute.

Jim Blasingame is the author of The 3rd Ingredient, the Journey of Analog Ethics into the World of Digital Fear and Greed.


Print page