9 Strategic Questions to Ask Yourself to Simplify Life’s Puzzles.

Insights from COVID-induced puzzling

We were sheltered-in-place. The backyard was useless due to torrential Texas rain. Three boys were bouncing off the walls — ages 8, 13, and 42.

Somewhere something shattered.

The boss too hit her breaking point.

“Sit down. All three of you,” my wife commanded. “You’re doing this puzzle. Now.”

And so, my boys and I began a 2,000-piece Star Wars puzzle. For twenty minutes, anyway. I soon found myself alone.

13-year old: “This sucks. Way too many pieces. I’m out.”

8-year old: “Darth Vader’s giant helmet is all black. Outer space is black too.”

So I was left with my OCD and 2,000 mostly black, indistinguishable pieces. Three days later I was traumatized by this puzzle. This experience, however, produced a series of valuable questions for thinking through the larger strategic issues in my business.

To save you time and torment, here they are:

1. Have I thought through a methodology to execute this?

I flipped the box upside down and sighed. Roughly half the pieces were upside down, as you’d mathematically expect. I began methodically flipping over 1000 tiny pieces.

If it sounds tedious, it was.

Once done, I had a thought: How would an expert puzzler go about this?

I then realized my phone was in the kitchen. The thought passed.

Poor choice.

Turns out thousands of puzzle nerds have shared their methodologies online, all very available to me with a few simple keystrokes.

According to the Kolbe A Index — and my team — I score high on the “Quick Start” dimension when it comes to getting work done.

The Quick Start mentality can be distilled down to this:

Step 1: Think of new idea.

Step 2: Begin executing new idea.

The upside is that exciting projects begin quickly and gain momentum. The downside is that the step labeled Think through entire project often gets skipped — as it did here.

For professional projects and puzzles, the investment in thinking through the project completely — to the bitter end — and writing it down is hardly tedious, it’s essential.

2. Have we identified the borders first?

After flipping over 1000 pieces, I had zero desire to search through all the pieces again to identify the edges.

Enough of the drudgery — I wanted to feel progress.

So I started hunting for the face pieces of the attractive lead (Jyn Erso played by Felicity Jones in the Rogue One prequel, if that rings a bell) in the center.

My wife popped in to check on my progress.

“Find all the edge pieces yet? Do that first.”

I mumbled something about helping me do just that while I mined the table for this girl’s face.

My wife shook her head no and left.

In puzzling (yes, it’s a gerund), separating the border pieces first establishes the constraints. Projects without constraints may seem like freedom, but the tyranny of choice will destroy you.

Constraints — clearly establishing what is within the borders and what is outside them — drives creativity as everyone narrows their focus to specific aspects of the project.

Hours later after numerous misinterpretations about spacing, I decided to search for all the edge pieces. My wife chuckled as she walked by, evaluating my lack of progress.

“Find all the edge pieces yet? You should do that first.”

3. Do I have all the necessary pieces for this to be successful?

On Day 2, my wife reported bad news. While helping my non-puzzling boys clean the playroom, she found something troubling.

“Lemme guess,” I said. “An empty box of Oreos under the couch filled with Texas-sized cockroaches?”

(That happened before.)

“Worse,” she said. “I found these.”

In her delicate hands she cradled seven (seven!) crucial pieces to this dreadful puzzle. Her face betrayed how much she knew those pieces meant to me. And the concern that there were untold other orphans far, far away from my dining room table workshop.

I immediately pondered the future.

After investing dozens of hours, would I then learn my effort was for naught as 5? 10? 30? pieces would be missing?

This seems like an obvious step — thinking through what products and expertise will be needed to successfully complete a project.

And yet, this step is often overlooked. An executive will say, “Well, when we get to that point, it will be a good problem to have.”

Still a problem.

Or someone will say, “Let’s keep the momentum going. We’ll cross that bridge when we get to it.”

That’s the problem.

There may be no bridge.

You’ll have to double back and spend countless hours of energy-sucking rework to get back to where you once were.

4. Is it possible I’m looking at this wrong?

As progress was being made, dozens of pieces would be unique enough to catch my attention. Struggling to fit them in after the tenth time (“This has to be the right piece for here!”) it would dawn on me . . . maybe I am totally wrong about this assumption.

It’s not Jyn’s gun . . . it’s the gun of the evil Lieutenant Commander Krennic, the Director of Advanced Weapons Research for the Galactic Empire!

To the annoyance of my wife, every thirty minutes or so I would show her the growing chunks of my puzzle progress.

“Now, I’m fairly certain this goes here,” I’d start, exposing my full vulnerability. “Is it possible I’m looking at this wrong.”

Multiple times she instantly recognized I was way off. It hurt to fail so often, but my progress always made an immediate leap.

Same rule applies in business. Who on your team has your permission to speak candidly when you may be looking at the picture incorrectly?

5. Am I too close this?

On multiple occasions I learned I was too close to the project.

Literally.

The light above the dining room table cast a wicked glare, forcing me to drop my face a few inches off the table to peer at the pieces at an angle.

Once I stepped away from the puzzle — on the rare occasions I left to stretch or use the bathroom — I would instantly recognize color combinations that had previously eluded me.

The same problem exists in business. We get so close to the details that we lose the perspective of the bigger picture. Once you step back, you may instantly realize, “Oh wow. That is certainly not correct.”

For executives and other professional delegators, there is a corollary here. Sometimes you’re too far away from the action to truly understand the details.

You may need to visit the jobsite or walk out into the lumberyard.

Go see for yourself — get your nose down in there for a moment.

6. What would have to be true for this to work?

As the puzzle surpassed half-assembly, the pool of possible pieces for specific areas narrowed. This particular puzzle I learned was a “ribbon cut puzzle” — there were only a few shape variations with uniform rows and repeating patterns.

This meant I could separate specific pieces by their common shapes.

I would often be puzzling over a specific piece when I’d realize it couldn’t possibly fit. It was identical in shape to the one I was trying to connect it to.

Examining the differing shapes, I would then ask, “What shape would this have to be for it to fit?”

This effort of inverting the problem often leads to new insights.

Before you shoot down an idea or say, “I doubt that would work here,” consider a different method of examination: “What would have to be true for this to work here?”

7. What criteria will determine if/when I abandon this project?

Late on Day 3 the wife gave this diabolical puzzle project a deadline.

“Tomorrow we’re having family over,” she informed me. “We’re going to need this table for dinner.”

“No way — I ain’t leaving TIL IT’S DONE!” I yelped unexpectedly (by both of us).

I was pot committed as they say in poker. Thumbs together . . . I was all-in.

She made me a deal.

“I’ll give you 8 hours — working alongside you all day — and if we’re not close,” she closed her eyes solemnly and paused, “. . . then you shut it down.”

“Deal,” I said. “Start with the Resistance X-wing starfighters in the corner.”

Obviously I did not expect this puzzle to kick my ass so violently and persistently. Now I was forced to ponder when and how I would decide to abandon this project.

Business legend Peter Drucker often posed this famous question to his clients: “If you were not already engaged in this line of business, would you choose to enter it now?”

This question is designed to highlight The Sunk Cost Fallacy. Whatever time, energy, and capital has been poured into this project already, it is gone.

Whether it’s $20 million or twenty hours of my time, it is gone.

And it ain’t coming back.

Continuing this endeavor simply because of previously invested resources is irrational. The only relevant question remains, “Do I continue to invest more into the project?”

As our 8-hour timeline neared its end, I transitioned from this question to a related one . . .

8. What is the opportunity cost here?

The torrential Texas downpour of 72 hours ago was long gone.

The sun was out. Kids were playing in the pool.

The opportunity cost here — what I could have been doing had I chosen not to hover over this stupid puzzle? — was sizable.

I vocalized my hatred for this dark, dark puzzle.

Loudly.

My wife pushed away from the table and asked . . .

9. Is this fun anymore?

It was not.

When fun ceases, that can be a sign things have changed. Obviously your job may not be an endless series of euphoric activities, but you should be enjoying what you’re doing 50 hours a week.

If you’re not having fun, it’s a sign.

Slow down and read it.

Am I done with puzzles?

I am not.

Moving forward, however, I will thoughtfully consider these 9 questions ahead of time. Despite the anguish delivered by this rogue 2000-piece puzzle, the upside is new thinking around my business challenges and opportunities.

So what did I do with this puzzle?

I walked to the fridge, opened a bottle of Blood & Honey, and uttered a phrase that had been echoing in my mind for some time.

“This sucks. Way too many pieces. I’m out.”