What Wordle taught me about my management style

Using trial and error comes naturally to me, but it had never occurred to me that I could get locked into ineffectual behaviors when the patterns in the world around me don’t do what I expect them to.”

Doug Phares, managing director, Silverwind Enterprises

I, like many people, identify as a Wordle Person. If you’re not familiar, The New York Times hit game, released in 2021, gives you six chances to guess a five-letter word. You get hints as you go — a green letter means it’s the correct letter in the proper space, yellow is the correct letter in the wrong space, and grey means that letter isn’t in the word.

It’s a simple enough game, but I became completely addicted during the height of the COVID-19 pandemic. And, because I’m me, I approach it methodically every day with the same approach. I begin with my designated Opening Word, which features a selection of statistically popular consonants and vowels. Then, depending on how many hits I get, I choose from a few different second-round words that will help fill in the gaps.

Most days, this process is enough for me to get the correct answer in three to four guesses. But some days, things just don’t work out that way. I stick to my system, and after all my well-reasoned, educated guesses, I’m left with one yellow letter and no idea where to go from there.

That is when my methodology falls apart, and I resort to brute force.

It’s not pretty. I start playing words that I know couldn’t be right to get more information. I make dumb guesses just so I can get to the next step with, hopefully, an extra scrap of information. Most often, this “strategy” doesn’t work out, and in a pique, I end up blowing all of my guesses just trying to make something happen.

I still get the Wordle in 3.6 guesses on average, so I can’t be too upset that sometimes I flame out. But one day, I was stomping down this familiar spiral, getting heated up as I stared down row after row of grey on my third guess, when I suddenly received a horrible splash of cold water right to the face with a chilling realization: This is exactly like my management style.

With a blend of experience and research, I’m well-equipped to manage people and finances effectively. I can recognize patterns and plan three to five moves ahead to achieve my goals.

But sometimes, the patterns don’t appear as I expect. When that happens, I can start making moves that I know won’t get me there. However, I do them anyway, because I’m frustrated with the situation and insist on moving forward, hoping that something will work and provide an answer.

This was revelatory for me. I’ve had a long career, and I’d never noticed this behavioral pattern. Using trial and error comes naturally to me, but it had never occurred to me that I could get locked into ineffectual behaviors when the patterns in the world around me don’t do what I expect them to.

I’d love to leave you with a pithy answer about how to break this cycle and get out of your own bad habits, but I’m still grappling with the realization that I’ve done this behavior for X-odd years and never realized it. I hope to break this cycle one day, but I’m not at that point yet.

Instead, I leave you with a question: Could you be stuck in a box without seeing it? I certainly was, even when this pattern was manifesting in different areas of my life. Whether you’re a Wordler or not, it could be worth it to critically examine your thought process in some areas not related to how you manage. You may be surprised by the patterns that unveil themselves and how much they overlap with your approach to problems in your profession.

Doug Phares is the former CEO of the Sandusky News Group. He currently serves as managing director of Silverwind Enterprises, which owns and provides management services to small businesses. He can be reached at doug@silverwind.biz.