Guessing

I’ve been around long enough to remember when a business owner’s decision-making process could be summarized in two words: “gut feeling.” Today we have data analytics, AI, dashboards, consultants, and enough reports to kill a small forest. In many ways, that’s a good thing. We have access to better information than ever before.

I still think many of our decisions are based on little more than guessing, in spite of all our advanced technology. Better guesses, perhaps. But guesses nonetheless.

Many important decisions still happen at the intersection of intellect and intuition. The spreadsheets get a vote. So does the little voice in the back of our heads. Which one carries more weight is largely determined by who we are as individuals.

Years ago a business owner might have simply announced, “I’ve got a hunch this is the right thing to do.” That gut feeling I just mentioned. Today the same owner arrives with a seventeen-page PowerPoint deck, three spreadsheets, a market analysis, and a consultant’s report before making exactly the same guess.

The only difference is that now the hunch comes with footnotes. Lots and lots of footnotes.

We seem to have developed an aversion to the word “guess.” Nobody makes guesses anymore. It seems unprofessional to even say it. Today we engage in predictive forecasting, strategic modeling, trend extrapolation, or probability-based outcome analysis. Sounds like somewhere along the way guessing hired a public relations firm.

Then there’s artificial intelligence. AI can analyze more information in a few seconds than I could absorb in a lifetime. It can spot patterns, identify trends, and make recommendations based on mountains of data. That’s impressive. What it can’t do is eliminate uncertainty. At some point, someone still has to lean back in their chair, stare at the ceiling, and say, “Well, I think this is my best bet.” In other words, somebody’s guessing.

This isn’t a new problem. Kurt Vonnegut understood it. In his commencement address at Hobart and William Smith Colleges in 1974, he observed, “Oh, there have been lots of brilliant guesses. But honest, educated people have to identify them as such—as guesses.” I like that. The problem isn’t guessing. It’s pretending we’re not.

The best leaders I’ve known gather facts, listen carefully, study the options, and seek wise counsel. Then, after all the available information has been exhausted, they make the best decision they can and move forward. They know the future isn’t available for preview. They’re simply making higher-quality guesses.

So, the next time someone tells you they possess a data-driven, AI-enhanced, statistically validated, algorithmically optimized strategic solution, remember this: It might be a very good guess. But it’s still a guess. That shouldn’t make us uncomfortable; it should make us humble.

We all make decisions with incomplete information, but the quality of our preparation matters. The quality of our thinking and character matters. And yes, the quality of our guesses matters too. Guess wisely.