Don't Outsource Your Judgment

Post 2: Experience Meets Intelligence Series

Leading in the Age of AI

One of the greatest responsibilities of leadership is making decisions.

An Original Boardrooms & Backroads Leadership Series

One of the greatest responsibilities of leadership is making decisions, particularly when the information is incomplete, the consequences are significant, and reasonable people disagree about the right course of action.

Throughout my career, both in the military and in financial and operational leadership, I've learned that good decisions rarely come from having all the answers. They come from asking the right questions, understanding the risks, listening to the people around you, and having the courage to make the call when the outcome is uncertain.

During my time in Army aviation, we trained extensively for situations we hoped would never happen. Procedures, contingency plans, and preparation were essential, but training also reinforced an important lesson: circumstances rarely unfold exactly as anticipated. Equipment can fail, conditions change, and information that seemed reliable minutes earlier may no longer apply. When that happens, you have to assess the situation, trust your training, consider your options, and exercise judgment.

That lesson has stayed with me throughout my professional life.

Today, artificial intelligence can analyze complex information, identify patterns, evaluate alternatives, and produce recommendations in seconds. It's an extraordinary capability, and one I'm increasingly incorporating into how I work and think.

But it introduces a challenge that leaders need to recognize. When answers become easier to obtain, we must become more intentional about questioning them.

A Recommendation Is Not a Decision

Consider a situation familiar to many organizational leaders: evaluating a significant capital investment.

You have financial projections, construction estimates, operating assumptions, potential risks, and competing strategic priorities. You provide that information to AI and ask it to evaluate the investment. Within moments, you receive a professional-looking analysis, complete with financial comparisons, alternative scenarios, risk assessments, and a recommendation.

It's impressive, and it can save an extraordinary amount of time.

But I've spent enough years working with budgets, capital projects, and organizational priorities to know that even the most sophisticated financial model is only as reliable as its underlying assumptions.

What happens if projected revenues fall short? What if construction costs increase? What if the implementation timeline changes or an anticipated funding source is delayed?

And beyond the numbers, what happens if an investment makes financial sense but the organization isn't culturally or operationally prepared to execute it successfully?

These are the questions that experience teaches us to ask.

AI can help evaluate financial scenarios, identify potential weaknesses, and compare alternatives. But it cannot independently understand every relationship, institutional commitment, or cultural consideration that might influence the decision.

A well-written recommendation is not necessarily a well-reasoned decision.

That's where leadership begins.

The Danger of a Convincing Answer

One of the things I've learned through my own use of AI is how confidently it can present information, even when that information is incomplete or incorrect.

I've asked AI to evaluate issues, develop recommendations, and challenge my thinking. Sometimes its responses are remarkably insightful. Other times, I've questioned an assumption, requested supporting evidence, or approached the issue from another perspective and discovered that the initial conclusion needed revision.

That experience has changed how I interact with the technology.

Rather than asking AI simply to provide the best solution, I increasingly ask it to explain the assumptions behind its recommendation, identify the strongest arguments against it, and describe the circumstances under which its proposed solution might fail.

Those follow-up questions often reveal more than the initial answer.

There is a broader leadership lesson here. Most of us have experienced situations where the first proposed solution seemed reasonable, only to discover that an overlooked detail or an alternative perspective changed our understanding of the problem.

The same principle applies to AI. Its ability to present information clearly and confidently can be valuable, but it can also make an incomplete recommendation seem more credible than it deserves.

Confidence does not equal accuracy, and speed does not equal wisdom.

Experience Requires Humility

There is another side to this discussion, particularly for those of us who have spent decades in leadership.

Experience can be an enormous advantage, but it can also become a limitation.

Over time, we develop instincts based on what we've seen, the decisions we've made, and the consequences we've experienced. Those instincts frequently serve us well. They allow us to recognize patterns, anticipate problems, and make decisions without having to analyze every situation from the beginning.

But experience can also lead us to believe that because something worked before, it must be the right approach again.

That's where I see one of AI's greatest opportunities for experienced leaders. It can introduce perspectives we haven't considered, identify weaknesses in familiar approaches, and challenge assumptions we've accepted for years.

Of course, that only works if we're willing to listen.

If we use AI simply to reinforce what we already believe, we're not strengthening our judgment. We're using powerful technology to validate our existing biases.

I've always appreciated the wisdom found in Proverbs 18:13:

"If one gives an answer before he hears, it is his folly and shame." — Proverbs 18:13 (ESV)

That principle is as relevant to modern leadership as it was thousands of years ago.

Whether we're listening to an employee, a colleague, a board member, or evaluating information produced by artificial intelligence, we should resist the temptation to reach a conclusion before we've fully considered the evidence.

Wisdom requires humility, and humility creates room for better judgment.

Organizations Aren't Spreadsheets

As a CFO and COO, I spend a significant amount of time evaluating financial and operational decisions. Numbers matter. Budgets matter. Financial discipline matters. Organizations cannot fulfill their missions for very long without sound financial management.

But I've also learned that organizations aren't spreadsheets. They're people.

A decision to reduce expenses, restructure a department, change an operating process, or invest in new technology may appear straightforward when evaluated strictly through financial analysis.

Yet every organizational decision affects people, relationships, expectations, and culture.

Sometimes the most financially attractive solution isn't the best organizational decision. A change that creates immediate savings might weaken employee morale, disrupt essential relationships, or undermine the trust that took years to build.

Other times, the right decision requires making a difficult change despite the discomfort it creates.

Leadership requires understanding the difference.

AI can help us analyze costs, assess alternatives, and evaluate potential outcomes. It may even help us recognize perspectives we initially overlooked. But the people responsible for leading an organization must still weigh those findings against its mission, values, and long-term interests.

And sometimes the most important part of a decision happens after the analysis is complete, when we sit down with the people who will be affected and have an honest conversation.

Technology should help us prepare for those conversations, not replace them.

The Final Call Is Still Yours

I believe artificial intelligence will continue to transform the way leaders gather information, analyze problems, evaluate alternatives, and prepare to make important decisions.

I welcome that opportunity.

But the more capable the technology becomes, the more intentional we must be about protecting the judgment and accountability that leadership requires.

We need to know when to trust the analysis, when to challenge the assumptions, when to seek another perspective, and when to recognize that the issue requires more than a technically correct answer.

In the Army, the responsibility for a decision did not disappear because someone else developed the plan or provided the intelligence. The person responsible for executing the mission still had to evaluate the information, make the call, and accept the consequences.

Organizational leadership is no different.

When a decision doesn't produce the outcome we expected, we cannot simply say, "That's what AI recommended."

The responsibility belongs to us.

Artificial intelligence can inform our judgment, challenge our assumptions, and help us see possibilities we might otherwise overlook.

But it should never become a substitute for the experience, character, wisdom, and accountability that leadership demands.

Use AI to strengthen your judgment.

Never outsource it.

Backroads Reflection

The next time artificial intelligence offers a recommendation, consider this question:

Am I convinced because I've critically evaluated the answer, or because the answer sounds convincing?

There is an important difference between the two.

Artificial intelligence may help us make decisions faster, but the responsibility to make them wisely will always belong to us.

Go Be The Reason.