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Crossing the Rubicon

By Trever Cartwright

When was the last time you made a Rubicon decision?

As you think about the types of decisions you’ve made over time, chances are there are only a few that rise to the level what I call true Rubicons.

Rubicon decisions have a certain physicality to them. As we move through the process of making them we feel distracted and maybe a little anxious. When we share the Rubicon with our organization, they predictably make our hearts pound and maybe our palms sweat a little. Whatever our physical reaction, suffice to say, Rubicon decisions demand our full attention every step of the way and can be emotionally draining.

Rubicon decisions are indelible. Once we cast our die, their impact is irreversible and will forever change the course we’re on. It makes sense that they would be so insistent of our time and energy. Thank goodness we don’t have to make them every day. But when we find ourselves standing in their shadow, we need a way to effectively rise to the occasion and meet the challenge they present with courage and conviction.

There are many remarkable examples of what I call Rubicon moments throughout time. While doing research on the topic of courageous decisions, I came across one in particular. The story of Julius Caesar, widely considered one of the most significant warriors the world has ever known, was frequently referenced.

On January 10, 49 BC, Caesar made the momentous decision to lead his army across a shallow stream that wound its way through a portion of northeastern Italy. This stream, known as the River Rubicon, marked the boundary between Cisalpine Gaul province to the north, and Italy proper to the south.

An ancient Roman law forbade any general from crossing the River Rubicon and entering Italy proper with a standing army. To do so would be considered an act of treason, punishable by a torturous and agonizing death. The purpose of the law was to protect the republic from internal military threat. Crossing the Rubicon would reveal Caesar’s ultimate aspirations and mark a point of no return. In this moment the Roman Empire was born and the course of history was forever altered.

As he stepped into the River Rubicon, Caesar declared, “Jacta Alea Est.”, which is Latin for, “Let the die be cast.”

The phrase “crossing the Rubicon” has endured through millennia to refer to anyone committing him or herself irrevocably to a high-stakes course of action in which the risks and rewards are extreme.

I have found that one of the most common challenges many leaders face is not necessarily making the Rubicon decisions that need to be made in their organizations, but rather having the courage to set those Rubicons into motion—to actually walk into the river despite the extreme consequences however risky or rewarding they believe them to be.

As you think about the big decisions waiting to either be made or to be put into motion in your organization—those Rubicons that may be keeping you awake at night, consider the following suggestions. They’ll help you find the perspective you need in order to take the best steps forward and not get caught in the inertia of inaction.

1. Your organizational values have great utility in a decision-making context.

As you move through your decision-making process, take time to honestly and thoughtfully filter your potential decision through your company’s values, one by one, giving equal weight to each of them. Ask yourself, “How would (this decision) align with or support (Y) value?” or, “If I were to announce (this decision) to my team, how would I connect it to each of our organization’s values?”

Remember, your organization’s values are what define the soul of your company and shape the content and character of its culture. As a leader, any decision you make needs to be values-driven, clearly reflecting the beliefs that inform how your business shows up in the world.

2. Sometimes best is right.

It’s easy to fall into the trap of finding the right decision. Understandably, being right is something most people care very much about. But Rubicon decisions can be elusive, making “right” much harder to determine. Before you know it, time—and your competition—pass by and disappear into the distance. You find yourself hoping the big decision that needs to be made will simply go away or somehow solve itself. It won’t. And you know that.

Instead of hand ringing over the right decision, focus your time and energy on making the best decision. To be clear, there are certainly times when the precision of a dead- right decision is necessary. However, in most cases, the best decision can be made based on careful consideration of the information you already have.

The next time you find yourself lying awake searching for the right answer, stop the madness for just a moment. Breathe. Step out of the details and look at the situation as a whole. By not falling into the quicksand that often comes with being dead right, you’ll be avoiding the unintended consequence of allowing your organization to be anchored by indecision.

3. If your company had a voice and could talk, what would it say it needs most from you in this moment?

It’s a counter-intuitive way to think about your company—as having a voice that you can actually hear. Organizations don’t talk. Nonsense, right?

When you think about it, it actually makes a lot of sense. Organizations do in fact talk and there is great wisdom in what they say. It’s a leader’s responsibility to be deeply attuned to what his or her organization is saying at any given moment and to consider this guidance when making any decision, let alone a Rubicon decision.

I’ve found that this simple, clarifying question can lead to great breakthroughs and can be a powerful catalyst for clarity and purpose. I’ve asked many leaders this question over the years and have always been amazed by the sense of calm that washes over them when they share their answer. Gradually, all the pressure and stress of the matter dissolves and the path forward—the decision—emerges.

Inevitably, the answer this question reveals is unencumbered by office politics or the doom and gloom of imagined negative reactions or blowback. It has the power to break down seemingly insurmountable barriers and shed a bright light on a range of possible solutions to the most difficult organizational challenges. If, after asking yourself this question, the best decision is clear, then all that is left is developing your plan to communicate and then implement it.

I read somewhere that of all the activities that take place in an organization, leadership is by far the hardest and most important among them. In my work with leaders—all of whom are faced with making important business decisions every day—I’ve found this to be a universal truth.

As a leader, it’s likely you have found yourself standing on the banks of your own Rubicon, just as Caesar did as he considered the consequences of forging ahead or stepping back. We all know what his decision was and what would follow as he uttered those now infamous words, “Jacta Alea Est.”

As you ponder the big decisions waiting to be made in your organization, ask yourself whether any of them represents a pivotal Rubicon moment, not only for your organization, but also for you as its leader.

And for the one or two that do in fact rise to this level of significance, what is the best decision you can make?

Will you hesitate at the river’s edge waiting for the right answer to grant you permission to pass? Or will you step into the water—emboldened by the information you already have, inspired by the clarity of your organization’s values and driven by your belief in what is best for your company?

The decision is yours. Either way, whether you step back or forge forward, the die is cast.