“By three methods we may learn wisdom: First, by reflection, which is noblest; second is by imitation, which is easiest; and third by experience, which is the bitterest.” – Confucius

In high school, I was impressed with an older student named Curtis. He was charismatic. A natural leader, an athlete and funny.

But what really caught my attention was how he seemed to make the “right” decisions.

That stood out to me. I often didn’t make the “right” decisions.

I reacted. I pinged. If a stray thought went through my head, I chased it.

Curtis didn’t do that. At least not according to my 9^th and 10^th-grade perspective.

Over and over again, I’d watch him stop if pranks or jokes were starting to go too far. He’d consider choices before he made them. He’d think of ways to be caring towards people.

He made decisions that I never even considered as options.

He was an example. An archetype. His approach to decision making was rare.

He was learning to exercise judgment. He was learning wisdom.

Now, 30 years later, I find that good judgment from leaders is still too rare.

Many leaders still ping. They react. They jump to conclusions or pile onto bandwagons.

They are driven by fear, anger or blind ambition as opposed to providing leadership.

What Is Needed to Cultivate Leadership Wisdom?

Merriam-Webster defines wisdom as The ability to discern inner qualities and relationships, good sense, to make wise decisions.

Leaders don’t intentionally make poor choices. But not many leaders intentionally cultivate the ability to make good choices. Not many leaders intentionally develop their ability to be wise.

Now, leaders often learn technical skills. In fact, most leadership development programs focus on technical skills. But very few teach what is needed to develop good judgment.

Wisdom, or good leadership judgment, is a skill. And like most skills, it’s developed and honed with practice.

How to Cultivate Leadership Wisdom

1. Center on Clarity The more you practice creating clarity, the easier it will be to make good decisions. Clarity in three specific areas is key:

a. Principles: Another way of saying principles is The greater the clarity and alignment between your core values and the values of your organization – the easier decision-making will be.

The better you understand how to apply these principles of values to various situations, the more wisdom you’ll display.

b. Purpose: Staying centered on your purpose or your “why” is critical. Along with principles, clarity of purpose (in the big and small picture) supports good decision-making.

Many decision-making conversations drift. They wander. They become driven by a strong personality or an urgency or a source of agitation. Purpose gets lost in a laundry list of “to-dos.” Stay centered on purpose.

c. Priorities: When leaders have defined priorities in advance, decision making becomes much easier. When those priorities are in alignment with your principles and your purpose you build a way of quickly measuring good decisions from poor ones.

Sometimes priorities need to change. But when change is intentional – as opposed to being due to distraction or urgency – even the change process becomes an exercise of good judgment.

2. Effective Evaluation Knowing how to identify and assess options well is at the core of any good decision-making process.

a. Stay Objective: Everyone has a bias in decision making. This might be expressed in the kinds of decisions we prefer. It might be expressed in the kind of decision-making process we prefer. Either way, it’s there.

Objectivity isn’t easy. Emotion and preferences aren’t wrong. But better decisions come from being able to set aside (at least temporarily) our biases and emotions.

b. Informed by Experience (Yours and Others): There is nothing new under the sun. It’s helpful to learn from your own past experiences, as well as the experiences of others. Leaders who see themselves and their situation as completely exceptional and unique typically crash hard.

Books, professional associations or publications can be very helpful. Committees are often derided, but they can be great sources of experience and objectivity. Mentors and coaches are often able to fill gaps in experience that you or your organization may not have.

c. Identify Options: Most people come to decision-making with one or two options in mind. Maybe there is indecisiveness or a conflict between the two. The reality is that there are usually many options. We just haven’t thought of them yet.

When working with clients, I have several tools I use to help them quickly generate more options. Use your Principles, Purpose, and Priorities as a screen for selecting good options. They nearly always end up choosing an option that is different than what was originally considered.

3. Take Action Good decisions that are never put into action are pointless. Some leaders content themselves with thorough decision-making processes – but then never implement. That isn’t exercising wisdom.

a. Decisiveness: Wisdom doesn’t equal perfection. Out of fear of making the wrong or unpopular decision, too many leaders never make a decision at all. Instead, they keep putting decisions off until it’s too late or something else forces a decision. This isn’t wise and it is poor leadership.

I agree with the old saying, “Haste makes waste.” However, I’ve found that decent decisions— executed quickly—produce better results than perfect solutions—executed too slowly.

b. Reflection: Reflection is the discipline of pausing after an action, looking back and then looking forward again. Leaders who build the habit of acting and reflecting grow. Leaders who don’t reflect tend to repeat mistakes.

Reflection is as simple as making a point to regularly ask questions such as:

• What happened?
• What did we intend to have happen?
• What accounts for the difference between the two?
• What can we learn from this?
• What will we do next?

c. Accountability: Accountability is the process of doing something with your answers to your Reflection Making the changes that need to be made. Stop doing what isn’t producing value. Keep doing what is.

The best accountability systems are planned and are part of your action planning. There should always be a planned time for reflection and adjustment after an action is taken. This ensures that problems are caught early and addressed. It ensures that uniquely successful approaches can be fully leveraged.

Leadership Wisdom Is Easy to Learn. But 9 out of 10 Leaders Won’t.

As you can probably see, building leadership wisdom isn’t ethereal, difficult or subject to chance. It’s mostly just a matter of discipline.

I don’t think Curtis had a list like this that he thought through. But I do believe that he had somehow been taught and internalized most of the items on this list.

If you put these disciplines into practice, you’ll find that the quali7ty of your decision-making will quickly improve. Wisdom will become internalized.

The big distinction is that most leaders just practice the above disciplines. Whatever their reasons are for not doing it – they don’t need to be your reasons.

Ultimately, learning to make wise choices, is a choice itself. Are you willing to make that choice?

Take good care,

Christian

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