How Leaders Can Develop Good Judgment

Posted by Jack Warren, Chase Oaks Chief of Staff, on Jun 16, 2022

How Leaders Can Develop Good Judgment

I often speak of five elements, or tools, of leadership: character, self-leadership, drive, judgment, and
influence. Good judgment is built on character, self-leadership, and drive. Like a fine wine, it takes a combination of the right elements to work together over time to produce. Can leaders actively develop good, sound judgment? Or is it just something that is acquired from experience—especially mistakes?

I think judgment can be developed over time, and it should be a priority for every leader.

Recently, a school principal shared this perspective on the importance of judgment: “We get paid for our judgment.” He meant that if we are a leader, our education, reputation, experience, and interviewing skills may have gotten us in the door. But it is the soundness of our judgment that allows us to continue to lead and to be invited into more leadership opportunities.

If our influence is going to grow, then our judgment must keep growing. Even more importantly, if
our judgment declines or lapses, we lose our influence, our impact, and our credibility. So how do we grow and develop good judgment?

Here are a few practical actions we can all take:

1. Ask God for it.
James 1:5 reads, “If any of you lacks wisdom, you should ask God, who gives
generously to all without finding fault, and it will be given to you.” God is the source of all truth and wisdom.

Wisdom is found throughout the Bible in the “wisdom” books (Psalms, Proverbs, Ecclesiastes, Job, and Song of Solomon). Wisdom can be found in the historical books of the Old Testament, in the lives, mistakes, and hard-earned lessons of others. Wisdom is also found throughout the Gospels where we find the teachings of Jesus, and throughout the Epistles of the earliest followers of Jesus. Wisdom is literally in every book of the Bible.

We can gain wisdom by reading the Scriptures, and we can also gain it as we ask God for it. Asking God
for wisdom isn’t a one-time prayer. I pray for wisdom multiple times a day because I don’t trust my judgment on my own. I honestly need wisdom from God hourly, so I ask Him for it a lot!

2. Learn from a person who has traveled the road you are on.
Many will call this person a mentor. While I agree that mentors are amazing, I rarely meet people who feel qualified to wear that label. However, there are tons of people around who have experienced the situations we are currently going through. I believe we need multiple mentors; these mentors likely have
regrets and past failures, and even better, they know and own their past mistakes. A humble, authentic person with successes and failures makes a great mentor. They just tend to shy away from the mentor label.

3. Seek feedback.
You have likely heard the phrase “We can’t smell our own selves.” Or, said another way, we all have blind spots in our lives—things about us that others can perceive but that we are not fully aware of.

Humble, hungry, and smart leaders know that they have personal areas which could hinder good judgment. As a result, they seek ongoing feedback to identify those areas. So, seek feedback whenever you do anything in front of a group. Seek feedback before you finalize a tough decision. Seek feedback when crafting sensitive communication. Feedback will save you every time.

4. Dissect past situations with a “Four Helpful Lists” exercise.
Our Chase Oaks staff are accustomed to using these lists after events. Here they are, along with what to do with the lists once they are made:

  • What was right? Repeat it!
  • What was wrong? Fix it!
  • What was missing? Add it!
  • What was confusing? Clarify it!

We can do this exercise in a matter of minutes, and we will improve as a result of it. This can train us to be wiser in our judgment and in our evaluations.

5. Listen to your gut.
This is listed last for a reason. Our gut instinct is there for a reason, but it alone can’t be trusted to provide the judgment we need. Past traumas and triggering situations can cause us to react in negative ways and hinder our judgment. Even so, when we have that pit in our gut, we need to pay attention and test our possible actions using some of the above options.

Know that I wish for you to employ the wisest judgment as you lead. I pray that God showers wisdom on you as you ask, and that He surrounds you with the right people who will provide feedback and learnings from their past successes and failures. We don’t go it alone, and we get better as we lead together.




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