People often mistake humility of manner with humility of character. As a result, we often encourage people all the more to try to build a humble manner without dealing with the deeper issues of humble character. After years of observing a person though, it sometimes becomes clear that a humble external manner may, in reality, have nothing to do with the humility of his heart and character.
Some people who seem slightly arrogant in their manner may be deeply humble. Others with the more humble external manner can be seething with pride.
Some people who seem slightly arrogant in their manner may be deeply humble. Others with the more humble external manner can be seething with pride. This happens often enough that we shouldn’t think of these two states as outliers. I’m not trying to destroy the rule by alerting you to a remote exception. These two examples are actually quite common.
Defining “humility” and the internal state of “self-forgetfulness” will have to be saved for another time. The question I want to address is: “How do I know if someone is really humble?” I suggest two checks.
Do people of substance and character become more or less loyal to this person over time?
When a person is not humble at the core, that reality will surface over time in spite of a humble manner. People will be attracted to those people at first but lose confidence in them over time.
When a person is slightly arrogant in his external manner but is deeply humble at heart and full of integrity, he will win increasing loyalty from people of character and substance, often to the point of fierce loyalty. Look for this. It can be one of the most revealing tests of humility in possible leaders that you could follow.
Are they paying the traditional costs of pride in their life?
Those costs come in many forms. Few and shallow friendships. A lack of equal colleagues. A grumbling distrust in the lower followers of the hierarchy. Obviously un-dealt with major areas of sin to which they seem oblivious. A lack of accurate self-knowledge. Can he or she be with people for a long time and not really know them? Do people resist sharing deeply with her because she doesn’t really listen? Maybe people aren’t candid with him, or they tend to flatter him. They don’t like being the butt of jokes, even funny ones. They don’t have a deep and trembling reference for God, so their relationship with God lacks intimacy. And so on.
If you know what to look for, real pride is obvious. Recognizing it is an integral part of mature Christian discernment.
These two tests for real humility are exceedingly difficult for someone who internally is proud to pass. If you know what to look for, real pride is obvious. Recognizing it is an integral part of mature Christian discernment. That is not to say that pride doesn’t affect us all. Pride is at work in everyone to a certain extent. But it can be subjected consistently to the control of the Spirit in line with Gospel truths which make us self-forgetful. Pride can only work energetically when the lie of our own self-importance is given root.
The right medicine for the right disease
Many people will also say that you can test inner pride by how someone responds to criticism. This is true only to the extent to which fear is also pride. If you suspect the pride of superiority, a defensive response to criticism can be a false positive. If a person responds defensively to criticism, it may not be because of the pride of superiority, but from a pride of inferiority, what we call fear.
This distinction is important, because these two kinds of pride require different remedies and should be treated in different ways. One needs to resubmit self in repentance to the supremacy of Christ in putting us down. The other looks to his supremacy which lifts us up. In both cases, Christ frees us from self-importance and releases us into the courageous power of self-forgetfulness. If you mistake the one kind of pride for the other, you may very well issue a rebuke when encouragement is required, thereby deepening the disease of fear by confirming that a fear of man is warranted.
How good are you at discerning pride? In yourself? In the leaders you follow and work with?
How good are you at helping people treat the problems of self-importance with the message of the gospel? How vigilant are you about this yourself?
Do you see fear as a kind of negative pride, or something to which you are fundamentally entitled and for which others are responsible?
Engage & Equip 
“Do people of substance and character become more or less loyal to this person over time?”
I see this positively playing out with our Elders. They are humble men who love God, love Jesus’ church, and sacrificially serve. As I worked with them, I continued to be more and more drawn to follow them because at their core, they know God is God, and they are not.
As to this question… “How good are you at discerning pride? In yourself? In the leaders you follow and work with?” … I think it can be difficult at times to put your finger on when it’s pride. Usually there is a feeling that something is just not lining up or is not right about a person – but I’ll have a hard time figuring out what it is. After reading this, the “something” may be pride issues.
“If you know what to look for, real pride is obvious. Recognizing it is an integral part of mature Christian discernment.” – This is true, yet I think most Christians fear the idea of claiming to have any kind of discernment because they themselves don’t want to come across as prideful – proclaiming to have discernment is to see something as right or wrong, and this is often viewed as a lack of humility in the culture (even church culture) that we live in. Even the most mature Christians will often keep quiet when it comes to making these types of judgment calls. I think this lack of confidence and trust in the Spirit’s leading is what keeps the church body from making bold strides to do what the Lord calls us to do. Often times we see a problem or potential problem but would rather keep our thoughts to ourselves instead of bringing up potential conflict.