Will vs. Skill: Why So Many Leadership Challenges Are Misdiagnosed
By the middle of the school year, leadership challenges tend to feel familiar.
The same conversations resurface.
The same behaviors create tension.
The same questions linger: Why isn’t this working yet?
At this point, it’s easy to assume the issue is motivation—or worse, attitude.
But in early childhood, many challenges that look like a lack of will are actually gaps in skill.
And confusing the two can quietly undermine trust, morale, and growth—especially midyear, when energy is already stretched.
Why This Distinction Matters—Especially Midyear
When leaders interpret challenges as will-based, responses often sound like:
“They should know better by now.”
“We’ve talked about this already.”
“At some point, people just have to try harder.”
When challenges are skill-based, the response looks very different:
Clarifying expectations
Modeling the behavior
Practicing together
Providing feedback and support
Midyear is when this distinction matters most—because patterns are established, but growth is still possible.
Mislabeling a skill gap as a will problem often leads to frustration, disengagement, and unnecessary conflict. Correctly identifying the difference creates relief and forward movement.
What ‘Will’ Challenges Look Like
Will-related challenges are about choice and commitment.
They show up when someone:
Understands expectations but consistently chooses not to follow them
Has the skills but resists responsibility
Avoids accountability even with support
Undermines shared agreements
These situations require clear boundaries, accountability, and follow-through—not more training.
But true will issues are less common than we think.
What ‘Skill’ Challenges Look Like
Skill-related challenges are about capacity and support.
They show up when someone:
Wants to do well but struggles to follow through
Is unclear about expectations
Has never been taught or modeled the skill
Becomes dysregulated under pressure
Avoids difficult conversations because they don’t know how to navigate them
In these cases, accountability without support feels punitive—and often backfires.
Skill gaps call for clarity, practice, and relational safety.
Why Leaders Often Get This Wrong
Under stress, leaders are more likely to:
Default to assumptions
Attribute behavior to character instead of context
Move too quickly to correction
Midyear pressure amplifies this tendency. When time feels tight, leaders may skip curiosity and move straight to consequences.
But effective leadership pauses long enough to ask:
Is this a will issue—or a skill issue?
That question alone can shift the entire tone of a conversation.
A Midyear Leadership Checkpoint
Rather than adding another strategy, take a moment to reflect:
Where am I assuming resistance instead of checking for understanding?
Which recurring challenges might actually be skill gaps?
How does my interpretation shape how I respond?
What would change if I led with curiosity first?
This kind of reflection protects relationships and standards.
A Tool to Support This Reflection
To help you slow this distinction down in real time, I created a Personal Leadership Reflection Guide focused on identifying will vs. skill—especially in recurring or frustrating situations.
⭐ Download the Personal Leadership Reflection Guide
(Designed to support clarity, not judgment.)
You can use it privately, with a coach, or as a lens for preparing difficult conversations.
Where This Leads Next
Understanding will vs. skill is a turning point.
It sets the stage for:
clearer expectations
more effective accountability
stronger relational trust
fewer unnecessary power struggles
Next week, we’ll build on this foundation by exploring Vision & Purpose—and how clarity at this stage of the year can reconnect teams to why the work matters.