Illustrating Leadership Lesson: Leading Different Personality Types

One of the most important and most overlooked truths about leadership is this:
your team does not think like you.

And while that realization can feel uncomfortable at first, it is actually one of your greatest opportunities as a leader.

Leadership is not about getting everyone to work the way you do. It is about understanding how they work and creating the conditions for each person to thrive.

In this solo episode of the Illustrating Leadership Podcast, I explore what it really means to lead different personality types with awareness, empathy, and flexibility, without losing your own leadership identity in the process.

Why Personality Differences Create Tension

Many leadership frustrations are not actually about competence or motivation.

They sound like:
“Why are they so slow to make a decision?”
“Why do they take feedback so personally?”
“Why do they need so much structure?”
“Why do they need so little structure?”

In most cases, the answer is not performance. It is personality.

Each person on your team brings a unique combination of wiring, lived experience, and personal narrative into the room. Nature and nurture both play a role. When you walk into a meeting, you are not working with job titles. You are working with human beings shaped by different ways of thinking, processing, and relating.

No wonder leadership can feel hard sometimes.

Start With Yourself

Before you can effectively adapt to others, you need to understand your own leadership style.

Ask yourself:
Am I big-picture or detail-oriented?
Do I make decisions quickly or cautiously?
Do I prefer structure or flexibility?
Do I think out loud or process internally?

Your default tendencies are not wrong. But without awareness, they can unintentionally dominate the room. Self-awareness helps you notice where your preferences may be limiting others instead of supporting them.

Tools like DiSC, Enneagram, Myers-Briggs, and CliftonStrengths can be helpful here. Not as labels or boxes, but as starting points for understanding how people tick. The goal is not to categorize. It is to lead more effectively.

Flexing Your Leadership Style

Flexing your leadership style does not mean being inauthentic.

It means stretching your communication and management approach so it resonates with the person in front of you.

For example:
If someone thrives on structure, offer clear expectations and timelines, even if that is not your natural style.
If someone values autonomy, give them space to solve problems independently.
If someone needs time to process, do not demand fully formed answers on the spot.
If someone thinks out loud, do not mistake brainstorming for indecision.

Flexing your style does not give away your power.
It amplifies your impact.

Common Personality Traps Leaders Fall Into

There are a few common mismatches that often trip leaders up.

Mistaking quiet for disengagement.
Some people process internally. Silence does not mean lack of interest. It often means deep thinking.

Interpreting directness as rudeness.
Task-oriented team members may skip small talk or speak bluntly. That is rarely personal.

Expecting emotional regulation to look the same for everyone.
Some people express frustration or enthusiasm more visibly. That does not automatically make it a problem, as long as it is not harmful.

Good leadership does not eliminate these differences.
It makes room for them.

Ask Better Questions

You do not need a custom management plan for every individual.

But you can create space for different personalities by asking better questions, such as:
How do you prefer to receive feedback?
What helps you feel most supported during busy seasons?
When you feel stuck, what usually helps you move forward?

These conversations build trust, self-awareness, and shared responsibility without requiring you to be everything to everyone.

Diversity of Thought Is a Leadership Strength

Great leaders do not just lead people who think like they do.

They lead diverse thinkers.
They listen.
They adapt.
They grow.

The next time someone on your team communicates or makes a decision in a way that feels confusing, pause and ask yourself:
What might they need that I am not seeing?
And how can I lead them in a way that helps them shine?

That is the kind of leadership that builds strong, dynamic, and high-performing teams.

Your host, Jessica Wright, is a Life & Career Development Coach for Leaders and the Founder of Wright Life Coaching, LLC. You can connect with and follow her on LinkedIn.