The 3 Questions I Ask Myself Before Making Any Major Leadership Decision


Leadership is filled with moments that demand clarity when emotions, expectations, and pressure are at their highest. Whether it’s a staffing change, a policy shift, or a decision that will ripple across an entire organization, leaders often find themselves at a crossroads where every path seems right and wrong at once.

Early in my career, I tried to find comfort in the idea that good decisions were clear-cut. I’ve since learned that most of the best ones rarely are. They live in the gray space, where empathy meets accountability, where listening meets leading, and where doing what is right is not always the same as doing what is easy.

Over the years, I’ve developed three simple questions that I ask myself before making any major decision. They serve as anchors that keep me grounded in purpose, people, and perspective when the winds of leadership start to shift.

1. Does this decision align with our purpose?

Every organization and every leader has a “why.” It’s what transforms management into leadership. Before making any significant decision, I pause and ask: Does this move us closer to our purpose, or does it pull us away?

When a decision aligns with purpose, it builds trust even if it is unpopular. People can respect a difficult choice when they understand it is grounded in something bigger than preference or convenience. Purpose keeps leaders from drifting toward reactionary leadership. It reminds us that direction matters as much as speed.

2. Will this decision strengthen or weaken relationships?

Empathetic leadership requires seeing people, truly seeing them, not as positions or titles but as individuals with hopes, fears, and potential. Every choice we make sends a message about what and who we value.

When I reflect on my own experiences, I have learned that the most lasting progress happens not through authority but through relationship. Before deciding, I ask: Will this decision build trust, connection, and collaboration, or will it fracture them?

That does not mean avoiding tough calls. It means approaching them with empathy, clarity, and respect, ensuring that even hard truths are delivered with dignity and that they encourage growth.

3. What legacy will this decision leave behind?

As leaders, we are constantly building a legacy, whether intentionally or not. I often picture a future version of our team, years down the road, looking back at this moment. What will they say we stood for? What did we model in how we handled challenge and change?

When I ask this question, it reframes my mindset from short-term problem-solving to long-term impact. It helps me slow down, breathe, and lead with both courage and care.

Leadership is not about being perfect. It is about being principled. And principles hold up best when we choose them before we are forced to.

Leading with Purpose, People, and Perspective

The next time you face a difficult decision, I encourage you to pause and ask yourself these three questions. They will not make leadership easy, but they will make it meaningful.

Purpose keeps you grounded.
Relationships keep you connected.
Legacy keeps you intentional.

And when those three align, you do not just make decisions. You make a difference.

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