Why Most Leaders Fail the “Why Test" (and Don’t Even Know It)

As leaders, we’re constantly making decisions. Some are small. Some are seismic. Whether we’re approving a budget line, launching a new initiative, or shifting priorities mid-year, each decision has a ripple effect that touches our people, our culture, and our results. Yet too often, we make these choices without fully considering whether they align with the vision we’ve committed to pursue.

This is where the Vision Filter comes in.

The Vision Filter is a deliberate pause before action. It’s the practice of running every choice - yes, every single one - through your “Why Test": Why are we doing this? Why now? Why is this the best path toward the vision we’ve committed to?

If the answers keep you connected to your “why,” you move forward. If they don’t, you stop and reevaluate.

Why This Matters for Sustainable Leadership

In my Sustainable Leadership framework, the first pillar is Clarity. It focuses on knowing what matters, where you’re going, and why you’re going there. Without clarity, leaders and organizations drift. Priorities shift not because they should, but because they can. Time, energy, and resources get poured into well-intentioned actions that don’t actually advance the mission.

The Why Test strengthens clarity by forcing leaders to stay anchored to their purpose. It protects against distraction and “shiny object syndrome.” It creates consistency in decision-making so that staff, students, and stakeholders know what to expect and trust the direction you’re leading.

Sustainable leadership is about playing the long game. That means every decision needs to be more than a quick fix or a feel-good moment. It must be intentional, strategic, and aligned.

The Cost of Skipping the Why Test

We’ve all seen leaders, and maybe even been those leaders, who bypass the Why Test. A new program launches mid-year because it looked great at another school. A policy changes overnight because of one customer complaint. A big investment is made without measuring its actual impact.

When the Why Test is missing, three predictable outcomes occur:

1. Initiative Overload – Too many disconnected programs and projects cause burnout, confusion, and diminished results.

2. Inconsistent Culture – People aren’t sure what the “real” priorities are, so they default to doing what feels urgent rather than what’s important.

3. Erosion of Trust – Staff and stakeholders lose confidence when leaders’ actions don’t seem to match the stated vision.

   
   

The truth is, you can’t lead sustainably if you’re constantly reacting rather than intentionally acting.

How to Apply the Vision Filter with the Why Test

The Vision Filter works best when it’s baked into your daily leadership habits. Here’s how to put it into practice:

1. Start With a Crystal-Clear Vision

If you can’t articulate your vision in a few sentences, it’s too vague. Your vision should describe not just what you do, but why you do it and what success looks like. This clarity makes it easier to measure alignment.

2. Run Every Decision Through the Why Test

Before committing to anything new, or deciding whether to keep something in place, ask:

• Why does this decision matter to our mission?

• Why is this the right next step right now?

• Why will this choice create the biggest impact with the resources we have?

  
  

If you can’t answer clearly and confidently, pause.

3. Consider the Opportunity Cost

Even good ideas may not be right for right now. Every yes requires a no somewhere else. The Why Test helps you weigh whether this is the best use of your finite time, budget, and capacity.

4. Involve Your Team

Invite trusted team members to challenge whether a decision passes the Why Test. Healthy debate ensures you’re not just justifying a choice because it feels good in the moment.

5. Document and Review

Keep a record of how major decisions passed the Why Test. This builds accountability and gives you a tool to review whether those choices delivered as intended.

A Real-World Example

Several years ago, I was part of a leadership team faced with a tempting opportunity: a well-funded district initiative that promised significant resources for our school if we joined a pilot program. The catch? The program’s focus didn’t match the priorities we’d already established for the year.

It would have been easy to say yes. After all, who turns down resources? But when we ran it through the Why Test, the misalignment was clear. Implementing the program would pull our staff in a different direction, disrupt current progress, and likely erode trust.

We declined the offer. And while it wasn’t the popular choice at the time, it was the right one for sustaining our focus and honoring the commitments we’d already made to our community.

Overcoming Common Challenges

Even with the best intentions, applying the Vision Filter and the Why Test can be tough. Here are three common hurdles and how to address them:

Pressure to Please – Leaders often feel obligated to say yes to higher-ups, board members, or influential stakeholders. The key is to reframe the conversation: a “no” isn’t rejection, it’s protection of the vision everyone agreed to pursue.

Fear of Missing Out – It’s easy to think that if you don’t act now, you’ll lose an opportunity forever. In reality, the best opportunities are those that fit your vision and timing. If it’s meant to be, it will resurface when it makes sense.

Unclear Vision – If decisions are hard to filter, it may mean the vision needs refining. In this case, the work isn’t just to apply the filter. It’s to sharpen what you’re filtering for.

Why This Is Non-Negotiable for Sustainable Leadership

Without clarity, you can’t lead with confidence. Without a vision filter, you can’t ensure that your clarity translates into consistent, purposeful action.

In the Clarity pillar of the Sustainable Leadership framework, the Vision Filter and the Why Test is more than a tool - it’s a safeguard. It keeps your leadership intentional, prevents the slow drift into misalignment, and ensures that every decision, big or small, reinforces the future you’ve committed to building.

When leaders embrace this discipline, they create stability in uncertain times, consistency in shifting conditions, and trust in the face of change.

Your Next Step

The next time you’re faced with a decision - whether it’s approving a new initiative, responding to a problem, or considering a shift in priorities - pause and ask:

Why are we doing this? Why now? Why is this the best step toward our vision?

If you can’t answer with conviction, hold off. Refocus. Realign. Because sustainable leadership isn’t about doing more. It’s about doing what matters most, over time, without burning yourself or your team out.

If you’re ready to go deeper into tools like the Vision Filter and learn how to strengthen Clarity, Capacity, and Care in your leadership, I invite you to:

• Pick up a copy of my book on Sustainable Leadership to explore the full framework in depth.

• Join our Skool community, where leaders like you are having real conversations, sharing strategies, and building the habits that make leadership sustainable for the long haul.

  
  

Your vision is your compass. The Why Test keeps you on course. Use it, protect it, and lead with purpose.