The Six Questions Every Leader Should Ask

Dear Leaders,

Great leaders don’t just make decisions—they think critically. In today’s fast-moving world, asking the right questions can be a game-changer. It’s not about having all the answers but knowing how to frame the challenge. What, Where, When, Who, How, and Why—six simple yet powerful questions that bring clarity, focus, and direction. Let’s break them down with real-world examples from both military and corporate leadership.

1. What? – Define the Challenge

Start with what. What’s really going on here? What are we trying to achieve? What obstacles are in our way? Think of this as setting your GPS—without a destination, how do you know where to go? The clearer the what, the easier it is to chart a path forward.

A military commander stepping into a battlefield doesn’t react blindly. They assess: What’s the terrain? What’s the enemy’s strength? What’s our best strategy? A CEO facing declining sales does the same: What’s driving this trend? What’s our competitive edge? What must change to regain momentum? Defining the challenge is half the battle.

2. Where? – Spot the Impact

Where is this issue occurring? Where are the biggest risks and opportunities? Where should we focus our efforts? Understanding the where helps leaders pinpoint problems and direct resources where they matter most.

For a general leading troops, the where is critical—Where is the enemy strongest? Where do we have an advantage? Where can we position ourselves for success? In the corporate world, leaders ask where to find the highest-growth markets, the best talent pools, or areas of inefficiency that need fixing.

3. When? – Timing is Everything

When did this issue arise? When does action need to be taken? When is the right time to pivot? Timing can be the difference between success and failure. Acting too soon can lead to hasty mistakes; waiting too long can mean lost opportunities.

Military leaders rely on when to launch operations at the perfect moment—timing air support, troop movements, and counterstrikes. Business leaders do the same, whether it's deciding when to enter a new market, launch a product, or respond to a PR crisis. Are you acting at the right time, or are you reacting to pressure?

4. Who? – Get the Right People Involved

Who is affected by this? Who has the expertise to help? Who is accountable? Leadership is never a solo act—it’s about bringing the right people together.

A military leader must know who to trust with specific tasks—Who leads the assault? Who handles negotiations? Who provides logistical support? Likewise, in business, knowing who to involve can mean the difference between a struggling team and a high-performing one. Who is missing from the conversation? Who will challenge our assumptions? Getting the right people in the room is often the first step to success.

5. How? – Find the Best Approach

How do we solve this? How do we make it happen? How do we measure success? This question moves leaders from strategy to action.

A general planning an offensive must think through how to execute it efficiently—How do we minimize risk? How do we sustain momentum? How do we ensure clear communication? In business, the same logic applies: How do we optimize our supply chain? How do we implement this strategy effectively? How do we measure progress? The right how ensures execution matches vision.

6. Why? – The Heart of Leadership

Why does this matter? Why are we doing it this way? Why not try something different? This is where leaders dig deep.

In the military, why fuels motivation—soldiers don’t fight just because they’re ordered to, but because they believe in the mission. Why is this mission worth risking lives for? Why is this strategy the best choice? In the corporate world, employees don’t just work for a paycheck—they commit when they see the purpose behind their work. Why should our customers care? Why do we exist as an organization beyond profits? A strong why creates alignment, energy, and resilience, ensuring that people push forward even when challenges arise.

Why These Questions Matter for Your Organization

When leaders and teams make these six questions a habit, the results are profound:

• Sharper decision-making by looking at challenges from every angle.
• Stronger collaboration by ensuring the right people are involved.
• Smarter problem-solving by identifying root causes instead of just symptoms.
• Greater agility to navigate uncertainty with confidence.
• Higher engagement as people feel connected to a shared purpose.

The best leaders don’t have all the answers, but they know how to ask the right questions.

The next time you face a challenge, take a step back and ask: What, Where, When, Who, How, and Why?

These six questions have shaped history’s greatest military and corporate leaders, and they can transform your leadership too.

-So, what’s a leadership challenge you’re facing right now? Which of these six questions will help you see it differently?

Yours Sincerely,

Lt Cdr Sadhanaa Giri

Founder LEADerSHIP DecK

Author -Emotions Decoded