*“How to”* questions focus on tactical, surface-level solutions rather than deep transformation. These questions imply that there’s a specific formula or step-by-step guide to solving complex leadership challenges. leadership isn’t about following a manual—it’s about shifting perspectives, developing emotional intelligence, and leading with authenticity in situations that are unpredictable and nuanced.
*Here’s why “how” questions miss the mark:*
*They Assume There’s One Right Way* : When you ask “how,” you’re looking for a fixed answer or a quick-fix solution. leadership is deeply personal. What works for one leader might not work for another because each leader’s context, personality, and challenges are unique. Asking “how” oversimplifies this complexity.
*They Avoid Self-Reflection:* True leadership growth comes from looking inward, identifying your values, strengths, blind spots, and mindset shifts. “How” questions bypass this inner exploration by seeking an external solution. For example, instead of asking, “How do I motivate my team?” a more powerful question is, “What is it about my leadership that may not be inspiring my team right now?”
*They Can Create Dependency:* “How” questions often reinforce the idea that someone else has all the answers, which can make a leader dependent on someone else’s guidance rather than trusting their own judgment and instincts. There is no handbook of leadership, even though everyone will give you theirs when you ask “how” questions.
*They Close Off Possibility:* Leadership is about navigating ambiguity and complexity. Asking “how” limits thinking to one route or solution – to what is already known or achieved in the past. It keeps us in the realm of incremental improvements rather than opening the door to disruptive, exponential growth.
In contrast, open-ended questions like “What’s possible?” or “What’s standing in my way?” expand thinking and open up a world of possibilities. aThese types of questions lead you into the realm of “what you do not know that you do not even know.” In leadership, this is the fertile ground where breakthroughs happen.
*They Focus on the Symptoms, Not the Root Cause:* “How” questions often address the immediate problem rather than exploring the deeper issue that’s causing it. If a CEO asks, “How do I improve team communication?” they can instead explore, “What beliefs or behaviors are currently hindering communication in the team?” This leads to more lasting change.
Many of the world’s greatest innovators, like Steve Jobs or Elon Musk, didn’t ask “how.” They asked questions like, “What if?” or “Why not?” These questions break the mold and allow creativity and visionary thinking to thrive.
Examples
Here’s a table that contrasts weak “how” questions with more powerful, expansive questions that unlock greater possibilities:
| Weak “How” Questions | Powerful, Expansive Questions |
|---|---|
| How can I grow my business by 10% this year? | What’s possible if I remove all current limits on my business growth? |
| How do I get my team to meet their goals? | What would it take for my team to consistently exceed their goals? |
| How can I solve this problem? | What am I not seeing that could transform this situation entirely? |
| How do I become a better leader? | Who do I need to become to lead in ways that create exponential impact? |
| How do I scale my company? | What new markets or opportunities could 10x my company’s growth? |
| How can I motivate my team? | What kind of leader do I need to be to inspire my team to self-motivate? |
| How do I manage this challenge? | What’s standing in my way, and how can I leverage it as an advantage? |
| How can I improve my product? | What could I create that revolutionizes my industry? |
| How do I get more customers? | What untapped audience could I serve that I haven’t even considered? |
| How do I increase my efficiency? | What systemic changes would allow us to operate on a whole new level? |
| How do I handle this conflict? | What deeper issue or opportunity is this conflict revealing? |
| How can I make time for everything? | What truly matters, and how can I focus on that to maximize impact? |
| How do I manage my workload? | What am I doing that no longer serves me or the bigger vision? |
| How do I deal with competition? | What new paradigm can I create that makes competition irrelevant? |
| How do I prepare for next quarter’s results? | What bold moves can I make now that would disrupt next quarter’s expectations? |
This contrast shows that while weak “how” questions tend to focus on specific, immediate tasks or problems, powerful questions invite broader thinking, challenge existing assumptions, and open up pathways to exponential growth.
Who Not How
The phrase “Who Not How” is a powerful mindset shift popularized by Dan Sullivan. This concept emphasizes the importance of focusing on who can help you achieve your goals rather than getting bogged down in the how of accomplishing them.
” How ” questions can indeed become a trap in certain situations, particularly when they focus too much on the process rather than the people involved.
“How” questions often lead to:
The Trap of “How” Questions
- Overthinking : They can cause people to get bogged down in details and processes.
- Limiting creativity : By focusing on the “how,” we may miss innovative solutions.
- Overwhelm : Complex “how” questions can paralyze action due to perceived difficulty.
- Individual burden : They can imply that the person being asked must solve the problem alone.
The Limitations of “How” Questions
“How” questions can hinder leadership and growth in several ways:
- Promotes Micromanagement : “How” questions often focus on specific processes or methods, which can lead leaders to become overly involved in day-to-day operations.
- Limits Creativity : By focusing on the “how,” leaders may inadvertently restrict innovative thinking and problem-solving approaches.
- Creates Dependency : When leaders constantly provide answers to “how” questions, it can create a culture of dependency where team members always look to the leader for solutions.
- Narrows Perspective : “How” questions tend to focus on immediate solutions rather than encouraging broader, strategic thinking
The Power of “Who” Questions
In contrast, “who” questions can unlock unlimited growth for leaders:
- Encourages Delegation : By asking “who” questions, leaders shift their focus from processes to people, promoting effective delegation and empowerment.
- Fosters Collaboration : “Who” questions naturally involve others in problem-solving, leading to more diverse perspectives and innovative solutions.
- Develops Team Members : By identifying the right people for tasks, leaders can provide growth opportunities and develop their team’s skills.
- Expands Networks : “Who” questions encourage leaders to look beyond their immediate circle, potentially uncovering valuable connections and resources.
- Promotes Strategic Thinking : Instead of getting bogged down in details, “who” questions allow leaders to focus on high-level strategy and vision
Examples
| Weak “How” Questions | Powerful “Who” Questions |
|---|---|
| How can I grow my business by 10% this year? | Who can help me achieve 10x growth this year? |
| How do I build a marketing strategy? | Who is the best marketing strategist I can partner with? |
| How can I scale my team without burnout? | Who can help me design a scalable and sustainable team structure? |
| How do I create more time in my schedule? | Who can I delegate tasks to that free up my time for higher value activities? |
| How can I improve my leadership skills? | Who can mentor me to become a more effective leader? |
| How do I solve this technical problem? | Who has the expertise to solve this technical problem quickly? |
| How can I motivate my team? | Who can provide insights on how to inspire and lead my team effectively? |
| How do I manage all these projects? | Who can take over managing these projects so I can focus on the big picture? |
| How do I get more sales leads? | Who is the best at generating high-quality leads that I can work with? |
| How can I raise capital for my business? | Who can connect me with investors or help me with fundraising? |
| How do I handle conflict in my team? | Who can help mediate and resolve conflicts effectively within my team? |
| How can I improve my product design? | Who is a product design expert that I can collaborate with? |
| How do I expand into new markets? | Who has experience in these markets that can guide our expansion? |
| How do I improve team communication? | Who is the right person to help implement better communication systems? |
| How can I innovate in my industry? | Who are the top innovators that I can learn from or partner with? |
| How do I manage my time better? | Who can help streamline my schedule and manage non-essential tasks for me? |
This table illustrates how focusing on “who” instead of “how” allows leaders to leverage the strengths of others, enabling faster growth, more efficiency, and bigger breakthroughs.