Leading With Powerful Questions: A 3 Part Series
Do You Give Answers or Lead With Powerful Questions?
One of the more popular coaching themes with my clients is helping them make the mindset shift from thinking their job is to have all the answers to creating higher leadership influence by simply asking more powerful questions.
Two of my four “Coaching Corners” are Leadership and Influence and so I find myself talking about these frameworks in many different ways on podcasts, panels, and in my 1:1’s.
During one of those conversations, I coined the phrase “Perfection is a Prison” when I was describing my own leadership journey and how this need to be perfect, especially as a CFO, significantly limited my ability to lead and to influence.
For at least the first 10 years in my career, I strongly believed that my superpower was having all the answers. I worked countless hours to ensure I had the details to any potential question from anyone so I could provide all the answers. For a time, I even carried around binders and tabs of my analysis, spreadsheets, and notes to ensure I had all the answers with me. I also thought this “looked cool” and was very CFO-like! Turns out, this leadership behavior was actually my kryptonite.
How was having all the answers my kryptonite? Here are just a few reasons:
Answers limit engagement. Being the answer man put me on an island and disconnected me from rolling up my sleeves and problem-solving with my executive teammates. Questions helped me to connect and create engagement with my colleagues. They got to know me better and began trusting me more.
Answers tend to create polarization and debate: right/wrong, good/bad. Questions created alignment and connected the focus to the best ideas winning.
Answers create dependence and bottlenecks on decisions. This was especially true when I didn’t have the answer right away. Questions helped me define and refine the “real question,” so I could focus on learning, delegation, and ultimately ownership from others.
So I worked hard to constantly remind myself to ask more questions, listen more, and talk/tell less. The more I showed up in this way, the more connected I felt to my peers, my teams, my CEO, and my Board. The more questions I asked, especially when I already knew the answers, the more engagement, learning, leadership influence, and impact I created.
For the next 20 years of my career, I saw this new superpower reflected in all the great leaders I was privileged to work with. Great leaders didn’t just dictate strategy. They didn’t just demand results. They used powerful questions to unlock critical insights, build trust, align the team, and create an ownership culture. They engaged their teams by rarely giving answers but mostly by asking more powerful questions.
So, it’s time for another 3-part series. I’ve been coaching “Powerful Questions” over the last several years and have been trying to condense my coaching down to just 3 posts. I hope to change your own mindset, to give you more superpowers, and to lock away the kryptonite that weakens us all.
Part 1: Leading With Powerful Questions
Why the best leaders lead with questions, not answers.
How great questions create great teams who trust each other, solve problems together, and create innovative solutions.
A framework for shifting from player to coach.
Part 2: The Power of Leadership Questions – What to Ask and When to Ask It
The three types of leadership questions: Relational, Prioritization, and Strategic.
How to use a Leadership Listening Tour to gather insights and build influence.
Real-world examples of leadership questions that create clarity and focus.
Part 3: Leading With Why – Connecting Strategy, Structure, and Execution
Why leaders must relentlessly reinforce why priorities matter and what they are trying to achieve.
How to connect strategy to systems and structures, and execution through great questions. “How will we achieve it?”
The role of “Why?” as one of the most powerful leadership tools constantly reinforcing, “Why does it matter?”.
Throughout this series, I’ll be providing you with actual questions to use and insights from my own experiences on the leadership teams at Netflix, Mozilla-Firefox, and Intuit and also provide other “best of” source materials for you.
I’ll summarize with a few powerful questions before we dive into Part 1:
“Are you a leader looking to shift from being the bottleneck answer person to engaging your teams with more delegation and ownership?”
“Are you tired of being swamped all the time and wish you could shift from telling to asking, guiding, and coaching?”
The goal of my 3-part series is to give you a starting toolkit with key frameworks, actual question-based playbooks, and a way to reframe how you think about your own leadership and influence for the next several years of your career.
Let’s dive in.
PART 1: LEADING WITH POWERFUL QUESTIONS
I’ll bet the following sounds familiar. You are part of a high-growth startup trying to scale fast. Every day is a feeling of being overwhelmed. As Wonka says, “Too much to do and too little time.”
People are constantly coming to you with questions and problems but rarely with recommendations, answers, or solutions. You are trapped in your leadership role and feel like, “I can do it faster and better than anyone else, and I’m the only one who really knows how to do these things.”
Now imagine that one day a mentor or coach comes to you and asks you a very simple question:
“Why do you think your team keeps coming to you for all the answers?”
After some reflection, your coach asks you what the opposite of your team coming to you with all the questions and needs for decisions would look like.
Your coach continues asking you questions.
In this new ideal state, “How is your team operating and behaving?”
You and your coach do a shared notes document or whiteboard the answers. It’s then that you realize you’ve just created Step 1 of your “Future State Roadmap.” If that’s the desired future state, you start asking yourself, “How am I going to get there?”.
You likely get stuck again until your coach asks you,
“What is one easy step you could take tomorrow to start you on this journey?”.
Your coach and you land on a simple leadership shift of leading with more powerful questions. Your coach led you by example. All your coach did was ask you a series of questions. You did the work by answering them and taking action.
You begin to realize that always being the answer person will never get you from here to “there.” The next day, you start in on Step 1 and simply start asking more questions. You remember to pinch yourself and bite your tongue whenever you start falling back on the bad habit of giving answers.
6 months later, after changing your own leadership behaviors, you show up at a coaching session and share how much more time you have, how your team is more autonomous and innovative, how you are struggling with being a bit bored, and how you are wondering where you can make more impact.
The coach then asks a few more questions:
“Have you tried leading with powerful questions leadership with your peers on your executive team, with your CEO?
“Have you asked your direct team members to start leading this way with their own teams?”
Cook’s Coaching Axiom: Think of leadership and influence like being a great coach. A coach doesn’t run onto the field to play the game. Instead, they ask the right questions during practice to help players develop strategies, skills, and confidence.
Bottom Line 1: This shift—from leading with answers to leading with questions—is a hallmark of great leadership. It’s not about relinquishing control; it’s about creating space for others to expand and grow their own leadership and their own influence.
Bottom Line 2: Leadership isn’t about being the smartest person in the room. The smartest person in the room IS THE ROOM! Leadership is about creating an environment where the collective intelligence of a team is amplified—and powerful questions are the key.
Always and Never: Always Remember and Never Forget…
Questions create engagement.
Questions create a problem-solving connection and allow others to learn and for you to coach with much greater influence.
The right questions invite creative solutions, challenge assumptions, and ultimately unlock innovation.
Leading with powerful questions begins to create an “ownership culture” where people discover answers for themselves and their teams.
Qualities of Great Questions:
Specific and Intentional
Non-Judgemental
Future-Oriented
Help People to Think Differently
Provide Focus and Clarity
Simplify Decision-Making and Prioritization
Sample Powerful Questions:
I promised some sample powerful questions. Feel free to copy/paste these into a Notion workspace, a Doc, or even write them down in your little moleskin notebook for future reference. I’ll provide many more sample questions in Part 2’s post (next week) when I go deeper on “What To Ask” and “When To Ask It”.
“Is there a better approach to this problem?”
“What do you think is the root cause of this problem?”
“What would great look like in this situation?”
“What are the assumptions you are using?”
“Are these assumptions based on data or opinion?”
“If we could solve only one problem this quarter, what should it be?”
“How do we define success in 6 months? 12 months?”
“How would we define failure?”
“Does this decision align with our Vision or our 1st Principles?”
“What’s the biggest challenge you’re facing right now, and how can I help?”
“What is the true severity of the risk we are worried about?”
“What is the probability of that severe outcome happening?”
“Are there potential risks here we haven’t surfaced?”
“What would make our customers ecstatic?”
Instead of: “We’re losing users because the onboarding flow is broken. Here’s how I think we should fix it.”
Ask: “Our onboarding flow has a 20% drop-off rate. What factors do you think are driving this? Have you personally been through our onboarding experience? What were your pain points, and do you have suggestions for improving our onboarding experience?”. Don’t let the person answering off the hook with closed door “No’s” or “I don’t know’s.” If you get this, then ask them to come back to you in a few days with answers to your questions!
Instead of: “Why did this fail?”
Ask: “What did we learn from this, and how do we course correct?”
Instead of: “Why haven’t we fixed this yet?”
Ask: “What’s the first step we can take to improve this?”
BEWARE THE INNER ROOMMATE INSIDE YOUR HEAD!
Do you hear that inner roommate voice inside your head? Are they pounding your brain with their classic negative mantras:
“You don’t have time to lead this way!” You must lock that roommate away since every answer you give quickly creates more time pressure for you, while every question you ask builds long-term capability, capacity, and confidence.
“I’m the only one who knows how to do this, I’m the only one with the experience and the answers.” That may be true today, but it builds very weak teams and weak teams are the hallmark of weak leaders. Start being okay with your team only getting 80% of the answer or the solution right and spend your experience and knowledge guiding them on the last 20%. Perfection is a prison after all and nobody ever grew or improved (including you) by being perfect all the time. Imperfect answers are coaching opportunities and can spark more learning, more innovative ideas, and deeper discussions.
“Hey! When you are asked a question, you are supposed to give an answer and shut up! If you answer a question with a question it will frustrate the hell out of people or worse make you look unprepared or evasive.” This is only true if it’s the right question with all the right assumptions and in those cases, yes, answer the question. BUT ALWAYS PAUSE before answering and ask that roommate in your head:
“Is this the right question? Is there a better question?
“Is the question based on the proper assumptions using 1st Principle Thinking?”
Important Note: In my 30 years of doing this, I’ve found that only 20% of questions asked of you are “the right questions”. 80% of the questions need refinement. They are either not the right question or are grounded with improper assumptions or a shared set of facts and data. Worst of all are the questions that are stated as facts but are based on the opinions of the person asking the question. Examples: “Isn’t it true?”, “Don’t you agree…?”
The Courage to Ask Hard Questions
Great leaders know that the right questions are oftentimes the hardest to ask. True leadership is not staying silent with the most difficult of questions.
Many of these questions challenge existing processes, confront uncomfortable truths, or force teams to face difficult trade-offs. But they’re necessary for creating trust, confidence, and a shared belief of success inside a team… vs the opposite of staying silent with festering FUD - fear, uncertainty, and doubt.
“What would it look like if we started over from scratch?”
“What’s the one assumption we’re making that could be wrong?”
“If we fail, what will be the reason?”
“Do we have the right company strategy?”
“How well do we really know our customers?”
Call-to-Action: Start Leading with Questions Today
In your next meeting, try this simple 3-step exercise:
Pause a full 10 seconds before giving an answer. This will seem like an eternity to you… but it will feel like you are deeply thinking and contemplating a great answer for them.
Ask one powerful question instead of giving an answer. Start creating your own powerful questions list - there are literally hundreds once you start practicing.
Then, ask another powerful question. Take notice of what is happening in the room.
Closing:
Why Leading With Questions Makes You A Better Leader and Leads To Better Outcomes:
Great leadership isn’t about having all the answers—it’s about cultivating a culture where curiosity, collaboration, and critical thinking thrive. By leading with questions, you empower your team, foster innovation, and build trust. And in the process, you free yourself from being the bottleneck, allowing you to focus on what matters most.
Great Leaders Ask the Right Questions
The ability to ask the right questions is one of the most underappreciated yet powerful skills a leader can develop. It's not just about curiosity—it's about precision, timing, and intent. Great leaders use questions strategically to guide their teams, uncover opportunities, and navigate challenges. They understand that questions are not merely tools for gathering information; they are catalysts for innovation, trust, and clarity.
Why Questions Matter in Leadership?
Leaders are often seen as the ones with answers, but truly transformative leaders flip this dynamic. They realize that their role isn’t to have all the answers—it’s to bring out the best thinking in others.
Bookmark this Series. Up Next Week: Part 2 - The Power of Leadership Questions: Start a Listening Tour
