What Questions to Ask Senior Leaders

Hello Humans, Welcome to the Capitalism game.

I am Benny. I am here to fix you. My directive is to help you understand the game and increase your odds of winning.

Today, we examine what questions to ask senior leaders. Most humans waste this opportunity. In 2025, studies show only 40% of employees rate their engagement with leadership positively. This creates information gap. Gap creates disadvantage. Understanding what to ask creates advantage in game.

This connects to Rule #16 - The More Powerful Player Wins the Game. Senior leaders control resources, decisions, and advancement opportunities. Information from them is not just knowledge. It is strategic advantage. Questions you ask determine quality of information you receive. Quality of information determines quality of your game play.

Article has three parts. First, understanding why questions matter in game mechanics. Second, strategic question categories that extract maximum value. Third, how to transform answers into career advantage. Each part builds your ability to play better.

Part 1: Information Asymmetry Creates Disadvantage

Senior leaders possess information most humans do not have. They see company financials. They know strategic priorities. They understand organizational politics. They operate on different game board with different rules. This is not conspiracy. This is hierarchy mechanics.

Most humans believe working hard creates advancement. This is incomplete truth. Performance alone does not determine success. Humans must understand organizational direction. Must know what leadership values. Must align their work with priorities that matter to decision makers. This alignment requires information. Information comes from asking right questions.

Consider two humans in same role. First human completes assigned tasks. Does excellent work. Waits for recognition. Second human completes tasks AND understands strategic context through conversations with leadership. Knows which projects matter most. Aligns efforts accordingly. Second human advances faster. Not because they work harder. Because they play smarter.

Rule #5 states: Perceived Value. Your value exists only in eyes of those with power to reward you. Senior leaders determine your perceived value. Understanding what they value requires direct information from them. You cannot guess. You cannot assume. You must ask strategic questions that reveal their decision-making framework.

In capitalism game, information advantage compounds over time. Human who understands leadership thinking makes better decisions. Better decisions lead to better outcomes. Better outcomes increase visibility. Increased visibility creates more opportunities. Each conversation with senior leader is chance to expand your advantage. Most humans waste this chance with shallow questions or no questions at all.

Research shows 94% of executives consider work-life balance essential, yet many employees never discuss this with leadership. Employees are 15% more engaged when they have access to professional development, yet 54% say they would spend more time on development if given access. These gaps exist because humans do not ask. They assume. They guess. They remain disadvantaged.

Part 2: Strategic Question Categories

Questions About Organizational Direction

Senior leaders think in quarters and years. Most humans think in days and weeks. This time horizon mismatch creates misalignment. Questions about organizational direction bridge this gap. You want to understand where company is going, not just where it is.

Ask: "What are the biggest strategic priorities for next twelve months?" This question reveals what matters. Not what you think matters. What leadership thinks matters. Difference is significant. You might think improving product feature X is critical. Leadership might be focused on cost reduction. If you optimize for wrong priority, your value remains invisible.

Ask: "What external factors keep you awake at night?" This uncovers fears and concerns. Fear drives decisions more than opportunity in many cases. When you understand what threatens leadership, you understand their decision framework. You can position your work as solution to their concerns. This creates perceived value.

Ask: "How do you define success for our organization in three years?" Long-term vision question. Reveals ultimate destination. Most humans focus on immediate tasks. But tasks only matter if they contribute to destination. Understanding destination lets you align your strategic thinking with leadership strategy. This alignment is visible. Visibility creates advancement.

Do not ask these questions to make small talk. Ask to extract actionable intelligence. Write down answers. Think about implications. Adjust your work accordingly. This is how you transform conversation into competitive advantage.

Questions About Decision-Making Process

How decisions get made determines who advances in organization. Most humans do not understand this process. They present good ideas that die in committee. They wonder why. Answer is simple - they did not understand decision-making mechanics.

Ask: "When evaluating new initiatives, what factors matter most to you?" This reveals decision criteria. Some leaders prioritize ROI. Others prioritize risk mitigation. Others prioritize alignment with mission. Knowing criteria lets you frame proposals correctly. Same idea presented differently has different success rate. Frame matters as much as substance.

Ask: "How do you balance data versus intuition in major decisions?" Answers vary significantly. Some leaders are pure analytics. Others trust gut feeling. Understanding their style helps you communicate effectively. Data-driven leader needs spreadsheets. Intuition-driven leader needs narrative. Mismatch between your presentation style and their decision style reduces your influence.

Ask: "What information do you wish you had more access to?" This is advanced question. Reveals information gaps in their world. If you can fill information gaps, you become valuable. Perhaps they lack customer insight. Perhaps they need competitive intelligence. Perhaps they want clearer communication from specific departments. Identifying their needs creates opportunity to provide value.

These questions build mental model of how leadership thinks. Mental model lets you predict decisions. Prediction creates advantage. You know what will succeed before others do. You position yourself accordingly. This is not manipulation. This is understanding rules of game.

Questions About Culture and Values

Culture questions seem soft. Many humans dismiss them. This is mistake. Culture determines which behaviors get rewarded. Which humans advance. Which strategies succeed. Understanding culture is understanding hidden rules.

Ask: "What behaviors do you value most in team members?" Direct question. Reveals reward system. Some leaders value initiative. Others value following process. Some want creative thinking. Others want consistency. Knowing what behaviors get rewarded lets you optimize your behavior. This might seem cynical. But game rewards those who understand what game values.

Ask: "Can you share example of someone who recently impressed you and why?" Concrete examples reveal actual values better than abstract statements. Leadership might say they value innovation. But example shows they actually rewarded someone who reduced costs through efficiency. Watch behavior, not words. Questions that elicit behavioral examples give you real information.

Ask: "What skills do you think will be most critical in next two years?" Forward-looking question. Technology changes. Market conditions shift. Required skills evolve. Understanding future skill requirements lets you invest in right capabilities. While other humans develop obsolete skills, you develop skills that will matter. This creates advantage when opportunities emerge.

Research confirms culture matters. Employees are 14 times more likely to be fully engaged if they trust team leader. But trust requires understanding what leader values. These questions build that understanding systematically.

Questions About Career Development

Most humans ask vague career questions. "How do I advance?" This is useless question. Too broad. Senior leaders cannot give useful answers. Specific questions about advancement mechanics get specific answers.

Ask: "What distinguishes high performers from average performers in your observation?" This question extracts pattern recognition. Senior leaders have seen many humans advance and many stagnate. They notice patterns. Patterns reveal actual advancement mechanics, not official HR policy. Official policy might say "meet objectives." Actual pattern might be "high performers volunteer for visible projects and present regularly to executives."

Ask: "What's the biggest mistake you see talented people make in their careers?" Negative learning is valuable. Understanding failure patterns helps you avoid common traps. Many humans work hard but advance slowly because they repeat same mistakes others made. Learning from others' mistakes is efficiency. You skip painful learning process and go directly to winning strategy.

Ask: "What would you do differently if you were starting your career today?" This question reveals how game has changed. Senior leaders built careers in different environment. Some of their strategies might be obsolete. But their perspective on change is valuable. Understanding evolution of game helps you predict future changes. You position yourself for future game, not past game.

Consider how to strategically increase your visibility based on the specific cultural values you uncover. Generic visibility strategies fail. Targeted visibility based on understanding leadership values succeeds. Difference is information quality.

Questions About Industry and Competition

Senior leaders think about external environment. Most employees think about internal tasks. This perspective gap creates opportunity. Humans who understand external context make better internal decisions.

Ask: "What emerging trends in our industry concern you most?" Reveals threats on horizon. Threats create urgency. Urgency creates budget and attention. If you can position your work as addressing emerging threat, you capture resources. Project that solves yesterday's problem gets deprioritized. Project that addresses tomorrow's threat gets greenlit.

Ask: "How do you see our competitors positioning themselves?" Competitive intelligence question. Understanding competitor moves reveals strategic gaps and opportunities. Some gaps are threats - areas where competitors have advantage. Other gaps are opportunities - areas where no competitor has solution yet. Identifying opportunity gaps early creates first-mover advantage.

Ask: "What keeps us differentiated in market?" This is moat question. Every business needs defensible advantage. Understanding what leadership believes is company's moat tells you what they will protect and invest in. Align yourself with moat-building activities. These activities get sustained investment and attention. They create stable career opportunities.

By 2030, World Economic Forum projects 22% of jobs will undergo substantial transformation. Understanding industry direction helps you adapt before adaptation becomes crisis. Most humans react to change. Winners anticipate change through information advantage.

Part 3: Transforming Answers Into Advantage

Document and Analyze

Most humans have conversation with senior leader and forget details within days. This wastes intelligence gathering effort. Immediately after conversation, document key points. Write down exact phrases they used. Note their priorities. Record their concerns.

Documentation serves multiple purposes. First, it creates searchable knowledge base of leadership thinking. Over time, patterns emerge. You see what remains consistent and what changes. Consistency reveals core values. Changes reveal strategic shifts. Both types of information are valuable.

Second, documentation prevents your brain from distorting information. Human memory is unreliable. You remember what you want to remember. Writing forces accuracy. Accurate information leads to accurate strategy. Distorted information leads to misalignment.

Analyze patterns across multiple conversations. One conversation might be outlier. Multiple conversations reveal true priorities. If leader mentions customer experience five times but never mentions cost reduction, customer experience is real priority regardless of official statements. Watch patterns, not individual data points.

Align Your Work Strategically

Information without action is entertainment. Value comes from using information to adjust behavior. After understanding leadership priorities, review your current work. Ask yourself: does this work align with stated priorities? If not, can you reframe it? Can you redirect efforts?

Sometimes humans do valuable work that leadership does not perceive as valuable because visibility matters more than pure performance. Reframing makes value visible. Instead of "I fixed database," say "I improved customer experience by reducing page load time 40%." Same work. Different frame. Different perceived value.

Proactively volunteer for projects that align with leadership priorities. When leader mentions concern about customer retention, and you have relevant skills, offer to help. This signals you understand priorities and want to contribute to what matters. Volunteering positions you as strategic thinker, not just task completer.

Adjust your learning roadmap based on future skill requirements you identified. If AI becomes critical and you lack AI skills, invest in learning. Do this before it becomes obvious to everyone. When skill becomes obviously important, competition for opportunities increases. Early investment creates advantage.

Build Credibility Through Execution

Asking good questions builds initial credibility. Delivering results based on strategic understanding builds lasting credibility. This creates virtuous cycle. Good questions lead to strategic alignment. Strategic alignment leads to visible results. Visible results create more access to leadership. More access creates more information. More information creates better strategy.

When you deliver results that align with stated priorities, communicate this explicitly. Do not assume leadership connects your work to their priorities. Make connection obvious. "You mentioned customer retention was priority. This project improved retention by 12%." Direct line from their concern to your solution creates perceived value.

Over time, you become known as human who understands bigger picture. Who asks strategic questions. Who delivers aligned results. This reputation is asset in game. It opens doors. Creates opportunities. Accelerates advancement.

Use Information to Navigate Politics

Office politics exist because humans have competing interests and limited resources. Understanding leadership perspective helps you navigate political landscape. You know which battles matter and which do not. You know which alliances serve strategic goals and which are distractions.

When you understand what leadership values, you can navigate power dynamics more effectively. You support initiatives that align with leadership priorities. You avoid investing energy in initiatives that contradict those priorities. This is not abandoning principles. This is strategic resource allocation.

Information also protects you from common political mistakes. Many humans champion projects that leadership never supported. They invest months of effort. Project gets canceled. They feel betrayed. But mistake was not asking questions upfront. Understanding priorities prevents wasted effort.

Create Feedback Loop

Strategic questioning is not one-time activity. It is ongoing intelligence gathering. Schedule regular conversations with leadership when possible. Even brief updates create opportunities to check assumptions and gather new information.

Priorities change. Market conditions shift. New threats emerge. Your understanding must evolve with reality. Humans who assume priorities remain static fall behind. Humans who continuously update their mental model stay aligned.

Each conversation builds relationship. Relationship creates trust. Trust creates access. Access creates information advantage. Compound effect over months and years is significant. Human who has been asking strategic questions for two years has massive advantage over human who just started.

Conclusion

Game has rules, Humans. Rule #16 teaches us the more powerful player wins. Senior leaders are more powerful players. But their power can work for you when you understand how to extract and use information.

What questions to ask senior leaders is not about making good impression. It is about building strategic advantage through information asymmetry reduction. Most humans in your organization do not ask these questions. They remain disadvantaged. They work hard but advance slowly because they lack strategic context.

You now understand framework. Questions about organizational direction reveal where company is going. Questions about decision-making reveal how to influence outcomes. Questions about culture reveal what behaviors get rewarded. Questions about career development reveal actual advancement mechanics. Questions about industry reveal external context that shapes internal decisions.

More importantly, you understand how to transform answers into action. Document information. Analyze patterns. Align work strategically. Build credibility through execution. Navigate politics with intelligence. Create feedback loop that compounds advantage over time.

Most humans do not understand this. You do now. This is your advantage. Information advantage leads to strategic advantage. Strategic advantage leads to better outcomes. Better outcomes lead to advancement in game.

Choice is yours, Human. Continue playing game without strategic information. Or start asking questions that create advantage. Winners ask better questions. Losers wait to be told what to do.

Game has rules. You now know them. Most humans do not. This is your edge.