550 Questions to Ask Senior Leadership

Ever wonder what’s going on in the heads of the big bosses at your company? You’re not alone! Knowing the right questions to ask senior leaders can give you a sneak peek into the future of your workplace, help you understand what matters most, and even guide your own career. 

So, let’s dive into some smart and fun questions you can ask to get the lowdown!

Questions About Company Vision

  1. What’s the company’s mission in simple terms?
  2. How has the vision changed since the company started?
  3. What are the most important values for the company?
  4. What’s the big goal for next year?
  5. How do you plan to grow the company?
  6. How do you want the company to be remembered?
  7. What makes our company different from competitors?
  8. What’s the most exciting project coming up?
  9. How does the company support innovation?
  10. How do we stay ahead of market trends?
  11. What’s the role of sustainability in our vision?
  12. How important is customer satisfaction?
  13. What legacy do you want to leave?
  14. How does the vision align with current projects?
  15. Are we looking to expand internationally?
  16. What kind of partnerships are we interested in?
  17. How do we adapt when things don’t go as planned?
  18. What’s the backup plan if we don’t meet our goals?
  19. How do we measure our progress?
  20. How can employees contribute to the vision?
  21. How often do we revisit the company’s vision?
  22. How do you communicate changes in vision?
  23. How important is social responsibility to us?
  24. What are the biggest challenges we face?
  25. How do we balance profit and purpose?
  26. What keeps you excited about coming to work?
  27. What’s your personal vision for the company?
  28. How do you keep the vision alive during tough times?

Questions About Decision-Making

  1. How do you make tough decisions?
  2. What’s the biggest mistake you’ve made?
  3. What did you learn from it?
  4. How do you gather information before making a decision?
  5. How much do you rely on your team’s input?
  6. What factors are most important when you make a decision?
  7. How do you deal with stress during decision-making?
  8. Can you share an example of a successful decision you’ve made?
  9. How often do you change your mind?
  10. How do you prioritize tasks and projects?
  11. How do you decide what to delegate?
  12. What’s the role of data in your decisions?
  13. Do you make decisions quickly or take your time?
  14. What do you do when you realize you made a wrong decision?
  15. How do you balance short-term gains and long-term goals?
  16. Do you take risks? 
  17. How do you evaluate them?
  18. How do you weigh advice from others?
  19. Do you consider employee feedback when making decisions?
  20. How do you handle uncertainty?
  21. What role does intuition play in your decisions?
  22. How do you keep everyone on the same page?
  23. How do you set project deadlines?
  24. How do you manage expectations?
  25. How important is consensus to you?
  26. What’s your approach to solving complex problems?
  27. How do you balance being fair and being effective?
  28. How do you assess the outcomes of your decisions?
  29. Do you ever involve clients or customers in decisions?
  30. How do you deal with decision-making fatigue?
  31. How do you know when to step back and let others decide?
  32. How do you evaluate the success of a decision?
  33. What’s your backup plan if a major project fails?
  34. Do you believe in having a Plan B for big decisions?
  35. How often do you consult with external advisors or experts?
  36. What do you wish you knew before making past decisions?
  37. Do you think failure is a part of the decision-making process?
  38. How do you manage pressure from stakeholders?
  39. What role does company culture play in your decisions?
  40. How do you ensure your decisions are ethical?
  41. Do you involve junior staff in any decision-making processes?
  42. How do you handle decisions that affect employee morale?
  43. What’s your approach to making time-sensitive decisions?
  44. How do you manage competing interests among departments?
  45. How transparent are you about your decision-making process?
  46. What’s the most difficult type of decision to make?
  47. What do you think about crowd-sourcing ideas before making a decision?
  48. How do you keep track of all the decisions that need to be made?
  49. How do you deal with the emotional aspects of decision-making?
  50. When a decision fails, how do you manage accountability?

Questions About Work Culture

  1. How would you describe our work culture?
  2. What qualities do you look for in a new hire?
  3. How do we deal with conflicts?
  4. How is teamwork encouraged here?
  5. How do you handle underperforming employees?
  6. How often do we have team-building events?
  7. What’s your approach to work-life balance?
  8. How does the company support employee well-being?
  9. What’s the best way to get recognized for good work?
  10. Is it okay to make mistakes here?
  11. What kind of training programs do we have?
  12. How do you handle office politics?
  13. Are employees encouraged to speak up?
  14. How do we celebrate successes?
  15. What’s the policy on remote work?
  16. How does the company support learning?
  17. What opportunities are there for career growth?
  18. How important is punctuality?
  19. Do we have any mentorship programs?
  20. How do we handle stress and burnout?
  21. Is there a focus on diversity and inclusion?
  22. How are promotions decided?
  23. What’s the role of humor in the workplace?
  24. How are new ideas encouraged?
  25. What’s the policy on taking breaks?
  26. How often do employees get feedback?
  27. How do you make sure everyone feels included?
  28. What’s the best part about working here?
  29. Are there opportunities for skill development?
  30. How do we maintain a positive work environment?
  31. How does the company support mental health?
  32. What role do values play in day-to-day operations?
  33. Is it easy to move between departments or roles?
  34. How does the company handle negative feedback?
  35. Do you think our work culture attracts top talent?
  36. What’s the policy on sabbaticals or long-term leaves?
  37. How do we keep everyone updated about what’s going on in the company?
  38. Are there volunteer opportunities through work?
  39. How do we stay connected when everyone is busy?
  40. Is there an open-door policy with senior leadership?
  41. How do we maintain culture when hiring a lot of people quickly?
  42. What steps are taken to ensure a harassment-free workplace?
  43. Do employees have a say in company policies?
  44. What are we doing to be more eco-friendly?
  45. How do we ensure fairness in workload distribution?
  46. How often do you, as a leader, interact with employees at all levels?
  47. What are the most common reasons employees stay long-term at the company?

Questions About Financial Stability And Growth

  1. How does the company plan for long-term financial stability?
  2. What’s the company’s strategy for revenue growth?
  3. How are we adapting to economic changes?
  4. What are our major sources of income?
  5. Are there any upcoming mergers or acquisitions?
  6. What financial risks is the company currently facing?
  7. How is the company preparing for potential downturns?
  8. Are there plans to diversify our product or service offerings?
  9. How much do we reinvest in the business versus taking profits?
  10. What’s the strategy for managing operational costs?
  11. How are we approaching debt management?
  12. What are our financial goals for the next year?
  13. How is the company handling investor relations?
  14. Are there any plans to go public or issue new stock?
  15. How do we compare financially to our competitors?
  16. What kind of financial training is available for employees?
  17. How transparent is the company about its financial health?
  18. How do we prioritize different areas of the business in terms of funding?
  19. What’s the policy on bonuses and raises?
  20. How is the budget set for each department?
  21. Are there any cost-cutting measures in place?
  22. What percentage of revenue goes into research and development?
  23. How do we plan to expand into new markets?
  24. Are there any significant capital investments planned?
  25. What’s the strategy for increasing shareholder value?
  26. How is success measured in financial terms?
  27. What are the biggest challenges to achieving our financial goals?
  28. Are there any planned changes in pricing strategies?
  29. How often do you review financial forecasts?
  30. What are we doing to improve our financial literacy as a company?
  31. How does the company deal with financial emergencies?
  32. What’s the plan for scaling the business?
  33. How are profits distributed among stakeholders?
  34. Are there any tax incentives or benefits we’re leveraging?
  35. Are we meeting the financial benchmarks set for this quarter or year?
  36. How does the company ensure financial compliance and ethics?
  37. What steps are taken to mitigate financial fraud or risks?
  38. What is the strategy for maintaining a healthy cash flow?
  39. Are there any plans to seek additional funding or investors?
  40. How is the financial team structured within the company?
  41. What are we doing to stay financially agile?
  42. What role do analytics and data play in financial planning?
  43. How often is the financial health of the company audited?
  44. How does the company adjust to fluctuations in the market?
  45. How do you prioritize spending on infrastructure versus human resources?
  46. Are we investing in sustainable or green initiatives?
  47. What’s the company’s strategy for managing currency and exchange rate risks?
  48. How do you keep employees informed about the company’s financial status?

Questions On Employee Growth And Development

  1. How does the company identify high-potential employees?
  2. What are the essential skills the company values for growth?
  3. How do you plan to develop leadership from within?
  4. Are there any upcoming training programs?
  5. How are career paths structured here?
  6. What’s the process for performance reviews?
  7. How does the company help employees reach their career goals?
  8. Do we have programs for continuous learning?
  9. How does the company support educational goals?
  10. What opportunities are there for cross-training?
  11. How are new skills integrated into work roles?
  12. Is there a framework for measuring employee growth?
  13. How often can employees expect to receive career advice?
  14. Do you have a policy for job rotations?
  15. What kind of support is there for newcomers?
  16. Are there clear steps for advancement?
  17. How does the company deal with skill gaps?
  18. Is peer-to-peer learning encouraged?
  19. Are there any partnerships with educational institutions?
  20. What kind of recognition can employees expect?
  21. Are there leadership development programs?
  22. How does the company support women and minorities in their career growth?
  23. Do you support employees who want to switch roles or departments?
  24. Are there options for part-time or flexible work to aid development?
  25. How can an employee contribute outside their job description?
  26. Do you encourage employees to attend industry events or workshops?
  27. How does the company help prepare employees for future industry changes?
  28. Are there any mentor-mentee programs?
  29. How do you measure the success of employee development programs?
  30. What are the biggest challenges facing employee growth?
  31. How do you support employees who want to gain leadership skills?
  32. Are there opportunities for employees to work on special projects?
  33. How do you accommodate different learning styles?
  34. What happens when an employee hits a career plateau?
  35. Is there a process for employees to share their career aspirations with managers?
  36. How do you ensure that promotions are fair and unbiased?
  37. Are there any programs for financial literacy or personal growth?
  38. What resources are available for self-directed learning?
  39. How do you keep employees motivated about their career progression?
  40. What’s the policy on job shadowing within the company?
  41. Are employees encouraged to pursue certifications?
  42. How do you keep track of each employee’s development journey?
  43. Is there a feedback loop for employees to comment on the effectiveness of growth programs?
  44. What career paths are most common within the company?
  45. How does the company support employees during role transitions?
  46. How important is networking within the company for career growth?
  47. Are employees encouraged to take on stretch assignments?
  48. How do you help employees prepare for retirement or career changes?

Questions On Team Collaboration

  1. How is collaboration built into our work process?
  2. What tools do we use to make team collaboration easier?
  3. How do we deal with conflicts in a team setting?
  4. How do teams across different departments collaborate?
  5. Are there any team rituals that help with bonding?
  6. What’s the process for giving and receiving feedback within a team?
  7. How do you ensure that all voices are heard in meetings?
  8. How flexible are team roles?
  9. How do you deal with teams that aren’t performing well?
  10. How are teams kept informed of company-wide goals and changes?
  11. How are collaborative efforts recognized and rewarded?
  12. How does leadership support team initiatives?
  13. Do teams have the autonomy to make decisions?
  14. How do you ensure the team stays aligned with the company’s mission?
  15. Are there channels for cross-team communication?
  16. What’s the approach to handling remote or distributed teams?
  17. How often should teams be meeting?
  18. How does the company handle team burnout?
  19. Are there best practices for project management?
  20. How does the company promote creative collaboration?
  21. How do you balance individual work vs. teamwork?
  22. What kind of challenges are given to teams to encourage growth?
  23. Are there opportunities for teams to work on self-initiated projects?
  24. What are some team success stories?
  25. How do you build a sense of trust within teams?
  26. How important is it for teams to celebrate small wins?
  27. Are there strategies for improving team morale?
  28. How do you integrate new members into established teams?
  29. How do you keep long-term projects exciting?
  30. What happens when a team misses a deadline?
  31. How do you handle communication gaps between teams?
  32. What’s the approach for sharing resources among teams?
  33. How do we ensure everyone is accountable in a team setting?
  34. How are high-performing teams recognized?
  35. Do teams have budgets for team-building activities?
  36. How does leadership ensure that teams are diverse?
  37. Are there guidelines for effective team meetings?
  38. How does the company support teams during high-pressure situations?
  39. Are there any systems in place for teams to share best practices?
  40. What role does transparency play in team collaboration?
  41. Are there any team training sessions that focus on collaboration?
  42. How do you rejuvenate a team that’s lost its spark?

Questions About Customer Satisfaction

  1. How is customer satisfaction measured?
  2. What’s the strategy for improving customer loyalty?
  3. How do we handle customer complaints?
  4. What are the most common points of praise from customers?
  5. What are our customer retention rates?
  6. How often do we update customer service training?
  7. What role does technology play in customer satisfaction?
  8. How do we ensure product or service quality?
  9. Are there plans to improve the customer experience?
  10. How are customer insights integrated into decision-making?
  11. What’s our approach to handling negative online reviews?
  12. How do we make sure our customer support is top-notch?
  13. How do we exceed customer expectations?
  14. What steps are being taken to personalize the customer experience?
  15. How do we keep track of customer preferences?
  16. Are there any loyalty programs or incentives in place?
  17. What’s our approach to customer feedback?
  18. How do you ensure consistency in customer interactions?
  19. How often do we review our customer satisfaction metrics?
  20. Do we have a process for following up with customers?
  21. Are there plans to expand customer support channels?
  22. What’s the policy for returns or refunds?
  23. How do we maintain a relationship with customers post-purchase?
  24. How do we handle customer data privacy?
  25. Are there collaborations with other companies to enhance customer satisfaction?
  26. What are the future plans for customer engagement?
  27. How do we manage crisis situations that affect customers?
  28. What role does social media play in customer satisfaction?
  29. Are there any plans to launch new customer-focused initiatives?
  30. How do we ensure employees are motivated to provide excellent customer service?

Questions About Innovation And Adaptability

  1. How does the company foster a culture of innovation?
  2. What are the latest technologies we’re adopting?
  3. How do we prioritize areas for innovation?
  4. Are there any projects focused solely on innovation?
  5. How are employees encouraged to think creatively?
  6. How is the company adapting to the digital landscape?
  7. What are we doing to remain agile in our operations?
  8. How are we leveraging data analytics for better decision-making?
  9. Are there innovation metrics that we track?
  10. What plans are in place for digital transformation?
  11. How are we incorporating customer feedback into innovation?
  12. How do we ensure that innovation aligns with the company’s goals?
  13. Are there any examples of recent innovations within the company?
  14. What role does cross-functional collaboration play in innovation?
  15. How are we encouraging experimentation and calculated risks?
  16. What is our strategy for staying ahead in technological advancements?
  17. How are we managing failures or setbacks in innovative projects?
  18. How do we keep up with changes in consumer behavior?
  19. What are we doing to stay ahead of emerging industry trends?
  20. How are we utilizing AI and automation?
  21. Are there opportunities for employees to be part of innovation committees or teams?
  22. What challenges do we face in implementing new ideas?
  23. How does the leadership support innovation initiatives?
  24. What’s the process for employees to submit their innovative ideas?
  25. How do we balance innovation with operational efficiency?
  26. Are there specific budgets allocated for innovation?
  27. How do we measure the ROI of our innovation efforts?
  28. What training is available to help employees build innovative skills?
  29. How are we innovating in our marketing strategies?
  30. Are there partnerships aimed specifically at fostering innovation?

Questions About Crisis Management

  1. How prepared is the company for a financial crisis?
  2. What is our plan for data breaches or cyberattacks?
  3. How does the company deal with sudden changes in regulations?
  4. What contingency plans are in place for supply chain disruptions?
  5. How are we prepared for natural disasters affecting operations?
  6. Are there crisis communication protocols in place?
  7. What is the process for escalating a crisis within the company?
  8. How often do we conduct crisis drills or simulations?
  9. How do we ensure the safety and well-being of employees during a crisis?
  10. What role do external partners play in crisis management?
  11. What are the immediate steps in case of a PR crisis?
  12. How do we manage information and decision-making during a crisis?
  13. What resources are allocated for crisis management?
  14. What is the backup plan for system failures?
  15. How do we handle a sudden drop in market demand?
  16. What is our plan to manage labor disputes or strikes?
  17. How do we safeguard against legal issues or lawsuits?
  18. Are there specific teams trained for various types of crises?
  19. How do we engage with the public and stakeholders during a crisis?
  20. How are we prepared for leadership transitions during a crisis?
  21. How do we keep shareholders informed during a crisis?
  22. What is the strategy for reputation management in times of crisis?
  23. How do we ensure continuity of services to customers during a crisis?
  24. Are there any lessons learned from previous crises?
  25. How do we manage the financial impact of a crisis?
  26. How do we deal with international crises affecting our global operations?
  27. What’s the plan to bring operations back to normal post-crisis?
  28. How do we assess the effectiveness of our crisis management?
  29. How are we updating our crisis plans based on current events?
  30. Are employees trained on what to do and whom to contact during different types of crises?

Questions About Diversity And Inclusion

  1. What is the company’s approach to diversity and inclusion?
  2. How diverse is our current workforce?
  3. What are the plans to recruit a more diverse talent pool?
  4. How do we support employees from underrepresented groups?
  5. How is diversity considered in promotions and career development?
  6. How are we educating employees about unconscious bias?
  7. What steps are being taken to create an inclusive work environment?
  8. How do we ensure pay equity across all groups?
  9. Are there any diversity and inclusion training programs?
  10. How are diversity and inclusion measured?
  11. Are there any diversity goals or benchmarks?
  12. How do we support the mental health of all employees?
  13. How does the company ensure a discrimination-free workplace?
  14. What is being done to make company events and activities inclusive?
  15. How do we handle issues of harassment or discrimination?
  16. Are there employee resource groups focused on diversity and inclusion?
  17. How do you keep employees accountable for maintaining an inclusive environment?
  18. How do we celebrate cultural diversity within the company?
  19. How are leaders trained to manage diverse teams?
  20. How does diversity impact our product or service offerings?
  21. Do we conduct regular surveys to measure employee sentiment on diversity?
  22. How do we accommodate employees with disabilities?
  23. Are there any partnerships with organizations promoting diversity?
  24. How is diversity and inclusion discussed in team meetings?
  25. Are we doing anything to encourage diversity in leadership roles?
  26. How do we address language and communication barriers within the workforce?
  27. What role does empathy play in our approach to diversity?
  28. What feedback have we received from employees on our diversity initiatives?
  29. What are the challenges the company faces in being more diverse and inclusive?

Questions About Overcoming Challenges

  1. What has been the biggest challenge for the company in the last year?
  2. How did we overcome unexpected obstacles in a recent project?
  3. What are the ongoing challenges in talent management?
  4. What is the company doing to deal with supply chain issues?
  5. How are we handling competitive pressure?
  6. What strategies are in place to tackle declining market share?
  7. Are there any issues with client retention, and how are we addressing them?
  8. What challenges are we facing in terms of employee engagement?
  9. How are we handling challenges related to remote work?
  10. Are there any internal communication challenges we’re working on?
  11. What steps are being taken to improve product quality?
  12. How are we dealing with the challenges of rapid growth?
  13. What are the hurdles in adapting to new technologies?
  14. Are there challenges related to regulatory compliance?
  15. How do we handle challenges in team collaboration?
  16. How are we dealing with data security concerns?
  17. What’s the biggest challenge in maintaining a positive company culture?
  18. Are there challenges in training and skills development?
  19. How do we overcome setbacks in meeting financial goals?
  20. What is the strategy to tackle high employee turnover?
  21. How are we managing customer service challenges?
  22. What are the main obstacles to meeting deadlines?
  23. How are we dealing with limitations in resources?
  24. What are the challenges in maintaining a work-life balance for employees?
  25. How are we addressing the challenge of outdated systems or software?
  26. Are there any reputational challenges we need to be aware of?
  27. How are we handling any ethical dilemmas or challenges?
  28. What are the difficulties in sustaining partnerships?
  29. Are there any challenges we face in hiring top talent?
  30. How do we ensure business continuity despite challenges?

Questions About Sustainability Efforts

  1. What is the company’s sustainability mission?
  2. How are we reducing our carbon footprint?
  3. What initiatives are in place to minimize waste?
  4. Are we using any renewable energy sources?
  5. How do we consider sustainability when choosing suppliers?
  6. How are employees educated about sustainability?
  7. What’s the plan for reducing water consumption?
  8. How do we incorporate sustainability into our products or services?
  9. Are there sustainability targets that the company aims to meet?
  10. How do we measure the impact of our sustainability efforts?
  11. Do we have any partnerships with environmental organizations?
  12. How does the company report on sustainability?
  13. What steps are taken to make our supply chain more sustainable?
  14. Are there any plans to make our offices or facilities greener?
  15. How do we engage customers in our sustainability efforts?
  16. Do we consider the environmental impact when making business decisions?
  17. What is the company doing to reduce plastic use?
  18. Are employees incentivized to participate in sustainability programs?
  19. Are there any sustainable practices in our manufacturing process?
  20. How do we keep track of our energy consumption?
  21. What policies are in place for responsible sourcing?
  22. Do we have any sustainability certifications?
  23. How are we reducing emissions in our operations?
  24. Are there opportunities for employees to volunteer in environmental initiatives?
  25. How do we promote eco-friendly commuting?
  26. What investments are we making in sustainable technologies?
  27. How do we collaborate with other businesses for sustainability?
  28. How do we offset our environmental impact?
  29. How do we ensure sustainability in long-term planning?
  30. What are the biggest challenges we face in becoming more sustainable?
  31. Are there any plans to collaborate with the government on sustainability initiatives?
  32. How are we engaging shareholders in our sustainability goals?
  33. Do we offer eco-friendly options for customers?
  34. How do we ensure that our marketing materials are sustainably produced?
  35. Are there any grants or awards that we’re aiming for in sustainability?
  36. How do we consider the life cycle of our products for sustainability?
  37. Do we have a dedicated team focused on sustainability efforts?
  38. How are we minimizing the use of hazardous materials in our operations?
  39. Are there any plans to update our facilities to be more energy-efficient?
  40. How do we support local communities in our sustainability efforts?
  41. What steps are we taking to protect biodiversity?
  42. Are we conducting any environmental impact assessments?
  43. How do we encourage suppliers to adhere to our sustainability standards?
  44. Are there any sustainability-related perks for employees, like incentives for biking to work?
  45. How are we ensuring that our remote work policies are also sustainable?
  46. Are we working on any projects to restore natural habitats?
  47. How are we reducing noise and light pollution from our operations?
  48. What are we doing to make our packaging more sustainable?

Strategic Questions To Ask Senior Leadership

  1. What is the company’s top priority for the next year?
  2. How are we adapting to changes in the industry landscape?
  3. What’s the plan for staying ahead of our competitors?
  4. How are we leveraging technology to meet our strategic goals?
  5. How often does the senior leadership team meet to discuss strategy?
  6. What’s our approach to entering new markets?
  7. How are we innovating within the company?
  8. What metrics are most important for tracking strategic success?
  9. Are there any strategic partnerships we’re considering?
  10. How do we ensure our business model remains sustainable?
  11. What’s our backup plan if the current strategy doesn’t work?
  12. How does the company handle strategic risks?
  13. How are employees aligned with the company’s overall strategy?
  14. What are we doing to improve brand reputation and recognition?
  15. How does strategy vary for different departments or teams?
  16. How are new technologies affecting our business strategy?
  17. What are the upcoming milestones for the company?
  18. How do we prioritize projects and initiatives?
  19. Are there any plans for rebranding or shifting the company focus?
  20. What opportunities are we not taking advantage of?
  21. How do we plan to scale operations efficiently?
  22. How do we maintain quality while pursuing rapid growth?
  23. What’s our exit strategy in case of business failure?
  24. How do we address gaps in our product or service offerings?
  25. How do we ensure our system is flexible enough to adapt to changes?
  26. What role does data analysis play in strategy development?
  27. How does the company plan to deal with potential crises?
  28. Are there opportunities for employee involvement in strategic planning?
  29. How does corporate social responsibility factor into our strategy?
  30. How are we planning for future workforce needs?
  31. Are there any mergers or acquisitions in the pipeline?
  32. How do we safeguard intellectual property and other assets?
  33. What is the company doing to stay socially and environmentally responsible?
  34. How do we assess the effectiveness of our current strategy?
  35. What steps are being taken to improve operational efficiency?
  36. How is the company exploring new revenue streams?
  37. Are there any plans to go public or change the company’s ownership structure?
  38. Are there any opportunities for leveraging AI or machine learning in our operations?
  39. How do we stay aligned with our core values while executing our strategy?

Fun Questions To Ask Senior Leadership

  1. What’s the most interesting book you’ve read recently?
  2. What’s your go-to coffee order?
  3. What’s your favorite office snack?
  4. If you could travel anywhere right now, where would it be?
  5. What hobby helps you relax and unwind?
  6. Who’s your all-time favorite movie character?
  7. If you weren’t doing this job, what would you be doing?
  8. What’s your favorite sports team?
  9. What’s your most memorable career moment?
  10. What’s the most interesting place you’ve visited?
  11. Do you have any hidden talents?
  12. What’s your favorite type of music?
  13. What’s one interesting fact about you that few people know?
  14. How do you typically spend your weekends?
  15. What was your first job ever?
  16. If you could have dinner with any historical figure, who would it be?
  17. What’s your favorite season and why?
  18. Do you have any pets?
  19. What’s your favorite way to give back to the community?
  20. Do you have a favorite quote or saying that inspires you?
  21. What’s your favorite family tradition?
  22. What’s one thing on your bucket list?
  23. Do you have a go-to karaoke song?
  24. What’s your favorite genre of movies?
  25. Coffee or tea?
  26. What’s your favorite board game or video game?
  27. If you could have any superpower, what would it be?
  28. What’s your comfort food?
  29. How do you stay up-to-date with industry news and trends?
  30. What was the last concert or live event you attended?
  31. If you were a teacher, what subject would you teach?
  32. Do you have a signature dance move?
  33. What TV show are you currently binge-watching?
  34. What’s your favorite type of exercise or physical activity?
  35. What’s your favorite local restaurant?
  36. Are you an early bird or a night owl?
  37. What’s the most adventurous thing you’ve ever done?
  38. Do you like to cook? If so, what’s your best dish?
  39. What’s your favorite way to unwind after a long workday?
  40. If you could meet any fictional character, who would it be?
  41. What’s your favorite podcast?
  42. Do you have any favorite motivational speakers or influencers?
  43. What’s the last movie that made you cry?
  44. What was the last thing that made you laugh out loud?
  45. If you were stranded on a deserted island, what three things would you want with you?
  46. What’s the most challenging DIY project you’ve ever taken on?
  47. What’s your go-to order at a fast-food restaurant?
  48. If you could instantly become an expert in something, what would it be?
  49. Do you have any “guilty pleasure” TV shows or movies?
  50. What’s your most used app on your phone?
  51. What’s your go-to joke?

Frequently Asked Questions

What is senior leadership?

Senior leadership refers to the top executives and decision-makers in an organization. This often includes roles like the CEO (Chief Executive Officer), COO (Chief Operating Officer), CFO (Chief Financial Officer), and other high-ranking positions. They’re the folks responsible for guiding the company and making big decisions.

What skills are essential for senior leadership roles?

  1. Strategic thinking: Ability to plan for the future and see the big picture.
  2. Communication: Clear and effective communication skills, both written and verbal.
  3. Leadership: The ability to guide and motivate teams.
  4. Financial literacy: Understanding of budgets, financial reports, and financial planning.

How do you interview a senior leader?

Preparation is key. Do thorough research on the leader’s career, the company, and the industry. Know what you want to achieve with the interview.

  • Focused questions: Craft questions that delve into their experience, leadership style, and vision for the company.
  • Logistics: Arrange a suitable venue and time, ensuring all tech equipment is functioning for recording if necessary.
  • Be professional and courteous: Maintain a respectful tone and thank them for their time and insights.

How do you build trust with senior leadership?

Be transparent in your dealings. Honesty is often the first step to trust.

  • Deliver results: Consistently meet or exceed expectations to demonstrate your reliability.
  • Be proactive: Don’t wait for instructions; show initiative in solving problems or improving processes.
  • Seek feedback: Regularly ask for and act upon feedback, showing you’re committed to continuous improvement and value their opinion.


Knowing what to ask senior leadership can open doors you never even knew existed. It’s more than just getting the inside scoop; it’s about connecting in a meaningful way. So, don’t hold back. Take these questions and make your next sit-down with the bosses one for the books!

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Robby Salveron

Robby is a multimedia editor at UpJourney with a journalism and communications background.

When she's not working, Robby transforms into an introverted art lover who indulges in her love for sports, learning new things, and sipping her favorite soda. She also enjoys unwinding with feel-good movies, books, and video games. She's also a proud pet parent to her beloved dog, Dustin.