Questions for Leaders (book answers)

  • How to influence without authority?

  • How to voice your successes without bragging?

  • How to hold yourself to a standard but also not always put yourself down when you fail

  • How to read the room and pull comments out of people

    • cognizant and conscious

  • How do you deal with teaching/training “the same thing” over and over to new folks without getting demoralized?

  • How do you handle your emotions? (you team is always watching/feeding off your attitude)

  • How do you approach “chairing” or leading a meeting? how much do you try to be knowledgeable before entering?

  • When you are in a meeting or seeking input from your team (as a leader), what has been the best way to get honesty/candor from your team?

  • How do you manage the people/relationships who don’t report to you (without upsetting other branches of the organization)?

  • How do you build self-ownership in others/individuals?

    • Not just “delegating work” to them but they begin to take initiative on their projects and driving them the best way they can

  • How do you communicate your vision/goals effectively

  • How to build the environment for success?

  • How to apologize properly/successfully?

  • How do you lead someone who doesn’t want to follow/be a part of the team?

    • how to give feedback that sticks?

  • How do you learn to say no?

  • How did you learn to embrace risk-taking? or how do you approach decision-making with unclear answers?

  • How do you maintain strong relationships with folks over the long term (through career changes/moves)?

  • What makes a “good leader”?

  • How do you balance holding onto good people vs advancing their careers/training new folks?

  • How do you view the difference between managers and leaders?

  • how do you develop the people below you?

    • to succeed in their current job and to be successful in the future

  • What is your strategy/methodology for task or projects management?

  • What is your template for long-range vision/strategy planning?

  • How do you approach and handle difficult conversations with a team member?

  • Is there a specific situation where you went about dealing with Union folks wrong and got burned?

    • What did you learn about how to approach these situations?

Questions for Leaders about myself

  • How could I do X better? - I want to go from “good enough” to great

  • Where do you see my strengths?

  • What do you see as some of my blind spots and how can I improve?

  • How can I get feedback from people (above, below, around) me?

  • How am I viewed by leadership/folks at your level?

  • What opportunities/risks do you see for me?

  • How to improve my self-awareness? How can I find my issues before they become bigger?

Personal Questions for Leaders (stories)

  • What gets you out of bed/here? how do you stay motivated

  • How do you view your career?

    • Looking back? Looking forward?

  • What’s something you wish you knew early in your career?

    • What about common advice you think people should ignore?

  • What’s something you learned working at other sites/roles that you are using in your current spot?

  • What’s the next opportunity you’re looking forward to?

  • Was there a time you messed up and felt like you’d failed? How did you bounce back?

  • How did you learn to embrace risk-taking?

  • Tell me about a pivotal career decision you made, how did you weigh everything?

  • Which leadership skills were the most difficult to develop?

  • How do you view the industry? What drew you into it? and where do you see it going?

  • How do you keep up with the workload? how do you organize your time and mental to get everything done?

  • What level of the org did you feel the most power to change the “culture” in a positive way

  • How do you think about leading a group or your own personal leadership?

  • Who’s someone I should be building relationships that I might be overlooking?

  • Who do you go to when you’re needing direction/advice?

  • When did you overcome your “imposter syndrome”? but more likely how do you handle feeling it still?

  • How do you view your own leadership of your team (good/bad/effective?) What’s your approach to it?

  • How do you define your leadership style, and how has it evolved?

  • How do you think about the culture/atmosphere around you/your team? What do you try to do about fostering it?

  • Is there a historic figure you wish you could meet/talk to?

  • What is a talent you admire in other individuals? (in work/outside of work, maybe specific examples)

  • Who do you look to as a great leader (inside or outside of the company)? What about them do you admire/want to imitate? Is there a mentor you really grew under?

  • What is success to you?

some from Tim Ferriss

  • What’s a belief/behavior that change your life?

  • What’s the best small purchase that improved your life? (<100$)

  • How has a failure, or apparent failure, set you up for later success? is there a favorite failure you’re willing to share?

  • What’s been the best investment of your time/money?

  • What’s the book you come back to or enjoyed the most?

    • what about podcasts?

  • What is an unusual habit or an absurd thing that you love?

  • When you feel overwhelmed or unfocused, what do you do? how do you center yourself?