10 Questions Great Bosses Regularly Ask Their People

Great leaders ask great questions.

Too often leaders think they are the smartest person in the room, so they are quick to offer advice, give direction, and share their perspectives on how things should be done. Most leaders do this instinctively, because after all, it’s the type of behavior that caused them to rise through the ranks. But when you become the boss, your role shifts from being the one to make things happen to empowering your team members to get the job done. You can’t do that if you’re always dominating the conversation. You need to draw out the best thinking and performance from your team members, and the way to do that is through asking great questions.

If you’re not sure what questions to ask or where to start, give these a try:

1. What are you excited about in your job? The answer to this question allows you to understand what motivates and excites your team member. When you know the kinds of tasks, activities, or projects that energize your team member, it allows you to guide them toward current and future opportunities that are similar in nature. It results in team members playing to their strengths and interests which results in greater engagement and performance.

2. Why do you stay? This is perhaps the most important question that leaders never ask. Do you know why each of your team members chooses to stay with your organization? If you did, would it change the way you relate to them? I would hope so. Knowing the answer to this question will drive the way you structure job opportunities for those employees you want to retain. For employees who have “quit and stayed,” the answer to this question will give you insight into why they are choosing to remain stuck in their current position (usually fear of change, they’re comfortable, or they’re beholden to their current salary and lifestyle).

3. What might lure you away? This is the sister question to number 2. If you’re like most leaders, you probably don’t know the answer to either one. If you knew what would lure away your top performers, you would know what you need to do to get them to stay. Asking this question sends the signal to your team members that you know they are a valuable contributor and you’re not blind to opportunities they may have elsewhere. It lets them know you are committed to doing what you can to keep them happy and engaged with your organization.

4. What would we need to do to get you to stay? Don’t wait until your employee resigns and has one foot out the door to ask this question. By then it’s too little, too late. Ask this question on a regular basis as part of longer term career development discussions. Similar to questions 2 and 3, this question allows team members to express the things they think about their employment experience that they would never say to you in any other context. Just the very fact that the leader is willing to acknowledge the employee has the potential for other opportunities and cares about retaining him/her, causes the employee to feel valued and respected, which inspires loyalty and commitment.

5. What new skills would you like to learn? Most people want to keep learning and growing in their jobs, and in fact, this desire often ranks higher in surveys as being more important than getting a raise or other forms of recognition. Many managers are afraid to ask this question because they aren’t sure if they can deliver anything in return. Even the most mundane, clear-cut jobs usually have some room for creativity or improvement, but it takes a bit of work for the leader to think outside the box to uncover those opportunities. One good place for leaders to start is to examine their own jobs. What could you delegate or share with your team members that would allow them to learn something new?

6. Are you being __________enough for now? (challenged, recognized, trained, given feedback, etc.) You’re probably starting to see a theme to these questions by now, aren’t you? Along with the others, this question allows you to probe into areas of performance that wouldn’t normally surface in your typical 1on1 conversations. We all fall victim to tyranny of the urgent and tend to focus on the immediate tasks and deadlines we face. We have to train ourselves to periodically step back from the daily grind and have discussions with team members about the bigger picture issues that define their employee experience.

7. What is making your job harder than it needs to be? The people who usually know best about what’s working and not working in the business are those on the front-lines of the action. Ask your team members about the things that are holding them back from performing better or experiencing more joy in their work, and then get to work on addressing those issues. Leaders can often make a greater impact on employee performance by removing obstacles that hinder productivity, rather than spending time on trying to create new systems, processes, or skill development programs.

8. What are your ideas on how we can improve things around here? Do you like it when your boss asks your opinion? Of course you do! It makes you feel like the boss respects your knowledge and expertise, and values your perspective on issues. Then why don’t you do the same with your employees? It’s a truism that no one of us is as smart as all of us. The power of a team is unleashed when the leader leverages the collective wisdom and experience of all its members.

9. What should I be doing more of? Unlike the other questions, this one is about you, the leader. It opens the door for you to hear from the employee about what you’re doing right, and obviously, the things you should keep doing. You may not see much value in asking this question because you believe you already have a good sense of the answer, but I encourage you to ask it anyway. You may be surprised that some of the behaviors you consider insignificant are actually the things that carry the most weight with your team members (like asking them about their weekend, how their kids are doing, taking an interest in them personally).

10. What should I be doing less of? It’s important you know this critical principle about leadership — most people won’t speak truth to power unless they believe it is safe and acceptable to do so. As a leader, it’s incumbent upon you to foster a culture of trust and safety that allows your team to give you honest and unvarnished feedback. You do that by explicitly giving permission to your team to give you feedback, and most importantly, receiving it with openness and a willingness to modify your behavior. Too many leaders only receive feedback from their bosses during the annual performance review, and although it can be helpful, it’s often from a limited and biased perspective. Great bosses seek feedback from where it matters most — their team.

Being a great boss isn’t easy. If it was, the world would be full of them. Instead of relying on the natural tendency to solely focus on the here-and-now in your interactions with team members, take a step back and consider the bigger picture. Start incorporating some of these questions into your 1on1 meetings and watch for the positive impact it will have on your team members’ level of engagement and productivity.

24 Comments on “10 Questions Great Bosses Regularly Ask Their People

  1. If I would be the employee asked I would wonder that I don’t get paid for these kind of decisions …

    • Your statement above seems to indicate to me that you are a boss, who thinks employees are doing a job…or an employee who is doing a job…and getting paid for it… Perhaps it might be different if you consider your position as part of a career!
      I had a number of positions in a company for 30 years…I left it when it was clear my boss considered me to be someone doing a job.

  2. Amazing write up…However the real question is do people really know the answers for 2 and 3. Also for question 4, how realistic their expectations are and how to set them right without triggering them to look out … Challenging indeed!

  3. Regardless of the question a manger asks there is significant value in just engaging your people, especially if the interest is genuine. When that genuine connection is established, the questions aren’t necessary because the exchange is natural.

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  5. I am currently in the process of working my notice and ready to start anew. Yes, the pay will be a LOT better- probably the work career prospects too. But, I am happy were I am but not with my role as I have been given three new positions within 18 months. I do not see my latest role as meaningful.
    All this has been related to management- on deaf ears.
    Communication has always been an issue here for me- that is why I am leaving.
    I hope this aids your discourse?

    • Thanks for sharing your experience, Tony. It reinforces the need for leaders to have open communication with their team members and to be partners with them in their career development.

      Best regards,


    • Gee Tony that helps me! I am thinking about leaving my company because of several reasons
      – There is no place for me to move up (Double Masters and soon a PhD) and I am not allowed to lead. They pay me an “OK” salary to take out the trash and do other jobs that a person still in HS can do.
      -No salary raise for the past 12 years
      – Way too much drama with no support from administration

      I could go on, but I know…. you are asking why I stayed so long? Well, I’ll tell you. I earned my MHA & MBA and now my doctorate writing research papers on very poor leadership. But for me it was just the daily goings on—the papers wrote themselves. For example, my Masters thesis was based on a conversation I had in the hallway with sr. admin:
      Hi- How about if you give me 15 minutes and I will show you how to save $150,000?
      Administrator: No…we like things just the way they are. We do not need your input.

      Another conversation that I have dragged on for four months (because I needed information) will become the focal point of my dissertation. It will show how to increase efficiency and save the company over $2 million dollars. By the way- they have no interest in even listening on how to save the money or the changes to make.
      The company I am looking to move to has leadership openings all over the country.

  6. Randy, thanks so much for a great post!
    These are great questions, no matter what level of the organisation you are at! Imagine how great working life would be if these questions were more common!
    I think there are two reasons why it isn’t more common… first that even great bosses are still human, and experience the same insecurities and worries that the rest of us do – opening up and asking questions that might show you don’t have all the answers is really hard to do! Second, being sufficiently mindful so as to see the opportunity to ask the question/s when we’re all so very busy just putting one foot in front of the other.


    • Hi Rebecca,

      Thanks for the positive feedback. I agree with your two reasons why this isn’t a more common practice for leaders. It’s hard work!


  7. What makes people stay.
    It’s a great question.
    Liking your manager is a good starting point.
    If the relationship is not there and the comforting an reassuring feedback is Missing, with lack of direction comes the dissatifiers that slowly eat away at the sub ordinate to the point of leaving .

    Market forces also drive people away. Once an employee is in the door , the office politics for pay and compensation will kick in…. meritocracy will eventually catch up with the individual. Seeing no merit increases will harbour disdain for challenge . A self professing prophecy.

    In summary ask me all the questions you like , jf you are nice treat me with respect and pay me fairly I will work for you.
    Know what your people want support them in achieving their goals and don’t be afraid to let them grow in the organisation

    • Good points Enda.

      Paying people a fair wage and treating them with respect is a necessary starting point.


  8. Great article and comments are right on point. I had worked in middle management for 10 years and went through various types of company sponsored “coaching” courses and learned some really great stuff. The irony of that is the people that push the “coaching” don’t necessarily practice what they preach/are taught.

    We sometimes forget to just to be kind and understanding. Explain yourself clearly and most importantly listen to what your employees are saying and how they are acting. Engage them. The best bosses I have had said, “Thank you!” Worst bosses only cared about their own issues. If the conversation is only one sided most likely it is not going to make matters better. That just alienates your team.

    As employees we also have to remember that managers are people too. Not every decision is correct-I know that for a fact. Be at least willing to give the ideas some time to develop. Managers do sometimes have a good strategy. On the the flip side managers must be open to listen to criticism from their employees as well. Don’t take offense to what they are saying, be the bigger person that is why you were put into a position as a leader.
    Listen, think, and then react.

    Now go lead!!

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  10. Great Questions, very thought provoking useful material. arun malik

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  13. Ideally this article sounds awesome – However, we must remember what the tale of Boaty-McBoatface taught us: When we ask open ended questions with no parameters, we’re likely to get a response we’re unwilling or unable to implement. Fact is, as an employee, if asked these questions I would initially be delighted! Following my responses I would expect that my effort in responding would generate outcomes of real change. Frankly, if I were asked these and nothing changed I would be more frustrated and more likely to take action to leave than if I were never asked in the first place. My advice here is simple – don’t ask if you aren’t willing or don’t have the autonomy to take action on the responses. Most “Bosses” are middle management that may in fact not hold the horsepower to change, and therefore ought be cautious about asking open ended questions.

    • Hi Clint,

      I think the key is the manager setting the right expectations of what he/she may/may not be able to do with the suggestions. The point is to engage in meaningful dialogue and to solicit the input of others.

      Take care,


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