10 Questions Great Bosses Regularly Ask Their People

Guest Post by Randy Conley

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 one-on-one 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 one-on-one meetings and watch for the positive impact it will have on your team members’ level of engagement and productivity.