25 Thought-Provoking Questions Managers Should Ask Themselves

Self-reflection is the key to self-awareness. Asking thought-provoking questions helps us take a deeper dive into our thoughts, feelings, emotions, and actions. As a manager, it’s extremely important to practice self-reflection. Not only does self-reflection allow you to make personal improvements, but it also allows you to look outside of yourself to learn how your peers feel and how you can better support those around you. 

Asking thought-provoking questions is a crucial part of self-reflection. If you don’t ask questions, you won’t get any answers. To quote Jennifer Goldman-Wetzler, the CEO of Alignment Strategies Group, directly from the Supermanagers podcast:

 “Putting myself in their shoes and even asking the question, where might they be coming from that, you know, is a really important skill that without your self-awareness, can be sometimes a problem because we don’t want to over-empathize with other people.” 

When practicing self-reflection, we’re able to look inward through a different lens and adjust accordingly. In this article, we’ll outline 25 carefully crafted, thought-provoking questions that managers should ask themselves when they’re ready to start looking inward. 

25 questions managers should ask themselves

• Forbes’ must-ask questions 
• Manager performance tracking questions 
• Employee performance tracking questions 
• Personal well-being questions
• Team morale gauging questions

Forbes’ must-ask questions

1Am I spending my energy on the right things?

As a manager, it’s extremely important to identify whether you’re putting your eggs in the right basket. It’s no secret that managers wear many hats, and it can be difficult to identify which areas are most worthy of your attention. While you may have a variety of pressing action items, it’s important that you sit down and make sure you’re spending your energy on the right tasks. 

2How well do I understand my company’s business?

As a manager, you’re not just responsible for yourself. In addition to planning your own day and making sure you’re contributing to your organization, you also need to make sure that the team you’re managing is aligned and working towards the same North star. As such, it’s extremely important that you understand your company’s business. 

3Am I developing my employees to the best of my abilities? 

Self-reflection is key, and many managers fail to ask themselves this very important question. Reflecting on whether or not you’re developing your employees to the best of your abilities will help you identify the areas in which you need to improve. 

4Do I always set an example other employees want to follow?  

It’s extremely important that you set good examples for your employees. Not only are you responsible for yourself, but you’re also responsible for making sure your team does their best to work towards organizational goals while upholding company values. If you don’t lead by example, your team members won’t be inclined to follow.

5Am I holding my employees accountable for the results the organization most needs? 

This is a very powerful question that will help you determine whether or not you’re holding your employees accountable in an impactful way that leads to results. 

Manager performance tracking questions 

1What types of projects does [employee] excel at? 

Learning where your employees excel is extremely beneficial. Not only does this insight provide more context and guidance to help you ensure projects get done well, but it also helps you place people on projects they enjoy. You can even help senior management to gain more perspective by letting them know in what areas your direct reports excel. 

2How have I impacted [employee]’s ability to succeed and grow in their position?  

As a manager, it’s your job to make sure those you manage have what they need to succeed—whether this means making sure they’re equipped with the tools they need or ensuring they can approach you should they be facing any roadblocks. Understanding the impact you’ve had on your teammates will help you determine whether or not you’ve made an impact as a leader. 

3Has [employee] made positive contributions to the team or organization since the last review? If so, describe one.

It’s important to determine whether or not your employees are making impactful contributions. If an employee hasn’t, it may be time to make adjustments. You’ll have to identify whether you’re providing the employee in question with everything they need to succeed and pivot accordingly. 

4How has [employee] done with creating and meeting goals over the past few months?

Do you know if your teammates have met their goals over the last quarter? Understanding whether an individual on your team has been a valuable team member is imperative when planning for the next quarter. 

5Which company value have I seen [employee] emulating well in the last few months?

In addition to performance, it’s equally as important to ensure your employees have emulated your company’s values. If they haven’t, it may be time to lead by example or explore what may be holding them back. 

Employee performance tracking questions

1How have I helped my team achieve our company goals?

Employees aren’t solely responsible for their success. Without a proper manager, it becomes nearly impossible for employees to realize their full potential and therefore contribute to the organization’s overarching goals. Understanding if you’ve had a positive impact on your employees’ success is invaluable.  

2How can I better track success amongst my employees? 

As a manager, one of your main prerogatives should be tracking metrics and making sure your employees are on track to hit company goals and objectives. Learning how you can make iterations and improve tracking will ensure your teammates are organized and on track.  

3What would my teammates or clients say about their recent interactions with me?

This is a great question because it forces you to pause and reflect on your recent interactions. If you haven’t taken the time to reflect on the interactions you have with your team or clients, this question may serve as a learning opportunity or an opportunity to spark positive change.  

4How has my team been able to contribute to the company’s current goal of [goal]? 

Without a North Star, your employees will fall short. Ensuring you understand how their efforts contribute to the greater picture is a great way to make sure everyone’s aligned and working towards the same shared goal. 

5How satisfied were customers with all employee interactions this quarter? 

Customer success is a great way to gauge employee performance. If your teammate received a low score, it might be time to revisit your outreach strategy. If your team performed well and customers were happy with their interactions, it may be time to reward your team! 

Personal well-being questions

1Overall, how happy did I feel this week?

Understanding how you feel is invaluable. Not only does this self-awareness help you put things into perspective, but it also helps you determine which tasks drain your energy and which ones inspire you to do your best work. 

2Overall, how anxious did I feel yesterday?

If you don’t take the time to step back and reflect on how you feel, you won’t be able to make improvements. Understanding what made or didn’t make you anxious will help you make more conscious decisions moving forward. If something makes you anxious, you can address what’s causing the anxiety or find healthy workarounds. 

3Overall, how does waking up for work make me feel? 

The age-old saying goes, “if you love what you do, you won’t work a day in your life.” If you find yourself constantly drained, it may be a sign that it’s time to reevaluate your career. If you wake up feeling inspired, refreshed, and ready to take on the day, it’s a good sign that your work-life balance isn’t affecting your personal life. 

4Overall, how satisfied am I with my life nowadays?

Work isn’t everything. On a global scale, it’s important to understand how you’re feeling. Your personal life can spill into your work life and vice versa. Understanding how you feel on a global scale will not only help you manage your feelings, but it will also help you become a better leader. 

5Overall, to what extent do I feel the things I do in my life are worthwhile?

Feeling purposeful is one of the many keys to happiness. It’s important to gauge how you feel and understand where your work lies on this scale. 

Team morale gauging questions

1How can I incentivize my team?

While this question may seem simple, it can be quite powerful when followed up with meaningful action. Take time to reflect on what incentives your employees react well to; understanding what your employees believe to be a great reward will help you understand how to make them feel valued and appreciated. Taking the time to learn how you can incentivize them will not only help you understand how to motivate your team members, but it will also make your team members feel valued and understood.  

2What can I do to be more supportive of my teammates? 

Feeling supported is extremely important. Reflecting on how you can better support your employees and their teammates will help you unlock the insights you need to empower them to do their best work. 

3How can I reward my team if they have had an excellent week at work? 

Understanding how you can incentivize your team to do their best work is extremely valuable. If your team has had an excellent week, you may want to reward them to reinforce these positive behaviors. Understanding the ways you can reward your team members in a way that demonstrates your gratitude will ensure you provide a reward that makes them feel valued.  

4Do my employees feel supported and valued at work?

Understanding if your employees feel supported and valued at work is a must. If you uncover that they do not, it’s your responsibility to put measures in place that create a more positive environment. 

5Do my teammates have someone to talk to if they have had a bad day at work?

As a manager, it’s your job to make sure your employees feel safe and valued. As a result, it’s extremely important to make sure they have someone within their network that they can talk to should they feel as though they had a tough day at work. 

Are you ready to look inward and ask impactful questions?

Identifying which questions managers should ask themselves is the first step toward success. After you’ve identified which questions will spark positive change, it’s time to ask them! One-on-ones, standups, or even informal meetings with your employees all present a great opportunity to ask these questions.