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Managers Need to Ask Hard Questions

Conversations need to go beyond work to keep employees engaged.

Source: Etienne Girardet / Unsplash
Window into an office with the words What Is Your Story in neon letters.
Source: Etienne Girardet / Unsplash

When was the last time you asked yourself if you like what you do, if it builds on your strengths, or if your career decisions align with your personal goals?

When was the last time your manager asked you these questions? When was the last time you, as a manager, asked your people these questions?

Unfortunately, we are all too busy, too over-scheduled, and, for some of us, too burned out to do the hard work of reflecting honestly on where we are and where we would like to be, not to mention building in time to have these conversations with the people we manage. But if you want to be a great manager, this is some of the most important work you can and should do.

Reflective Conversations Matter

Intuitively, you probably know that there is value in reflection. Anyone who has worked in management or studied it has learned the importance of debriefing conversations, which assess what’s working and what could be improved upon. From activities like Stop-Start-Continue to SWOT (Strengths, Weaknesses, Opportunities, and Threats) analyses to environmental scanning to open brainstorming sessions, there is a multitude of reflective practices to ensure that organizations and teams use the collective wisdom of everyone to make strategic decisions. These are great practices for aligning work outcomes with organizational goals.

Reflection is also a key component of individual growth and learning that many people either forget to use in the working world or do not have time for. But as the saying goes, “Those who cannot remember the past are condemned to repeat it.” This is true for geopolitics, organizations, and individuals.

Reflection is one of the most important elements of experiential learning: First, you have an experience, and then you must reflect on what you learned from that experience and how you can use that knowledge to move forward (McCarthy, 2010). Otherwise, your life and career are disconnected actions with no greater meaning.

Reflection is everyone’s responsibility. You can and should build in a daily or weekly practice of reflection on your own. It is one of the most important tools managers have to develop strong relationships with their people, align the work with strengths and interests for greater engagement, and encourage intentional career development while also role-modeling the importance of regular reflective practice.

And as Stefano, Pisano, and Staats (2017) note, intentional reflective practices are key to improving work performance. These can be hard conversations and hard questions. But they might be the most important conversations with the people you manage.

Hard Questions Every Manager Should Ask

Intentional reflection should be built into one-on-one conversations with direct reports and team meetings to deepen learning and improve decision-making around the work. In addition to these task-oriented conversations, spend time talking with your direct reports about the following topics.

  • Questions About Strengths and Interests. What individual strengths and interests are unique to each of your people? What do they like and not like about work? Where do they find themselves energized, and what drains them? How do they want to spend their free time? Asking these questions lets you get to know your people better and provides critical information on redesigning work to better use their strengths and interests.
  • Questions About Capacity. Managers are fond of saying, “You can tell me if the workload is too much.” Has anyone ever responded honestly, “It’s too much"? Of course not. Instead, intentionally ask, “What needs to come off of the list?” and don't take “nothing” for an answer. Before you assign new work, ask, “How is your capacity right now?” Sometimes, we all have to do something, whether or not we can. But as a manager, you should know that burnout is one of the driving forces behind the current resignation crisis at work. Your people aren’t superhuman, and work shouldn’t fill every hour of the day. Be intentional about asking about capacity so that your people can do great work, not just work to be done.
  • Questions About Motivation. Why do your people come to work every day? I love the research into motivations or orientations to work: People either work a job, build a career, or pursue a calling (Wrzesniewski et al., 1997). There is no one right motivation to work. And the reasons your people show up daily may not be the same as your motivation. So ask them: Why do you work? Why do you work at this job, specifically? Not everyone has to be there for a higher purpose. By making it comfortable to have that conversation and encouraging them to reflect on how the work aligns with their motivation, you become a partner in their career development, not a hindrance to it.
  • Questions About the Future. For career development, you should have intentional conversations with employees about their future and how this role fits into that path. What are the gaps that need to be filled? Where do they see themselves in the next two to three years? How would they like to grow in skills or knowledge areas? You won’t always be able to provide everything everyone needs; sometimes, people must leave to move forward. As a manager, asking these questions and making it OK to talk about these topics leads to more intentional growth.

This is an ongoing, lifelong career. Remember that you should always reflect on your learning and how your work fits into your future, motivation, and capacity. It’s some of the most important work you will do as a manager and a person.


McCarthy, M. (2010). Experiential learning theory: From theory to practice. Journal of Business and Economic Research, 8(5), p. 131-140.

Stefano, G.D., Pisano, G., & and Staats, R. (2017). Learning by thinking: How reflection aids performance. Academy of Management Proceedings, 2015(1).

Wrzesniewski, A, McCauley, C., Rozin, P., Schwartz, B. (1997). Jobs, careers, and callings: People’s relations to their work. Journal of Research in Personality, 31(1), p. 21-33.

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