The Great Questions of Leadership

For those who might wonder just how effective their leadership is in their organization, let me introduce you to “The Great Questions”.  I work with a lot of leaders who are doing everythingquestion-mark-dice they know how to stay on top of the responsibilities that rest on their shoulders: from being great managers of work, to great managers of people, to making an impact and getting things done. And often, in the heat of the moment, with the pressure on, it’s easy to begin to fall into common leadership traps such as complacency (not really leading at all anymore) or naivete (not knowing what a leader is supposed to really do in the first place).

So every time I sit down to work with a leader, no matter what the chief complaint or symptom is that brought us together, I always begin with the “The Great Questions”:

  1. What is the purpose and/or mission of your organization, department, etc.?
  2. Are you accomplishing it?
  3. How do you know?

Let’s talk about the power of those three simple questions, from both the inquirer’s and the receiver’s side.

What is the purpose and/or mission of your organization, department, etc.?

This first question is meant to take all of the things competing for a leader’s time and attention, all of the distractions and all of the small stuff that has become big, and blow it away by regaining context of what this whole thing is about in the first place: why are we here and what are we supposed to be doing in the long run? Asking this question helps calm the seas, focus on what matters most, and quickly tells the interrogator how well the leader understands why the organization even exists in the first place. By doing so, we frame the important conversation and throw anything not directly related to it out the window, off the plate, persona non grata, etc.

Are you accomplishing it?

This is the point where leaders either have an immediate answer or pause to think.  If they have an immediate answer, it doesn’t necessarily mean that they are or are not on target, it just means that they think they are.  This question is not meant to be debated, it’s really a set-up for the next question by getting them to answer yes or no, and then slapping question number 3 on there for gut check time.

How do you know?

How do you know is a question about awareness, about measurement, about active inquiry into the ultimate question of “are we successful or not?”  It tells you so much about the manager or leader before you, and what may or may not be missing in their organization.  It also is a question about knwoledge vs. conjecture:  We are asking if they KNOW.  Often, it is difficult to really know, but we want to find out how they are framing their paradigms of the organization.  in 9 out of 10 organiztions, I will bet that the manager never really asks that.  Instead, it’s, “Am I doing what I need to do to keep my boss off my back?  Am I doing what I need to do to look good?”  Those aren’t wrong questions, rather they are more likely indicative of what the real organizational mission may be, rather than what the framed poster in the break room or company banner claims.

How do you know lets the interrogator see if the leader and their organization is measuring their purpose and mission – if not, then it probably is not being fulfilled, and the activities, systems, processes, people and focus within the organization are almost certainly out of alignment, are fragmented and disjointed.

Leaders who lead by “The Great Questions” tend to do less managing and more actual leading and torch bearing, thanks to the vision and clarity that working within the big three allow you to achieve.

So go on, ask them, of your self, of your direct reports and of those you report to.


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