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The Critical Questions Every Leader Should Ask

Robert Steven Kaplan
Posted: 09/06/2011

Do you think you have all the answers? Do you expect this from those in leadership roles? According to a new book by Harvard Professor Robert S. Kaplan, What to Ask the Person in the Mirror, there is a misguided and deleterious assumption that leaders must be vessels of information.

HRIQ is joined by Robert Steven Kaplan, author and Professor of Management Practice at Harvard Business School, to discuss how leaders may establish a clear vision and a set of priorities for the organization by asking the right questions instead of trying to have all of the answers.

HRIQ: Where do problems start in a company?


RSK: The problem often starts where people don’t quite understand what a leader actually does. A leader has to do many things, but for starters, a leader needs to ask the right questions. A leader needs to be able to step back, self diagnose and reflect and ask questions. The reason this is so challenging for a leader is when you’re junior, you’ve got people watching you and giving you feedback. I often go to a group of leaders in a company and ask, "How many of you have a coach?" you might see 15 hands go up in a group of 100. And I’ll say: "The rest of you don’t have a coach?" What I find is that they feel they don’t have a coach. They don’t know how to navigate and feel alone and isolated. Leadership is not about being superman or woman—it’s about asking the right questions so you can mobilize your team, get the feedback you need and drive the company and your career.

In your book, you refute the belief that good leaders must have all the answers. Obviously, not everyone is a born leader—so in your opinion, what does it take to be a fantastic leader?


It’s great to be born with some natural talents in terms of speaking, writing, charisma, intelligence. My experience is this: those don’t necessarily mean you’re going to become a leader. In fact, if you’re so gifted, you may actually struggle to become a leader. Leadership is a team sport. To be a leader, you have to do some things that actually may make you uncomfortable. If you’re highly talented, it actually may be easier to do some things yourself and not to coach people.

The bigger indicator is: are they highly motivated? Are they willing to learn? If someone is willing to learn, it may take them longer but they’ll eventually get there. Leadership skills are things you need to work out, and while everyone out there may seem as though they’re doing it effortlessly—they’re not. I struggled for many years and it took a lot of work and a lot of reflection. As someone who went through this myself, I understand better how I can help others do it.

You talk about "asking the right questions" and self reflection. What are the basic types of inquiry and some examples of questions that leaders have to ask themselves?

People often come to me with a specific problem they’re having. I’ll stop them and say, "Let’s back up. What is your vision for the business that you run?" A lot of the time, people can tell me, and a lot of times they can’t. Why? Articulating a vision is based on what your distinctive competencies are. As the world is always changing, many people have to think about that. They’re not sure. I try to stop people and ask: What are your distinctive competencies? What’s your aspiration? And then I ask: what are the 3-5 things you must do superbly well to achieve that vision? This is a very simple conversation, but often when a leader is having a problem, invariably they are not clear themselves and priorities, or they are clear but don’t communicate it enough to their people. It’s very hard to be a good coach if you’re not clear with your direct reports and subordinates, as well as lateral relationships. How can you coach them if you don’t really know what you what and where you’re going? Everything you do needs to align around that vision.

How will asking the critical questions improve the operations of their companies?

Let’s say you write down your vision and aspiration for your business. You write your 3 or 4 priorities. Now—think about the number of other things. Think about how you spend your time. Does it match those key priorities? Are you spending your time on those priorities? Are your people? Are you communicating—over and over—these priorities? You can see how it will affect company effectiveness. All of the sudden, you align people. The recruiting decisions you are making become clear. Expense reductions decisions become clear. If you know clearly your vision and priorities—it’s a lot easier to do. Everything in terms of company organizational effectiveness comes from aligning your coaching, time, hiring decisions, strategy decisions, leadership style around what you’re trying to accomplish. Once people understand that discipline and get their direct reports to have that discipline, you see company performance improves dramatically.

How does one develop and practice the skills necessary to be a great leader, and what obstacles do executives have to overcome to reach these goals?

A lot of people think: "I need charm lessons," "I need to improve my personality," "I need to be more effervescent," etc. Well, I don’t know how to do that and I don’t think it’s true. Break it down into five or six things that you need to do superbly well to drive your business or non profit.

To me, those big things are 1) Vision and Priorities; 2) Aligning your time with those key priorities; 3) Learning to delegate and coach your people; 4) Learning to get feedback and coaching. It’s not giving a fancy speech. It’s about knowing where you’re going and aligning your time and each of your key decisions.

I keep a list of about 4 or 5 priorities and when I’m struggling, I look at them and ask: "How am I doing on that?" Maybe the world just changed and we have a dramatic change among our competitors. Maybe we need to step back and rethink our strategy with a clean sheet of paper. It’s about making time as a leader for the things you need to do and learning to delegate and get rid of some of the things that are not part of your key priorities. In order to do that, you first have to decide what they are. That’s what makes a great leader, in my opinion.

Interview conducted by Alexandra Guadagno, Editor for Human Resources iQ

Robert Steven Kaplan
Posted: 09/06/2011