Leadership is solitude, leadership teams are introspection

Summary

Leaders are by the nature of their job, alone. Good leaders are thinkers, they explore and map their territory and lay out a course. That is they lead with vision. To develop a clear and confident vision leaders need to be able to concentrate on what’s important to take decisions with courage and conviction. Leaders don’t have the expertise to tackle every problem. Leadership teams have a wider expertise and should be structured such that there is openness and space to explore from a place of vulnerability. Good leadership teams are also good friends who are able to fearlessly point out mistakes and pitfalls. Leaders should go out of their way to create and maintain that culture of intellectual honesty in their leadership teams enabling the same kind of introspection as one would with close friends.

Good leaders are courageous thinkers

Leadership is a frame of mind. You don’t need to have a title to be a leader, but if you do have a title you better have the right frame of mind.

As a leader, you need to be able to think for yourself. Take in, organise, and make sense of data coming to you and then take a call. You also need to have a strong moral sense. This takes courage. It is trivial to let things proceed as they are or to con your superiors into generating a list of tasks for you to do. But to point and say that we need to do this and not that, takes courage and mental faculties to argue for your point in the face of opposition.

In books on leadership, one often reads saying “no” and creating time for yourself in your schedule, the main purpose of this is to give yourself time to think, to marinate in the data and ferment out decisions. Leaders (in my startup experience) are pelted with requests and activities that would easily fill up 48 hours every day if they let them. For people like me, who come from research, the importance of creating time to think and plot ahead is implicit and we naturally make that space.

Good leaders make that space, put in thought and make the tough calls.

Good leadership teams are capable, great leadership teams are capable friends

There is a central problem here. No leader can be an expert in everything. Even if data is staring you in the face, you may not (and often don’t) have the experience to correctly surmise what the next step should be. This is what the leadership team (or just your team) is for.

There is an excellent article by William Deresiewicz on Solitude and Leadership (here), where he talks about how being a leader is essentially an activity done in solitude. However there is also an important point he makes about the need for friendship as a means of self-discovery and solitude:

“So solitude can mean introspection, it can mean the concentration of focused work, and it can mean sustained reading. All of these help you to know yourself better. But there’s one more thing I’m going to include as a form of solitude, and it will seem counterintuitive: friendship. Of course friendship is the opposite of solitude; it means being with other people. But I’m talking about one kind of friendship in particular, the deep friendship of intimate conversation. Long, uninterrupted talk with one other person.[…] what Emerson meant when he said that “the soul environs itself with friends, that it may enter into a grander self-acquaintance or solitude.”

Introspection means talking to yourself, and one of the best ways of talking to yourself is by talking to another person. One other person you can trust, one other person to whom you can unfold your soul. One other person you feel safe enough with to allow you to acknowledge things—to acknowledge things to yourself—that you otherwise can’t. Doubts you aren’t supposed to have, questions you aren’t supposed to ask. Feelings or opinions that would get you laughed at by the group or reprimanded by the authorities.”

Leaders should go out of their way to be friends with their leadership teams. In my experience of running projects, large and small, without a tight-knit leadership team the projects are hopeless and fail miserably. The main reason for this is not the capabilities of the individuals but their ability to openly discuss and question assumptions. To an external observer this make look like the leader is generating a coterie or a clique around them, but that’s exactly what one needs. A good leader is nothing without a leadership team that is textbook definition of coterie: “an intimate and often exclusive group of persons with a unifying common interest or purpose“.

A good leadership team enables the leader to take tough decisions and make what seem like courageous calls from the safety of having thought things through.