Question everything

I’ve been thinking and reading a lot about leadership recently, and saw an article that picked up some interesting points.

Entitled Solitude and Leadership, it was the text of a lecture given in October 2009, by William Deresiewicz. He asked a really good question:

Why is it so often that the best people are stuck in the middle and the people who are running things—the leaders—are the mediocrities?

Think around the organisation you work for, or places you have worked in the past. Do you recognise the situation? I know I do. The greater the level of bureaucracy in a company, the truer the above statement tends to be. Deresiewicz suggests the reason for this:

Excellence isn’t usually what gets you up the greasy pole. What gets you up is a talent for maneuvering. Kissing up to the people above you, kicking down to the people below you. Pleasing your teachers, pleasing your superiors, picking a powerful mentor and riding his coattails until it’s time to stab him in the back. Jumping through hoops. Getting along by going along. Being whatever other people want you to be, so that it finally comes to seem that you have nothing inside you at all. Not taking stupid risks like trying to change how things are done or question why they’re done. Just keeping the routine going.

“What is rewarded above all,” he concludes, “is conformity.”

Isn’t that a soul-destroying picture of humanity, let alone leadership? But it’s how the world works, so we’d better understand it, and then try to transform it. Deresiewicz develops his theme:

For too long we have been training leaders who … can answer questions, but don’t know how to ask them. Who can fulfill goals, but don’t know how to set them. Who think about how to get things done, but not whether they’re worth doing in the first place.

In other words, we have managers, not visionaries; people who can keep the present running, but who can’t shape the future.

The first clause of the above quotation is the one that I find most striking – and most challenging. Every leadership course I’ve been on or book I’ve read teaches about setting goals, and about thinking about what your goals are, not just how to achieve them. But I haven’t come across the first before, or any guidance on how to develop the skill.

How do you ask the searching questions that are going to make people look inside themselves and really think things through? Some of the great leaders I know are very good at asking questions of themselves, of the people around them and of the culture. I’ve been the recipient of some such questions, and they’re an incredibly powerful tool, but I’m not very good at asking them myself.

One I’ve started asking myself is ‘what is this movie (or book or play or interview or lecture) really saying? What vision of the world is it selling? What underlying assumptions is it making about reality – and are they true?’ OK, so that’s multiple questions, but I find they’re really helping me to be more discerning about the world I’m absorbing.

I noticed a few days ago that several of my blog posts are entitled with questions. My first instinct was to try to stop doing that – didn’t I start blogging because I want to say things, not ask things? – but actually, no – I started blogging because I want to understand things and then change things. To understand them I have to ask questions about them. It may only be me answering the questions, but it’s better than never even considering them, in fact, even Einstein once said that “The important thing is not to stop questioning,” which I think is pretty good authority!

I’m making a mental note to start sharpening my questioning skills. I think they will be a powerful tool in the future. What do you think?

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  1. Dad
    on Mar 26th at 9:25 am

    Yesterday the Leader of the House of Commons was minded to reject a request for a debate on a particular matter on the grounds that the Member requesting it had not been present when the matter he wanted debated had occurred and therefore, as he had no knowledge of the matter, he should not be asking for a debate. The Speaker observed that it would set a precedent for The House if knowledge of a matter was a pre-requisite for debate.

    Therein, I think, lies the nub of your problem. Frequently, those who are supposed to be leading don’t know what they are talking about. Anthony Ashley, Lord Shaftebury, brought about lasting change for child workers in mills and factories. He only achieved it after he took himself away from his comfort zone and travelled to the industrial north to see first hand the conditions in which children were working. His subsequent pleas in Parliament were then irrefutable because he could say ‘I have seen it myself’.

    Now you could say that he was following the course you advocate – he was questioning. I suggest it was something a little different. To set the goals that bring about change requires the combination of being a scientist and a artist. The scientist side of his nature led him to investigate – not necessarily ask questions but to observe and see what happens. The artistic side caused him to view what he was seeing in a different light to what most others saw. The result drove him to restlessness until he could find expression for what had then become an emotional rage within him. If the function of a leader is to bring about change then it needs that motivational inner emotional rage. Think of Churchill’s blood, sweat and tears declaration. Could any passive person have led us through the conflict. Churchill was not a natural choice for Prime Minister – he was rejected at the Polls immediately after the war. What he had was a love for his country coupled with years of journalistic experience as a war correspondent. He had been there and seen it. He knew what war was all about. He knew the damage it inflicted on communities and nations. So he was able to be the leader for that particular situation.

    Finally I want to give you a question to ponder. Is a leader someone at the front, the back, in the middle, or on the sidelines? There are two theories about how to move a flock of sheep. One says you go to the front and they follow you, the other says you go to the back and drive them. Both know that a rogue sheep in the middle of the flock will cuase the flock to go off course. Maybe the rogue in the middle is the true leader. Or is the dog running around the sidelines?


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