The most important question for leaders to ask

I take part in lots of planning meetings and I have noticed that the quickest thing to get lost in such meetings is- the point. We rush to questions of what and how and miss the why. But I have come to believe that the why question is the most important question, the most creative question and the most releasing question.

This is a big part of the difference between leadership and management. Leaders are always asking the big questions of why, prompting imagination and drawing people back to the point.

The leadership discipline is to relentlessly make the point the central and defining thing rather than allowing the process or all the busy stuff to take over. Focusing on the why allows you to dream big and imagine better. Starting with the what or the how always closes down options, cuts off creativity and defines the action by what is deliverable rather than by what is imaginable. There are lots of times that poor implementation leads to failure but I strongly believe that the greatest weakness of most organisations is not poor delivery but insipid imagination. Our greatest need is for better dreamers rather than for more project management. Yet most organisations believe that their greatest need is for better implementation. Great delivery is obviously vital but it must follow great imagination. I have sat through countless meetings where an activity has been perfectly executed but missed the point. An IT system delivered but doesn’t do what the real users need. A perfect product that fails because nobody thought through why someone would engage with it. A detailed process that ticks every box but only inspires people to figure out how to work around it. All symptoms of forgetting the why.

Bureaucracies tend to get some other questions wrong as well. The answer to who? tends to be someone else or a consultation. It is hard to take responsibility and make things happen. There is a paralysis of permission seeking.

The answer to when? tends to be later. The fear of dong the wrong thing is greater than the fear of doing nothing. There is an inbuilt bias to being cautious and slow. There is a paralysis of action.

As Walter Brueggemann put it:

We need to ask not whether it is realistic or practical or viable but whether it is imaginable. We need to ask if our consciousness and imagination have been so assaulted and co-opted by the royal consciousness that we have been robbed of the courage or power to think an alternative thought.

In discussing Christian ministry Hans Kung wrote ‘Wistfulness is no substitute for daring’. That is the leadership discipline.