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Chapter 1 Leadership hats

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In my role as a manager and leader, I always feel as if I have to wear many different hats; sometimes it feels like I have to wear many hats at the same time! I believe that the essential skill of being a great leader is knowing which is the right hat to wear at the right time and in the right way to best deal with the situation being faced. In my experience, this choice is rarely straightforward, particularly when you are dealing with people and the challenges of their different perspectives, mindsets, preferences and approaches.

Fortunately, in my case this has always been the aspect of leadership that I have loved the most – the fact that when it comes to people there is never a ‘one size fits all’ answer to problems. You have to respond intuitively to situations that, on the surface, appear to be the same but often require a different approach because of the challenge of dealing with a diverse range of people. I have found that trying to work effectively with my team as a leader has brought me the most challenges as well as the greatest joy and rewards (and, of course, every emotion in between!), so in all honesty I have enjoyed the fact that there are rarely any easy answers.

Deciding what is the right hat to wear (i.e. what our response should be to a certain situation or person) is often not straightforward, and so typically our first response is often made in an habitual way that is easiest for us and fits within our comfort zone. From what I have shared with you so far, you will probably acknowledge that many people feel most comfortable, not surprisingly, with the ‘teller’ response and this will be the hat that they will bring to their leadership roles – on automatic pilot in many instances.

What I’d like to do to start our journey into building a business case for asking Better Questions is to share some insights into the most frequent hats we wear as managers and leaders. I hope that by doing this we will be able to recognise the key aspects of each hat in the hope that, going forward, it will help us to make more informed choices rather than automatic choices.

So, to start this exploration I invite you to consider a line, with one end representing the more typical ‘telling’ space and the other end representing the ‘asking’ space.


I ask in advance for your understanding in the explanations I am about to share with you; they may at times appear to be simplistic in their nature. I recognise that rarely is anything clear-cut in life, and usually there are many grey areas; however, if you can bear with me in my explanations, I hope to be able to clarify some important points that will enable you to glean more understanding about the key distinctions between the two approaches of ‘telling’ and ‘asking’.

Better Leaders Ask Better Questions

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