Career Guide


Reflections on leadership

What is wisdom? A common definition is that it’s something cultivated through experience over time.

It’s also often said that experience is what you’re left with after life throws at you what you don’t want, the implication being that we learn from the setbacks: what doesn’t kill you makes you stronger, and so on.

But if wisdom stems from accumulated experience over time, this would suggest that the older everyone becomes, the more wise-heads we see in the world. Alas, even the most furtive glance around us quickly confirms this isn’t so.

“Aha!” some might exclaim, “wisdom is what’s cultivated by reflecting on our experiences over time”. That’s certainly a step in the right direction. However, if the reflection is skewed towards the belief that “Everything I’ve done today was totally awesome”, it rather deals a blow to the cultivation of wisdom.

In the best leaders – those resonant leaders who truly inspire and empower others through their own example – we find in their actions what true wisdom consists of: authentic reflection plus deliberate contemplation over time.

Abraham Lincoln once said, “I am a slow walker, but I never walk back.” Lincoln was known for his humble stoicism, and the respect he garnered – even from his rivals – stemmed from his capacity to better understand himself, how the world works, and where he fit into the grand scheme of things.

Lincoln constantly sought to get a handle on himself, to understand what made people tick and, perhaps most importantly, persevere in discerning the appropriate course of action in relation to any given situation. Doubtless, he made mistakes – but he took those mistakes and used them as life lessons to help him change course and chart a new direction where necessary.

Whereas superficial reflection might say, “I messed up there – I’ll try to do better next time, can’t win them all,” authentic reflection digs deeper and asks questions of ourselves that we might not wish to ask.


Let’s take a closer look at the three components of wisdom and how we can tie them together to better serve ourselves and others:

- Authentic reflection is where we find the courage to ask ourselves, “Where could I have done better?” as well as “What did I do that I should carry on doing?” Just as we shouldn’t shirk from facing up to where we can improve, we should also have the courage to recognise and appreciate our strengths so that we might build upon them.

- Deliberate contemplation is similar to reflection, except it goes beyond ourselves and explores the people, the environments, the dilemmas and the challenges that exist externally. We might ask, “Why does this challenge exist?” and “What are some of the possible solutions that could be put in place – and how can I work with others to help alleviate the problem?” Deliberate contemplation focuses on what’s significant or important in the immediate future – it’s where we derive insights as to the most beneficial next steps to take.

- Time is what affords us the room to grow. It’s something we all share for a while. However, how we use the time we have determines how we grow and develop. It rolls on by regardless of whether it’s wasted or utilised. If we use it sensibly, we get the most from it in terms of who we grow to be.

The nineteenth-century Danish philosopher Soren Kierkegaard once said that, “Life can only be understood backwards; but it must be lived forward.” In leadership, reflection and contemplation are vital tools that allow us to chart the best course moving forward by understanding what has gone wrong before.

In a Washington Post article the late Eric Kail, former course director of military leadership at West Point, wrote: “Reflection requires a type of introspection that goes beyond merely thinking, talking or complaining about our experiences. It is an effort to understand how the events of our life shape the way in which we see the world, ourselves and others. And it is essential for any leader.”

Having said that, reflection doesn’t come easily to us. We are, in general, adept at presenting a crafted image to the outside world precisely because we are inclined to construct convincing self-narratives that justify rather than investigate, conform rather than question, and sit in comfort rather than seek to be curious.

Indeed, the past year has seen a torrent of twists and turns and has undoubtedly left us all with much to ponder. As with any year, what has been is gone and in its trail, we are invited to reflect, contemplate, and ask ourselves a potentially life-changing question: “What’s the best way forward from here?”


Sandy agrees with the idea that “an unexamined life is not worth living” but, being one for balance, he also believes that life should be enjoyed – especially during the festive seasons – with family and friends. To connect with Sandy, follow him on Twitter @RealSClarke

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