Why Getting Wiser Makes You a Better Leader – and How to Do It

How to Be Wise in Three Easy Steps

The primary way that leaders gain influence is through demonstrating good character, and one key element of that is wisdom, something that the human race has valued for thousands of years. According to Jewish tradition, a particularly interesting exchange about wisdom happened around 3,000 years ago, when King Solomon was offered anything he wanted by God.

He asked for wisdom.

Within that context historically and culturally, one would have expected him to ask for riches, or long life, or a never-ending supply of women, but instead, he asked for wisdom. The story goes that God was so pleased with his mature (and, paradoxically, wise) answer that he gave Solomon wisdom, and then gave him all of those other things as well.

What is wisdom?

Wisdom is best understood as the ultimate pinnacle of human understanding. We’re surrounded by analytical machines and data-driven organisations, and wisdom has to be understood as something that computers inherently can’t have, regardless of advances in machine learning. Humans are differentiated from even the most advanced system by their ability to be wise, because of our ability to access the highest level of the understanding curve, made up of the following four levels of understanding.

  1. Data is the bare bones of facts. On their own, they don’t really mean anything, such as ‘65 miles’, ‘14 November 1578’ and ‘Scott Milliman’. The journey into understanding is one way; without data, there is no understanding of any sort, and there is no inherent value in data alone.
  2. Information combines those granular elements into factual statements that actually mean something. Taking the data above as an example, the statement ‘Scott Milliman traveled 65 miles on 14 November 1578’ is a piece of information that carries meaning. We live at the level of information the majority of the time because it provides immediate context to understand stimuli that the world throws at us.
  3. Knowledge combines multiple pieces of information and applies logic to draw conclusions. This is where intelligence really starts being applied. At this stage, you’re gathering two or more distinct pieces of information and combining them to generate new statements. So you might look at how far every individual traveled on a particular date, and present a statement such as ‘15% of people traveled further than Scott Milliman on 14 November 1578.’ You could also take other information that you wouldn’t naturally be looking at and use that to draw conclusions. Knowledge statements tend to look like long information statements, and here’s why humans can be different from machines.
  4. From the perspective of a machine, once you’ve applied logic to some information and discovered a new piece of knowledge, that simply becomes new information that can potentially be used in future logical processes. Wisdom is the level at which you add lateral thinking to knowledge. Wisdom is comfortable with ambiguity and intangible concepts, and allows people to give genuinely good advice on something they know little to nothing about.

This was summed up beautifully in the 2017 TV adaptation of Louisa May Alcott’s Little Women when the wonderful feminist Josephine said to the kind-faced German Professor Bhaer, ‘You know so much more than I do,’ and his reply was brilliant:

That only makes me learned. It does not make me wise.

So wisdom is not simply more knowledge. In fact, the wisest among us are those who have learned to discern what data, information, and knowledge to completely ignore. Simply put, wisdom is the ability to identify the deepest principles from as broad a range of sources as possible, and apply those instinctively in ways that may not have been obvious at first. It’s wisdom that convinces a business owner to not sell her business when knowledge would advise her to do exactly that. The joy she derives from the work is intangible, but for her, that’s more important than money.

What can we do to increase wisdom?

Firstly, teach yourself to ask open questions. Something people really notice, and which stands out as being wise, is asking great questions. What makes a great question? A great question is something that gets you thinking, and that will rarely happen with a closed question. Try to observe yourself and others in conversation, and you’ll notice that most people use closed questions most of the time. Even when someone asks an open question there’s a tendency to immediately follow it up with a further question before the other person can respond that does nothing other than turn the open question into a closed question. Like the other day, when a colleague asked me: ‘So, what are your plans for Christmas? At home with the family?’ Opportunity lost!

When you’re having a normal, relaxed conversation with a friend, asking closed questions makes little tangible difference, because we tend to answer closed questions as if they were open. On a Monday morning, Susan turns to Jane and asks, ‘Good weekend?’ Jane answers, ‘Yes, on Saturday we…’ Susan hadn’t asked what Jane had done, but she answers that way anyway. Think about it, though. If Susan follows up Jane’s answer with an open question: ‘Oh, and how does that compare with work this morning?’ the conversation can suddenly go anywhere. Jane could make a funny comment, she could open up about an emotional issue at work or at home, or she could even discover something about herself in terms of her attitude towards work and home life she wasn’t previously aware of.

Open questions are powerful, even when they’re very simple – in some cases, particularly because they’re very simple.

Secondly, listen to understand rather than to reply. Normally, as the other person in a conversation is speaking, I’m thinking up my response. Sometimes it might come out immediately, sometimes I might hold onto it in my head, and perhaps be forced to drop that thought as the conversations moved on or may forget it, but that’s as far as my listening goes. Rather than listening to reply, I’d like to encourage you to listen to understand.

This can feel unnatural because when the other person finishes speaking we might not have something to say. Give it a go anyway. If someone says something and you’re genuinely listening to understand, there will be a question you’d like answered. So when Paul tells Tim he’s got a job interview in the morning, Tim doesn’t need to tell Paul about his last job interview, despite the fact that his brain is prompting him with stories he could tell. Instead, he can ask a question: ‘What do you like about the new job opportunity?’ ‘When did you start thinking about leaving?’ ‘What could your current employer do to convince you to stay?’

Combining open questions with listening to understand is like combining flames with fire-lighters on the barbecue of wisdom. You’ll get more knowledge out of that conversation than you would have done otherwise because your listening is focussed on increasing your understanding, and also the other person will have benefitted from deeper insights derived from exploring their own thought processes.

Thirdly and finally, practice self-reflection. Set aside time to think about how you’ve acted in a particular scenario, and how you could improve next time. It’s tempting to feel that we can give others advice on any area of their lives they ask us about. We’re generally quite comfortable telling people that they should stay in a relationship, quit their job, move house, or get out of debt. It’s also tempting to feel that we’re aware enough of ourselves to not need advice from others. Those two outlooks can’t be true simultaneously unless you’re part of an impossibly tiny group of elite perfectionists, who probably need to learn a lesson or two about humility.

Let's summarise.


In summary, wisdom is the deepest understanding of a broad range of knowledge sources, combined into one consistent and applied worldview that’s helpful to yourself and others. Wisdom helps you understand where people are coming from, which gives you a better opportunity to suggest solutions they’ll agree to. It helps you appreciate new ways of working and makes you more open to good ideas, even when they’re unfamiliar. And it helps you come up with new solutions that others won’t have considered until that point, potentially speeding up conflict resolution and improving the quality of the decisions that are ultimately made.

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