To make no mistakes is not the power of man, but from their errors and mistakes the wise and the good learn wisdom for the future. Plutarch

“I don’t know what to say. I don’t have anything valuable to add, so I just stay quiet.”

I looked across the table with my eyebrows raised. Here was a successful leader who was one of the brightest minds I’d ever met, with a track record of helping teams deliver project after project. She had a rare combination of being highly technically competent and great with people. Liked by all who worked with her, she had just been promoted to an executive position which by all accounts – mine included – was an excellent appointment.

Yet given this new platform to shine, she was struggling to make an impact. While she had been decisive and confident in her previous roles, the feedback she had received was that she was too quiet and too timid in senior leadership meetings.

As we explored the issue during coaching, it was clear she was wrestling with the “Am I good enough?” question. For her, the struggle to answer this question was causing her to doubt the value she added to the senior leadership team. Because she could not articulate to herself the value she contributed to the team, she couldn’t intentionally and confidently provide that value in the boardroom. So she stayed silent, engaging as little as possible, just looking to survive leadership team meetings without saying anything others would see as stupid.

This was a shame because she had so much value to add to the team. She just needed some help to realise it.


One of the greatest sources of value leaders can provide is the hard-earned wisdom they have gained from their experience. Every leader has had an experience they can learn from. Whether they be successes or failures, the ability to draw lessons from past experiences and apply those lessons to the future is a key ability for leaders to be both wise and successful over time.

It is often difficult to conceptualise what wisdom is. It is a word surrounded by connotations of mystical sayings emanating from a wrinkled face cropped with grey wispy hair or written down by the hand of someone long dead. Yet you don’t have to be dead (or even half dead) to possess, use and share wisdom.

Wisdom is simply the ability to adopt a meaningful perspective that allows you to articulate and apply lessons learned from experiences of the past that are useful in the future. You might like to think about wisdom in terms of hindsight, insight, and foresight.

  • Hindsight is where you look back and reflect on past events. With the knowledge of how things played out, you can identify what the best course of action would have been. Often, it is hindsight allows us to identify the lessons we learn from our past experiences.
  • Insight is the ability to see into present events and identify what is really going on in the current context. It’s about recognising which lessons from yesterday can help you make good decisions today to get a good outcome tomorrow.
  • Foresight is the ability to look forward and based on your past experience anticipate potential future events and plan accordingly. It allows you to identify opportunities to proactively apply lessons previously learned to avoid poor outcomes and increase chances of success.


While John Maxwell writes that, ‘Reflection turns experience into insight,’ I believe reflection helps develop hindsight and foresight as well. You will notice that at the core of each ‘sight’ listed above, are the lessons learned from experience. To be intentional about developing sharing and applying wisdom, you need to first clearly articulate what lessons you have learned.

It’s a bit like teaching someone how to tie a tie. For those of you who do wear ties, if you’re like me you have no problems tying your own. You can do it quickly and efficiently without thinking. However, if you must explain to someone else how you do it, you struggle. Because you have never clearly articulated to yourself how you do it, you struggle to communicate to others the steps you take. To teach someone else, you need to first articulate to yourself what is required. It is the same with the lessons we have learned.

This process starts with reflecting on our experiences. By analysing past scenarios, we can understand what occurred, why it occurred, and how things played out. We can assess decisions that were made, consider possible alternatives, and determine what would have provided the best possible outcome. This deeper level of understanding will allow you to identify the lesson (or lessons) to be learned from that experience.

Deconstruction creates knowledge; recombination creates wisdom. – James Clear

I’ve written before that the lesson must leave the learning in order to be leveraged. It is only once a lesson has been articulated as a stand-alone principle, independent of the specific circumstances in which it was learned, that it can then be applied in the present or future. It’s only when you can clearly articulate lessons from your past that you can effectively communicate them to others.

A simple framework to help this process is STAR+.

  • Situation – What was the situation?
  • Task – What were the tasks required from the individuals involved?
  • Action – What did you and others decide and/or do?
  • Result – What was the outcome as a result of the decisions made and actions taken?
  • Alternatives – What could have been done differently to get the best possible outcome?
  • Lesson – What is the stand-alone lesson to be learned?
  • Future – What are the future applications of this lesson?

If you repeat this process for all the most significant of experiences throughout your career and life, you will end up with an entire list of lessons to be applied in the future. This is your wisdom bank. This is the value you bring. It becomes much easier to answer the “Am I good enough?” question and quell your doubts about the value of your contribution when you can look, see and hold a large list of valuable lessons.

The result is that you’ll be more confident around other leaders.

That was the case for the executive I was coaching.

It can be for you too.