How often do you admit to having weaknesses?
To yourself?
To others?

That is the first step.

So, here goes. I’m not particularly good at selling myself. In business, it is without doubt a weakness. It isn’t that I have any issue with sales per se, with money or with rejection – none whatsoever.

It is specifically around prospecting – around reaching out to random souls to see if they may be interested in investing in my services. It feels like an intrusion. I perfectly understand that this can be recast as doing the world a disservice by hiding my light under a bushel, but it just isn’t the type of conversation I enjoy. It is specifically around having to prove my worth in a vacuum – I would prefer to let the work speak for itself rather than talking about it.

However, this is only a weakness in a world in which I work alone. Once I combine my skillset with a top-class salesperson, my weakness becomes a strength because it means I wholly focus on serving and delighting clients.

In practice, as opposed to philosophically, a weakness is only a weakness insofar as it does us a disservice. Once we can reconfigure the situation, we may well find we can turn it into a strength.

Questions in the Image:

  • What can I learn from my weaknesses?
  • i) What weaknesses can I admit having?
  • ii) In what circumstances are they weaknesses?
  • iii) How might they be strengths?

Want to Read More Around This Topic?

The Gifts of Imperfection by Brené Brown (link to This book encourages readers to embrace their vulnerabilities and imperfections, viewing them as catalysts for courage, compassion and connection rather than simply as weaknesses.

Nurturing Curiosity – Daily Practice: This is part of the Nurturing Curiosity series of tools, insights and questions designed to help nurture curiosity as part of our daily practice. In point of fact, every interaction we have is an opportunity to question what we are observing and how we and others are seeing the world. Also remember that questions come in many forms throughout our day. In fact, I am currently waiting for someone to drop off a package and every 10 seconds my brain is going – Are they here? Are they here? Not only will the drop-off interrupt my thinking, but I am amplifying it by continually interrupting myself. In short, my concern about being interrupted is triggering my brain to interrupt itself. How does that make sense? How might I stop interrupting myself? What is my deeper concern here?

About Tom O’Leary

My mission is to help others think differently – meaning more broadly and deeply – and thereby make better decisions. The key to thinking differently lies in our curiosity.

The more we question, the more possible answers we uncover, and the more we expand what we thought possible. Life has taught me that possibility lies not so much in seeking answers but in learning to ask better questions – the ones that help prioritise what is truly essential.

And yet, in a culture obsessed with efficiency and productivity, the paradox is that much energy and resources are wasted by a bias towards action over contemplation. If you are answering the wrong question, it doesn’t matter how ‘hard’ you work, you are still answering the wrong question.

That is why I am a big advocate of nurturing curiosity and innovative thinking at all ages, particularly amongst leaders because of the impact they have on us all. In my vision, leaders aren’t boxed in by traditional thinking or established playbooks. They are curious, open to fresh ideas and diverse perspectives, fostering a culture of exploration and learning.

How Might Tom Help?

  1. My first invitation is to take maximum advantage of the free content on this site.
  2. I also endeavour to answer every email so if you have any queries do reach out – you will find my address if you are curious. Your future self will thank you!
  3. If you would benefit from a face-to-face conversation, consider signing up for a Decision Coaching package (initial call plus follow up call).
  4. If you feel you would benefit from a chat without having to sign up for decision coaching, click on the button below to join the waiting list for the opportunity to speak face-to-face. No charge! You just need to make a case as to why we should speak.