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Humbleness and Entrepreneurship

By Sonja Montague Mackay

What role does humbleness play in shaping leaders of the future?  How do you create a humble mindset and why is it important?

During an emotional culture workshop with Skalata Ventures, an Australian seed investment program, we dove deep into the importance of humility.  Humility was one of the top five desired feelings identified as important for their portfolio companies.

The beauty of working with the emotional culture deck as a way to facilitate conversations around feelings and emotions is the opportunity to reflect on what is really important.  Often what arises is not what anyone expected.

It is not every day that leaders and teams take the time to pause and pose questions such as “how do we want our people to feel?”, “what does our success rely on them feeling?” and of equal importance “how do we not want them to feel?”

Skalata Ventures shapes future leaders. Through their program, Skalata is cultivating and nurturing leadership across all levels of their portfolio companies’ businesses.  By taking the time to identify the core feelings they want their portfolio companies to experience during their program they are creating an environment where talking about feelings is welcomed and leaders of the future are supported.

How do you adopt a humble mindset and why is it important?

If you are humble, you are open to learning, not assuming you have all the answers.

We’ve found that great leaders exude a strong sense of humility. Humility and selflessness are closely linked. You cannot be selfless without humility, and humility without selflessness is false humility.

Humility is a direct way of keeping your ego in check and developing a healthy sense of selflessness. 2

The power of humility.

How can leaders support their people, their teams to feel a sense of purpose, to have high motivation, energy, and creativity? The answer humility.

“How Humble Leadership really works” Dan Cable writes about how to enable this sense of purpose “one of the best ways is to adopt the humble mind-set of a servant leader.  Servant leaders views their key role as serving employees as they explore and grow, providing tangible and emotional support to do so”.  1

This allows the creation of a culture of learning, encouragement and the sharing of expertise.  No one knows it all, servant leadership ensures we all learn from each other and remain open-minded whether you are a two-person start-up, the CEO of a multinational organisation or the Prime Minister of a nation.

A ritual to encourage humility

With humility identified as a one of five feelings that Skalata Ventures wanted their founders to feel, the question arose of how?

What is a ritual that can be utilised to instill and evoke humility?  We workshopped the importance of founders’ active participation in fireside chats, roundtables, and interaction with those who are one step ahead or even further along on the founder journey.

We all learn from one another, this is a tenant of servant leadership and one that can be forgotten when you have deadlines to meet and emails to send (which at the time feel the most important thing you have ever had to do.)

One Takeaway

With Skalata, we explored the concept of “one takeaway”, after attending a leadership retreat in the USA over twenty years ago, at the end of each session of speakers we were asked to reflect on what was our one takeaway.  This way of approaching all meetings, workshops, fireside chats, pretty much everything in life has stayed with me ever since.

Simple I know yet powerful.

What can often happen is hubris takes hold and our humbleness get forgotten.  Hubris can be described as exaggerated pride or self-confidence.  I don’t need to attend this because……

Whatever the founder is currently doing is more important than the learning opportunity.  I get it, we can all become overwhelmed with the volume of work and think that not attending a fireside chat or a roundtable discussion is ok as “we know what they are going to say”.

What if we shift to a mindset of humility, servant leadership, openness to learn and adopt the principle of one takeaway?

It is unlikely you will leave any meeting without some form of takeaway.  You will learn something by actively participating.  You may actually have the breakthrough you have been searching for or identify a way of working that you never ever want to implement..good to know.

By sharing your one takeaway with fellow program participants you get to see the lens with which each other views the world and perhaps learn more than you realised.

And so, the importance of humility becomes much clearer.

When leaders are humble, show respect, and ask how they can serve employees as they improve the organization, the outcomes can be outstanding. And perhaps even more important than better company results, servant leaders get to act like better human beings”.2

And so I ask, what is your one takeaway from this post?


Dan Cable “How Humble Leadership Really Works” April 2018 Harvard Business Review

Rasmus Hougaard & Jacqueline Carter “The Mind of the Leader: How to Lead Yourself, Your People, and Your Organisation for Extraordinary Results