Leading with compassion

We know it’s time to step up and become the leaders we’ve been looking for.

But it’s not always that simple.

Our inability to recognise the difference between our emotions and the stories we tell ourselves about them can hold us back in both our ability to lead and in our personal growth.

One way we can overcome this is through "radical self-inquiry" - the non-judgmental exploration of our unconscious beliefs and motivations.

It’s a term coined and exemplified by our returning guest, Jerry Colonna.

The author of Reboot: Leadership and the Art of Growing Up and REUNION: Leadership and the Longing to Belong, Jerry has worked with CEOs and changemakers from around the world.

We’re huge fans of his work, which is deeply rooted in the concepts of radical self-inquiry and the healing journey towards becoming more conscious, aware, and compassionate leaders.

In part two of our conversation, he offers a holistic formula for developing effective and resilient leadership, one rooted in practical skills, deep self-reflection, and the courage to vulnerably share our experiences.

He calls bullshit on the masks some of us wear to pretend that our businesses are “crushing it”.

And he challenges us to let go of what we hold dear to create a more equitable world.

If you missed it, check out the first half of the conversation here.

This one’s for you if…

• You want to develop more effective and resilient leadership through integrating practical knowledge, deep self-reflection, and vulnerable sharing.

• You're curious about the unconscious drivers behind toxic leadership behaviours and how cultivating compassion can help address them.

• You want to create spaces where people can vulnerably share their struggles, breaking down the cultural norms that often trigger isolation and silence.

• You're ready to engage in the transformative process of radical self-inquiry to uncover your unconscious beliefs and motivations.

Here are nine takeaways from the conversation:

1. Emotions and feelings are different

So many of us use the terms emotions and feelings interchangeably. 

But Jerry highlights the importance of distinguishing between them.

“Emotions are these sensations in the body, and the feelings are the stories we tell about the emotions.”

He encourages us to get curious about the emotions underneath our reactions, rather than getting trapped in the limiting narratives we create in our minds.

2. Unlock what’s really driving you

We like to think that we’re behind the steering wheel when making decisions. But more often than not, our unconscious is running the show.

To counteract this, Jerry emphasises the transformative power of ‘radical self-inquiry’ - a non-judgmental exploration of the unconscious beliefs and motivations that shape our behaviour. 

“Radical self-inquiry is the skillset that we're the least likely to have developed as children, and it's arguably the most important.”

Honing this ability is crucial for developing self-awareness and breaking free from our unhelpful patterns.

3. Curiosity reframes the dumb stuff we all do

Toxic behaviour can come from an innocent place. Jerry suggests approaching our own and others’ behaviours with the spirit of non-judgmental curiosity.

“We want to feel safe physically, existentially, emotionally, spiritually, and we want to know down to our bones that we belong. 

It starts to shift the conversation when we see toxic behaviour through the lens that might occur when we say, ‘Well, that's just a five-year-old kid trying to seek love, safety and belonging.’

It doesn't excuse the behaviour. But it makes sense of the activities.

And when we ourselves fail to be the leaders that we want to be?

If we look with curiosity and that radical self-inquiry at our own behaviour and say, ‘Oh, I was just trying to keep myself safe. 

Boy, that's a knuckleheaded way of doing it.

But that's what it was. I'm not a bad person.

I'm just trapped in a five year old's body, trying to make sense of the world.’”

This perspective shift unlocks a deeper understanding of ourselves and others, and develops our ability to make sense of even the most challenging dynamics.

4. Practical skills + Radical self-inquiry + Shared experiences = Enhanced leadership

Jerry offers a simple formula for developing effective and resilient leadership that integrates practical skills, deep self-reflection, and the courage to vulnerably share one's experiences with others.

“‘Practical skills’ plus, what I refer to as ‘radical self-inquiry’, plus something that I think you do quite well, ‘shared experiences’. 

Those three equal enhanced leadership and, most importantly, greater resilience.”

5. Nobody is crushing it

It’s easy to feel inadequate when you see how others appear to be doing and hide what’s actually going on for you. 

“When I first started doing this work, I used to stand up in front of people and say, ‘Nobody's crushing it.’ 

People would say, ‘How's it going? How's your startup going?’ ‘Oh, we're crushing it.’ 

You know it's bullshit, right? And yet there's still this culture that persists because we're trying to make sense of, ‘Why do I do it? If it's so hard, why do I throw myself into this ring?’

I would argue that the most radical and perhaps the most transformative part of that entire formula is the ability to share in community the true story of what we're experiencing.”

6. Compassion fixes our urge to fix

When we’re faced with another person’s suffering, we want to stop the hurt. Often, because we’re the ones feeling uncomfortable. 

Jerry emphasises the importance of cultivating compassion - the ability to witness another's emotional experience without the impulse to immediately fix it. 

“Compassion, etymologically, breaks down into two words; ‘com’, ‘passion’. 

‘Com’ means to be with. ‘Passion’ refers to feelings.

It does not break down into fixing feelings.

It literally means to witness someone else's experience, labelled as a feeling.”

Being able to ‘be with’ a difficult experience this way offers a path for deeper connection and self-exploration.

7. A better way to measure your leadership

There’s so much talk about how to be a good leader. But how do you measure how effective you’re truly being?

“I would ask, ‘How many leaders have you helped create?’

What are the conditions in your organisation such that those innate leadership skills, and the people with whom you work, start to rise?

What would happen if everyone within an organisation felt enough love, enough safety, and enough belonging that they could be their greatest, most actualised human self?

Now, I can't guarantee that it's going to create the best financial return on investment.

But what an extraordinary organisation it would be.”

8. What are you willing to give up for systemic change?

If you’re reading this, you’re probably a change-maker. But there are some hard truths to face about how we’re “complicit in creating the conditions” and how we may benefit from them. 

Jerry knows that this can be deeply uncomfortable, but argues that this very discomfort is a necessary step towards personal and societal transformation.

“I get it's uncomfortable. Imagine who has been bearing the emotional load of systemic oppression, and imagine how uncomfortable it is for those folks.

Because I think that there's a core question, which is, ‘What is my responsibility to the world outside of the meat sack of me?’ 

And equally important, ‘What am I willing to give up that I love .. including my own love, safety, and belonging, so that someone else can feel those things?’ 

I think that there's a moral responsibility to ask those questions, to strive for those answers.”

9. We don’t need to do this on our own

When contemplating what’s our work to do and how to lead by example, it’s not just community we can lean on.

While it’s easy to react against negative role models, positive ones can be energising. 

In Reunion, Jerry talks about turning our ancestors into elders as a way of creating systemic belonging within an organisation.

While recommending many of his books, he spoke lovingly about his relationship with his mentor, the American author, educator, and activist Parker J Palmer.

“I literally will say myself at times, 'Well, what would Parker say in this moment?' And that's really a powerful guide.”

There is huge value in finding mentors and “elders” who can serve as a powerful guide in moments of doubt or confusion.

And for many of us, our new mantra might be: What would Jerry say?

Jerry Colonna isn’t afraid to challenge us to go beyond what feels comfortable when exploring the importance of self-awareness, vulnerability, and compassion in leadership and personal growth.

All in the service of making it a better world - for everyone.

Do you want to join other like-minded people who want to make a positive difference in the world? Join our community, dip your toes in with a Masterclass, or dive into transformation at one of our life-changing events.

Notes

Many thanks to the wise and hugely inspiring Jerry Colonna for his time, yet again. We could talk to you forever.

Check out his books Reboot: Leadership and the Art of Growing Up and Reunion: Leadership and the Longing to Belong, his start-up podcast, and his resources at Reboot.io.