What kind of leader do you want to be?

As leaders, our responsibility is to make the world a better place. This work starts with getting to know ourselves.

What kind of leader do you want to be? This should be easy for any leader to answer, but it only becomes easy once you spend time exploring it.

Jerry Colonna is one of the thinkers who shaped my understanding of what makes a good leader. In Reboot, his first book, he made a powerful argument that “better humans make better leaders”:

Radical self-inquiry is how we learn to become more of ourselves, more like ourselves, more authentic. More human.
And better humans are better leaders.
This is what great leaders do. Great leaders look unflinchingly in the mirror and transform untamed hungers and unruly compulsions into moments of self-compassion and understanding. In doing so, they create the spaces for each of us to do the same, turning our organizations into places of growth and self-actualization.

By getting to know ourselves and becoming more ourselves and more authentic, we become better humans and leaders. Then, we turn our organisations into places of growth and self-actualisation for others.

There’s nothing about money in this definition, and I don’t believe it’s an accident. In fact, the poem on the website of Reboot, a coaching firm Jerry leads, states in its first line.

It doesn’t matter to me how much you’re worth on paper,
or who you know or hang out with.
I want to know what your heart values
and what courage – perhaps dormant –
awaits
inside of you
to dare to pursue that for which your heart truly longs.

Great leadership is never about money. It’s not that it doesn’t matter, but the work doesn’t stop there. The work of a great leader is to understand what their heart values and what courage awaits inside them. Instead of being a self-indulgent exercise, this work of radical self-inquiry helps leaders see the effect of their leadership on others, as Jerry writes in Reunion, his second book:

What’s needed is nothing short of a transformation of the traditional notion of leadership. It is no longer sufficient to measure success by financial return on investment, for example. Good leaders must also use the experience of leadership to confront demons. They must encounter and understand the subroutines that define their lives and see the ways such inherited belief systems shape the positive and negative experiences of those whom they are called to lead.

If we don’t do this work, we build organisations and teams where the leader is focused on the endless pursuit of more power, money or other achievements, while those we lead don’t feel safe enough to belong.

The full measure of a leader is more than return on investment, it’s a continuation of the expectations built on the anxious and insecure need to constantly prove worth by measuring our lives in what we have colonized, what and who we have dominated, and the toys we’ve collected at the end of our days. One measure of a true leader is the number of people who feel safe enough to belong.

What might it look like in practice? A one-sided focus on drive and motivation at the expense of making your team members feel insecure and not good enough. I can think of more than one leader looking to instil “a sense of urgency” without fully realising that they’re doing it by making their team members more insecure (or choosing not to think about it).

An inevitable result that comes sooner or later is people choosing to leave, with the leader left wondering: “But they were so driven and motivated…”

Part of the great myth of business leadership is that the power of never enough can be channeled and mastered into drive and motivation, traits so often seen as sacred to the pursuit of a goal. The myth is that we can cherry-pick the good known as motivation while leaving behind the devastating negative of not good enough.

Taking it a step further, if we, as leaders, focus on growth and productivity as self-evidently good goals, we build organisations that are not a place where others can feel they belong.

Urgency, speediness, and, for many organizations, the persistent need to “scale” for no discernible reason, other than the presumption that bigger is better, is unchecked extractive capitalism. This stands in opposition to the need and respect for rest and recovery. It also fosters a view of the self that highlights productivity and rational, objective results even as it strips away the humanity of a community of co-workers, wildflowers all, undermining any semblance of systemic Belonging.

Growth or productivity by themselves isn’t a problem. They become a problem if a leader myopically focuses on them without asking what kind of leader they want to be and without doing the kind of work that makes us better humans with bigger hearts.

[T]he most likely cause of a leader’s failure is their inability to read and meet the needs of their employees, to heed their longing to belong. You can ignore the strident calls from folks like me but look at the data. When your employees want you to take a stand for Black Lives Matter, for instance, they want you to lead with your heart, with empathy. They want you to give a shit.

Be warned. Expanding the definition of successful leadership to include having a heart that is filled with compassion, that cares about a world in which fourth graders and innocent Black men are murdered, in which gender-questioning children and adult women are denied healthcare, causes a reckoning not only with the systems of oppression with which you may have benefited. It will cause a reckoning with your own sense of self. It will cause you to do your work.

I remember a client wondering whether to make a statement to the team about yet another horrible atrocity that everyone was reading about in the news. Not to say anything felt wrong, given the scale of the horror. To say something invited the question of which atrocities to acknowledge and which to ignore. After all, his CEO job isn’t to comment on every atrocity we see on TV.

My invitation to him was not to try answering this question rationally but rather to inquire into what kind of leader he wants to be. The invitation was to feel the pain of the world and of his team members, some of whom might have been indirectly affected, and get a sense of what kind of leader he wanted to be.

And then, from that place, choose the next step, trusting that it will be the right one, made not out of greed, desire to dominate or insecurity, but genuine care for others and a desire to be a better human and a better leader.