Self-inquiry transforms leaders into better humans, and better humans into better leaders.

This radical inner journey is the proposal that Jerry Colonna, author, CEO and founder of Reboot.io, makes to anyone who finds themselves in positions of authority – those among us who face the challenge of caring for others in the organisation without needing to sacrifice their own peace.

In an exclusive interview ahead of TechHR India 2024, People Matters spoke to Jerry about radical self-inquiry: a concept of self-awareness that might seem out of place in the context of business environments but has massive potential to build emotionally adjusted and empathetic leaders.

Radical self-inquiry prompts individuals to ask: “Why do I do what I do?” Jerry pointed out. For instance, why does a leader get upset when a colleague makes a particular decision? Why does a high-achieving CEO feel constant anxiety, and how does this anxiety impact the entire organisation?

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By understanding their own desires and anxieties, however, people can create a culture of empathy and support, mitigate conflicts, and foster a collective sense of purpose.

“If you use radical self-inquiry to understand the way an organisation operates, [you’ll find] most of the toxic behaviour within an organisation stems from people – either with power or without power – seeking to feel loved, safe, and that they belong,” Jerry said.

“There’s a connection between me doing my inner work to grow up and be the best human I can be, and me meeting the needs of my organisational colleagues, so that they can feel safe, that they are loved, and ultimately that they belong.”

Reconciling our inner and outer states

In professional settings, as in so many other facets of life, human beings tend to project their inner states onto their actions and decisions. Yet, there are also moments when disparity between between our inner and outer selves causes us to ask tough questions to get at our truth.

One poignant example is Jerry’s own story. Despite his success as a venture capitalist, he battled severe depression in his late 30s. His external achievements did not align with his internal struggles, prompting a deep dive into self-inquiry.

“The more success I had, the worse I felt. To the point that a lifelong relationship with depression, which began in my childhood, came back with a vengeance. In my late 30s, I was at a pinnacle in my career and suicidal. So the two things, simultaneously,” he recounted.

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“In that moment, at 38 years old, I had a choice. I could continue living what felt like a lie or I could radically inquire within to say, essentially, what’s going on with me?”

Jerry believes his emotional state at the height of his success was counter-intuitive: “The narrative that we all grow up with is, ‘achieve, achieve, achieve’ and it’ll be rainbows and pots of gold for the rest of your life. The truth is, far from that.”

Through meditation and studying Buddhism and psychoanalysis, Jerry reconciled his inner state with his outer success, achieving harmony between the two.

“As a result of that, I ended up in this place where, for the most part, I feel good about myself,” he said. “I ended up with this synchronicity between the inner and the outer.”

Radical self-inquiry: a step-by-step journey

Through honest introspection, leaders can acknowledge their motivations and unhealed wounds and, from there, develop their potential to drive businesses better.

A self-aware leader takes charge with a sense of purpose and respect for individuality. Conversely, however, a leader without self-awareness may lack empathy and be ineffective.

As a coach, Jerry is dedicated to guiding leaders find deeper meaning in their mission, both inside and outside the corporate sphere. He believes that, by understanding personal barriers, leaders can better manage their emotional states, creating a healthier work environment.

The logic is straightforward: the inner work that requires an individual to address their personal turmoil can almost always alleviate the pressures of most human interactions in professional settings.

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Self-inquiry, according to Jerry, also involves recognising the privileges of leaders themselves. It means asking oneself, “What am I willing to give up to make it safe for others and help them feel they belong?”

Jerry believes undertaking this courageous inner journey entails spiritual work and requires leaders to embody the values of kindness, compassion, and respect. It also draws on the wisdom of traditions that emphasise treating others as one would like to be treated.

Radical self-inquiry, Jerry believes, is not merely a personal endeavour but a powerful tool for transforming leadership and organisations.