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Season 2 · Episode 26 · English

Unlock Authentic Leadership by Knowing Your Shadow

Steven D'Souza Author of Not Knowing, international executive educator

Prefer audio

I think many of us recognize that we live in an era of "performative leadership"; a curated world of toxic positivity where leaders feel pressured to always have the answer, always smile, and always project certainty.

But the cracks are showing.

From the collapse of toxic corporate cultures like Boeing to the quiet burnout of high performers, the cost of ignoring what lies beneath the surface is becoming too high to pay.

This conversation challenges the binary idea that we must hide our "darker" sides to succeed. Instead, it proposes a radical truth: true executive presence doesn't come from suppressing your shadows, but from integrating them. If you want to understand why talented leaders derail and how to cultivate a resilience that goes deeper than a mindfulness app, this episode is the blueprint.


Guest:

Steven D’Souza is an influential executive educator whose career provides a powerful foundation for his insights. His journey moves beyond conventional business training, starting with studies for the priesthood and work with young offenders in high-security prisons, before pivoting to coaching the C-suite of global corporations.

As an award-winning author, his book Not Knowing won the prestigious CMI Management Book of the Year, and he has been recognized by the Thinkers50. He serves as an Associate Fellow at Oxford University’s Saïd Business School and an Executive Fellow at IE Business School. This background allows him to expertly connect the spiritual, the biological, and the systemic, offering a perspective on leadership that is both intellectually rigorous and deeply human.


Key Insights:

The high cost of the hidden

Research suggests up to 70% of leaders derail within their first 18 months. This rarely happens due to a lack of technical skill, but because strengths under pressure mutate into toxic behaviors (e.g., decisiveness becoming impulsivity). How do you identify your "shadow drivers" before they sabotage your tenure?


The power of "Negative Capability"

In a business world addicted to speed and certainty, the most effective leaders possess what the poet John Keats called "Negative Capability" - the ability to exist in mystery and doubt without reaching for irritable facts and reason. Is the capacity to pause and not know perhaps the ultimate strategic advantage in complex systems?


Your gifts are hiding in the dark

We often assume the "shadow" only contains our worst traits (anger, jealousy, greed), but it also holds the "Golden Shadow" - the talents and desires we were shamed out of expressing as children. Are you unknowingly suppressing the very creativity that could define your next breakthrough?


The danger of "Good Vibes Only"

Enforced positivity leads to emotional labor, burnout, and a loss of genuine connection. Steven explains why real psychological safety requires the space to express the full spectrum of human emotion (including anger and grief) and how suppressing them can fuel toxic organizational cultures.


Leadership is biological, not just intellectual

We tend to treat leaders as "brains on sticks," ignoring that we are embodied creatures driven by hormones, sleep cycles, and physical needs. How does ignoring the biological reality of the human body lead to disastrous ethical drift and decision-making?


Listen now to stop running from the shadows and start leading with wholeness.


www.thinkroompodcast.com

www.linkedin.com/jgronstedt

www.grail.works

Read the full transcript
Johan00:00:00

I think you have such a fascinating life story and in order to, to understand this conversation, um, I think it might be a good idea to, to explore a little bit about how come you ended up writing your latest book, The Shadows at Work Uh, and I would imagine that your life story has been a pretty big part of, of ending up where you're today.

Steven00:00:25

Yeah. Thanks. So I think The Shadows at Work Book is about looking at our dark side, as it were. Dark has not in negative but more hidden. And i think there were th main reasons i chose to write about this topic.

Johan00:02:50

that

Steven00:02:57

Many of them came from minority communities and from deprived backgrounds.

Johan00:04:07

definition of derailment when you speak about it?

Steven00:04:10

don't succeed in their role You don't succeed in your role. And you know, one question to why? Obviously there's multiple factors. Of example, people are recruited into their role uh, based on prior success, at managing job, but not necessarily on potential uh, to do a new and more complex role.

Johan00:05:22

reason for leaving as far as I understand the statistics

Steven00:05:25

Yes, exactly. And the third broad reason is around the societal uh, relevance. There there are two commentators Edmond Lau and Matt Klein and they wrote an article called Dark Mode Shift.

Johan00:07:48

Two things that that pops up into to my mind in periods of, of increased, um, external stressors as I think we, we experience in our society right now.

Steven00:08:23

know my shadow and my light. So would i last be whole?

Johan00:08:29

Yeah. And that speaks about integration. right? It's not about hiding. Um. The dark sides, then then I'm not whole. And I I think the the society that at least I grew up in, in um, puts a premium on the light side, and everything else must be hidden.

Steven00:08:47

Part of it's, you know, there's a lot written on toxic positivity. Positivity. Yeah. And you know, uh, we we live in a a culture almost like of emotional labor, where in some professions you know, staff are uh, paid to be polite, to paid to smile.

Johan00:15:02

very interesting.

Steven00:15:24

Yeah, i think every culture has its own. Um, you know, shallows, for example, in, in Japan culturally like, uh, women are not, you know, it's culturally inappropriate to laugh, so you always find people covering their mouth and in other cultures, you know, sexuality might be suppressed or other.

Johan00:17:09

Yeah, and I would imagine that these uh, different lenses are, are deeply intertwined as well. Yeah. Do you find that, so if we take the subgroup leaders, because everybody will carry their shadows, uh, but do you find that there are, are certain shadows that are more prevalent amongst that specific group leaders?

Steven00:17:29

A

Johan00:18:25

Yeah.

Steven00:18:26

Give back to those in power and well, less able to to receive it because of that difference in, in status.

Johan00:19:07

i would imagine since you do so much consulting also to organizations, that there are systems to put in place to, um, kind of decrease the risk of derailment.

Steven00:19:22

Yeah, I think, uh, the, the main one is probably for human resources in terms of, uh, who do they promote and, uh, why. So there's a lot of research that shows that we promote, uh, very poorly and we promote based on overconfidence rather than on capability. It happens particularly on a gender basis, so there's a a good uh, piece of article, actually it's the most read HBR article by uh, a colleague, Thomas Ari Music. He wrote an article called, Why do so many incompetent men become leaders? And In his research it shows that you know, because we judge overconfidence for competence Mm. And, and that's uh, uh, partly down to what we uh, conflate such as charisma, uh, talking time with ability and and that sorts, that's clearly being challenged and they're not uh, causal.

Johan00:20:53

most

Steven00:21:29

I think uh, there's a woman called Susan Fowler who wrote an article about her strange year, year in Uber.

Johan00:21:35

Okay.

Steven00:21:35

And

Johan00:22:36

people that that gets the, the, the dressing down right,

Steven00:22:39

equally, his peers that he didn't feel were off the, of his, uh, intellectual caliber, let's say, or his, uh, quality. So, you know, he was ferocious in his, uh, attacks, but he was also, um, a good producer.

Johan00:25:24

about

Steven00:25:59

You are, you are, right. Uh, I think you have to look at the cost of ignoring the shadow for an organization.

Johan00:30:27

to make this even more practical.

Steven00:30:49

Yeah. So I think in, in, uh, my early. i remember one time my manager saying to a colleague of mine, he was a new colleague, I, I'm really glad you're here. And inside I felt, uh, a sense of pain. Why is he saying, I'm really glad you're here to my colleague, but not to me. Hmm. And the d

Johan00:31:09

came forward.

Steven00:31:11

I recognize its shadow when, uh, our reaction is disproportionate to the situation and somebody may have acted in a different way.

Johan00:31:33

It's almost a practice as well to kind of just notice that this is probably a disproportionate reaction.

Steven00:31:40

It's, yeah. It's, uh, recognizing, you know, asking yourself. Yeah. wow.

Johan00:36:51

like

Steven00:37:44

Mm-hmm.

Johan00:37:45

Do you agree with that?

Steven00:37:46

Yeah, I do. Like, uh, now Most shadows were formed because of shame.

Johan00:39:00

It's

Steven00:39:12

A simple example is at school. I remember loving art, you know and loved painting.

Johan00:39:45

relationship to, to dance. It was something that I, uh, I don't think it was anybody who explicitly told me that you shouldn't dance, but it's something that's during, during growing up, uh, i identified as not being a dancer, right?

Steven00:40:41

I think it's about listening to our desires And, uh, longings as well, and not, uh, dismissing them too quickly. Mm-hmm. And, you know, i gave the example of, you know, choosing career options early in our, early in our careers for prestige or for security. Uh, I remember I've applied, I think four times to be a school teacher, and I got accepted at Cambridge University in the uk and i didn't choose teaching because i felt it was not rewarded in, in the UK as a profession. uh, financially and also politically.

Johan00:43:30

four lenses, did you find was most difficult to write about in the, in the context of leadership? You mentioned sex, for example.

Steven00:44:25

I think you've touched on, you know, because sex often correlate to it, shame. It's almost like we have no space for it in organizations.

Johan00:46:18

No and I think that's so sad. Uh, Let's explore power and strength, for example, because it might be... Easier to talk about than than the the sexual dynamic power is something again that as a society where we we more often talk about it as power corrupts for example as we spoke about today I've had really interesting conversations on this podcast that that the most dangerous type of power is an unconscious relationship to power Yes. so I've had for example people that has come from um, experiences in, in more of the martial arts community and they say that there's nothing as calm as an aura to be around around people that has a very very conscious relationship to their physical power Uh, and I think the same is probably true for all of these kind of hidden shadows that the danger is not being aware is not power in itself Yes.

Steven00:47:19

Yeah, I think, uh, you're right. Uh, we, we have negative associations with the word, whether it's anger, whether it's sex whether it's power, and that's not helpful. i love the way you put it. Unconscious relationship is what's dangerous. But I, I do boxing. I took it up in later life at 45 years old, and i I practiced now for five years. So by far I'm not, uh, an expert. But I notice when I, when i fight somebody who is a beginner, complete beginner, it's far more dangerous than fighting somebody who's conscious because they throw everything.

Johan00:49:00

point around uh, brains at work uh, I think it's such a simplistic way of of looking at humans, right? Um, yes. Just maybe a fun point to to not completely close out the sex chapter but imagining a, a deeply sexually frustrated manager like yes, you can't really turn that off.

Steven00:51:01

There's another meditation similar to the dynamic one, that's, uh, almost like you express each emotion like for a period of minutes, but totality. So for example, you might express playfulness for a few minutes in your body, may with others socially. So it's more of a, a socialness then you might experience, let's say, uh, tears and sorrow.

Johan00:53:39

And i think the, there's, i don't know if you agree with this. i feel that there, there's a, um, kind of blending in what, what's within psychology and personal development and different type of meditations and so forth. i feel that there's a lot of leaders that are a little bit afraid of, of even entering into that space. It feels like it's, it's completely like, it's too heavy lifting. i need to rebuild the whole foundation. And then maybe you see the, the types of people that are, are mostly in these worlds have sometimes a tendency to almost turn away from, from the world of, of more professional pursuits.

Steven00:55:18

I do wonder about this, you know, and I think this is generational as, as well, Johan, like, you know, I, I've read that in the past, you know people didn't expect as much from their work, you know, work was something they did uh, for a portion of their day, and then they spent time with family, as time with friends, doing other things, and uh, over the decades, the expectations that we have of work have changed.

Johan00:55:45

think the quality of of the life outside of work has gone down, we see uh, uh, a lot around, again, coming back to sex, we have less and less sex, and you talk about that, it's dopamine is so freely available on the mobile phone or on the Netflix or whatever, So, so just the quality of friendships are going down over time, So, so like the balancing forces are also less balancing in in a sense.

Steven00:56:08

Yeah, I, I agree with you. I think this is probably where in a society that encourages shadow behavior. Yeah. You know, performative, performative leadership may be distracted.

Johan00:57:03

Can you say an example of, of what leading from the dark actually means, maybe through somebody you've worked with or something like that

Steven00:57:11

Well, A

Johan00:59:10

example of uh, negative capacities In the context of leadership Do you think?

Steven00:59:16

Simple

Johan01:02:06

I

Steven01:02:57

I've seen a rise of, you know, Mindfulness.

Johan01:03:28

as a coping mess mechanism.

Steven01:03:30

Yes. And it can be used as a, a me mechanism for almost like getting more productivity as a, than necessarily, uh, helping an individual and changing, you know, it's like in, it's like helping somebody get used to a dark room without helping them open, you know, the window thing and letting the natural heat in, so i I think it can be helpful, but in, you know.

Johan01:04:37

i heard the definition at retreat. i was at speaking about the exact same thing that was, meditation is anything that you do with your full intensity. And i think for me, that, that something kind of clicked there.

Steven01:05:55

I see that, but I also think, you know, distraction is a part of meditation and, you know, it's

Johan01:06:01

Yeah, that's right.

Steven01:06:02

You know, it's not, we don't have a clear mind, you know, we're not like a, a tranquil lake the time and that, the proof of being aware, okay, I'm distracted and coming back, that, that equally as Asian and I think too many, almost like pressures on ourself to be able to so-called meditate or do things right.

Johan01:08:07

But

Steven01:08:47

Yeah, it's not normative. You're right. End up, up to stopping, waiting, et cetera. But I think these are, uh, these are the negative capabilities that I think are really helpful to develop.

Johan01:10:10

Yeah.

Steven01:10:10

and

Johan01:10:41

Yeah, curiosity is, is such an interesting trait and skill, especially now in in an environment that is changing so quickly, I, I strongly believe that curious leaders will be high performing leaders in the coming years treating uncertainty not As risk but as opportunities comes very close uh, in in terms of mindset being more curious so I would love to hear more about 'cause the example that you just gave is, it is a tool for uh, encouraging curiosity in teams what are more tools that you use to encourage curiosity

Steven01:11:22

I think ask more questions you know as a, as a child if a, a child you know we're always asking questions you know why, what, you'll be familiar with this Your young children.

Johan01:11:45

penalized quite clearly. I, I've read studies around this that, that the teachers say that they want curious children but in in reality they treat them worse and worse the more questions they ask.

Steven01:11:56

Yeah, it's almost like seeing as attention or you know, we're not rewarded. And so as adults, known to stop asking questions. And we don't ask enough questions or we don't, you know, we only stay within our narrow frames. So part of, of

Johan01:12:11

the style

Steven01:12:34

Yeah. In, in a practice called adaptive leadership, one of their practices is to ask conflictual questions. So meaning questions that are more difficult to ask. So rather than, you know, oh, that's great, how did you do? It's more, uh, or the question is, what part did you play in the mess and how did you contribute to this, uh, problem?

Johan01:13:11

also difficult to do this in a, a management team, let's say, or in, in a team, because questions that are important, they also take time.

Steven01:13:34

uh, You can make time for this so you know, I I worked with an organization that you know, they ran uh, coaching circles which were just focused on questions and they were with people who are not in your area so if you tend to have people who have, you know, they work in your department, they tend to see uh, problems through the same frame as you, and therefore have tending to see solutions and questions, ask questions around the same angle, the, the way this works is that people from different departments would get together uh, once a week for 30 minutes only and each person would have a a challenge they're facing and they had to speak, speak the challenge, but then they would remain silent and then each other person, let's say there were four, four or five in the group they would ask an open question To that person, and that person didn't have to answer, you know, their job was just to listen and write down the question because often we wanna give a reply Yes, but I've tried. Yeah. And they, they, they were questions like, well, have you seen this before?

Johan01:15:06

kind of

Steven01:15:27

know. Yeah. I agree. And there's also this idea that, you know, we always seem to want to answer and solve questions. Mm. But p pe uh, children don't ask questions for information, I mean, they ask questions for discovery to your point around confirmation or cur, uh, or, you know, curiosity. So there's a concept called The Beautiful Question, and it's, uh, by a poet who works a lot with corporations called David White. And, uh, he said, often beautiful questions are questions that you can ask yourself that don't require immediate answers, but that these, the answer to those questions evolve, you know, over your life and over your career. But they're, they're, they're deeper questions such as, you know, what's my purpose? You don't answer that once And forever.

Johan01:17:09

Yeah,

Steven01:19:08

Yes. And hopefully they're teaching it to you as well by their, you know, by their question and their, their curiosity in their, in, uh, zen there's a, there's a phrase, it says in, in the beginner's mind.

Johan01:20:21

I would wanna, before we we end out the, the podcast, to explore a little bit more about the spiritual lens and, and how you've come to think about like, some other concepts that we don't especially in the Western world, have a pretty conscious relationship to is is ideas of like destiny, purpose. We we're, we, We like to frame it more as... um. If we have a conscious relationship to we more frame it more as as perhaps vision where I'm the, the agent in, in this in this journey.

Steven01:20:58

Yes, Um, you know, there are many ways of thinking. That one is you know, life happens to you. Uh, The other perspective is life happens through you. And then another one is life happens as you. So rather than, and i think that that's, uh, you know, the evolutions almost in, in thinking about your relationship to, to life.

Johan01:22:01

And

Steven01:22:02

i think. For, for, for leaders and being able to attend to our own humanity, our own sense of grief, our own sense of sadness, our own, uh, lust, ambition, uh, jealousy, all of these human, uh, human uh, capabilities, I think makes us more whole.

Johan01:22:58

Yeah, absolutely. And what was the quote that you started the podcast with? i thought it was so beautiful. i would want to end the podcast on the same.

Steven01:23:05

Sure. So the quote was by Sir Michael Tippet and it's, I would know my shadow and my light. So would i at last behold.

Johan01:23:17

Beautiful. Thank you so much, Steven, for coming on.

Steven01:23:21

Yeah, thanks Johan, it was my pleasure.

This episode lives on thinkroompodcast.com.