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04:45: Curiosity about “stuckness” and how we get free

12:45: How curiosity informs my approach to coaching

15:00: Why I welcome resistance in a coaching session

17:30: Our ideas about work, and where they come from

20:45: Work and the difference our superpowers make

27:04: Courage to be curious — how fear gets in the way

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Pearl:

So it is rare these days to find people who are more interested in authoring original thoughts, and that's someone like you, Dalglish. It's a real pleasure speaking with you on this because you strike me as a “quiet rebel.” Someone who doesn't believe in public likes and opinions and retweets, but rather investing time, building original thoughts and words. Would it be an accurate assessment of you?

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Dalglish:

Yeah, it's wonderful. So first of all, thank you for having me on. I think I've always identified as an introvert. I'm sure people who've known me for a while know that I tend to be on the quiet side, more reserved, so I don't hanker after visibility. It’s hard for me to be loud, I think.

You mentioned my writing: it's so interesting, because since writing my blog on my website, I've gotten some feedback. Some people say: “If you would just use fewer words, write it more simply and, you know, be a bit more snappy, you would have a larger audience.” And I do think it's hard to get visibility and readership, especially in this attention economy where there's just so much content asking for our attention.

At the same time, I've kind of kept to my style of writing because I like to think that I write in a way that rewards readers who are willing to spend a bit more time with what I'm offering. So, as much as I feel the pressure that people give me to maybe be snappier or quote unquote “write for the internet,” I still think there's something to doing the kind of work and thinking and writing and reflecting, that takes a bit more time. Also, GPT3 and AI have been in the news a lot lately, so AI can write now, right? So I suppose it's also a bit of me wanting to make sure that I'm writing something that an artificial intelligence cannot recreate.

But the flip side, I think, of what you said about public likes and opinions: I will say that as an introvert and someone who's more quiet, something I've struggled and continue to work with is this tension between visibility and invisibility. Because I think I have spent a lot of my life in hiding; I'm very comfortable being invisible, and for a long time I felt, well, I'll participate or I'll show up or I'll speak up when I'm smart enough, when I'm good enough, when I'm capable enough. But more and more, with each passing year, I've started to realize the time is now. I mean, I may never be more qualified or capable than I am now. So I do live in the tension of, on the one hand, wanting to be quiet and reserved, but also making sure that I'm showing up for people when it can be most helpful and impactful.

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Pearl:

It sounds like a fine balance, isn't it? (Yes.) And that's the beauty of curiosity, I think. You know, when you are in the space of introspection, digging deeper and thinking a little bit more on some of the issues. And I think that's what you really embody in your writing and the things you share. I think curiosity really puts you in a kind of “forward mode” as well something outside of your usual introversion. Would you say that curiosity is your driving force in such scenarios?

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Dalglish:

Yeah. I think the way you phrased that makes me think that, if my tendency by default is to be more reserved and introverted, the one thing that does draw me out and towards people, is my curiosity about what's going on in their heads, interpersonal dynamics, how people relate to each other. And because I'm a coach, these days my attention goes to how people get stuck. How do we come unstuck from the patterns and habits that hold us back? Because that's more or less all of the work that I do with my coachees. And what I mean by stuckness is just this basic sense of waking up every day, doing the same things over and over, retreading the same ground over and over, causing ourselves and others the same suffering and pain without knowing how to stop it, or how to get out of it.

And so, and there are many varieties of stuckness, right? There can be professional, personal stuckness. So obviously as a coach these days, I work mostly with the professional variety. For example, founders or leaders who know that they have a perfectionistic tendency, and that they'd be so much more effective if they could let go, but they find it so hard.  Or founders and leaders who feel the need to know everything, they feel most secure and comfortable when they have expertise. But that's also holding them back because as you scale and build your company, it's not possible to know everything. So, over and over you see varieties of stuckness. People who are in compulsive habits and patterns who know they want to get out of it, but can't seem to quite help themselves. So when you talk about curiosity, that's where my curiosity goes. I get very curious about varieties of stuckness: why people end up there, and what it might take to help them get out.

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Pearl:

And where does your own curiosity come from?

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Dalglish:

Gosh, I think there is a very personal side to it. So growing up – so I grew up in Singapore –  I grew up in a fairly privileged but kind of chaotic family. There was just a lot of conflict, and I think just growing up, watching those dynamics and realizing, wow, there's just a lot of pain, a lot of suffering that we're causing each other. And it would just be so much better if we could all just agree to behave differently tomorrow. And sometimes you have that intention and aspiration, right? You'd say, tomorrow I will be different. But then the next morning comes, someone says something to offend you and you're right back in your pattern. So I think I just grew up really sensitive to that dynamic, and really feeling the costs of that kind of stuckness. And also with that curiosity and interest around why it’s so hard to change. How can it be that intelligent, rational, well-intentioned adults know that they have to be better for others, and yet something brings them back over and over to the stuckness.

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Pearl:

And that calls for a level of awareness, doesn’t it? For people to realize that the behaviors that are either self-inflicted or damaging to others, that are repeated – I think not a lot of people get that. Is that something you strive to get them to be aware of before they change? Or would you have a different approach when it comes to recognizing such behaviors?

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Dalglish:

Yeah, so I think, in terms of changing or getting out of this stuckness – it's a huge question. Like how do you actually get out of it? I think the first step is just awareness. So, for a lot of kinds of stuckness, sometimes we're not even aware that we're stuck. There are people, I mean, I think a lot of people will know or have had the experience of working with leaders where we all know what their problem is. We tiptoe around their ego, we know what not to say to trigger them, we know how to “handle” them, but the leaders themselves seem completely oblivious to what's going on.

So I think number one is just wow, having that awareness: Do I have an issue? Is this my impact on other people? And sometimes you could say, just having that awareness can be 50% of the problem. And that's where feedback comes in. I think, if most people already know what the problem is and it's an open secret, often, all you have to do is just ask the people around you: “Hey, is that my impact on you?”

And the second thing I would say is, even if you have awareness, sometimes that awareness alone doesn't mean that you wake up tomorrow and you know what to do. I was reading an example recently, an example of people with heart disease. So plenty of people with heart disease know “I need to change my diet and eat healthy and exercise three to five times a week.” And the stakes are so high. Either you do this or you die, right? You have a shorter life. The stakes couldn't be higher, and yet we all know it's very common that people still struggle to make those changes. So that's one extreme example.

But I think it shows up in many of the leaders and founders that I coach. Like the examples that I gave you just now, I do see leaders who struggle. “I know I'm being perfectionistic. I know I'm getting into weeds. I know I'm micromanaging, and yet, even though I have this intention not to do those things, when push comes to shove, it's just so hard to let go.” So there, I think, you have the awareness, but the problem lies a bit deeper. Usually with these patterns, there's a lot of safety and security wrapped up in them.You know, we develop these strategies, which sometimes can be strengths, but we use these strategies to keep us safe and that's why it's very hard to let go of them. And when we grow up – we develop these strategies when we're younger – we grow up and we continue defaulting to them, even though there's a part of us that obviously knows we're adults, that we can choose. But it's just a pattern that we keep going back to.‍

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Pearl:

That does make a lot of sense. A lot of our behavior is actually determined by the childhood that we had, and I know the term “childhood trauma” comes out quite a fair bit when we talk about behaviors in our adult life. But a lot of what we go through forms who we are.

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Dalglish:

Yeah, absolutely. I think the one thing I would say about what you just said is, I think it is a positive thing that these days, all over the world in the US and in Singapore, people seem more comfortable using psychological language, talking about therapy, and talking about trauma. I think it's been a very positive development, but I do want to underscore that the thing I said  – that we have patterns that we develop when we're young and then these lead to problems later in life – it doesn't have to be trauma. It doesn't mean that if there wasn't trauma in your family of origin that you don't have these issues.

So some examples: For example, if you grew up and as a child you were just praised a lot for people-pleasing, because you knew how to make other people happy, and you knew how to diffuse conflict. So you got a lot of praise for that as a child. Well, guess what? When you grow up and you enter the workforce, guess what strengths you're going to use. And that's a great thing – it's a gift to have that sensitivity and to know how to make people happy. But the problem comes when you have no choice, when that's the only way you know how to solve problems, because you only know how to make people happy. And then when you overuse those strengths, there is a dark side.

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Pearl:

I think that's what most people default to, right? There is a standard way and probably a most comfortable way of handling things in life. And most people default to that. Overcoming that requires a sense of awareness, which you spoke about earlier, which is a big part of EQ. Do you take curiosity as a lever to increase awareness, or do you have other approaches that you work with them (coachees) on in this equation of EQ?

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Dalglish:

Yeah, that's really interesting framing. I think the first thing I would say is, in some ways, curiosity is fundamental to the job of a coach, because you could say that all we do is ask questions, right? So if you're not curious, it's almost impossible to become a coach. So there's just something fundamental about curiosity being the basis of coaching.

Now, in terms of the question about my approach, I could say a few things about my approach. The first is I tend to be less directive than other coaches. Some coaches, if you look online, they'll have a 10 step program. Like, “Here's my syllabus and you go through these steps with me, then you'll have the solution to your problem, whatever that may be.” That tends not to be my approach. I've started thinking about the way I work with clients in these words: I think what I do is help leaders do the inner work that's required to unlock outer growth. And that's quite a broad statement, but for me, what it means is that I'm willing to go pretty deep with my clients.

As you can guess from some of the things I've said in our sessions, we will look at your old emotional patterns, we will look at your relationship attachment styles, and where those come from. And they usually do not come from work; these come from your childhood. So it may seem very separate, like “What does all this have to do with how I show up as a C-suite leader or as a manager?”

But I really do believe, from my own experience and experience of those I've coached, that it really is all connected. Yeah. And the other thing I would say is I hold the goal and outcome of coaching a bit more loosely. I think it's a bit of a journey. I think a client may come in and say, “Hey, I have this particular issue with this specific employee or team member, and that's the one I wanna work on.” I usually find that once you peel back the onion, the problem may lie elsewhere. You scratch beneath the surface and you go deeper and you realize, wow, there's a much bigger pattern here. So the question we started with may not be the one we end up working with.‍

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Pearl:

I can only imagine that your clients might have some resistance to that. What do you do when you face resistance?

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Dalglish:

Yeah, it's so interesting. Gosh, I think the thing I would say is almost everything in a coaching relationship is a product of both the coach and the client. And I know that’s … let me talk through what I really mean. So when there's resistance that comes up in a session, and of course it does, I always think of it as “How are we creating this resistance together?” Because it's usually not just the client.

So a specific example: There was a period of time in my coaching journey where I was seeing a lot of startup founders who were having real trouble in the fundraising environment. It's very brutal. They're pitching their company to hundreds of investors and getting disappointed and rejected left, right, and center, and they were coming to me for coaching. And there was a period where I was doing my job, I was asking the right questions, I was doing the sessions, but I kept hitting a wall. I kept thinking, why am I not helping, I don't feel like I'm really helping them. I don't feel like I'm really getting through to them. And of course, there's a part of me that thinks, oh, okay, well the client's not ready, they're not ready for coaching, they're not ready to change, and so it's something about them. But when I have that thought, I immediately say, oh, okay, well, what's going on with me that I'm thinking that? And if I dig deeper, there's something about the issue they're bringing to me that probably reminds me a bit of myself, right? Like it's hard – there's probably a part of me that thinks, gosh, am I good enough to help them? Is there a bit of a rejection, my fear of me being rejected by my clients because I'm not helping them. Maybe I am also feeling not up to the task. I give this example because I think, if there's curiosity in the coaching relationship, it's something we create together. If there's resistance, it's also something we create together. So the resistance, itself, becomes the thing we talk about, the thing that we work on as part of the coaching relationship. And it's also material for my own personal growth because I think if there's resistance in a coaching relationship, it also points me to where I'm not able to hold a client's experience because I'm not holding my own experience. And so that tells me where I need to continue doing my work.‍

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Pearl:

I think it speaks to the deep level of awareness and reflection that you have. I'm gonna ask a question about work, so a lot of people tend to feel stuck at work, and work sometimes connotes negativity because it sounds like that, exactly that, hard work. Can that be changed?

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Dalglish:

Yeah, I mean, I think you're asking like the million dollar question of our time, right? It's all over the news. We keep hearing about the great resignation, “quiet quitting,” you see all these surveys that say Gen Z really wants engagement, purpose, and meaning in their work. And so you're asking me, can this be changed? When I think of that question, the first thing that comes to mind is just, gosh, we need to really acknowledge that what we're working with are extremely old and durable ideas about work that have a long history and culture.

So, for example, you said, well, work is labor, work is drudgery, work is suffering, well, where does that idea come from? You can go back, as you know, as far as the Bible, where labor was punishment for the fall of Adam and Eve. So that's how old that idea is. And then obviously, since the Industrial Revolution, we have the idea that work or labor is the commodity that we sell in order to be able to get money to buy the things we need to survive.

So anyway, the idea has been with us for a long time. But the opposite idea that work should have purpose and meaning – that's also not new. Gen Z didn't create that. If you think about it – I mentioned the Bible — we can think about Catholicism, the idea of “vocation.” So in today's vocabulary, we think of “vocation” as a job. That's what it means. But if you look at the root of the word “vocation,” it actually means “calling” from God. And also the Protestants have the Protestant work ethic, where work is the way we serve others.

Anyway, I give this little history lesson because I think it's important to take the long view. These debates are not necessarily new, they didn't come just in 2022. So it's important to realize that, you know, this kind of push back and forth over the generations has been happening for a long time now. So I think that contextualizes a bit the question of change.

That said, I think on a more micro, personal level, where my attention goes is, okay, there are these different ideas of work, but sometimes people get stuck. They don't seem to realize that there are different ways of understanding work, even though they have a choice. And so around choices, it’s also important to note that for many people in society, they don't actually have a choice to think of their work as purposeful and meaningful. Think of all the essential workers during COVID. We acknowledge that their work is important, but we don't want to pay them more. So for many people, let's just acknowledge that work is still just really a way to survive. The question of purpose and meaning and joy doesn't even come up.

But that makes it even all the more surprising that for people who have choices, all the white collar professionals, the people I used to work with, I didn't quite understand why they seem to only think of work as suffering, right? “This is the way work is, of course it's unpleasant, this is why I'm paid.” And the idea that suffering is a necessary cost of staying alive. So it's interesting for those people, if you have a choice, why is that the only way you can look at work?‍

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Pearl:

So personally, what does work mean for you?

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Dalglish:

Oh, man. Well, the first thing I will confess is, I talk about these white collar professionals who suffer for a living. I mean, that was me, right? I spent many years as that person. I mean, honestly, there were times when I thought to myself, my ability to bear suffering, which you can, if you want to use a nicer word, you call it resilience – I thought that was what people paid me for. I thought that was why I was successful. And so it took me a very long time to even imagine that there was another way.

I think these days, if I think of what work can be, I think what the best kind of work is when you can tap into your unique gifts – What comes easily to you that doesn't come easily to others? Or put more simply: What is your superpower? What have you been put on this earth to do? And I think work where you tune into that superpower and show up and benefit others, that's probably work in its best form.

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Pearl:

Is it hard to uncover your own superpower?

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Dalglish:

I think it can be easy or difficult. I've always envied people who seem to just know – the prodigies who are really talented in music, or sports people. I've always envied them because they just kind of know, and then that's what they're gonna do. For me it's taken a lot longer, and I've had a longer journey to coming to what my superpower is.

I think the challenge is that there are layers and layers of psychological or mental barriers to get through in order to even realize what your superpower is. So I'll give you a couple examples. Just to use myself as an example: I mentioned I was a sensitive child, that I was very attuned to what people were thinking and feeling. And of course it's a gift I use today as a coach with my clients.

But you know, as a teenager or as a child, you would not have been able to convince me that that was a gift. First of all, I would've said, “Wait, isn't everyone like that?” I was so convinced that everyone was picking up on what I was picking up on, and I didn't realize that it was something I was doing that was different from others, and more importantly, it didn't feel good. It didn't feel like a gift. It felt like a curse. I didn't want to be sensitive. I didn't want to know what other people were thinking and feeling. I wanted to be like everyone else. So I invite everyone to think: your superpower may not even feel like a gift! It may be actually a place of pain or suffering that needs more attention.

So I think that’s one way. I think the other thing that stands in our way, I like to – I have a cute name for it, I call it an “inner venture capitalist.” You'll see what I mean. So, when you invest in companies or you invest in founders, you ask the founders a lot of tough questions. Like: “How are you gonna make this big?” How are you gonna make a billion dollars? How's this a defensible moat? “And I think we all have a little bit of that inner venture capitalist in us that we apply to ourselves, because the moment we have an inkling of what our superpower or gift might be, immediately, that voice comes up and says: “Are you gonna be the best at it? Are you gonna build a big business around it? Are you gonna make a lot of money around it?” And then of course, under all that pressure, whatever spark, or little realization we might have had just completely dies.

So I think, to put things in perspective, if you are an investor in other people's companies, you should ask those tough questions because you might lose a lot of money. But hey, if you're reflecting on yourself and your superpower are you really saying that there's a world where you won't invest in yourself? I mean, that's pretty cruel, right? So I think that we really need to look at that, and quiet or maybe diffuse that voice a little bit.

And I think the last thing I would throw in is there's a cultural piece. Of course. I'm sure all your Singaporean listeners will sympathize: we grew up with parents who had very good intentions in telling us, study this because at least a great career, don't study that because it doesn't go anywhere. Don't spend too much time on sports. Right? Because that's not helpful. So I think there are also a lot of messages and stories that we've received about what is worth doing and what gifts are worth having. So we need to unpack that to really, really access what our superpower is in order to show up in the world and do the work.

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Pearl:

So you’ve held different positions in your career from a researcher to being a teacher, and you were a management consultant as well. Which role did you feel has allowed for curiosity the most?

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Dalglish:

Hmm. I don't know. I think I will say that my instinct is that curiosity is more of an internal orientation rather than unique to a job. Because, for example, you would think that to be a researcher, to get a PhD, you have to be pretty curious, right? You have to ask big questions. But that was not my experience, actually, even in academia if this is  the method or the discipline or the department, there are some questions you can't ask. Because that's the way things have always been done. So I tend not to think about it as a curious or not curious job. That said, I do think institutions have a role to play. You might be working for an organization where there's no psychological safety, where you can't take risks or you get punished. Where you can't ask the wrong questions or you’ll be looked at differently. So then that kind of situation can really discourage curiosity. But you know, no matter what the institutional context is, I do still go back to curiosity being more of a quality that we can bring. And it requires courage, because you're essentially asking questions that no one dares to ask. And if people don't dare to ask a question, there's probably a good reason, there are probably real consequences to asking those questions.‍

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Pearl:

Yeah, and that's so true. A lot of conversations I’ve had about curiosity actually bring up courage. Is that something you feel is a prerequisite for curiosity? Is that something that we can further build upon?

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Dalglish:

Yeah, absolutely. When I think about courage, my mind almost goes to the flip side. Because I think courage is the opposite of fear, perhaps? And so the question – if I'm not curious, or if I don't dare to be curious – the question is, what am I afraid of? And I think there're so many reasons why one might be afraid and not willing to be curious.

So the first might be the fear of retaliation. We're scared of authority, we're scared of punishment. You know, again, your Singaporean listeners might sympathize a bit more with this – if I asked the wrong question, there might be severe practical consequences for me, my family, or my future career. So there's that kind of fear. A second kind of fear might just be – my reputation, how people look at me. If I get curious about the quote unquote “wrong” things, people might think I'm stupid or people might think I'm a troublemaker. So there's that kind of fear as well.

But honestly, the fear – maybe the deepest one, or the most interesting one, to me is:  “I'm afraid of finding out the answer.” Just to give you an example: I might be curious about what impact my job really has? This job that I show up to every day from nine to five, Monday to Friday. One could say, it's good to be curious about that. Well, are you really contributing to the world? Are you really benefiting others? You could be curious about that, but on the other hand, you might be afraid of finding the answer. You might be afraid of the idea that, oh my gosh, what if I find the answer and it's that actually I'm not making a difference? So I would rather just not ask at all. That maybe is the third kind of fear that I will point out.‍

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Pearl:

So last but not least, a question of personal philosophy. What does the term “rebel curiosities” mean for you?

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Dalglish:

Wow. So I've been thinking about it since you told me the name of your podcast, way back when. So I think my response to it is that it’s an interesting two words that you've chosen. Because I think of them as being in a productive tension. When I think about “rebels” or “being rebellious,” there's a bit of an external orientation –  having the courage and bravery to challenge, to fight, to move against what's in the way.

And then on the other hand, curiosity, as I said just now, I feel it's more of an internal orientation. It's open. It's non-judgmental. Some people can be very curious about what's going on in themselves and you would never be able to tell. So, when you put the two together, I think it creates a very interesting tension.

So, I think what's great about the name you've chosen is that I think the world needs both. The world needs people and leaders who are willing to be curious and open-minded and do the deep work of self-inquiry that it takes to understand themselves and others. At the same time, you can't just do that because once you've done that, or as you're doing that, you also need to show up in the world. You need to take what you've learned and the realizations you've had and actually show up for people and make a change in the world. You actually need to show up for other people, challenge the status quo, and create change. So I think the name you've chosen is very interesting and embodies the two things probably that we need most right now.

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