[Interview] Why Creating Space Matters More Than Efficiency | Simon Dowling on Intentional Leadership

Simon (00:00.652)

I think if you're purely reactive, that's management, but leadership has to be anchored in choice. The very basic, right? know, if I'm in an emergency ward in hospital, you know, was working with a medical team where they were having this very conversation. We don't have choice about what we're doing in the heat, you know, when we've got all of these inpatients being admitted, new emergencies arriving, et cetera. But we do have choice about how we approach.



All of those situations, we have choice about how we engage with the patient. We have choice about how we respond to the families. We have choice about how we engage with the paramedic. We have lots of choices, how we engage with each other. They're all micro choices, micro moments.



Digby (00:51.342)

Whatever leadership isn't about having all the answers, but about creating the right space for people to thrive. And one of the outcomes from meetings weren't just about being efficient and effective, but also about being engaging and expansive.



Well, today I'm joined by a guest who brings a fascinating blend of legal precision and improvisational creativity to his work with leaders. We explore how the most impactful leaders intentionally shape the emotional quality of the environments they create, not just to get things done efficiently, but to generate genuine energy and connection. And we get into that classic tension between the desire for control and the opportunity that exists when you let go. So whether you're a



Leading a team meeting or a major transformation, this conversation will change how you think about the spaces you create and the choices you make within them. Hi, I'm Digby Scott, and this is Dig Deeper, a podcast where I have conversations with depth that'll change the way you lead.



Simon (01:49.806)

you



So the other day, Simon, you mentioned a question that you used as an opening for a leadership workshop. And that question was, if you're going to be on a podcast today talking about leadership, what would you want to talk about? So why don't we start there? Simon, if you're going to be on a podcast today talking about leadership, what would you want to talk about?



Wow. I hate it when your own questions are used back at you. They're not designed for that.



I don't want you to hate it, so apologies for that.



I don't hate it. Just makes you nervous. Because you feel like when you ask questions, you should, and I'm not kicking the can down the road here, but you do when you're asking questions, they come from a place of you knowing what answers you actually want from people. But in fact, as a facilitator, you don't. It's just to see what it sparks. So in fact, I think what would I want to talk about? I would want to talk about space, how leaders create space for people.



Simon (02:58.03)

and the kind of space they create and choice as well. Like they're the two big words that are on my mind at the moment, I think, when it comes to leadership, the leaders I work with.



Cool. I love when you say you ask the question to see what sparks. So that's what sparked by the sound of it. And you listen to that rather than went into what should I say?



I love the experimentation around questions. I use this term, and I'm sure I'm not the only one, this term catalyst questions, like what's a catalyst question? And I often encourage leaders to think about what are the questions you ask that catalyze something. So they catalyze thinking, they catalyze a response, obviously, but they catalyze thinking more importantly, they catalyze energy, they catalyze something beyond the immediate moment. And I think



certainly my work, and I'm sure this is the case in your work too, you're constantly thinking, okay, what might I be able to catalyze through the questions I ask and through the contexts I create for people? That's the art of facilitation, right? Warren Berger, his book, A More Beautiful Question, I think, talks about this, and I love that.



That's a book I want to read. I've come across him. I've listened to his podcast he's on and it's a great title. Isn't a more beautiful question. It's in fact, we were talking in a workshop a couple of days ago, a group of people, we were practicing asking good questions and it's interesting when we did the debrief afterwards and not using your language of catalyst, I love that idea of catalyst. You know, what were the questions that really shifted the room or other people and. a



Digby (04:39.97)

They weren't questions that came from the head. They were questions that came from the gut. No, more importantly, they shifted something, not in the head, but in the heart or the gut. And it tapped emotion rather than intellect. Was one I remember, was sort of a coaching style question that one person asked of another in the room. What would the sneaky cheeky version of you do? It was because she was sort of trying to do the right thing.



She's a senior leader and she's trying to get some influence happening. And she was all about, no, what's the right way to do it. And this question came from left field. What would the sneaky cheeky version of you do? And you could see her face light up and she went, Ooh, okay. That gives me a few new avenues, which is what you're talking about, which is what catalyzes energy or thinking. And I would add to that emotion. Yeah.



How does this question make you feel? And just as you're saying that, I'm realising the power of a question is to actually allow people to try on. It's like being in a clothing shop and if I go shopping with my wife, she'll hand me bits of clothing and say, try this on. I go, no, I've never tried that on. That's not me. Just humour me. Just try it on. Let's see. And I love a question that does that as well. Like what's the sneaky cheeky version of you allow? Like what if it's like that classic coaching



question, which just, sounds cliched, but it's so often yields a great response, which is if you did know the answer to this, what would it be? Which often is off the back of someone saying, I don't really know. So what is it about that question? It gives people either permission to know without the fear of judgment, or does it give them permission to pretend they're someone other than themselves?



and to throw caution to the winds. All those kind of possibility questions, they catalyze a different way of thinking too. That's really cool. Which is where, actually that was where the podcast question came from, Diggs. Like when I asked that group, and I was sharing this with you the other day, I literally, like they were in the room and they were already having a warmup and I'd given them a question that was totally unrelated to the reason we were there. And I thought, I need another question that bridges us into the day.



Digby (06:37.016)

Yeah.



Simon (06:58.712)

And so I literally just opened up the deck of slides and thought, what could I ask them? And I looked at them and I just thought, let's just pretend they're all in fact the experts. Mean, this is the end of a 12 month programme. Let's pretend they're the experts. So that's where the podcast kind of conceit came from. And I think that's where catalyst questions or great questions as leaders often come from is what are you trying to precipitate in the room? What are you trying to change emotionally, energetically? And now just find a question that might get you there. Play with that.



Yeah, I'm a big believer in having a question bank and you know, I'm imagining with your slides, what went in through my mind, you was talking about opened up my slides and you having a list of 50 questions and you, that's the one for this group. Now I suspect it's more in your head than on your slides, that stuff, right? And you make it up on the spot.



Yeah, in this case, that's exactly it. Literally typed it in live thinking of it. What do I want to ask? Yeah. But I like the idea of a question bank. I need one of those.



It's a bit more about building your question muscle, isn't it? Right. It's to be able to ask as Warren Berger would say, more beautiful questions. And I often talk about, I tend to have four different types of questions as your what questions, which are your orienting setting, the same questions. Like, what are we here for? What roles do we need? What time do we have? All that sort of stuff. And then there's what is questions, which are you. The interrogating what's happening and what do we actually want and what's the real issue and really getting into a deeper understanding of the challenge.



Then is your what if questions, which is what you were just talking about, like the possibility generating questions and the unlocking questions and the creating potential different ways forward. And there's your what next questions, which are, okay, so what do we do with this? Right. And to me, what I see a lot of groups do and people do in conversation and meetings is stay in the first and the last ones, you know, the what questions and then the what next questions, but they don't get into the real meat of something.



Digby (08:56.406)

I see you as a real master at the second and third questions. And actually the fourth ones too, right? That pragmatism that you bring. Looping back then, and there's definitely a link, right? Cause you responded to that first question and you said, I'd like to talk about space and choice. And obviously they're linked. Which way should we go? What's your sense of where we take it?



I space, feel like the space is the natural build off what we're talking about here. And maybe choice will fall out of that as if they're separate topics. They're not. When I use that word choice, if you tracked me in workshops and rooms with people and coaching sessions at the moment, and you tracked my language and did a word cloud of what are the words that pop up the most, I think they are the two words. And choice often translates as choiceful, which is, you know, how to lead us.



step into a place where they're really clear on their intention and they're very conscious about those choices that they're making in the moment, not just at a mental level, but in any given moment. And I think that connects with the question of being really intentional about what kind of space you want to create for your teams, for people. In the same way you're right here, for example, your choice of questions is very choiceful. Like, what am I trying to create here with Simon, this guy I know? We're colleagues, but we're friends.



And how do you design a podcast? Well, the only way to do that is through the choice of question.



Absolutely. Let's stay on space. So what do you mean by space? When I say space or when we say space, what's your definition of that?



Simon (10:31.182)

space more than anything is a context. You know, because obviously you can think of the physical space, but it's a context where people can be something or do something or achieve something or feel something. And I think the quality of a space, that's like, you know, you go to a restaurant and, know, often they'll ask you to rate the ambiance or, know, when you read a



review of a restaurant, they'll talk about the ambiance as a critical factor in the overall dining experience. So there's the food on the plate. There's the quality of the service. There's the cutlery, the drinks, the wine, the cocktails, but all of that sits within this bigger context. And it's one that you detect from the moment you walk in to the restaurant. Some people perhaps more conscious of it than others. Like my wife and I, when we sit in a restaurant, we're really.



attuned to all the factors that are creating the vibe. It's the vibe of the thing to quote that classic. Your honor. Aussie movie. Yeah. And I think space is that it's the ambience and that context, but with a really clear purpose attached to it, which brings us back to the word choice. So it's not just about the feels or the vibe. It's a space that is designed to dot finish this sentence.



It's a space designed to encourage experimentation. It's a space that is designed to allow people to connect and collaborate, reenergise or regenerate energy. It's a space that is designed to, and you could get going, right? So I think the interesting thing for leaders is how do you create those different contexts, those different spaces with intent? And some leaders have a default towards one more, the others, like, you might have a leader who is very



very strong on creating a space where we get shit done. You just call it productive space, but it's the getting shit done space because they're very clear on, what are we here to do? How long are we got? What are the goals? That language, because I think that's where space, that's a huge indicator of the kind of space a leader creates is the language that they use, the questions that they ask. That might be their default mode. Then I think, you the interesting thing in that is how does a leader become more attuned to the other spaces they're not?



Digby (12:26.286)

Yeah.



Simon (12:51.384)

creating. And build that as a muscle.



What's coming up as you talk is it started in my mind, at least with space as a physical place, as in the restaurant or the meeting room or whatever it is. And because of the setup of that, that allows a certain ambiance and a certain vibe. And then you add intent or purpose to it, which to me then broadens the definition of space to a feeling of spaciousness as opposed to the space.



I'm curious about the, when we say space, it's not just the four walls around us and the gap in between. There's something about a feeling element to space as well. Right. Does that make sense? And I'm wondering what your take is on that.



Yeah, I think that's absolutely right. There's a few thoughts sort of flying through my head. There's a really kind of common expression that's used at the moment, which is a safe space. This is a safe space. You know, does this space feel safe? And I think, and I, you know, I've got a whole kind of thing around that, like, you know, how many times have we been in a workshop or something where someone at the beginning says, now this is a safe space. It's like, is it really like, you can't just call it that we'll see, because really that should be the



Huh.



Simon (14:13.652)

language I might use to describe the emotion, feeling, but do I feel that way? Does it feel like a safe space? So I think that's an emotional quality for sure. But I'm just sort of going through this and going, you know, if I go into a conversation with you, Digby, there is a space immediately between us that is created by the history of our relationship.



characterised by trust, characterised by just the intimacy of listening and so forth. And all of that learned experience, lived experience between us gives this whole thing an emotional quality. And instantly that defines the space. Like we jump on a call like this and the conversation is immediately shaped by that kind of space, but it's unique to us. It's different from, you know, another friendship or a colleague where I know the space is more defined by



Is this an emotion? But the emotion is we've kind of got to catch up with each other. Like we've got to just know what each other is doing. So we go through this rapid fire of like, so what have you been up to? What are you doing? How's work? What are the kids up to? And it's like this laundry list of the stuff we've got to cover off and tick off. I wonder what the emotional quality of that is. It feels again, just defined by the history of that relationship and the dynamic of conversations.



Yeah.



Simon (15:34.914)

That feels a bit more productive, more, you know, are we making progress on this friendship?



Yeah, it's interesting, isn't it? You've the productive a few times and I think there's different ways of interpreting that. Coming back to intent and so there's the kind of the physical, but there's also the leaders language you mentioned and what are the outcomes that we actually trying to create here and the outcomes don't have to be tangible outputs. That's one outcome, but there's also, does the team feel closer?



Do we feel creative? Is there a momentum beyond this room in terms of team camaraderie, for example, right? And therefore what space and spaciousness can I create as a leader to do that? It's such an interesting idea. This, this idea of space. Cause my guess would be that there's plenty of leaders who don't necessarily give this a lot of thought. It'll be more about, okay, we've got an hour. We've got to get this decision made.



go. You know, in your professional work, how do you circuit break that or work with that sort of drivey? Let's just go without having given a lot of thought because in some ways in your role, you are the leader as a facilitator, yet you're not the leader of the team or the organisation that you're working with. How do you work with that dynamic?



The first thing that comes to mind on that is that, yeah, often you are working with teams who they engage you as a facilitator or as a coach, because they know someone knows that they kind of need to slow themselves down a little bit. Problem is, is they don't bring you in. Someone's going to drive them all towards a particular outcome. And, know, I've had a recent experience of this with one team, and this is not the only one who's done it. Right. But they wanted to.



Simon (17:24.046)

facilitate a conversation about the future of the organisation, strategy, and so forth. And in the lead up to this, one of the leaders in the team kind of pulled together all of their thoughts on a questionnaire and then got AI to distill that down into big themes and then got AI to translate that into a draft strategy document and shared that with me as if to say, okay, so we've done the work.



to this point. Now what do we need to do when we come together? We just need to verify this draft. Don't we? That AI is created and there's a classic moment, right? To go, hang on, clearly we want an outcome, but what are the beats we need to go through to get there? And what space essentially do we need to create for the team in order for them to feel comfortable with that outcome? Yeah. Because there are some phases we haven't gone through. So this feels efficient.



It even feels effective because the document it's creating is smart, but is it generating an emotional, a positive emotional response for people that makes them go, this is exciting. This is inspired. Feel connected to it. I feel like I own it. So really, I think what you're inviting people to do is yes, we need to get an outcome. So now what is the quality that we need in that outcome? It's not just, it correct?



So yes, we're achieved it. So we need to finish with an outcome, which by the way is the, think one of the most common fears with facilitators and it's one of the points of resistance I hit across a lot, which is the fear that you're going to give them great conversations, but they're going to walk away with nothing other than some crumbs from the muffins they ate and a bunch of post-it notes on the wall. I think the first thing you need to honor and respect is the fact is we need an outcome. So.



We're going to have to hold space and time for distilling and clarifying that. But now, yeah, what are the other things that will allow us to get to that end point? Because the other qualities we need are we need shared ownership of that. We need buy-in. We need people feeling ready to talk about it and take it into the rest of the business. We need it to be a strategy that has asked the right questions and has thought beyond



Simon (19:41.238)

our default.



I love this. I've not thought about it in this way before. And I think plenty of leaders listening to this will get some real value here. I've written down efficient, effective and emotional. So efficient is speed to outcome. Did we move it at the right pace to get to something effective is, is it the right outcome? Right. And I rather, you know, we might be really good at climbing a ladder fast, but did we go put it against the right wall sort of thing? Right. Yep. And then the.



Emotional is the quality of the outcome, which is how you describe it. Love that. Know, does it have buy-in excitement energy around it? Right. And there's something about that as a set of questions, right. And not just for us as facilitators, but also for any leader who's bringing people together. This idea of, all right, so where am I focusing my attention across those three E's? Is it just about efficiency?



Or is it actually about the higher end game of energy and excitement and emotion? I'm using lots of E words.



I wrote those down because I'm feeling like there's one missing there too. And I don't know whether it's part of it, but if I had to make it an E word, I'd say expansive. In other words, it's thinking beyond the default or evolutionary or something. Now I'm stuck in your E palette.



Digby (20:54.253)

Yeah.



Digby (20:58.894)

Yes.



Digby (21:03.374)

The power of alliteration, right? It's good. Yeah. That's brilliant.



There's this question I sometimes ask almost always, in fact, not sometimes, ask people at the beginning of a conversation. So a leadership team, if they're talking about strategy, I'll ask them, what are the qualities that we need in the output? So what will make the output a good output? So not in terms of its content, but in terms of its qualities. Or I might ask that in terms of a team saying, what are the qualities of the output of this conversation today?



we're going to cover a lot, before we get there, what do you want? How will you measure the success of this day? And usually, I literally take time to just say, I want to hear from everyone on this. Like it'd be interesting to hear. And cause one of the things that often does highlight is people go, that's really interesting to hear those guys talk about this. Cause I wasn't thinking of that, but now that I hear it, yes, it's important. So you'll get those in the room that are saying, it needs to be clearly worded.



It needs to align with our global strategy. They're thinking, they're thinking effectiveness. Whereas the, those that are saying it needs to be an opportunity for us to have had some conversations or debates that we haven't been having, or it'll be great to bring in the voice of the customer, or it would be wonderful to think that this is.



They're head-worth.



Simon (22:30.99)

whatever we share, when people ask us, what did you talk about today? When we share that, that they will be excited by it, not just informed by it. Like what great things to be talking about in the first 15 minutes of a day. Cause then you got that up on the wall going, all right, we need to make sure we move through some spaces or beats, whatever you want to call it. I call it space, but we need to create space to be able to lean into all of those things. Cause they're not going to be created through a single type of conversation.



In your years of experience of doing this, you've had heaps of opportunities to observe whole lots of different groups and be parts of those different groups. Tell us a story if you can, access that experience bank of a turnaround of a group. Hopefully that's not much of a challenge. Where perhaps you started with resistance and what are we here for? And by the end, there's a complete shift into that higher quality outcome.



I'm not going to overthink this because I always freeze when I have to think of examples. It's like in those classic, you know, feedback conversations. Can you give me an example of that? No, one doesn't come to mind, but I know the feedback's true. But I did think instantly, as you asked of an example, and it was only three weeks ago, we were having a conversation around the teams. They wanted to have a purpose statement. Well, they already had a purpose statement. And so



purpose.



Simon (23:57.41)

The leader of the team said, let's start this session with just a reflection on is our purpose statement still fit for purpose? Like, are we good with it? That's a tick and flick. Any words you'd want to change. And a couple of people said, you know, is this word right? Is that word right? And I said, I feel like we're going about this the wrong way. When you ask the question, is the purpose statement still right? I'm not sure that was meant to be an editing exercise. it like.



Surely that has to go closer to the heart. And I said, can I propose something else? And this isn't in the agenda, but can I propose that we spend some time and we broke off into a few little groups. And I said, I want you to kind of picture that you're sitting around a campfire and you're just sharing some stories with each other about, I call them, that's what I'm talking about stories, which is.



Stories of things that have happened, anecdotes, experiences with customers, conversations, bits of work we did that says, that's what I'm talking about. That's where the goal is. That's where we are doing our best work. That's what makes us us. That's the essence of what it is we're here to do. The difference we're here to make. And so I proposed this as an activity and the, the leader in the team sort of looked at me as if to say, no, we know our purpose really. And a couple of them sort of looked at each other as if to say,



some eye rolling.



Simon (25:19.19)

Is this a good use of time?



Who is this woo woo facilitator



And I said, purpose exists in the day to day lived kind of experience of what this team does. I said, give it a go. So here you go. So they went off and did this and it didn't take long and only took 20 minutes. And at the end of their stories, I saw as say, as each person tells a story, just people fire off. What are the words or the things that come to mind about, you know, what that story is really about capture some of those we came back and the mood in the room had changed completely. God, it felt good to hear some of those stories.



Gosh, I now I better understand what some of the others in this group are doing. Now I look at that purpose statement and the words are right. It just makes more sense. So I think the question is, are we telling the story of that purpose right? Not is the purpose statement right? And it was like, as a facility, the moment's where you want to go, I told you so, but you don't. Because this is what you're there to do to help people have conversations they don't normally make space for.



And that's what it would have felt like, right, to them. It's like, oh, do we have time for that? We're smart. We know what this is. It's like, yeah, but you're asking the wrong question.



Digby (26:33.618)

it's moving from head to heart again. You know, that story is awesome as a, yeah, yeah. You know, we'll do some editing, which is head stuff into feeling and emotion, which is the heart stuff. And that's where the power is. Right. I wrote a blog yesterday after noticing I'm in the process of planning to move house in the next month. And you've been there a couple of times recently and I noticed in my busyness.



How, you know, all the logistics, all the planning, all the packing stuff, right? It's all head stuff, right? Got to get the moves over to check out the house and how many boxes will get all this stuff. Right. And I noticed it's so head and I was, it was just exhausting me. It was so tiring and there wasn't a lot of fun and I haven't been sleeping well as a result. And my mind has been just worrying with all this decision making and.



I wrote this piece about that I'd noticed that this was happening and how exhausting it was and where's the deeper meaning behind it, right? I'm not tapping into that. I'm just talking about getting stuff done. And then it got me thinking about in leadership, this challenge of being in headland the whole time where we just, what's next? What do have to do? What decisions we have to make and all this and how disengaging that is not just from your own.



deeper sense of meaning and purpose and joy, but also how that is then projected out to your team and your organisation, right? And the risk of that, if we just in headland. So what you're talking about this idea, as I've written it down, going from efficient to effective to emotional feels really, really key. And what I would love to know is how do we not rely on people like you and me as the ones to slow us down?



That's one of my eternal questions around how do we create unhurried productivity? I don't have an easy answer. What? But I know that the practice is critical.



Simon (28:37.944)

Yeah.



Simon (28:44.14)

I mean, before we keep riffing on that, you know, the other word that immediately spring to mind as you were just sharing that is we live in this achievement orientation all the time. Like it's achieve, achieve, achieve, or, know, to use that expression I use before get shit done, because the lists are huge. The to-do lists are massive. Like we're moving house. There's so much to coordinate. You're running a team or a business. There is so much to get done. And it feels like the pace of that has just gone up. People have.



More to do than they can possibly get through. And so I think that's the other thing to just sort of pick up on here because I don't want to lose it, which is the sense. Think, you know, when I talk about space explicitly with leaders, that there's often this sense that we, yeah, I love the idea of space, but you should see my, my world. Yeah, we don't have time to stop. We don't have time to breathe.



There's always a but, right?



Simon (29:40.31)

And so I think the assumption is in order to create space, we've got to have a two day retreat and go into, you know, the Hills.



You swing the pendulum massively, right? The other way.



Yeah. So we will do space when things are quieter. When's going to be?



That might be when you're dead, right?



When I retire that week. So I think the real question here is how do you create space? And this goes to our point your point, right? It can't depend on what we're gonna book a facilitator for a day or two Because I need to create space within the busyness within the work as well



Digby (30:18.146)

Yeah, that's how I think about it. Example, right? It's Friday today. Usually it's quite a day, but given the moving stuff, I've got three different contractors coming over this afternoon for various reasons or related to the move, which compresses my day. before we recorded, I had a few choices. I did a bit of work this morning and then I was like, what's the best thing I could do now to make this conversation as good as it possibly can be.



And it's as enjoyable as it possibly can be. And I went for a walk for half an hour. I found space in the day to do that rather than do the next thing on my list because I think I was focusing more on the emotional quality of the outcome of this that I wanted rather than the efficiency of how many things could I get done today. And it came down to me giving myself permission to do it in the face of all these made up



other things that I could be doing and other people's expectations. And there's something quite powerful about that.



giving myself permission, such a good, well, cause now we come to that word choice, right? Like if you assume that you are choiceless, that you lack agency, that you can't make choices because you are dictated and shaped entirely by the inbound traffic. I simply have to react to that. I don't think that can ever really be leadership. Think if you're purely reactive, that's management, but leadership has to be anchored in.



choice. The very basic, right? You know, if I'm in an emergency ward in hospital, you know, was working with a medical team where they were having this very conversation. We don't have choice about what we're doing in the heat, you know, when we've got all of these inpatients being admitted, new emergencies arriving, et cetera. But we do have choice about how we approach all of those situations. We have choice about how we engage with the patient. We have choice about how we respond to the families. We have choice about how we engage with the paramedic. We have lots of choices. How we



Simon (32:23.222)

engage with each other. They're all micro choices, micro moments. And the tragedy of busyness is people often either use it as an excuse, not consciously necessarily, but an excuse to say, I haven't got time to be aware of what's happening right now. I just have to go on autopilot. I think that's where we get into trouble.



It reminds me of some research McKinsey published a couple of years ago. It wasn't their work, I think, but they were the distribution point for it, which was called Dual Awareness. I think it's a book called Dual Awareness, which is as leaders developing the capacity to have Dual awareness, which is one part of the jewel is the awareness of your state, your language, the way you're being. What are you thinking? How you feeling? What are you doing? What are you saying?



And the other part of dual is the awareness of our environment. So the vibe, the responses to what you're saying, the relationships that are happening in the meeting between people, how they're relating, you know, and simple stuff like this, temperature of the room. Okay. Right. But all of this stuff, paying attention to it, that the key point I took from that idea was that you need to be able to do it in the moment, not afterwards.



Oh, I wish I hadn't said that. I mean, you can learn from that to be able to notice in the moment is the highest form of awareness and then to be able to respond appropriately. And I think when we get too busy into efficiency and task mode, we miss all of that because it's just what's next, what's next. And that gives us a little dopamine fix, but is it really serving the context? Which is what we're there to do as leaders. Right? So it's a very powerful idea, this idea of.



dual awareness, I think.



Simon (34:12.792)

There's a permission thing in that as well, which is, remember the very first blog post I wrote when I started my practice, which was 13 years ago, was titled, Out of Your Head and Into the Moment. And it was probably a message to myself more than anything. That concept, that idea had come from verbatim from the world of improvisation and improvised theatre, which is part of my background and training. I spent many years doing improv.



And one of the most powerful lessons, and I stuck with it for a long time because it was just filled with so many powerful lessons for life. And this was one of them, get out of the head and into the moment, because if you're improvising, so you picture improv on a stage in a theatre context, you're co-creating with colleagues in the moment for the benefit of a paying audience as well. But the worst thing.



is being on stage with someone who is so in their head that they're worried about what's going to happen next. They're three lines ahead trying to plan. We'd often call them dirty rotten planners. They'd often call me dirty rotten planner because I'm trying to control and fix things always. I'm managing the scene as opposed to just being totally attuned to what the scene needs and what



Great.



Digby (35:30.498)

Yeah.



actually my other performers are doing and what they need from me. That's a much more powerful state to be. So if you translate that, like, I love that thing. If you've got to be in the moment and noticing stuff, cause that's a muscle and it takes, it actually takes practice. And I'll talk with leaders often about how's he noticing muscle? Like, is it flabby or is it well toned, well honed?



No one wants a flabby noticing muscle.



because I don't think a lot of leaders have a practice.



Yeah. How do you do it? Let's get real here because we're not perfect, are we?



Simon (36:08.494)

I'm far from perfect. The reason I do all of this is to try and coach myself.



Exactly. You're your first client, right? Yeah. What are the challenges you face with that? And where do get in your own way around this stuff? Or how do you get in your own way?



I'm a filthy planner. am terrified of things going wrong. I had to use every muscle in my bones to not prepare some notes of things I wanted to say with you today. Because even though some people might go, well, being prepared is good, isn't it? Yes, it is. But I know for myself, if I'm well-prepared, I'll be more worried about, we covering off the things I wanted to prepare? yeah. Than what is this conversation actually about? Like, where are we going?



What does this need? What's possible here? Like what, what offers are being made here that we could pick up on. So I'm very aware of it. And I would say some days it's a losing battle. Like if I'm facilitating a workshop with a group that feels, if I sense in any way that I could lose a group, am very quickly fear-driven very quickly. And that leads me to be very.



conservative and very controlling in terms of the conversation and the flow. I know that's when I stopped picking up on the stuff that actually needs to happen. And I've had some great clients that have called me out on it.



Digby (37:28.174)

Yep. And they're the best, right? Yeah. They are gold. it's the whole stop trying to be a hero here, you know, and it's shift back into host mode, but I'm the same. I was running a workshop for Christmas a few months ago and yeah, the energy was flagging in the room and I started to get nervous about that. So I started to counter it by being even more energetic and it wasn't really working. And in hindsight, and I remember it about



20 minutes later or something, someone just said, Hey, can we just get outside for a bit because it's hot and we're a bit tired. Can we just go and shift the state? I'm like, yeah. And coming back to something you said right at the start, so this idea of let's pretend they're the experts. And I really liked that. It's this, well, if you're in front of a group, you don't have to have the monopoly on what's going to happen and how it's going to happen. and who says what, you know, pretend they're the experts. It's like, let them.



take it where we need to take it, which is I guess what I tried to do when I, you know, I asked you the question, if you're in a leadership podcast, what would you want to talk about? It's like inviting you to step into the space and let's go there because I have two pages of questions that I wanted to get into. And I've been dual processing. Where's this conversation going? What does it need? And also, Ooh, what else could we bring in that I'd already



pre-prepared, which I think is preparation is helpful, right? Because it's like we could go those ways. Yeah. Another little story, actually. You gave me feedback on a video I put on LinkedIn last week and he said, I think that's one of the most natural videos you've ever done. Yeah. Yeah. And then I said to you, yeah, I did about 10 takes of it. And the version that you see is the one where I threw away the script.



Yeah.



Digby (39:21.102)

And it wasn't because I'd memorised it all from those other nine takes. It was because I just went, this is too hard trying to memorise all the words. And it was more like, what do want to say? How do I want to land? And let's just say that and do that and be that. so I threw the script away and it was interesting to your feedback because it was like, okay, yeah, more of that, please.



Yeah, there's a trusting yourself in that. I think part of it is, so we talk about noticing, but I think in order to be willing to notice stuff, you also have to be able to let go a little bit, let go enough for there to be enough space to see things and to think that they're relevant to where we're headed. Like, sorry, this sounds esoteric, I guess now, but it's like, I've got to be prepared to just let go of control and trust myself in the group that



We will find our way to this conversation or through this. We will find our way to an outcome. And perhaps the worst thing I can do is, is make the assumption my prepared agenda is going to get us there because maybe it's the very thing, the very thing that is preventing us from getting there. As you were just sharing your example, another example that came to mind for me was working with a group and saying, right, it was, could sense there was, there was unspoken tension in the room. It was a fairly big group. So I always get nervous about allowing.



I don't understand to come to the surface in a big group because of the potential for it to explode and then I lose control and I'm not doing my job and that was a situation where a client said there are conversations that need to be had in this room and we're not having them. How are we going to get there? And all of my responses were fear based. It was like, I agree with you, but you if we don't know what they are, you know, this old adage, don't ask a question you don't want the answer to and it's all control, control, control.



And I said, let me go for a walk. Need to think. I, cause I just, could sense this version of me kicking in. That was like, you are being so unhelpful right now. So just get the hell out.



Digby (41:24.14)

What I admire Simon is that you had enough awareness to be able to go, this fear based version of me is kicking in.



Right. That's that dual awareness thing you were just...



Yeah. And a number of people would maybe not even realise that. Well, they may realise that afterwards and there may not be another option. So be able to tune into what's going on for me here and what choices have I got. So you modeled some of that right there. There's an unexplored part here, which is who is this Simon Dowling fellow, right? So usually you'd start a podcast conversation with, so.



what's your background and where'd you come from and all those things. We went right into this whole space of leadership and everything. And I suspect people listening are going, I love a bit of his backstory because I heard improv, right? What we haven't heard is former lawyer, right? And, and I'm looking at your face now going, do we really need to go there? I'm curious about, cause the stereotypical image of a lawyer is almost the opposite of



yeah



Digby (42:30.998)

A lot of the stuff we've been talking about, nothing against lawyers. There's more of a, hmm, that's an interesting journey. It's a bit like me starting as a chartered accountant, right? We both came into this professional services field and now we're in this quite different space, still professional services, but of a different ilk. I really want to ask you what drew you into law, but I think I'm probably more interested in what drew you away from law into this.



So couple of things, one is I always had wanted to be a teacher. So there was the teacher DNA in me. That was, I don't know, but if you did know what would the answer be? I think the answer is probably some teachers I had when I was young at primary school level who were just great. They were really good at teaching. I still kind of, I carry them with me in, in, you know, who I am.



Where does that come from?



Simon (43:29.096)

And so I was inspired by that and something obviously appealed about the idea of teaching and helping others learn. So I wanted to be a teacher. I grew up in a world where, no, you know, you don't want to teach. If you get the marks, you should do something else. Yeah, it's just such a tragedy. Know, anyhow, ended up doing law for that reason, because I got the marks basically.



Aim higher young man.



Simon (43:58.498)

but knew almost from day one that this was not the long-term plan, found a way to do some teaching. So it was running seminars for clients and stuff until I eventually decided, you know what, I am going to teach and resigned and was going to go off and do a dip head and become a secondary school teacher. I was accepted into that. I'll never forget, you know, in my suit, I'd come from my, my office. I was standing in the queue, putting in, cause this was the day we had to do it all manually. Right.



footing in my application to teach. And there I was in the queue going, my gosh, this is such a different world. Like, this is after six years, five or six years of legal practice. Anyway, while I was waiting, A, for my DIP-Ed to start, the study to start, and also to finish working, because I'd handed in my notice, I came across this consulting company basically that placing these ads and then they gave me a call by



pure coincidence because they were looking for someone preferably with a legal background because a lot of their clients were lawyers, but they were looking for someone to help them teach conflict management, negotiation, mediation skills and so forth. So I ultimately decided to give that a crack and put my deep head on hold. And the thing that appealed most was within the first year, I was going to be doing some teaching in a university context and also with corporate clients. So it sort of seemed to tick all those boxes.



That's the literal story of how I got into that, this line of work. And if you think about those first, I was there for 11 years, right? The first few years of that was really teaching negotiations. was very skills-based learning. But then towards the end of my time there, I had some clients say, off the back of the work you do, really love the way you facilitate. Could you come, we've got an offsite or we've got a leadership team that just, need a facilitator. And I literally did not know what that meant.



Yes, right.



Simon (45:51.66)

I literally did not know what is a facilitator. You know, I thought that was a term we used because we didn't like describing ourselves as trainer. But if I haven't got content and slides, what do want me to do? And I didn't know this work existed. So before I know it, I'm on this offsite with this senior leadership team, working with the HR person who partnered with me on this to say, let's design an agenda. This is where we want to get to. But your job is just to help them have great conversations. And



I was in there, I had a serious imposter syndrome because it was like, who am I to do this? And secondly, I've never done it before and I'm pretending that I can, but suddenly I realised this is what I just feel in my element doing, right? Which is helping people and noticing and helping people have important conversations. Yeah. And I came out going, my God, more of that. Yes, please. That was magical. And it went.



Thought you had wide for it.



Simon (46:47.98)

really well. So was a great kickoff point. And I think I should go back to the improv background. So while I was studying law, but I also was studying performing arts at uni. So that was my combined degree, which was an arts degree, but with a major and a focus in performing arts, because I had done that at school. I loved acting. I loved theatre. And I was doing it more for kicks than anything.



But so coming out of uni, I had done a lot of theatre at uni, a lot of plays and stuff, but I didn't really have time to get involved in theatre productions because I was working as a lawyer. I was way too busy for rehearsals and stuff, but ended up getting involved in improvised theatre because there was no script to learn, just workshops to attend and then performances to do. And that's where I started to really learn the skills of people being able to co-create things without a script.



And that's when I went, my God, this is magic. But I was really bad at it because I was a lawyer who loves control and scripts.



Those two things, is a duality there.



So that duality is one I almost carry with me every day now, right? It's like am I lawyer Simon or improviser Simon? And in fact, does it have to be either or how do I blend this?



Digby (48:08.056)

How does lawyer Simon show up?



sensible, critical, pedantic, details oriented.



And they're all can be strengths, right? Particularly when you're working with a group and they need the output, they need a closure, they need all that practical stuff,



Yeah, thank you. Yeah. So that's true, right? So that version of me is also say, hang on, this doesn't feel like a clear commitment. It's the pragmatist. The duality here is pragmatic, Simon, you know, really fearful of people walking away without outcomes that are meaningful and can be acted on versus, yeah, but I believe deeply that the best way to get to those outcomes now is to do that in a way that's playful, fun, vulnerable, self-deprecating, silly.



Yeah, that's right.



Simon (48:58.382)

Joyful but fully expressive as well. You the opportunity to explore experiment fail Celebrate the failures all of that stuff, which is the stuff I learned in Improv and now just believe is so valuable



It's an incredible combination of bridging two very different worlds. suspect that's what makes you special and why people really like working with you because it's that we know that the people who need the pragmatism are going to get that. people who want to explore and be more open in their orientation to where we take things, they're going to get that. And you can seamlessly blend and dial up or dial down what's needed in the room. And that's.



That's an incredible range of skills to have, I So go you.



Thank you. That's very nice to hear that. That's lovely. Well, and you know, so there's two things that just want to share off the back of that. First of all, I'll never forget the moment I was running. This was back when I was running negotiation programmes and stuff. And one of my clients by complete coincidence had seen me in a show a couple of weekends before an improv show in the comedy festival. So I was performing in the international comedy festival in Melbourne. We were doing this improv show. She was in the audience.



And I didn't know until I rocked up for this gig two weeks later. And she said, Simon, I saw you in this. And my instinctive reaction was, my God, I've been exposed. Like I've lost credibility in this room. So up to that point, I'd been holding those worlds separate. It's almost like this is secret Simon. is professional Simon. Cause I thought they couldn't coexist. Mean, this is the nonsense of it. Right. And I think it's probably something in that for a lot of us until she said,



Digby (50:45.088)

I so.



Can we please have more of that Simon here?



Mm-hmm.



And at first I didn't even compute. What are you mad? Like, it's got nothing to do with this sensible, important, intelligent work. Of course it had everything to do with it. What a gift to have that moment to say, stop holding them as binary choices and instead it's the combo that is you. And it seems so blatantly obvious, but again, the fear of living up to people's expectations and dealing with senior tough crowds at times going,



I've got to match their critical thinking. I've got to match their sensibility. And I overindexed towards that.



Digby (51:28.334)

think what you do is you show a different way that's credible and relatable. And I think that's what leadership is really to say, here's a different way. And if we can tap into the emotion for people, not just the head, then there's something very powerful. I'm wondering if there's stuff we haven't talked about.



You're the one on the list of questions we denied.



I a lot of questions, but I want to put it in the middle for us,



There is something I think we should come back to and that is you put this question of like, you know, getting practical, how do leaders work this noticing muscle? Because I think this, this is easy to understand conceptually, but I think the work in this is important because it's not just nod and agree with this stuff. And there's a couple of things that I'm just thinking about. Like one is having this kind of almost avatars of yourself is really useful. Like what are the different versions of me? So having a lawyer, me and improvising me is really useful for me because



I can keep an eye on both of them and how they're showing up. And I'll often do this with leaders is talk about, you know, what are the different, if we had three versions, three cards that we were turning over and say, this is the three versions of you that we might typically see in stressful, difficult moments, what are they? And also in glorious, joyful moments. And let's keep those three avatars in close check. But there's also then the work of noticing, being able to notice in the moment. And I think that is



Simon (52:55.488)

It's got to be some sort of grounding practice. whether it's yoga, in my case, it's at the moment, it's yoga. It's the thing at the moment. I'm much more attuned to what's going on in a moment. If I've done yoga on a given day.



There's a ripple effect, right? You do that, it has a ripple effect.



It anchors you for the whole day. Yeah. Used to meditate, used to journal, still do occasionally, or whether it's going for a walk and setting yourself a goal of noticing 10 things on the walk. I can't turn on the podcast. Can't turn on the radio or the music until I've noticed 10 things.



Yeah.



Digby (53:33.29)

I think that's a really powerful one is removing distractions and seeing what you notice. I deliberately, when I went for my walk before this, there was no music. was no input besides what I saw and heard. And it was very helpful. Any other practical things, tips for leaders to be this way?



The other one, this is again one that I use on and off when I remember to, but I have introduced this to a few different leadership groups who enjoy it, which is just having a real simple kind of check-in for how are we going? And the how are we going could be as simple as having a kind of a question that you'd love to ask two or three times, which is in you, in fact, you're really good at this, D.B. How is this conversation going? How are we tracking?



How are we feeling about this conversation? Is it going where we wanted to? Is it touching? You just did it a moment ago, right? Is there anything we haven't explored that we would have liked to? So that kind of meta check in, the go to the balcony moment, I think is powerful. And I couple with it or trio with it three things, which is what does the moment need? What do I need and what do they need? a moment, me and them.



Well



And that's one that I'll use more often silently, which is what is, I'll write it literally, it's a triangle on a bit of paper moment, me, them. What is this?



Digby (54:53.42)

Yeah, brilliant. Yeah. And I talk about four lenses of listening, listening to the personal, which is yourself listening to the relational, which is them listening to the directional, which is where's the conversation going, how are we tracking and listening to the contextual, which is the, what might be informing how we're showing up and how we're being today, where are we adding each of those and



That's great. That check-in is such a beautiful window into the awareness and noticing in the moment, both of those things coexist.



How do you remember to ask those questions? I think that's often the thing, right? You sometimes remember that you, I wish I'd asked them. That would have helped if I had asked.



So I think there's some structure around, you've got half a day or a couple of hours, whatever. Yeah. It's like, to me, it's whenever there's a natural pause point, it's to go, all right, these are things I'll remember to ask myself and then also ask the group again, like the flabby muscle versus the tone muscle. I think it's one of those things. It starts off with structure that, you know, I go to the gym three times a week, whatever it is, then it becomes just part of how you operate.



So to me, the structure thing is key and build it into the agenda to be able to ask those questions. You know, I'll often do what I call a thermometer, which is, you know, hold your thumb up and then turn it into a kind of like a, dial that you might see on a car dashboard, you know, with a, you know, pointing down all the way up to pointing up with how's your energy. And I'll just get people to do a show of energy thermometer, right across that scale. Then things like that.



Digby (56:39.564)

I'll always do after a break, sometimes before a break. At the natural break points, I think is what matters.



I love that like hard wiring some stuff in. That's when we talk about space before, when we talk about noticing, maybe the big thing is and leaders stop trying to be perfect at this. Like make it easy for you to set a timer to go off loudly with like energy check, energy check, energy check.



And make it fun and not too bonus. Keep it light.



Be imperfect, be bad at this.



Simon, there's a question I love to ask at the end of a conversation.



Simon (57:20.886)

not the end already, isn't it? aren't we just going? aren't we just getting going?



This is part one, my friend. My God. Well, we talk a lot. We, think we have to press record more often with these conversations. No, it's rich, a rich vein of gold. What's happening, I think. But the question I want to ask you is if you think back over the last hour, what have you learned or been reminded of during this conversation?



Feel free to edit.



Simon (57:48.538)

I think for me, it was really useful to bring back up to the surface, the power of reflecting on that duality as we were just talking about the two versions that can kick in. Because if you don't regularly reflect on that and talk about it, like this conversation has been super helpful for me because I'm now thinking about how those two versions of me will play out in a gig I've got next week, for example, or how they're playing out in the context of.



the busyness of home at the moment. So I think what that's reminding me of is the power of just having someone you can sit down and talk about this stuff with regularly and say, how are you tracking with that? So not trying to do it all alone. And, you know, if I take our conversations, not just the recorded ones, but that's the power of our conversations, someone that allows you to talk about that stuff.



That's one thing. The other thing I'm being reminded of is I talked about those spaces before and I'm suddenly going, oh my gosh, amidst the busyness, there's so much to achieve on the home front as well as the business front at the moment. Like we've got a lot going on. There are some spaces that I'm not holding because it feels we don't have time for it, but I'm going, that's just false logic connection space, the space to just have time sitting, expressing thoughts, just hearing about what's going on, just the space to breathe.



returning to some of those habits and rituals that allow that in our family, I think is powerful and important. And conversations like this are good to remind you that it's so easy to talk about this stuff, but it's very easy to omit to practice it in your own world. So yeah, that's a gift. Thank you.



Thank you. Yeah. The stuff we've been talking about clearly goes beyond the work of leadership in a work context, right? This is life skills stuff. So thank you. If people wanted to learn more about you and what you do and what you think about, how do they find you?



Simon (59:51.18)

I'm in Melbourne, so I'll maybe next Wednesday stand on the corner of King Street and William Street.



With a little sandwich board, right? Yeah.



I'll set up a table, I'll bring some sandwiches and anyone who wants to join.



You heard it here. Get in first, get in early, folks.



You know, but if that doesn't work, I'm in Auckland in my, no. Okay. So I'm on, I'm online. I mean, it's pretty easy these days, isn't it? I'm on LinkedIn. I post regularly on LinkedIn. I'm there. Just look me up, but connect with me, send me a message. Love hearing from people. We're in a world where people like to on LinkedIn observe each other, but they don't reach out and use it for what it's really there for, which is to create connections, make links and networks. Yeah. Make a connection. My website, Simon Dowling.



Simon (01:00:41.838)

com.au. You can find out more about me there and again reach out to me and it's got all my contact details in there. So always welcome someone's email or phone call if they want to have a chat about anything or you're interested in something I've talked about and you say hey have you got any resources on this? Just reach out.



And there are plenty of resources, as you've heard, you know, folks listening that he's a wealth of pragmatism as well as heart.



And I recently recorded a podcast with Digby Scott on his podcast, Deeper, which you can listen to that. Hang on. probably tip if you've got this far. Thank you.



The improv is there every time, isn't it, mate?



the idiot.



Digby (01:01:27.406)

Don't start with I you choose. I love it. Simon, thank you. It's been rich. It's been warm as ever, mate. We'll see you again soon. Thank you.



Thanks, Heapsticks.



Digby (01:01:43.31)

a couple of quick reflections before we finish up. I'm really struck by the idea of the quality of the outcome that you want when you've brought people together. It could be just about efficiency, were we efficient in our time? It could be about the effectiveness of the outcome, was it the right outcome? And then also, this is new stuff for me, is this idea of what's the emotional quality of the outcome? Are we bought in, are we excited and energised by this? Has it got energy around it?



And then Simon suggested perhaps it needs an expansive collage as well. How has it changed or shifted our perspective in some way? And I love those ideas. It's something I reckon I'm going to start to build into my work when I facilitate, when I bring people together. And perhaps it's something that you as a leader could think about too. I'm really curious about what this has got you thinking and what you might be led to do now as a result of this. Here are a few practical things you could take some action on.



First thing is to listen to episode three with DK, who is a former TEDx curator, all about the deliberate design of spaces for people to have a positive experience. We go deep on that. A couple of other things you could do, there's two blogs, I'll put them in the show notes, these are blogs I've written, one called The Moment of Choice and another one called Develop Dual Awareness, where I go into those ideas in more depth.



You could also subscribe to my weekly newsletter where I go into some sort of depth with some practicalities around ideas around leading people well, making change happen and living life deliberately. And that's at digbescott.com forward slash subscribe. I'd love it too. If you could share this episode with someone else who you think might get some real value from it. Perhaps you could also follow it in your feed to say you get every single episode coming through.



I'm Digby Scott, this is Dig Deeper and until next time, go well.