Alanna Irving on leadership, decisions and money in bossless organisations

Ep. 35


Alanna Irving is a facilitator, entrepreneur and community builder and is the Executive Director of Open Source Collective. We talk about her chapter in the new book Better Work Together about growing distributed leadership, working together in bossless organisations, collaborating with money, and her own journey, including how to run Agile Scrum on your personal relationship.

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Lisa Gill: Alanna - hello. Let's start with bossless leadership. I know that's one of your interests and areas of specialty, so what does bossless leadership mean to you?

Alanna Irving: Bossless leadership is a phrase that I just started using. The concept of leadership in much our society is really wrapped up with this hierarchical, positional authority. And I'm very interested in what leadership is when you start to unpick that and start to decouple it from that positional authority idea. And get to the essence of what is that leadership, apart from that?

So I started using the term bossless leadership just to point at that. But I feel like there is no perfect term for what I'm trying to say because there are so many connotations that everybody brings with them into these conversations. Hopefully, though, the idea of bossless leadership is weird enough that gets people to look up and go 'oh, wait - what would that be like?'

Topics in this question

Lisa Gill: It's hard because I don't think there are perfect terms for any of these things. But I think it's finding something that people can relate to, or connect with - at least initially - and then get their interest. I also wanted to say congratulations on the Better Work Together book because I know you were one of the many authors. And I really loved your chapter about growing distributed leadership. I was wondering if you could share some some of the principles that you outlined in that chapter for listeners. That seems a great way into bossless leadership and distributed leadership, and how we can start to cultivate that in organisations.

Alanna Irving: I started thinking about how to grow distributed leadership when I was working with Enspiral, which is a non-hierarchical network of social entrepreneurs. At the time, there was a cohort of us around the same age who would come up together for a few years. And then there were new, younger people coming in. And we were thinking a lot about how we could best serve these younger people who have so much to give and also so much that they want to learn. And also about how we could continue to challenge ourselves to grow - how do we find mentors that are more experienced than us in a way that is non-hierarchical, and that doesn't come with this patronizing connotation to how that all works.

So I was thinking a lot about that, and I started asking a lot of questions about leadership and coming to terms with the idea that I was good at this leadership thing. And if I could redefine it in a non- hierarchical, non-coercive way then that leadership thing is what I would do. So I started sticking by both of those things and asking questions like, 'well, if there's no pyramid that you're climbing up, if there's no sort of ladder that you're climbing, what does it mean to grow as a leader in this environment?' For those of us who are thinking systemically about growing leadership across the whole network, what does that look like and how do we grow more leaders? How do we grow more leadership among everyone here?

Suddenly those questions sparked this whole line of thinking that ended up with this model that I developed that has helped me to think it through. It basically just talks about the different levels at which leadership grows. The pre-requisite level is about shared power. If you're in an environment where you can't talk honestly about power dynamics and that's not an ongoing genuine curiosity that people are open about - if there isn't genuinely a desire for shared power - I think it's like pretty much a non starter. There's no point in trying to grow distributed leadership unless you have some of those prerequisites.

If you've got that, then the stage that comes up next is what I call self-leadership. This is all about how I continually grow professionally and personally, how I challenge myself, how self- aware I am. Do I understand how I want to work? What kind of collaborator should I be and can I be? Being a good team member, basically. And also that skill of looking around and figuring out how I can add value without necessarily being told what to do.

After that, the level up from there, which is sort of a meta level if you think about it, is leading others. And this is, I think, how leadership is often thought of in wider society. It's about the person who is the leader of a team but in an environment without that coercive positional hierarchy. So what does that look like?

I think it's facilitative leadership, bottom-up leadership, servant leadership, there are lots of terms coined to gesture at that whole area. And that includes things like facilitating good communication, reflecting back to the group, helping the group figure out how to delegate tasks, noticing when other people are blocked, and asking good questions that help other people develop or get to the next level.

Then, if you zoom out another meta level there's leading leaders, which is a meta level up from there. How do you grow the skills that allow people to be good, non-hierarchical, facilitative servant leaders. And this often involves designing processes that can work without your direct involvement that can scale beyond an individual leader managing it - that everybody can engage with and iterate, change and interact with. I think that is a big part of it.

It's also key to just think carefully about leadership development pathways in your network - how do people gain these skills? How can we facilitate more people to have access to these skills? And looking at whether certain kinds of people are ending up as leaders. Do they all look the same or have a similar background? Why might that be? Are some people being left out? Are we not doing a great job with valuing diversity and really inviting all of the different kinds of leadership that we're going to need here? Those kinds of questions.

And then the final level - which I think of as ecosystem leadership - is a very wide view of how we are progressing our understanding of the very nature of leadership on a much bigger level. How are home networks relating to each other in ways that increase our collective agency? How can we intersect our work with the big forces in society that serve to privilege or oppress certain people from opportunities for leadership? These kinds of questions - and cross- pollinating on the widest levels - I think of those things as ecosystem leadership.

So, ironically, this non-hierarchical leadership idea ended up in this really hierarchical model. And that's why I chose this metaphor of a flower, when I describe it in the book - and the soil and the seeds and the sprouts and flower and the pollination. That was my attempt to say, 'how do we have a non-hierarchical metaphor for this thing?'

Anyway, I ended up being able to boil that down to a one-page visual, which I felt really good about. I don't think it's the answer to all of like, 'what is leadership?' It's not about that. But it may be a useful model to hold up and go, 'oh, cool - well, how do I fit into this?'

I recently did a workshop on how to go to distributed leadership at a conference. And it was really cool because I talked through the model, and then I just started inviting people on stage to do a fishbowl style workshop clinic thing. And I invited some audience members to come join inside the fishbowl as well. And it just happened to work out as a facilitator. And it is so nice when this happens.

The first person who came up was right on the cusp of self-leadership going into leading others and taking their social entrepreneurship onto a team level. And we talked all about that. And the next person who came up was in a bigger team wondering about how their organisation could involve their wider community of users and supporters. And then, finally, we had a couple of really amazing ecosystem leaders that we got to talk to. So, yes, I find that being able to boil this down into such a clear model does help facilitate those conversations to really dig into all the complexity and uniqueness of every situation.

Lisa Gill: Yeah, I really like that model. And I hear from a lot of people in self managing organisations, that they're kind of stuck with this question of - well, if there's no career ladder or pyramid to work my way up, what does progression look like? How can we codify how people can develop?

Some people will develop their technical expertise, and that's perhaps easier to talk about. But this more human, less tangible area of leadership - I think this model gives a really nice, clear, potential map for some of those skills or capacities that people can develop - and to place yourself. You know, where am I? And what would it look like if I wanted to progress to the next stage?

So it's really nice to have that. I was looking at Buffer - they have this open source document about how they promote and reward individual contributors versus managers. And it's been fascinating to me to watch their journey from fully on board with Teal and self management. And then they went wow - and went back a bit to more hierarchy, but more conscious hierarchy. But I was kind of disappointed with this document, because how they were describing the management capacities - like the skills and what it is to be a leader at this level. And this level was really quite oldschool. And it said a lot about supervising and getting involved with technical matters. And so it left me with this question of, well, how can we describe leadership - if not through that mechanistic lens and micromanaging or supervising lens. So I think this offers a really nice alternative.

Alanna Irving: I think there's something in there about the work that we all need to do to work through and let go of the very strong baggage that we are handed in our culture about hierarchical leadership. A lot of people grow up and their families are dictatorships. And they go to school and that's a dictatorship. And then they go to work and that's a dictatorship. So until we have just as much research and writing and dreaming about this other model as we do for MBAs currently learning all this stuff and however many business schools there are teaching about hierarchy - it's going to take a lot of unwinding and unpicking.

There's something complex about our relationship with power dynamics, our relationship with taking responsibility for ourselves, our relationships with taking responsibility for each other in a conceptual, healthy way - which is just so hard. And it's never easy. It's hugely rewarding, but it's never easy. Walking those roads is never straight, it's never easy.

So I'm constantly tripping up on my own internal, 'oh, actually that was my ego coming out again', and like, 'oh, actually, I'm afraid to take responsibility for myself' or 'I actually did want to talk and tell person what to do', or 'I am actually really attached to a certain outcome'. All those things are ongoing. So I think that these questions are roadmaps for how we can develop or to ask ourselves at different stages, which can be helpful. Plus, working with peers who can consistently reflect to us and challenge us in healthy ways. I don't have the answers. I just kind of know what the shape of the journey looks like.

Lisa Gill: Yes. You've mentioned power dynamics and, and coercive power a few times. And I know through your experiences at Enspiral and beyond - and in the work that you're doing currently - that's something that you look at. What have you learned about power and the nature of power and how we can start to become more aware of it and question it and call it out?

Alanna Irving: I think power is some sort of law of nature. It's like, water - something that exists and has certain properties that you can observe. And sometimes you can channel it and it tends to pool in certain areas, or it reacts in different ways to different environments. But power is not something that we can ever get rid of. Every human group inherently has power dynamics.

So I think the question we then have to ask is how are we going to relate to that? What does that mean to us? What are we going to do with those power dynamics? How are we going increase our skills for observing them, understanding them and talking about them - and figuring out if they're working for us the way we want them to, and how we might go about changing them or improving them.

There is sometimes a knee-jerk reaction - a rejection of power itself. But I think that's a little bit self defeating, because it's inescapable. In fact, if we try to escape it or avoid it - or don't want to look at it or talk about it - that's when power can get extremely dangerous and quite dark in ways that we don't always intend. That's when you can get these unspoken rules, hidden hierarchies and weird power dynamics. I think everybody's probably had that experience and it just feels really uncomfortable. And you're not sure what's going on, or you know that somehow you don't have access to certain power, and you can't talk about it because it's not explicit.

So I just think it's a constant process of surfacing - 'what's going on with our power dynamics?' or 'is it working for us?', is almost the best you can do. And from there you can build certain processes and try to make certain things explicit which makes them easier to talk about or easier to iterate on. But because human groups are hugely dynamic and constantly evolving things, anything that you put in place - any snapshot that you take of making it explicit (like roles or our roles or relationships) - is only going to be sure for the instant that you name it. And then it will immediately begin evolving. So it's a constant process of continually working on those skills of communication and self awareness and other awareness, and just being in relationship and constantly reflecting is the only way I have found to really approach power that feels genuine.

Lisa Gill: Yes, it's hard to have those conversations. But it's the only way I can think about it as well - to just keep trying to bring it up, making it visible and talking about it. So that it's explicit. And I guess connected too, because I know you've also written a lot a lot about decision-making. And that comes up a lot in self-organising or self managing teams and organisations. Where are you currently in your thinking around decision-making? Have you come across or developed any models for that which you think are useful?

Alanna Irving: Decision-making is another one of those things that you never fully figure out. It's a constant ongoing learning journey. I think one thing I've realised more and more in the last couple of years since branching out in my work is that it really depends on the group of people that you're working with.

For example when I was working with a Lumio team for about five years, it was a fantastic team. And Lumio is a decision-making tool, obviously. So it was a bunch of decision-making nerds being in a company together. And we were all facilitators, activists and technologists who were very interested in these same questions. So, of course we talked a lot about decision-making and it was a big focus for us. We had a lot of very sophisticated decision-making protocols and group practices that we would undergo to get us to a good place and strategy day facilitation run sheets and all this kind of stuff - and that's all really good. And that's in the Loomio Handbook for anybody who wants to use it.

Whereas now I'm working with this team with Open Collective which is just way more free-form. It's a fully remote team. Whereas for Lumio being together was very important for our relationship, the Open Collective team is much more emergent and less explicit on how decisions are made. But it works. And it's great learning for me to be much more comfortable with very emergent decision-making or less explicit processes. And just trust it. It's more the approach of 'ok, hire people that have good skills and are good communicators, and then just let them do their thing and talk to each other and figure stuff out'.

I think there may be times in the future for Open Collective where we do want to roll out some of those more explicit decision-making protocols. And I'm really glad I have those in my toolbox. Because when the day comes, I know that I can pull them out and say 'why don't we try this process?'. And I've done that a little bit - I have run strategy workshops where we trying to make it a little bit clearer what we were going to focus on over the next few months. And that sort of thing is just super hard for a remote team to really converge on. Especially when communication is disjointed and we're in so many different time zones.

Anyway, I think the point with decision making is that there is no one answer. There's only a tool belt that you can develop. It's really useful to know the names of many different decision-making protocols and to know that there are decision-making protocols. And probably you're using certain ones. Whether you intended to use a protocol or not, you'll find that if you don't make a different choice you'll default to this decision-making protocol. And I just think it is really useful to have a bit of a vocabulary and a toolbox around that so that you can step back and go, 'oh, is this the decision-making protocol that is most suited to what we want to do here?' Are we defaulting to listening to the most charismatic communicator every time who makes the decision? Or are we defaulting to unanimity? When actually what we should be doing is devolving power so that certain people are able to run ahead without everybody agreeing? I think that's a useful skill and vocabulary to develop.

Lisa Gill: That's helpful, yes. Could you say a bit more about Open Collective and the work that you're currently doing?

Alanna Irving: Open Collective started as a crowdfunding tool for open source software projects. But it's evolved quite far beyond that now. Because it started with open source software projects it's built for distributed collaboration, which often doesn't naturally want to or can't take the shape of, for example, a legal entity that one person owns. It's actually something which is unknown or owned in common among a whole group of people, and needs to be managed that way.

So if you look at the website, Open Collective looks like a crowdfunding platform, except it's all transparent - where the money comes from and where it goes. Then, if you lift up the hood, and dig around a little bit at how this thing actually works you'll see that it's sort of a tool for Fiscal Sponsorship. So using legal entities in really creative, flexible ways.

Basically, you can have one legal entity - so none of those projects have to create their own legal entity or get their own bank account or worry about any of that stuff. They can just focus on making open source software. And we take care of all that financial admin in the background. Then there are other umbrella organisations - for example there's a great one called Brussels Together in Belgium, which is for grassroots citizen initiatives. Civic responsibility work and environmental groups - and those kinds of groups.

Those groups are not owned by anyone either. They don't want to be bogged down in the paperwork of figuring out a bank account and a legal entity and hiring an accountant and worrying about taxes. So instead, this Brussels Together organisation takes care of all of that, and can fiscally and legally host all of these groups. So there's lots of those umbrella organisations in different geographies that focus on different missions or different communities of collectives.

Lisa Gill: It sounds super interesting. I feel like I'm not quite clever enough to understand all of this. But what it brings to mind is something else that I know you're interested in - and I think is sometimes a bit of a taboo topic in terms of distributed and decentralized organisations, which is money and how we collaborate with money. What has been your journey with that and what have you learned? What are some insights that you could share with listeners about collaborating with money in a non hierarchical way?

Alanna Irving: Collaborating with money has become a really big theme in my work over the last few years. And that was not exactly intentional. It's something that really emerged. Then I turned around and went, 'wait a minute, all of the work that I've been attracted to in these few years has been around this theme'. So that was interesting to notice.

I think it, started with the work we were doing at Enspiral. Money was naturally a part of it, because we were running businesses. And that was just inherent to the work we were doing. So we were thinking about money as just another type of information or just another resource that we could play with - that we could understand and get to know in different ways.

We were very much in the habit of taking everything and deconstructing it and saying, 'Oh, governance - let's deconstruct that and rebuild it in a different way', or, 'Oh, company structures...'. We were in a very experimental mode and so quite naturally just did the same thing with money. Also as a group of people it was very much about generosity and helping each other out. Money is a natural way to do that.

So we started doing a lot of interesting experiments with money and Enspiral. What emerged was the whole collaborative funding Cobudget thing. Cobudget is a tool for making a budget together. Essentially, you put up projects and people can control different amounts of the money and decide what to do with it. And see what collectively emerges. What do we want to prioritize? How much money do you want to spend on different projects?

So Cobudget is a software tool that helps groups do that. And that came out of how we were doing budgeting in Enspiral. We needed ways to involve large numbers of people transparently in budget setting. So I did a lot of the behind the scenes sort of work figuring out how you actually make that happen. How do you actually move money around in bank accounts? I was doing all the admin and a lot of the legal entity company structure work behind that. A I wondered how you hack things that are made for one way of looking at business and collaboration for a completely different sort of paradigm. The status quo is just really time consuming, expensive and requires talking to lawyers and asking accountants questions and so on.

I remember, luckily, we had accountants at Enspiral who were totally aligned with us because I was asking them questions like, 'Can this company just give money to this other company?' And they said 'Oh, no, generosity is not in the text'. So out of that I really felt the power of money. I think a lot of people feel like money is very powerful. But it's kind of like 'money's out there and it's having power over me' sort of feeling.

I tasted an inverting of that - like, 'Oh, money, we can control how we want to use it, we get to say what the dynamics of our internal economy is'. And that's very empowering. So I got very interested in that.

Open Collective is basically a tool to automate all the things that was super hard that I was doing manually at Enspiral. So when I heard about what they were doing and they reached out to me, I was just like, 'thank you - somebody is building a software tool to do this thing that I've been painstakingly doing on spreadsheets and driving us crazy to actually fit in the law'. So that was really great, and that's why I decided to start working with them.

I always feel for and think about the back office admins - the people behind the scenes who actually make this thing work, beyond whatever the shiny headlines are. I'm very interested in the nitty gritty behind the scenes processes. And Open Collective is very much a tool for that stuff - and for basically radically bringing down the overheads of it. So that more people can feasibly work in these ways without pulling their hair out or having to pay lots of expensive lawyers and accountants.

Also I've recently been dealing more and more with the whole crypto world. And of course dealing with money in new ways is very central to what a lot of what people are thinking about in the crypto world. So that's interesting. I'm not usually an early adopter type - I usually just wait and see what my friends think. And then end up coming to things very late.

So I only got really pulled into the whole crypto thing in the last couple of years. But it's really interesting and empowering to be able to take money and turn it into information, and then do lots of creative and highly flexible things without all the baggage from all the systems we use to manipulate money in mainstream society. And there are pros and cons to that. Some of the stuff that's been developed in mainstream society has been developed for a reason and when you throw those things out, things get messy. But other things are just huge weights on creativity, and lifting those things off can really open up possibilities.

Lisa Gill: I wonder what your advice might be to people listening who are in self-managing organisations. They've evolved a lot of really cool practices, and they're doing quite well. But the one thing that they haven't yet touched is salaries. Because that feels scary - to open up salaries, especially if you didn't start out that way if you transformed from a traditional organisation. What would your advice be to people who are who are curious about how they might approach money in that sense? How can you open the kimono?What are your thoughts?

Alanna Irving: Money has a lot of psychological power for many people in positive and negative ways. Talking about money is somehow this massive shortcut to talking about all of these very deep, important, complex issues. If you have a conversation about your relationship with money, it's often a conversation about how you were raised, and how poor your grandparents were and what some of the biggest mistakes you've made in your life are. And what your hopes for your children are. It's just huge. And also it's right next to what your values are as a human being - because we are up against this incredibly pervasive capitalist mindset that says we you the monetary value that you can claim. Nothing more, nothing less. Which is, obviously a hugely damaging and narrow way to look at a human being, but is massively influential in our culture and in our mindsets.

So I'd say first of all, don't blame yourself if talking about money gives you the heebie jeebies, that's normal and expected. If you're working in a self-managing organisation, you probably have a lot of practices for creating good containers for having hard conversations. So I'd encourage you to think about the money conversation similarly, and just think creatively about it. or, Who are the right people to speak to, what kind of container may hold them up well, what kind of questions may open up the right questions?

Good facilitation obviously helps a lot. I would also really encourage people to let go of the idea that there's any one answer about money. Just like there's no one answer about any other organizational process or decisions that you need to make. You have a feeling and say we'll try something, we'll experiment. And then we'll stop and reflect and see how it went for us, and then decide if we want to keep going in that direction or try something else. Or maybe we'll commit up-front to trying three very different experiments so that we can honestly say we really felt it out and can figure out what's working for us, be willing to loosen the sort of tight grip or super seriousness that people tend to hold around money, and see whether that's facilitated by putting timeboxes around things, or taking 10% of the budget and freeing it from our normal budget process and doing a really transparent, participatory experiment. Just to start practicing and playing with money together in lower stakes ways can be really helpful because then it will feel less scary to make the bigger, more serious decisions about money later on.

Lisa Gill: That's really good advice. Thank you. I'm wondering, as you look back through your journey with all of this stuff, what has been the most challenging or painful learning moment for you, do you think?

Alanna Irving: Wow. I think my experience leaving Enspiral was pretty challenging. It was a big combination of me burning out after many years of stretching myself too far and not having enough balance. And just working in an early stage bootstrapping startup and never having enough money and always feeling like we wanted to help everyone and we couldn't.

Plus, going back to some of what we were talking about earlier with leadership development, coming to terms with the idea that I felt like I was outgrowing my pot. I needed to break out and spread my branches and roots a bit more. But that was really sad for me too. To confront the idea that I may have reached some limits at that time for me in that place. And that's because of how much love and respect I have for all the people there. And how hugely influential and precious their peer mentorship has been to my leadership development. But also feeling like to actually grow I needed to step out, challenge myself in new ways, take some of the stuff I'd learned and apply it in new contexts and see what that's like.

I had to let it get to a point where the things that weren't working were right in my face before I actually let myself consider that that was going on. For every collaborative group who is doing highly experimental, brave stuff - it's dangerous and risky. I was just feeling like I had taken some risks, as a leader in that space and I didn't feel like I was getting the support that I needed. It wasn't because people didn't care or anything like that. It was just that the structures that I needed weren't there - or the understanding, or the culture, or the larger thing that I needed to be holding me to do what I felt like I needed to do for my next stage of development.

It was a very hard time, and I never completely left because, I still love all of those people and work with them and support a lot of those projects. And I went to the recent Enspiral retreat and it was great. So I guess I still feel like I have like one toe in. But it has been healthy for me. Important for me.

Also, as you know, I've gone through a bunch of life transition changes in the last few years. I had a baby, and we bought our first house, I got married, and life changes. I tend to be a person who, for whatever reason does things in extremes. I'm either traveling all the time doing trips around the world or not traveling at all for several years. And I'm constantly trying to like challenge myself to see how I can do things like in a medium way. So that's where I'm at right now. Is it possible for me to be in relationship with something in a less extreme way? I feel like that's the part of my personal growth that I'm confronting now.

Lisa Gill: Thank you for sharing that. I resonate with this challenge of extremes and burning out. And I think it's also something that a lot of people struggle with when when you are working in environments like this - that are much more decentralized and people are very passionate about it. It's experimental, and it's exciting, and it's purpose led. So it's much easier, I think.

I can remember talking to some of the nurses from Buurtzorg and one of the challenges there is that people love their work so much, and they have so much autonomy, that the shadow side of that is that people are burning out. And it's really challenging to support each other and to support yourself as well. And how to get the right balance and have some self care and awareness there too is hard. Have you distilled any lessons for yourself around that area or is it something you're still exploring?

Alanna Irving: Yes, I think I've probably made every mistake in the book at some point in terms of burning out or going too far or stretching too much, or saying yes to too many things, or having too much passion. I've done all of those things, in many ways. But I have learned a couple of things along the way.

I think some other life experiences that I've had have helped me reflect on it - some health issues, I have a disability. And that has forced me in a lot of ways to get really serious about balance and wellbeing. I've got much better at that in recent years. It just means that I can't fake it. I have to actually be doing the wellbeing balanced thing or I will just actually kind of fall apart. So that keeps me honest, I would say.

And also the psychological work that goes along with picking apart your worth as a human from your productivity or busyness or all of these things. I think when you're confronted with physical limitations that becomes very stark. I'm still working on that obviously, but I have had a lot of thoughts and processes that have helped me get to a better place with it. And then having a kid which isn't experience that a lot of people who have MS have. So I have no choice but to look after myself. Because I have to be there for this little person. And it's so incredibly clear that I am useless to her if I don't actually take care of myself - if I don't eat, sleep and breathe.

I think having a kid is another example of something that people are obviously very passionate about, and it's very personal. Just like hoq passion values driven work can be. So you have this urge to just give and give and give until you fall over. But on another level, you know that if you care about the long-term wellbeing of what you're trying to give to, then your wellbeing is a huge part of that equation. Because you want to be there to be able to keep giving years from now, whatever that looks like. So I think having a kid has helped me put some of these questions in starker relief. And realise, that there are some echoes here about how I feel about my work, which is very passionate and values driven as well.

Lisa Gill: I feel like I also owe you a big thank you because I came across the article that you wrote about running retrospectives on your relationship. And this was before I knew you. So I didn't realise until I was doing a bit of research for this interview that I've been using your article and doing that with my partner and running agile retrospectives on our relationship - and then I realized it was you that had written it.

Alanna Irving: Awesome. It was great. That article as taken off more than anything I've ever written. Honestly, it's so funny. It's taken on a whole life of its own. My partner and I do agile retrospectives on our relationship once a month. And we've been doing that since quite early on. We're total geeks caught up all these practices around building software and teams and so on. So I fully own up to how geeky it is but it's been really important for our relationship.

It really warms my heart that it's worked for other people as well. It's kind of funny - it may seem like an overly structured approach to emotional, personal communication. But paradoxically I think it's because we're quite sensitive, emotional people that we like these spaces. And there's an intentionality around the communication and a little bit of structure to create safety to maybe go deeper or open up a bit more.

Even if you're a sensitive person who feels things strongly, it's an ok place to be able to really bring that authenticity and those vulnerabilities. I think that's why it's been so good for us, and that's why we keep doing it. We've been together for six or seven years now. And we still do it every month. Maybe when our kid is a little bit older we'll involve her as well. You just don't imagine asking a kindergartner if they can think of any process improvements for our family. Like, should we be doing dessert more times a week? Or just in a discussion at that time? Can I ask how it has been for you?

Topics in this question

Lisa Gill: It's been great. I think what you said is exactly the value that we get from it. When I first approached Shaun about this I said it might be really geeky. But would you be up for trying this? And I was pleasantly surprised that he was like, 'Yeah, sure'. And then every time we do it - and we're not super disciplined about it, but we we always, every time we do one we get so much value from it - I think it's because the structure and those containers make it safe and intentional.

So we'll go for a walk and we'll talk about things like being grateful and expressing gratitude to each other. Things that we don't appreciate each other for - so often I just forget to do that in everyday life, but I notice the things that he's doing. So it's really nice to be intentional about that. And then to bring up really tough topics of conversation - but somehow it feels safe and ok, within that container, to do it. There is some sort of unwritten agreements already because the intention is that we're working on the relationship. We're committed to it working and so it's not coming from a place of criticism - it's coming from a place of commitment to the relationship. So it's been really wonderful for us. I'm super grateful that you shared that with the world.

Alanna Irving: Oh, well, thank you. I'm really glad to hear that.

Topics in this question

Lisa Gill: We have covered covered so many different topics. I'm wondering what is on the horizon for you. Do you have a learning edge at the moment? Or a question that you're holding on another topic or a juicy challenge that you're exploring currently?

Alanna Irving: In recent times I have been working in a more sustainable way. I have been being much more intentional about saying yes to fewer things. So that I can say yes to those things more fully. And having to say no to more things, which can be really hard. But that's allowed me the space, I think, to bring more intentionality to how I'm spending my time and attention. And I'm finding, work relationships and opportunities that really work for me, and I'm allowing it to be ok for me to have needs and set that bar and really look for that.

I think what that has opened up for me is space to be even more intentional about my work and inquiring into my values, and how I'm choosing to prioritise my time. Is that really matching with what I care about most? I think a lot more carefully about volunteering my time.

I am extremely lucky that I am constantly interacting with people who are doing all kinds of really cool stuff. I want to help everybody and I want to be involved in everything. But actually taking that step back and saying, 'ok, actually, it's more important for me to pick things that I think could have real impacts on social justice outcomes in my community, for example. Or following the lead of some amazing activists, women of color - I want to give them my volunteer hours, instead of saying yes to this and that.

So putting up some boundaries really allowed the space for that inquiry. But that's obviously ongoing all the time. And considering which fights are worth fighting, and which conversations are going to be amazing, and which ones were really not worth having. That's a constant question. I think one thing that's actually given me space to think more deeply about things like that has actually been working for somebody else's company - after many years of co-founding my own startups and building everything from scratch, andholding the entire existential weight on my shoulders.

It wasn't until I took that off and actually had roles where I have responsibility, and I really care, and I'm taking ownership for my stuff. Whereas an executive reporting to a board actually has some existential responsibility. Or in my current role with Open Collective I'm looking after a certain part of it, and that's great. And the two co-founders are having conversations with investors and I'm just like, 'hey, I'm so glad I don't need to do that right now'. Because I did that for a long time.

I think being willing to put some of that control down and take off some of those weights has opened up the space that I needed to actually live into my best way of working, align my actual work priorities and life priorities with my deeper values, and give myself some more space to be able to make choices instead of just being responsible all the time. I hope that was an answer to your question. It's something that's obviously still emerging for me.

Lisa Gill: Yes, it was. I think it's really interesting to transition from founder or co-founder to something else and noticing how that feels in terms of what you're holding onto - different weights and responsibilities.

Finally, what words of wisdom or advice or thought-starters would you give to listeners of the podcast who are somewhere on their journey perhaps to being a self-managing organisation or if they're starting to think about it or they're looking for the next level of development? What advice would you give them?

Alanna Irving: I think there's something there around sharing stories. That's what we were trying to do with the book we just wrote Better Work Together. It's very honest. It's not saying here's the answer or let me just follow this pathway - you can do both. But whatever we did, it's not like that at all. It's like, 'Hey, here's some real stories about things we tried. And this kind of worked. And that didn't, and this one was like this. And this question just led to more questions. And then this over here kind of worked a bit, you might want to try it'. And I think that was a really cool opportunity for reflection for me.

There were times at Enspiral where people were very excited about, 'oh, can we bottle this thing up and export it?' And can we copy and paste this into other cities? And what I've come to realize is I don't think you can. A truly vibrant, collaborative community is not built, it's grown. And each one grows differently, and has to be given that space - because what we're doing here is about emergence. It's about the cool stuff that we cannot predict - 'we're going to just go into this together and be in relationship and respond to what comes up, keep learning and keep building and we don't exactly know where it's going to go'.

I think that possibility and that space is super scary. But I think that's why we're in this thing - because that possibility space excites us. So I would say you can't copy and paste it, unfortunately. But every time that I have shared my stories - warts and all - I've been glad. And when I get to read other people's or hear other people's stories, it feels it's really important to feel that solidarity to know that many people are working on this bigger thing - I don't even know what you'd call it.

The speaker movement that we're in, this bigger paradigm that's emerging, it's not going to look like one way. It's going to look like a thousand different ways. But when we share the stories and start noticing some of the patterns - I think this is on the level of that ecosystem leadership that I was talking about.

It's our collective budget of noticing - where are some of the common patterns? What can we pull together? That could be a common story, or that could help us step back and look at what this thing is that we're actually in. I guess that's the project that I want to be in collaboration with all of you out there. I think that we need to be in this together to figure that out.