Alanna Irving on leadership, decisions and money in bossless organisations

Lisa: So Alanna, maybe 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: Bossless leadership is a phrase that I started using. I feel like the concept of leadership in a lot of our society is really wrapped up with this hierarchical positional authority, and I’m very interested in what is leadership when you start to unpick that and sort of decouple it from that positional authority idea and get to the essence of what is leadership apart from that.

So I started saying “bossless leadership” just to sort of point at that, but I feel like there is no perfect term for what I’m trying to say because there’s so much connotations that everybody brings with them into the conversation. But hopefully the idea of bossless leadership is weird enough that it gets people to kind of look up and go, “Oh wait, what would that be like?”

Lisa: Yeah, 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” because I know you were one of the many authors, and I really loved your chapter talking about growing distributed leadership. I was wondering if you could share some of the principles that you outlined in that chapter for listeners, because I think that’s really a nice way into what is bossless leadership and what is distributed leadership and how can we start to cultivate that in organizations.

Alanna: I started thinking about how to grow distributed leadership when I was working with Enspiral, just a non-hierarchical network of social entrepreneurs. At that time, there was sort of a cohort of us who were around the same age who had come up together for a few years, and then there were new younger people coming in. We were thinking a lot about how can we best serve these younger people who have so much to give and also so much that they want to learn, and how can we also 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 weird sort of patronizing connotation? How does that all work?

I was thinking a lot about that, and I started asking a lot of questions about leadership. I guess coming to terms with the idea that I was good at this leadership thing - if I could redefine it in a non-horrible, non-coercive way, then yeah, that leadership thing is what I do. So I started thinking about both of those things and asking questions like: okay, well, if there’s no pyramid that you’re climbing up, if there’s no sort of ladder that you’re climbing up, 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? How do we grow more leaders? How do we grow more leadership among everyone here?

So really, those questions sparked this whole line of thinking that ended up with this model that I sort of developed and that has helped me think it through. It basically just talks about the different levels at which leadership grows.

The sort of prerequisite 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, where there isn’t genuinely a desire for shared power, I think it’s pretty much a non-starter. There’s no point in trying to grow distributed leadership then, unless you have some of those prerequisites.

But if you’ve got that, then the stage that comes up next is what I would call self-leadership. This is all about: how do I continually grow professionally and personally? How am I challenging myself? Am I self-aware? Do I understand how I want to work? What kind of collaborator should I be? Being a good team member basically, and also that skill of looking around and figuring out how can I add value here without necessarily being told what to do. So there’s that whole self-leadership phase.

And then after that, sort of the level up from there, the meta level if you think about it, is leading others. This is, I think, kind of how leadership is often thought of in wider society. It’s about how this person is the leader of this team. But in an environment without that coercive positional hierarchy, what does that look like? I think it really looks like facilitative leadership, bottom-up leadership, servant leadership. There are lots and lots of terms coined to sort of gesture at that whole area.

That looks like things like facilitating good communication and reflecting back to the group, and helping the group figure out how to delegate tasks, and noticing when other people are blocked, and asking good questions that help other people develop or get to the next level - all those sorts of things.

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

And also just thinking carefully about leadership development pathways in your network. How do people gain these skills? How can we facilitate more people having access to these skills? Looking at: are certain kinds of people ending up as leaders? Do they all kind of 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? Are we 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 sort of a very wide view of: how are we progressing our understanding of the very nature of leadership on a much bigger level? How are whole 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. Cross-pollinating at the widest levels - I think of that stuff as ecosystem leadership.

So it’s kind of like, ironically, this sort of non-hierarchical leadership idea. In the book, I chose a metaphor when I describe it - I use a metaphor of a flower, like the soil and the seed and the sprout and flower and the pollination. That was my attempt to use a non-hierarchical metaphor for this thing. I ended up being able to boil that down to basically a one-page visual, which I don’t think is like THE answer to all of “what is leadership” - it’s not about that. It’s like, this is a useful model possibly to hold up and go, “Oh, cool, well how do I fit into this?”

I recently did a workshop on how to grow distributed leadership at a conference, and it was really cool because I got up and I talked through the model, and I just started inviting people on stage. It was sort of like a fishbowl style workshop clinic thing, and I invited some audience members to come join inside the fishbowl as well.

It just happened to work out - as a facilitator, it’s nice when this happens - but the first person who came up was right on that cusp of self-leadership going into leading others, taking their sole entrepreneurship onto a team thing, and we talked all about that. Then the next person who came up was in a bigger team, wondering about how their organization could involve their wider community of users and supporters. Then finally, we had a couple of really amazing ecosystem leaders up there that we got to talk to.

So I find that being able to boil this down into such a clear model does facilitate those conversations to really dig into all the complexity and uniqueness of every situation.

Lisa: Yeah, I really like that model, and I think I hear from a lot of people in self-managing organizations often this - they’re kind of stuck with this question of: well, if there’s no ladder, 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?

I think there are some people who will develop their technical expertise perhaps, and that’s maybe easier to talk about, but this sort of more human, less tangible stuff of leadership - I think this model gives a really nice, clear potential map for what are some of those skills or capacities that people can develop, and to sort of place yourself: where am I, and what would it look like if I wanted to progress to the next stage? So I think it’s really nice to have that.

I was looking at Buffer - they have this open source document about how they promote and also reward individual contributors versus managers. It’s been fascinating to me to watch their journey. They kind of went full on board with sort of teal and self-management, and then they kind of went “well” and went back a bit to more hierarchy, but more conscious hierarchy.

But this document was - I was kind of disappointed because how they were describing the management capacities, like the skills and stuff of what it is to be a leader on this level, this level, was really quite old school. It was a lot about supervising and sort of getting involved with technical stuff. So it left me with this question of: yeah, how can we describe leadership if not through that kind of mechanistic lens and micromanaging or sort of supervising lens? So I think this offers a really nice alternative.

Alanna: I think there is something there about the work that we all need to do to maybe 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 MBAs currently learning all this stuff in however many business schools there are teaching about hierarchy, it’s going to take a lot of unwinding and unpicking to get to a point where we really believe - I don’t know how to say it - like, it’s something complex about our relationship to power dynamics, our relationship to taking responsibility for ourselves, our relationships to taking responsibility for each other in a consensual, healthy way, which is just so hard. It’s never very easy. It’s hugely rewarding, but it’s not very easy.

And I just think that those that walk in those roads, it’s never straight, it’s never easy. So we’re constantly - I’m constantly - tripping up on my own internal “Oh, actually that was my ego coming out again” or “Oh, actually, I’m afraid to take responsibility for myself” or “I actually did want to tell that person what to do” or “I’m actually really attached to a certain outcome.” All those things are ongoing.

So I think these questions - maybe some road maps for how we can develop or key questions to ask ourselves at different stages 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 know that I kind of know what the shape of the journey looks like.

Lisa: Yeah, you’ve mentioned power dynamics and power and sort of coercive power a few times, and I know through your experience coming up in Enspiral 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 kind of question it and call it out?

Alanna: I think power is like some sort of law of nature. It’s like water. It’s 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 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 is: okay, how are we gonna relate to that? What does that mean to us? What are we gonna do with those dynamics? How are we going to increase our skills for observing them, understanding them, talking about them, 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?

So I think there is a sometimes kind of knee-jerk reaction, like a rejection of power itself, but I don’t think that’s a little bit self-defeating because it’s inescapable. I think, in fact, if we try to escape it or avoid it - “I don’t want to look at it and don’t want to 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 get these sort of unspoken rules and hidden hierarchies and weird power dynamics.

I think everybody’s probably had that experience where you’re like, it just feels really kind of icky and you’re not sure what’s going on, or you know that somehow you don’t have access to certain power but you can’t talk about it because it’s not explicit. So I just think a constant process of surfacing what’s going on with our power dynamics - is it working for us? - is almost the best you can do.

And I guess from there, you can build certain processes and maybe make certain things explicit that makes them easier to talk about or easier to iterate on or something like that. But because human groups are dynamic, constantly evolving things, anything that you put in place, any snapshot that you take of making it explicit like “Oh cool, these are our roles and these are our relationships” - it’s only going to be true 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, I think, and just being in relationship and constantly reflecting is the only way I found to really approach power that feels genuine.

Lisa: Yeah, I think it’s hard to have those conversations, but I think that’s the only way I can think about it as well - to just keep trying to bring it up and making it visible and talking about it so that it is explicit.

Connected to that, because I know you’ve also written a lot about decision-making, and that’s something that comes up a lot in self-organizing or self-managing teams and organizations - where are you currently in your thinking around decision-making? Have you come across or developed any models for that that you think are useful?

Alanna: Yeah, 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 realized more in the last couple of years, since sort of branching out in my work, is that it really depends on the group of people that you’re working with. Like previously, when I was working with the Loomio team, which I was working with for about five years - that was a fantastic team, and Loomio was a decision making tool, obviously, so it was a bunch of decision-making nerds being a company together. We were all kind of facilitators, activists, technology people as well, but 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, and we had a lot of very sophisticated decision-making protocols and group practices that we would undergo to get us to a good place - strategy day facilitation, all this kind of stuff. And that stuff was all really good, and it’s up on the Loomio handbook for anybody who wants to use it.

And then now I’m working with this team with Open Collective - it’s just way more freeform. It’s a fully remote team, whereas Loomio, being together was very important to our relationship. The Open Collective team is much more kind of emergent and less explicit in how decisions are made, but it works. It’s great learning for me to be much more comfortable with very emergent decision-making or less explicit process, and sort of just trust.

It’s more the approach of: okay, hire people that have good skills and are good communicators, and then sort of just let them do their thing and talk to each other and figure stuff out. I think that 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 go, “Cool, why don’t we try this process?”

I’ve done that a little bit - ran sort of strategy workshops and stuff like this where we try to make it a little bit more clear what we’re gonna focus on over the next few months and that sort of thing. It’s just super hard on a remote team to really converge that sort of thing, especially when we’re in so many different time zones - we can never actually [meet all together].

Anyhow, the point is, I think with decision-making, there is no one answer. There’s only a tool belt that you can develop. It’s really useful, I think, to know the names at least of many different decision-making protocols, know that there are decision-making protocols, and probably you’re using certain ones whether you intended to. Even if you think, “Oh, we don’t have a protocol,” actually you’ll find that if you don’t make a different choice, you’ll default to this decision-making protocol.

I just think it is really useful to have a bit of a vocabulary and toolbox around that so that you can step back and go, “Ah, is this the decision-making protocol that is most suited to what we want to do here?” Like, are we defaulting to listening every time to the most charismatic communicator who makes the decision? Or are we defaulting to unanimity when actually what we should be doing is evolving power to certain people to be able to run ahead without everybody agreeing? I think that’s a useful skill and vocabulary to develop.

Lisa: Yeah, I think that’s helpful. Maybe could you say something about Open Collective and what that is and the work that you’re doing currently?

Alanna: Yeah, Open Collective started as sort of a crowdfunding tool for open source software projects, but it’s evolved quite far beyond that now. Because it started with the open source software projects, it’s built for distributed collaborations which oftentimes don’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 unowned or owned in common among the whole group of people and needs to be actually managed that way.

So Open Collective - if you look at the website, what it looks like, it’s 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 look and dig around a little bit in how this thing actually works, you’ll see that it’s actually kind of like a tool for fiscal sponsorship, using legal entities in really creative, flexible ways.

Basically, you can have one legal entity on Open Collective which is kind of like an umbrella organization, and under that, you can have sub-organizations that do different things. We have one that’s for all the open-source software projects and that’s its mission, and it’s the fiscal sponsor for all of those projects - it’s like eleven hundred of them or something now. 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 focus on making open-source software, and we take care of all that financial stuff in the background.

And then there’s other such umbrella organizations. For example, there’s a great one called Brussels Together in Brussels, Belgium, which is for grassroots citizen initiatives, civic responsibility stuff, and environmental groups. All these kinds of groups are on there, and those groups as well, they’re not owned by anyone, they don’t want to be bogged down in paperwork of figuring out a bank account and legal entity and hiring an accountant and worrying about taxes. Instead, this Brussels Together organization takes care of all of that and hosts fiscally and legally all of these groups.

So there’s lots of those umbrella organizations in different geographies that focus on different missions or different communities of collectives.

Lisa: Right, 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 organizations, which is money and how do 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 sort of non-hierarchical way?

Alanna: Collaborating with money has become a really big theme in my work in the last few years, and that was not exactly intentional. It’s something that really emerged, and then I turned around and went, “Wait a minute, all the work that I’ve been attracted to 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’re running businesses, and that was just inherent to the work that we were doing. Thinking about money as kind of like just another type of information or just another resource that we could play with, that we could understand in new and different ways - like, we were very much in the habit of taking everything and deconstructing it and being like, “Oh, governance, let’s deconstruct that and rebuild it in a different way” or “Oh, company structure, let’s deconstruct that.” So we were in that very experimental mode, and money just quite naturally we did the same thing with.

Also, being a group of people, it was just 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 in Enspiral. What emerged from that was the whole collaborative funding Co-budget thing. Co-budget is a tool for making a budget together essentially. You can put up projects, and people can control different parts of the money and decide, what do we collectively sort of want to prioritize? How much money do you want to spend on different projects? Co-budget is a software tool that helps groups do that, and that came out of just how we were doing the budget 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 do you actually make that happen, how do you actually move money around in bank accounts? I was doing all the admin and doing a lot of the legal entity company structure admin behind that, and figuring out how do you hack things that are made for one way of looking at business and collaboration for a completely different sort of paradigm? That is just really time-consuming and expensive and requires talking to lawyers and asking accountants questions they’ve never been asked before.

Luckily, we had accountants in Enspiral who were totally on the vibe with us because I was asking them questions like, “How do we just - can this company just give money to this other company out of generosity?” It’s not in the tax code.

So out of that, I guess I’ve really felt the power of money, not in the sense I think a lot of people feel - like money is very powerful, but it’s kind of like “money is out there and it’s having power over me” kind of feeling. I kind of tasted this inverting of that, of like, “Oh, money is - we can control how we want to use it. We get to say what the dynamics of our economy, internal economy is.” And that’s very empowering.

So I got very interested in that, and then Open Collective is basically a tool to automate all the stuff that was super hard that I was doing manually in Enspiral. So of course when I heard about what they were doing, they reached out to me, and I was like, “Thank you! Somebody is building a software tool to do this thing that I’ve been painstakingly doing on spreadsheets and driving myself crazy to make 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 actually making this thing work beyond whatever the shiny headlines are. I’m very interested in the nitty-gritty, behind-the-scenes kind of processes, and Open Collective is very much a tool for that stuff, for basically radically bringing down the overhead of that stuff so more and more people can feasibly work in these ways without pulling their hair out or having to pay lots of expensive lawyers and accountants.

Then also, I’ve recently been dealing more with the whole crypto world, and of course, money and dealing with money in new ways is very central to a lot of what people are thinking about in the crypto world. So that’s interesting.

I’m not like an early adopter type a lot of times. I have like a natural “Oh, I’ll just wait and see what my friends think about that” attitude, and then I 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 of course, it is 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 used to manipulate money in mainstream society.

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: I’m wondering, what would your advice be to people listening who are in self-managing organizations, and 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 sort of scary to kind of open up, especially if you didn’t start out that way, if you transformed from a traditional organization? What would your advice be to people who are curious about how they might approach money in that sense?

Alanna: I think money has a lot of psychological power for many, many people in positive and negative ways. Talking about money somehow is this massive shortcut right to talking about all of these super deep, super important, super complex issues. If you have a conversation about your relationship with money, that’s a conversation about how you were raised and how poor your grandparents were and what were the biggest mistakes you’ve made in your life and what are your hopes for your children. It’s just massively huge.

And also, it’s right next to “what is even my value as a human being?” because we are up against this incredibly pervasive capitalist mindset that you are the monetary value that you can claim, nothing more, nothing less, which is obviously hugely damaging and not the only 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, that’s totally normal and expected. If you are working in a self-managed organization, 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 what kind of container may hold people well, what kind of questions may open up the right conversations. Good facilitation obviously helps a lot.

I’d 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 set of decisions that you need to make. Many people will be familiar with the idea that okay, 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 upfront to trying three very different experiments so that we can honestly say we’ve 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. Whether that’s facilitated by putting time boxes around things, or whether that’s about taking 10% of the budget and freeing it from our normal budget process and doing a really transparent, participatory experiment - just start practicing playing with money together in lower stakes ways. I think that can be really helpful because then it will feel not so scary and not so weird to make the bigger, more serious decisions about money later on.

Lisa: Yeah, 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: I think my experience leaving Enspiral was pretty challenging for me. It was a big combination of me sort of burning out after many years, stretching myself too far and not having enough balance - all the things that a lot of people do when working in early-stage bootstrapping startups, not having enough money, and always feeling like we wanted to help everyone and we couldn’t.

Plus, I guess 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. That was really sad for me to confront - the idea that I may have reached some limits at that time for me in that place, 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 actually feeling like, okay, to grow, I’m gonna need to step out, challenge myself in new ways, and take some of the stuff I’ve learned and apply it in new contexts and see what that’s like. I think I had to let it get to a point where the fact that things weren’t working was right in my face before I actually let myself consider that that might be what was going on.

I also think every collaborative group who is doing highly experimental, brave stuff - it’s dangerous, it’s risky. I guess I was just feeling like I had taken some risks, I would say, as a leader in that space and 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’s just 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 wasn’t there.

It was a very hard time, and I never completely left because I still love all of those people and work with all of those people and support a lot of those projects. I went to the Enspiral retreat this last time, and it was great. So I still feel like I work with one toe in, but it has been healthy for me, important for me.

Also, 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, and I got married before those things. Just life changes. I tend to be a person who, for whatever reason, does things in extremes. Like I’m either traveling nonstop, doing trips around the world, or I’m not traveling at all for several years. I’m constantly trying to challenge myself to do things in a medium way.

So I guess that’s where I’m at right now. Is it possible for me to be in a relationship with something in a less extreme way? So I feel like that’s some of my personal growth that I’m confronting there.

Lisa: Yeah, thank you for sharing that. I think 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 they are working in environments like this that are much more decentralized and people are very passionate about it, and it’s experimental and it’s exciting and it’s purpose-led.

It’s much easier - I remember talking to some of the nurses from Buurtzorg, and they say that’s one of the challenges there, that people love their work so much and they have so much autonomy. 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 in how to get the right balance and how to also have some self-care and awareness there. Have you distilled any lessons for yourself around that area? You said it’s something you’re still exploring.

Alanna: Yeah, I think I 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 guess some other life experiences that I’ve had have helped me reflect on it. I have 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 gotten way better at that in recent years, but it just means that I can’t fake it. I have to actually be doing the wellbeing balance thing, or I will just actually kind of fall apart. So that keeps me honest, I would say.

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 are 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, I think, get to a better place with that stuff.

And then also having a kid, which is an experience that a lot of people have had - it’s another time when I have no choice. I have 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 and sleep and breathe.

I think a lot of people having a kid is another example of something that people are obviously very passionate about, and it’s very personal, just like our passion values-driven work can be. So you have this urge to give and give and give until you fall over, but on another level, you know that if you care about the long-term well-being of what you are trying to give to, then your well-being is a huge part of that equation because you want to be there. 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 realize there’s some of that that goes there in how I feel about my work, which is very passionate and values-driven as well.

Lisa: 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 realize until I was kind of doing a bit of research for this interview that I’ve been using your article and doing that with my partner and running these retrospectives on our relationship. And then I realized it was you that had written this great article!

Alanna: Yeah, my partner and I, we do sort of agile retrospectives on our relationship once a month. We’ve been doing that since quite early on, and it’s of course because we’re total geeks and caught up in all these practices around building software and teams and stuff like that. So I fully admit how geeky it is.

But it’s been really, really important for our relationship, and it warms my heart that it’s worked for other people as well. I think it’s kind of funny - it can maybe seem like a really overly structured approach to emotional personal communication, but paradoxically, I think it’s because we’re quite sensitive emotional people that we like the spaces that that can create and the sort of intentionality of 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 feeling strongly that it’s an okay place to be able to bring that authenticity and those vulnerabilities. I think that’s why it’s been so good for us and that 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. I don’t just mean asking a kindergartner, “Can you think of any improvements for our family?” like “We do dessert more times a week.” How has it been for you?

Lisa: It’s been great. I think what you said is exactly the value that we get from it. There’s something - when I first approached Sean about it, I said, “This might be really geeky, but would you be up for trying this?” And I was pleasantly surprised - he was like, “Yeah, sure.” Then every time we do it - and we’re not super disciplined about it - but 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. We’ll go for a walk and we’ll talk about things like being grateful and expressing gratitude to each other, things that we want to 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 okay within that container to do it.

There’s some sort of unwritten agreements already that because the intention is we’re working on the relationship, we’re committed to it working, 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: Thank you.

Lisa: Gosh, we’ve covered so many different topics. I’m wondering, what’s on the horizon for you? Do you have a learning edge at the moment or a question that you’re holding about another topic, or a juicy challenge that you’re exploring currently?

Alanna: 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 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 finding work relationships and opportunities that really work for me, and allowing it to be okay for me to have needs and kind of set that bar and really look for that.

I think what that’s opened up for me is space to be even more intentional about my work and inquiring into my values and is my time and how I’m choosing to prioritize my time really matching what I care about most? For me, that’s looked a lot like thinking more carefully about especially my volunteer time. It’s very easy - I am extremely lucky that I am constantly interacting with people doing all kinds of really cool stuff, and I want to help everybody and I want to be involved in everything.

But actually taking that step back and being like, okay, actually it’s more important to 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 who I know, who I want to give my volunteer hours to instead of saying yes to this other thing.

So I think putting up some boundaries really allowed the space for that inquiry. But that’s obviously ongoing all the time - which fights are worth fighting, and which conversations are gonna be amazing and which are just really not worth having. That’s a constant question.

And I think one thing that’s actually giving me space to think more deeply about things like that has been working for somebody else’s company. After many, many years of co-founding my own startups and building everything from scratch and holding the entire existential weight on my shoulders, it wasn’t until I took that off and went into roles where I have responsibilities and I really care and I’m taking ownership for what I’m taking ownership for, but I’m an executive whose board actually has some existing responsibilities.

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. I’m just like, “Okay yeah,” 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, aligning 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 responsive all the time. I hope that was an answer to your question. It’s something obviously that’s still emerging for me.

Lisa: Yeah, I think that’s really interesting - to transition from founder or co-founder to something else and noticing how that feels and what you’re holding on to in terms of 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 organization or becoming or starting to think about it or they’re looking for the next level of development? What advice would you give them?

Alanna: I think there’s something there around sharing stories. That’s what we were trying to do with the book we just put together. It’s a very honest, I would say sort of naked kind of book. It’s not a book that’s like, “Here’s the answer. If you just follow this pathway, you too can do 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 works 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.”

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 and export it? Can we copy-paste this into other cities?” What I’ve come to realize is I don’t think you can. I don’t think a truly vibrant collaborative community is 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 gonna just go into this together and keep being in relationship and respond to what comes up, keep learning, keep building, and we don’t exactly know where it’s gonna go. I think that possibility 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-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 really important to feel that solidarity, to know that many people are working on this bigger thing. I don’t even know what you call it - this bigger movement that we’re in, this bigger paradigm that’s emerging. It’s not gonna look like one way; it’s gonna look like a thousand different ways.

But it’s in that - when we share the stories and we can 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 project 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 is this thing 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 we need to be in this together to figure that out.

Lisa: Thank you, Alanna. Thank you for sharing your stories, warts and all, and for sharing all of the things that you’ve learned. I think you contribute so much to this ecosystem with all of your writing and your sharing, and so thank you for all of that. It really adds huge value, and I really appreciate you. So thank you.

Alanna: Oh, thank you, Lisa. Thanks for doing this podcast. I think that’s a great example of like facilitating other people to share stories, and that’s a really amazing contribution. So thanks for having me on. I really appreciate it.