Why I’m hosting a leadership retreat this week

Shaping a collaborative leadership model that I’m proud to identify with

Jan 09, 2024

A few years ago I never would have guessed I would end up running a leadership retreat. But here I am, sitting in this lovely big farm house in the south of Spain, getting ready to welcome 12 leaders who are showing up tomorrow afternoon.

I first became politically active during the Occupy Movement, which was defined precisely by its leaderlessness. Since Occupy I’ve played key roles in Loomio, Enspiral, The Hum, and Microsolidarity. These are all organisations that work non-hierarchically; we build teams, technology, communities, networks, movements, and organisations with participatory culture and a bottom-up ethos. We’re all about horizontality, inclusion, and decentralisation. My political awakening started from a position of anti-hierarchy, and much of my identity and my expertise is tied up with collaborative, bottom-up ways of working together. So I’m not used to thinking about “leadership” per se.

I guess parts of me have always known that even in the most decentralised movements, there is a role for something like “leadership”. We need people who can imagine the future and mobilise around bold new ideas, people who can take a long-term perspective, take responsibility for the big picture, who can dig into the deepest levels of commitment and do what needs to be done when nobody else is stepping up. These are all “leadership” traits, even though I usually don’t use that terminology.

But because of my focus on non-hierarchy, I guess I have some cognitive dissonance. I have never closely examined the role of the “founders” or “leaders” in these organisations and networks. I have put all my focus on how to create systems to decentralise their power, to create inclusive decision-making, to elevate others.

But leadership is not the same as hierarchy, and hierarchy is not the same as domination. I do have a hardline stance against domination. But I’m getting curious about the appropriate use of hierarchy, and the appropriate use of leadership.

With this week’s retreat I’m turning my focus to that central role, the person who starts a new initiative, or who takes responsibility for maintaining it. I’ve been kind of avoiding the topic for years, so now I want to look at it head-on. I’m a founder of three organisations and a director of a fourth. I am deeply engaged in a kind of collaborative leadership and I want to take this opportunity to reflect and learn how I can hold that role more skilfully. And I want to play a role in shaping a collaborative leadership model that I’m proud to identify with.

I have loads of questions:

With the organisations that I’ve started, what boundaries should I hold tightly, and what should I let go of?
We ask everyone to “bring your whole self to work”, but how can I be honest about the anxieties, doubts, and ambiguities I face, without demotivating the team?
I try to be humble and elevate others, but I wonder sometimes if this posture of humility is actually undermining our mission. Would I be more effective if I were willing to take more of the limelight? Maybe we could mobilise more resources and have more impact if I were willing to play that game.
I know that power obscures my vision; people modify their behaviour around me. So how do I get good feedback? How do I encourage my collaborators to challenge me? So how do I assemble an accountability system around myself that is both loving and firm?
Where is my mentorship? How am I disqualifying myself from receiving the kind of support I need to really perform to my potential?

So I’m showing up to this retreat with my own leadership dilemmas. I need space to reflect on these tough questions. But I find it hard to reflect on my own, I avoid asking uncomfortable questions, or I get stuck looping round & around the same familiar thought patterns. So I need companionship. I need to be stimulated by other points of view. I want to take inspiration from your stories. I want to see what parts of me that are obvious to you and invisible to me.

So that’s why I’m delighted to have 12 amazing guests showing up tomorrow, to think about all this with. This group represents a diverse cross-section of actors in the landscape of European progressive social change, broadly defined. We have some people from the grassroots, and others working with institutions. Some of them have created new organisations from nothing, others have inherited an organisation with decades or even centuries of history. Some of them are radically decentralised, others are working within existing hierarchical structures. We have revolutionaries and reformists. What they have in common is a vision for progressive social change, from teams to workplaces to societies, and a commitment to leading in a “different way”.

Collaborative Leadership Questions

In interviews with me and my co-hosts, we uncovered some of the questions this new breed of leaders are showing up with:

How do I resource myself? How am I modelling self-care and sustainable work practices to my team? How do we centre health and wellness in our organising?
How do I lead in a team, or in a network of autonomous organisations, when nobody wants to be told what to do but everyone wants a clear sense of direction?
When should I bring others along, and when should I be decisive? How do I know when the group needs me to be assertive and create clarity? How do I make the right decision, knowing that it will sometimes go against people’s preferences?
When should I lean in with my power & experience, and when should I lean out and enable others to do it their own way, even at the expense of quality & efficiency?
How can we define a model of collaborative leadership that I’m proud to identify with, when the ‘leadership landscape’ is full of models I don’t resonate with, that are in fact contradictory to my values?
What is collaborative leadership excellence? Who are my role models? What traits am I aspiring to?
How do I make space for visionary work without getting overwhelmed by the operational workload? How do we enact our epic large-scale social mission in the day-to-day decisions and practices?
How can we do things differently while operating under organisational constraints, like a board who doesn’t “get it”, or bosses that I have no influence over, or complying with legislation that doesn’t fit us?
How do we decolonise our minds and work practices? How do I respond to growing & legitimate demands for liberatory practices, while I’m still growing as a leader, and swimming upstream against the status quo?
How am I supported to take a strong values-based line on contentious issues while negotiating between diverse stakeholders in an increasingly polarised political landscape?
How do we build a culture where difficult conversations are possible? How do we give each other feedback when we’re friends? How can you have a participatory culture if nobody challenges the leaders?
How do we nurture high-trust relationships when everyone in my team is working remotely and physically isolated?
Where am I in my life story? Am I doing the things that only I can do? What do I want to spend my remaining healthy active years on?
How do I know when I’m done with this role? How can I “leave without slamming the door”? How do we create a healthy succession plan when succession is a taboo in my organisation?

I don’t expect to come up with straightforward answers to many of these profound questions and paradoxes. But I’m anticipating a wonderful few days of reflection, companionship and inspiration as we chew on these questions together.