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To Pattern Hope For The Future, What Are The Leadership Essentials?

9 - 10 January 2023 

The Dialogue

What can you possibly learn at a Dialogue that you cannot search for online? When it comes to information, the answer is clearly, nothing.

However, when it’s about meaningful, positive change, a space to renew in the company of others who, and connecting with people in person, being in a Dialogue with all the multifaceted perspectives and experiences, participants say it ‘makes all the difference’.

This annual dialogue brings together leaders from diverse backgrounds, different approaches reflecting a rich range of perspectives. The power of the two-day dialogue is through the energy and commitment that each person brings to developing key questions that are given attention over the time together. The approach provides for a safe but challenging environment while maintaining flexibility, emergence and upholding individual responsibility.

We know the Leadership Dialogue is a valued experience for everyone involved because each person who participates is invested in getting together with other leaders who care about what they do and how they do it, and share a commitment to work with great questions.

The 2023 Dialogue

This year’s dialogue aims to create an experience that feels different, nourishing, expansive.

We will continue in the spirit of dialogue and to incorporate elements that allow us to lean further into the changing contexts we are operating in. On recent WLD events we have heard a call for strengthening relationships, for deepening the conversations that matter and for play and experimentation. In response to these calls we plan to make this year’s Dialogue a place where we can experience hope without ignoring the gravity of our situation, where we can embody a range of approaches towards the future and then each hone in on what’s most essential for us in our specific situation. Questions to explore within the context of Patterning Hope for the Future might include:

  • What to let go of and what to hold on to?

  • When to tighten and when to relax into uncertainty?

  • What’s really essential for leaders and leadership development?

  • To what extent is boldness, courage and embracing adventure core for the future?

  • What’s mine to do and what do I need from others to sustain and support me?

  • How does the role of ‘leader in a system’ impact future action?

We aim to generate and explore our key questions in an atmosphere of reciprocal relationships, deepening conversations and imaginative experimentation.

Previous Dialogues: Body


Leadership on a Shifting Dancefloor

Thoughts from a new participant before the dialogue. Click here to read.

After the Windsor Leadership Dialogue

On January the 13th and 14th 2020, I attended the Windsor Leadership Dialogue as an assistant rapporteur to Gillian Chivinge, the theme of which was ‘Leadership on a Shifting Dancefloor’. Leaders from the commercial, independent, and voluntary sectors attended the event at St. George’s House within the grounds of Windsor Castle. The dialogue was facilitated by a team of three custodians who were former participants and associates of the Dialogue.

The informing idea of the event is that a dialogue is a kind of collaborative thinking – and most importantly, that dialogue doesn’t need to lead towards an answer. It is instead an opportunity to think and to learn together, and to share space in an intentional way – with no specific end-goal or ‘target’ to achieve. Unlike a meeting at a workplace, for example, the Dialogue would not require that action was taken, there was nothing that needed to be done – the participants were free to just be together in a way that they found useful, exploring questions that felt pressing for them. My expectations were simultaneously off-the-scale and nought; I had no idea what a dialogue would actually look like when done by the ‘experts’. The Dialogue hoped to take people - who often had prestigious achievements – divest them of their rank in the hierarchies and order of society, and place them as equals, each with something to contribute and something to learn.  I was surprised and grateful to find that I was to be included in this ethos, valued and embraced as an equal amongst people I thought ‘great and good’, often at least 20 years older than me.

My lofty dream of observing perfect dialogue in action, of seeing the ‘experts’ perform, soon met with reality...

Read more

Previous Dialogues: Body


Re-imagining Leadership

What a 48 hours!

Key takeaway: there is no single ‘Self’, there is no one type of ‘Leader’.

Furthermore, I cannot get frustrated by people putting me in a box because in actual fact I am often the one drawing the lines and I am also the one with the power to rub them out.

The dialogue spurred so many emotions, which I will go into later. For now, let me see if I answered all my pre-WLD questions:

What makes the participants good leaders?

I did not ask this question outright. But from what I observed, I would say what makes a good leader is listening, questioning, potentially taking what may seem like a personal risk to do the right thing, and funnily enough admitting when you do not know the answer. Despite them seeming intelligent and well informed from where I was standing, they acknowledged: ‘I know I am not the wisest person here because I know that I know nothing’ – Socrates.

Why don’t I see myself in society’s visible leaders of today?

It was option 5 (mostly), perspective! It was immediately apparent to me that various leaders have various demeanours and personalities and I almost feel as though I had been ignorant assuming many leaders were so homogenous. While everyone had convened for a common purpose and perhaps had similar attitudes towards life, they were all so different and I managed to see elements of my own personality in almost all of them. What a relief!

Note: cognisant of the fact that it was an informal environment and that they were also the types of leaders who acknowledged that they still had things to learn, despite their titles.

Nevertheless, my experience was still sufficient for me to conclude that there are no personality traits that define a leader, probably just attitude.

What do I need to do to become a good leader?

Again, I did not know how to ask this outright. However, nuggets of advice that I did manage to pick up were: a) to be who I am but enjoy continuous growth, b) to work on my networks, and c) to take some professional risks.

Any other nuggets welcome at Outwith that, I will try to emulate what I observed as written under question 1.

I came away feeling the following:

Inspired – by the participants’ desire to try to make positive tangible change within society and by the fact that they were willing to grapple with the frustrating obstacles that life puts in the way.

Comforted – by the fact that such accomplished people not only acknowledged but actually embraced the fact that they still had growing to do and things to learn.

Relieved – because while working on my self-awareness and emotional intelligence remains important to me, I now know that I don’t need to obsess about knowing every aspect of one definitive version of myself. All I can be is who I am today and the destination itself is continued growth.

Energetic and excited – apparently I am already a leader! …so they said. As a result, there is no need for me to wait to take ownership of things until I have a grander title, it can all start (or continue) now!

Weird! – on Tuesday morning we created something that you can feel when a group of people give all their attention to a common task. For a moment, we were on a wavelength that created an atmosphere that cannot be described or quantified but was powerful, energising and outright bizarre. I am grateful to have been part of it, will not forget that sensation and look forward to experiencing it again someday.

Grateful – I am going away feeling very grateful to Nick for enabling me to have this experience, the leaders for embracing me, and to our hosts at St George’s House, Windsor Castle. Not only were the staff excellent, grounds beautiful, and choir spectacular, but there was also something about being stood in the chapel “within” centuries of history that made reflection different, easier and stronger.

Until next time!

Previous Dialogues: Body


Previous events have led to significant conversations and positive feedback.

Take a look at the video to get a taste of our events.

Previous Dialogues: Watch
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