Leadership retreats and the ongoing challenges of transformation

My leadership coaching company, Transcend.Space , recently held its first retreat in the stunning hills of Brecon Beacons (Bannau Brycheiniog) National Park in Wales. In gathering colleagues, partners and peers, the aim was to collectively explore some of the challenges we’ve come across in our industries and, on a personal level, reflect on our own abilities and directions as leaders.

Last month’s newsletter set out the context of the retreat. This edition is the second in a mini-series of three exploring some of the insights which emerged from it. In this newsletter, I look at the ongoing challenges of transformational leadership.

In today’s world, a business leader doesn’t just have performance functions to address - profitable growth, finance, procurement, offering the right products and services - but also external factors like climate change, technology and new types of competitors coming into their industries.

There is a constant flow of turbulence and if the events - COVID, Russia’s war, inflation, the emergence of AI - of the past few years have taught us anything, it’s that such disruption is no longer extraordinary. It’s part of the everyday.

To cope with this, organisations must be in a constant process of evolution (occasional transformations every two to three years) and that requires different skills from their leaders. They have a decision: do they sit on their old business models and products, or lean into the disruption to create something new? We’re at a point where the former is simply bad business practice.

Researching organisational transformations is a pillar of my work at the University of Oxford’s Sa?d Business School. I’ve previously discussed my recent research , carried out with EY, on the topic. But it’s actually something I’ve been exploring for nearly a decade, ever since a conversation with a CEO at Davos who told me:

“Over the last 30 years, I have been climbing a mountain. This mountain represents my own leadership, the growth of the company and the development of the industry. The problem as I see it today is that I'm standing on top of the mountain. In many ways, I should be incredibly pleased about what I and others have developed and the way in which the company and industry has made an impact on the world. However, when I look around me, I'm surrounded by fog and clouds and when I gaze beneath me, the mountain is starting to crumble. If I'm honest, I don't know how to plan for more than the next few months and cannot see into the years ahead.”

He was at a loss when considering how to ascend the next mountain and transform his company (see the fifth edition of this newsletter , published in 2021, for my detailed reflections of that exchange). And, eight years on at the retreat, there was a striking similarity in tone when I asked colleagues at a workshop: “What are you noticing about the journey of transformation that your organisations are on?”

Here are some of the (paraphrased) responses:

• “Change is happening so quickly. New types of competitors, COVID, ESG, diversity and inclusion. And now it’s AI! It’s just overwhelming.”
• “As a leader you are bombarded. Bombarded with content, bombarded with emails.”
• “My biggest frustration, looking between 1993 and 2023, is that we are following the same processes. It’s the same s*** with a different smell.”
• “Am I ready to say if my role becomes redundant?”
• “I haven’t seen enough honesty in my firm.”

One thing was clear from these anecdotes: transformations are not getting any easier. There is oft-cited 1995 research from John Kotter which found 70% of organisational transformations fail, with last year’s research I led with EY showing similar results: 67% of leaders told us they had experienced at least one underperforming transformation in the last five years.

However, these insights - with words like “overwhelming”, “bombarded” and “frustration” - were part of the beauty of the retreat. It was a chance for us all to step back from our normal worlds and… breathe.

Away from the glare of our phone screens, and the pings of Slack messages, it was a chance to think about what we were observing in our organisations and industries. It’s a process that is only realistically possible when a leader can get out of their day-to-day environment and create the spaciousness to see how the future might evolve.

It’s not to say the answers to their problems came from that exercise, or even necessarily the retreat itself. But when a leader can spend an extended amount of time in a constant state of “being” rather than “doing”, they are not so attached to the current way of working. They can therefore put themselves in a position to see what needs to go in their organisation, what needs to emerge, what that process looks like and how to lead people through it.

As my colleague Jennie McLaughlin , founder of Purpose Led Transformation, said as she reflected on the outcomes of the retreat: “The deeper you go on your own in a game, the better you can show up for those that you serve.”

It is in this place that we can see more clearly what our purpose is (beyond what we do today), how to create a psychologically safe space for both leaders and the workforce to have the right conversations, and then have the confidence to make the right decisions in the right way.

A message from the author

Thank you for reading the 53rd edition of the Leadership 2050 newsletter. You may be interested to know why I am writing it. As a senior fellow of management practice at the University of Oxford’s Sa?d Business School, my research and teaching focuses on how leaders transcend 21st century challenges such as disruptive technology change, the climate crisis and creating diverse and inclusive environments… alongside the ongoing challenge of delivering profitable growth. At Sa?d, I direct the Oxford Advanced Management & Leadership Programme and, in this capacity, work with leaders from many geographies, industries and governments. All this has given me a deep understanding of how good leaders create value - and bad leaders destroy it. One could argue that never before has this topic been so important on a global stage, hence why I am undertaking this work.