Playful Experimentation (Part 5 of 5)

by | Sep 23, 2025 | Agility, Complexity, Experimentation, Leadership, Reflection

Playful Experimentation, Reflection and Learning

This is the final part in this series where we will explore the role of playful experimentation so we can avoid the ‘authority trap’ when navigating complexity.

Up until this point, we have walked through the steps of:

  • Creating a holding space for navigating complexity – a space which is grounded in psychological safety with clarity of purpose and roles etc. enabling a space where people can fully engage – part 2
  • Bringing curiosity and encouraging others to bring curiosity also so we can purposefully and expansively explore and learn about the challenge at hand – part 3
  • Stepping back onto the ‘balcony’ to see the system and sense-make identifying working hypotheses on what might be going on – part 4.

I paint this as a sequence of steps, but in truth it is a more emergent process. Saying that, having stepped back to make sense of the emerging picture, you are likely to have some working hypotheses of what might be going on, areas you would like to learn more about or parts of the system which seem ripe to try something new. This is a great time to start thinking about helpful experiments that can be conducted. I use this term playfully in that it’s not about success or failure, but rather about what can be learnt along the way.

When thinking about experimentation, there are a couple of authors in this territory who have some helpful framing. Jennifer Garvey-Berger describes such experiments as ‘safe-to-fail’ – she suggests that we don’t start with high stakes ones which can have significant adverse consequences, rather this is about playing around the edge to gain some learning.

Prof. Amy Edmondson talks about the concept of intelligent failure – failure which is the result of consciously trying something new which leads to learning, even if it doesn’t go exactly to plan. I like the sound of this, but I recognise that the term ‘failure’ triggers many people as it can be uncomfortable. Amy suggests that we can think of it as pivoting rather than failing if that gets us over that concern.

Let’s explore with an example. Imagine that I am trying to shift the culture of my organisation and I have a clear sense of where we want to get to (the lived values, behaviours etc), but I am really unclear on how to get there.

A place to start could be to think about a variety of different initiatives that could be tried out. Experiments with these initiatives (even contradictory ones) can be run in different parts of the organisation to see what the results are before deciding how to proceed on a larger scale. Approaching experiments in a planned way whilst also encouraging curiosity is key. Then, the practice of stepping back to reflect on what happened and hypothesize about why it happened is a lovely piece of detective work that will lead to fresh insights and can inform further action.

There may be no clear end point to this process as complex challenges are not black and white, however when approaching such a challenge in this way I have found a real sense progress in the discoveries that emerge which help lay the path for how to proceed.

Reflections

In the early part of this series, I spoke of the pressures of bringing certainty when faced with complex challenges, to lead with a level of authority which gives confidence to those around you. My hope in writing this series is that the steps I outline can provide the comfort of a process to those navigating complexity, whilst also allowing next steps to emerge from listening deeply to those with different perspectives, making sense from the balcony and from playful experimentation. Whilst I have explained it as a step-by-step process, the reality is much more emergent – a process that allows for us to embrace and be curious about the grey.

I would love to hear your thoughts and questions along the way to make it as useful as possible, so do get in touch with your thoughts. Contrary perspectives are welcome also!

Eadine


Eadine is the founder of Resonate Leadership. She is a Harvard-trained leadership development professional, certified Leadership Agility® Coach and certified facilitator of the LEGO® Serious Play® method. We create spaces for navigating change and complexity resulting in growth, learning, innovation and problem-solving.

If your organisation is navigating complexity do reach out for a complimentary conversation about how we can partner with you.

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