Category Archives: Complexity Thinking

A Deliberately Developmental Experiment

When the founders at Upside approached me to develop a business-wide coaching programme, they were clear they wanted to do something different. It felt appropriate that a scaling company that puts talent and the development of talent at the heart of its organisation should embrace a new approach to developing its people. Fascinated by how we can build organisations and develop individuals for the future, and already drawing on Robert Kegan and colleagues’ work on adult development in my coaching practice, I introduced them to the concept of the Deliberately Developmental Organization (DDO).

This article unpacks how we developed a deliberately developmental coaching programme for Upside, and what we’ve learnt so far along the way. If you’re a leader in a high-growth startup who wants to know how to embed a deliberately developmental culture in your business, or if you’re interested in DDOs generally and would like to learn more about them through a real life example, then join us on this journey of discovery.

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Four Vertical leadership skills to help you thrive in a VUCA world

You’ve heard it already, we live in Volatile, Uncertain, Complex and Ambiguous (VUCA) world. But what does that mean for you as a leader? We’ll explore how traditional horizontal approaches to leadership, which focus on understanding the job to be done and the capabilities required to do it, fall short. In a VUCA world, we need to expand our capacity for leadership. To do so requires the development of vertical skills, to help make sense of the complexity that surrounds us and construct meaning within that complexity.

Drawing on the book Upgrade: Building your capacity for complexity, by Richard Boston and Karen Ellis, we’ll link VUCA with the four leadership capacities they identify that underpin vertical skills:

  1. Sensemaking – Observing, understanding and processing the complexity of a situation e.g. getting your head around all the different interconnected topics, data, issues or causal relationships.
  2. Perspective-shifting – ‘Zooming out’ to benefit from a more realistic and multifaceted understanding of a situation or relationship e.g. understanding the perspectives and agendas of the various stakeholders.
  3. Self-relating – Observing, understanding, regulating and transforming yourself e.g. making sense of your own reactions, thoughts and feelings.
  4. Opposable Thinking – Responding to the dilemmas and conflicting ideas that can create tensions within us and / or between us and other people e.g. working with opposing views.
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How Cynefin can help you become a better leader in a complex world

There’s no shortage of “how to” advice, playbooks, formulas and even secrets and guarantees for success (at least that’s what the gurus will have you believe). This can work well in complicated situations. But high growth technology businesses are not complicated, they’re complex. That requires a different approach to leadership, explored here through the lens of the Cynefin sensemaking tool.

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Beware the Illusion of Certainty

We like to think that our lives are ordered, predictable and subject to a great deal of control. The past is finite; we see only one outcome. We attach causality and narrative to it so that it makes sense. We roll our ability to make sense of the past over into the future, which is infinite; there are many outcomes, as yet unknown and unknowable. Randomness, chance, and luck influence us far more than we realize. Certainty is an illusion. Uncertainty is everywhere.

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