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Leadership2050 Edition 6, What is Your Leadership Context?


Welcome to this 6th edition of Leadership2050. Following the last newsletter, in which we looked at the mountain-to-mountain model and where you are located on this journey of transformation, in this edition I will examine how you can look more deeply at the leadership context that you are facing. This newsletter will be part of a three-part mini-series that will look at how to move forward from where you are today on the mountain-to-mountain model, to where you want to be in the future. The three assessment interventions that I will present within this mini-series are part of the core learning process of the Oxford Advanced Management and Leadership Programme (OAMLP) that I direct at Said Business School, University of Oxford. This programme is focused on how to be a 21st century leader, and brings leaders from over 100 different countries to the Business School. The OAMLP contains content that covers the following areas:

Your Proposed Leadership Initiative 

Your leadership initiative placed in today’s business, societal, and geopolitical contexts. Setting the trajectory to enhanced performance.

21st Century Challenges

Insights from cutting-edge research and new perspectives on how leaders make sense of, and thrive through, rapid political, social, and economic change. Key topics include trust in the digital economy; the impact of global events; and the climate emergency.


Developing and using scenarios to systematically explore the potential impact of these 21st century challenges on organisations and your leadership initiative.

Your Organisation’s Purpose

Working through a detailed analysis of the purpose of your organisation and the strategic choices that it compels; resolving paradoxes between purpose and performance in order to combine doing the right thing for society with long-term commercial success.

Your Organisation’s Performance Challenge

Translating purpose into performance through topics such as leading digital transformation, financing large-scale investments, strategic negotiations, sustaining competitive advantage and superior performance; and diversification and sustainable growth.

Your Leadership Initiative Redesigned

Examining successful execution, including adaptive leadership, presence and mindset. Bringing everything together to finalise your ‘Leadership Playbook’ of personalised, contextualised, and fully stress-tested strategies; consolidating your learning and using it as a springboard for innovative thinking, with action plans that will take your new leadership initiative forward.

So, let’s look more deeply at the first assessment tool, which focuses on your leadership context. This assessment process contains 10 questions that enable you to rapidly step back and understand the context that you are facing. They can be used by you, or with the team, and can lead to a very different type of conversation. This conversation can bring about a deeper sense of honesty about the challenges being faced and where people feel and think that the organisation is today. The questions and scoring mechanism, in themselves, are only the beginning; the real power of this intervention lies in the thinking and conversations that it can facilitate between executive teams. 

Using the assessment process in this way can lead to a greater diversity of perspectives, more honesty that comes through challenges from peers, and a stronger foundation upon which future changes might be based. 

The questions are listed below and, to begin with, I suggest that you score yourself from 1 to 5, where 1 is low and 5 is high. You could also think about the reasons for your score and this could act as the basis of content for the conversations that you need to have. On the Programme, we use this tool as a basis for case studies, presented by participants, which focus on the transformational challenge that they are facing as a leader.

1. How strong has your performance been over the last year? (1 = low, 5 = high)

2. How well-defined and understood is your organisation’s long-term purpose and strategy? (1 = low, 5 = high)

3. How clear are you about what you need to achieve in the next year? (1 = low, 5 = high)

4. How confident are you in your plan to deliver this? (1 = low, 5 = high)

5. How confident are you in your team’s ability to deliver this? (1 = low, 5 = high)

6. How confident are you in the culture that exists to support this? (1 = low, 5 = high)

7. How motivated do you feel as a leader? (1 = low, 5 = high)

8. How strong are your relationships with critical external stakeholders? (1 = low, 5 = high)

Once this tool has been used and completed, it provides a foundation for the other two tools that we use on the OAMLP: the Disruptive Leadership Readiness Assessment (DLRA) and the Leadership Playbook (LP). The DLRA focuses on identifying the major risks and opportunities that you face and then on how prepared you are as an organisation to address these. The LP helps to bring all of this together by providing a structure within which each participant creates their own playbook for how they will move forward with their transformational challenge. These two tools will be presented and discussed in the following two newsletters. 

In summary, any journey of transformation begins with a ruthless assessment of where you are today. Without this honesty, it is very difficult to move forward with addressing the right issues and prioritising resources. This takes courage and a CEO who is prepared to go through a difficult conversation before progress can begin to be seen. Without having somebody like this setting the context, it is very difficult for this conversation to happen, in an open and transparent way, with the right people. The second key ingredient in getting this assessment right is diversity of input. It may be that your executive team is too homogeneous, and you need to bring in voices from the wider organisation, as well as outside the organisation, to challenge some of the beliefs and assumptions that you have about this organisation and the world in which it operates and has an impact. The final ingredient here is knowing when to move from conversation to action. It is easy to become trapped in the complexity of the problems. Leadership is about finding ways through these problems and having the creativity, ambition and inspiration to move the organisation forward.