Simon Terry

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The Dread Pirate Roberts Problem

Man in Black: I can’t afford to make exceptions. Once word leaks out that a pirate has gone soft, people begin to disobey you, and then it’s nothing but work, work, work all the time.  

– From the film ‘The Princess Bride’

Many middle managers have the Dread Pirate Roberts Problem. Changing our organisations will require them to break from moulds of leadership that they have inherited with their roles. Middle managers need to invent the new path forward to more responsive organisations or disappear in the disruption of digital networks.

The Dread Pirate Roberts Problem of Middle Management

Man in Black: The name was the important thing for inspiring the necessary fear. No one would surrender to the Dread Pirate Wesley.

In the film ‘The Princess Bride” we discover that the Dread Pirate Roberts that has been terrorising the seas for 20 years is not a person, it is a role. The title Dread Pirate Roberts has been handed down from one player of that role to the next. Each player carries on the traditions and techniques of the role to maintain their effectiveness. When they tire of the role, they retire passing it on to the next person to play Dread Pirate Roberts with terror, ruthless efficiency and no exceptions.

Middle managers can experience the same challenge as the successors of the Dread Pirate Roberts. The role that they take on as managers in a hierarchy comes with cultural expectations that have been built up over years by their predecessors. Culture is an expectation as to patterns of interactions between people. The culture creates expectations of how managers will act, use their power and demonstrate leadership. In many cases those expectations can be no less fearsome than those of the Dread Pirate Roberts.

Many middle managers have not seen or been trained in any other models of management and leadership than those that have prevailed in the role or organisation. Asking or expecting these managers to break from these deep cultural expectations on their own is a vain hope. Even if they are given the skills to act differently, they will find their teams and stakeholders are disappointed that they no longer behave as the Dread Pirate Roberts should.  

The system pressure to return to type in this situation can be strong. Performance management & talent systems reward ‘strong leadership’, usually defined culturally by the existing role of manager. The risk of adopting another model is that any volatility of performance will be seen as failure of the new practice. Personal influence in the networks of ‘strong leaders’ can erode. Struggling to come to grips with new practices managers find management and leadership becomes ‘work, work, work all the time’. It hard not to see why many choose to just continue the traditions, enjoy the rewards and hang out for their chance to retire and pass on the role.

Why does Middle Management Need to Change its Approach?

Digital disruption and networked ways of working are threatening organisations and putting pressure on the traditional function of middle management roles. The role of middle managers as creators and filters of knowledge disappears as knowledge becomes a flow in networks and technology automates the functions.

Middle managers are increasingly facing a need to realise people’s potential in collaboration and create more responsive organisations. More and more organisations are focused on the fact that the poor engagement of people in traditional command and control models is a massive waste of human potential. Every disengaged employee is someone not helping to push the organising forward. More knowledge work demands better use of people’s purpose, passion, creativity and intelligence. Organisations increasingly want leadership in every role, a direct threat to command and control models. Managers need to leverage new mindsets, new questions and gather new knowledge & expertise from networks.

Embedding a New Model

However, when these changes require new management and leadership models, the Dread Pirate Roberts problem arises. A middle manager who is expected to manage by control and power will find a shift to the role of an engaging leader, let alone a network navigator, challenging and confronting. They are going to need to give up their traditional models of influence, perceptions of how they create value and ‘work, work, work’ to influence teams and stakeholders that a new approach works.

Middle managers need to accept the work & the risks. Leadership is work. In the new era of network disruption, leadership can’t be safe. Managers need to accept that they are the change management. Influence is critical and middle level managers need to use their networks and authority to lead that change collectively.

Senior organisational leaders can authorise and support these changes. Senior leaders can help reduce the work and risk of change. However, they cannot make change easier for middle managers. Senior leaders can’t order a change in culture. It will take a new shared story of leadership in the organisation, new capabilities & practices, new systems, and consistent role modelling for a new model of leadership to embed. Social collaboration inside organisations can help managers to accelerate this cultural change by acting as infrastructure of culture magnifying the change in culture and role modelling effective behaviours.

Middle managers need to embrace the opportunities to be leaders, culture change agents and to explore the network navigator role, particularly in networks in and around their organisation. These roles may well be the only functions of a middle manager in a future organisation. By experimenting and working collaboratively with their teams and leaders in this way they will discover the right path forward for their organisation & build critical capabilities for the years ahead.

Perhaps then all the managers playing the role of Dread Pirate Roberts in organisations can happily retire and hang up their boots.


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