Is your business ready to go ‘bossless’?

One of the main reasons I wanted to be an entrepreneur was for the feeling of freedom and autonomy it gave me. Is it possible for more conventional paid employment to offer the same sense of possibility? This question has preoccupied me over the past few months, as I’ve been experimenting with what best motivates my team.

Research on the subject of motivation suggests that members of Generation Y (or “millennials”; roughly speaking those born after 1980) are less tolerant towards “old-world” models of management, and tend to shun more traditional corporate career paths in favour of working in start-ups, or becoming freelancers or entrepreneurs. Dan Pink, a Harvard Business School professor and author of Drive, a book about motivation, suggests that this generation is driven less by money than by three other factors: mastery, autonomy and purpose.

In the pre-digital era, management worked as a hierarchy, with information distributed from the top down. In this model, employees looked upwards, deferred to authority and aspired towards promotion; they also had fixed “boxes” – ie job descriptions to which they conformed.

In today’s reality, the nature of people’s roles and responsibilities has changed, and workers need to be more adaptive to a fluid economy and constantly changing environment. But to a certain extent, young professionals are still conditioned to believe that if they deviate from their upward path – that of school, further education and university followed by a respectable graduate training position in a (preferably) large corporation – that they are, in some way, failing.

Our education system trains us for a hierarchical world where we are given predefined roles and tasks to complete. This might have been suitable in the industrial age, when people were expected to perform menial and repetitive tasks, but not for the knowledge economy we live in today.

The new world is a networked world where the linear career path is long gone; instead we are faced with a career helter-skelter. It is highly likely that most roles that are in any way repetitive will be replaced by machines or robots in the near future. Our most important assets are therefore our minds and our human potential.

How we unlock this potential is what fascinates me. In a connected economy, every employee should be seen as a node, an expert in their own domain. The role of the CEO should therefore be as a “chief energising officer”, providing purpose and broader vision that the team can rally behind.

In my own company, Enternships, we have tried to embrace this, and to adopt totally new ways of working. Rather than our developers blindly following the usual “agile” development model, which consists of two-week development sprints, we have decided to try something different.

Now my role is to set out a short-term (often one to two months) goal, not just for what we need to achieve, but for how and in what order the developers work. They have one guiding principle: “what can I do today to add the most value to Enternships?” This helps the team prioritise their tasks, feel less like “coding monkeys” merely performing one development task after another, and gives them more space to innovate.

We have only just started this new method, but the results are already encouraging. The developers are taking the initiative to create new tools – ones I hadn’t considered myself – and are often so motivated and excited that they end up working into their own time. I have noticed the team is happier and more motivated at work, which is my ultimate goal. This approach does come with some challenges to ensure external deadlines can be met, and we’re still working on perfecting how we implement it, but it’s an interesting experiment.

My feeling is that this way of working, which is more in sync with the millennial generation, ultimately boils down to trust. If you trust your team members, more often than not they will step up and take responsibility. It then becomes less about the structures you have in place, and more about the culture you wish to instil.

There is a lot we can learn from others who have blazed a trail in transforming their working cultures. Take Valve, a multibillion-dollar software company, which is often lauded as the poster child of a flat company with a “boss-less” structure. They have created a unique culture as well as that rarest of things: an employee handbook that is a must-read.

Another interesting innovation is Holacracy, a tool that lets companies structure themselves differently, avoiding conventional power structures. In the organisation’s own words, “everyone becomes a leader of their roles and a follower of others”.

Still, there is more work to be done in order to better understand the challenges and opportunities of thinking the structure of organisations. I would love to hear more examples of “good practice” from businesses around the world and start a discussion about how company culture and structure can be adapted for the new economy.

Rajeeb Dey is the chief executive officer of and a World Economic Forum Young Global Leader. This article was first published on the World Economic Forum’s blog.