Common Mistakes in Self-Management: Not Supporting People

Simon Mont
5 min readSep 24, 2019

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Transitioning to self-management is like taking the training wheels off of a bike. Those training wheels were really offering some support and stability, so taking them off will create some needs. We can’t just take off the training wheels, make no other adjustments, and expect to stay upright.

Its the same with organizations. When we take away old systems, we need create new systems that meet needs served by old systems, but meet them in ways that support the growth of people and the organization.

Bosses and hierarchies aren’t all bad. They were designed to support things like direction, coordination, and accountability, and often they do. The hang up is that boss-subordinate relationship also comes with a bunch of coercive dynamics that can stifle the subordinates creativity and leadership, subject the subordinate to inappropriate interpersonal behavior of the boss, and place the subordinates’ job security at the whim of someone who is not accountable to maintaining an authentic and dignified human relationship.

When we take away bosses, we are taking away a potentially coercive relationship, but we are also taking away the system that helped a lot of people orient to what they should be doing with their day and how they should be defining their success.

Some people will immediately thrive in this environment. They will be liberated by the invitation to move beyond specific tasks and begin to engage more deeply with the vision, strategy, and systems of the organization. Proponents of self-management often assume that everyone will thrive in this environment. That’s probably because most early adopters of self-management are themselves people who would thrive. But the reality is that plenty of folks don’t immediately love this new work arrangement.

There’s plenty of reasons this happens: It could be that the person would prefer to spend their time doing specific tasks assigned by someone else; it could be that the person doesn’t have the information they need in order to self-direct their work plan; it could be that there are dynamics in the workplace and culture that subtly discouraging or reprimanding that person but not others; it could be that the person hasn’t had the opportunity to develop some skills yet.

None of these things point to deficiencies in the people. Nor do they indicate that flattened hierarchies don’t work because people need bosses. They point to the basic truth that different people have different styles, needs, strengths, and preferences. We each thrive differently in different environments, and we need different kinds of supports in order to stretch and grow our capacities.

When I began working at a self-managed organization I loved the freedom to innovate and ideate. I loved the sense of empowerment and the room for creativity. But as some point I realized that I was often spinning my wheels, struggling to commit to priorities and execute, and I kept procrastinating on important but boring tasks. Underneath it all was an assumption that I should be operating mostly in a creative/visionary space and someone else should be tending to the nuts and bolts.

It didn’t take me long to realize that the assumption of what work I should be doing was intimately tied to the messages I’d received throughout my life, particularly the messages a formally-educated white man gets. This socialization fundamentally impacted how I showed up in the community. And the way it played off the socialization, personalities, and skills of others shaped who did what work. In a different structure, a boss may have made those work allocation decisions, they may have been biased or they may have intentionally created equitable leadership pathways, but without the boss we were all free to play out our internal conditioning.

And as it was all happening, I continued to not really contribute to the full extent of my capacity for the simple reason that I needed someone to help me stay focused and accountable. For me, there’s nothing like a deadline and a person I have to explain myself to in order get me to actually show up. I want that support to come in mutual peer relationship, but I need it in order to succeed.

One of the dynamics that amuses me the most is that many of the folks that feel like they thrive in these environments aren’t aware of the ways they are floundering, lacking direction, and needing support. It usually happens when there aren’t clear points of accountability, or when the person doesn’t realize how they could benefit from receiving coaching from a more experienced colleague. My millennial brethren and I find ourselves in this place often.

Some folks love the invitation to bring there full creavity to their organization. And, as we’ve seen, those folks need different types of support to make that happen in a good way. At the same time, there are plenty of folks who aren’t as interested in the invitation to co-create their organization in this way. Some days I find myself wishing that someone would just come give me a set of things to do so that I could just do the tasks, go home, and use my creative energy for my personal projects. There’s plenty of folks who view their jobs in exactly this way. So we need to design our systems to welcome them too.

The key thing to remember is that “everyone is a leader, responsible for their own work plan, and empowered to find where they want to contribute” is not actually inviting people into freedom. It is inviting people into a very particular work culture, a culture laden with assumptions that will resonate with some and not others, it will support and challenge each of us in different ways, it will make some things easy and it will make some things hard.

So if you want to remove the blockages to people self-directed leadership by removing bosses, also recognize that, in many cases, the bosses were also the source of clear measurable goals, support with work flow and prioritization, feedback on performance, and coaching. And lots of us, I would say most of us, need those things in order to thrive.

Removing these structures and saying “go figure it out” isn’t really setting people up for success. In order to create a system that unlocks the full participation of all people we need to listen closely to what people need. We need to design systems that meet needs such as coaching, encouragement, accountability, and thought partnership that don’t bring along the nefarious power dynamics associated with bosses.

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Read the other parts of the series:

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Simon Mont

A co-creator of just, joyful, and innovative workplaces. Reach out to simon@harmonize.work for consultation, training, and coaching.