Like a Boss: “How do I create structure in the workplace without becoming a tyrant?”

Welcome to Lattice’s advice column for new managers, “Like a Boss.” I’m your host, Jennifer Romolini. I’m an editor, an author (of the career guide “Weird In a World That’s Not”), and, yes, a boss who’s been managing other humans for the past dozen or so years at companies both giant and tiny, at quick and dirty startups and multi-layered corporations, with remote and in-office teams ranging from five to 45. I’m also a speaker who talks about succeeding at work even when you feel like a freak. And, sometimes, I give advice, like right now.  

Dear Boss,

I’m a co-founder of a new(ish) company. And while this is not my first job, it's the first time I’ve ever been in charge of this many people (we currently employ 15 full-time staffers along with 9 contractors). When we started the company, I guess I’d say my co-founder and I wanted to keep things loose in terms of leadership; we felt like without a lot of red tape and Management with a capital M, developers could be more creative and everyone’s ideas would be more readily heard. We never really set up any super-strict chain of command because we assumed our employees are adults and we should treat them like adults. But it’s not really working out the way we thought. 

In the past year, and particularly in the last six months since the pandemic, there has been a lot of infighting and bickering, a lot of complaints about who gets to do what on projects, a lot of necessary tasks slipping through the cracks. I’m spending more of my time counseling staff members about interpersonal issues and things “not being fair” than I am doing actual work, a situation which is obviously not sustainable. My business partner and I feel like we’ve created a quality workplace with all kinds of perks and great pay, and I really don’t want to end up resenting the people who work for us over something like whining. What’s my responsibility here? Should I just tell them to step it up?

Yours,
A Hard-Working Founder

Dear Hard-Working Founder,

Your question reminds me of a famous essay I read for the first time this week (though it was actually written 50 years ago) called “The Tyranny of Structurelessness.” In it, Jo Freeman, a lauded political scientist and feminist scholar, argued that structureless organizations, which are often formed to promote equality, usually do the opposite, creating more damage within teams than good. As she explains it, this is due to the fact that there’s actually no such thing as a structureless group. Instead, in the absence of defined leadership, employees will create their own hierarchy by necessity, forming implicit and even secretive structures on their own. 

Writes Freeman: “Thus structurelessness becomes a way of masking power... As long as the structure of the group is informal, the rules of how decisions are made are known only to a few and awareness of power is limited to those who know the rules. Those who do not know the rules...must remain in confusion, or suffer from paranoid delusions that something is happening of which they are not quite aware.”

Does this sound familiar to you? Because it does to me. When I was a new manager, I informally adopted a leadership style like yours — one where, theoretically, there was a voice for everyone and all opinions could be heard. I didn’t want to rock the boat, lord power over anyone, or do any of the uptight “bummer” things managers need to do (goals, expectations, feedback!, etc) and so, initially, I failed to set a proper workflow or a system of accountability. The idea being, “we’ll just all figure this out together!” 

The result was that only a few voices were ever heard. I was busy and so I favored and spoke more frequently to employees who felt comfortable speaking up or reaching out to me proactively (unfortunately that was often the whitest, most privileged members of the team), leaving others without this level of agency in the dark (often those from marginalized groups). Paranoia, chaos, and backbiting ensued — the employees who liked me really liked me because they had my attention; the ones who didn’t thought the system, such as it was, was inequitable. And the second group was right that, ultimately, no matter my intentions, there was a hierarchy. 

I, like you, was the one making final decisions and therefore it was my responsibility to set a fair, explicit, defined structure no matter if doing so made me feel like an uncool authority figure (side note here: if you are a person in power, your feelings are the least important part of the equation).  

The question you’re really trying to ask me today is: “How do I create rules and structure for my team without becoming a tyrant?” Your power over your employees is undeniable; there’s no healthy universe where you can push it off or pretend it doesn’t exist. You’re the boss. But what you do with that power will determine whether you create an efficient workplace where people feel safe and able to do their best work, or whether you allow your company to devolve into bitterness and chaos. 

My suggestion for you and your co-founder is to talk with your employees about what they think is working and what is not, and if their roles at the company, as they’re currently defined, make sense. Take their feedback seriously and keep it in mind as you thoughtfully and compassionately conceptualize and roll out a smart organizational structure with managers and job levels, new goals, expectations, workflows, and systems for accountability like one-on-one conversations and reviews (Lattice has a number of manager tools to help with this process, including goals and one-on-one tracking.) Be creative in your solutions and distribute power fairly — for example, rotate who should lead check-in meetings and brainstorms, have an inbox dedicated to employee concerns which you address each week.  

Implementing these changes may not be easy, and you will most likely endure bumps before the road becomes smooth. But as a leader that’s what you signed up for: helping your employees thrive while the company does, too. 

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