I recently did something I never thought I’d do: I killed off my company’s flat-management structure and assigned everyone a “boss.”

Four years ago, when I started ShortStack, I was committed to a flat structure where every employee had the freedom to manage themselves, had the opportunity to explore different job responsibilities in order to figure out a role that suited them, and felt comfortable coming directly to me with their ideas and opinions.

My vision was kind of like The Brady Bunch: Dad was in charge, but everyone was expected to figure out on their own how to be productive and get along. And for a long time, it worked.

Until one day, when it didn’t.

The problem with hiring independent, self-reliant people—the kind who thrive with little supervision—is they tend to have very strong personalities. When several employees started coming to me with the same issues, saying one department wasn’t getting something done fast enough and complaining about attitudes, I realized I needed to tweak the company’s structure so I didn’t have spend all my time being the referee.

It was time for managers.

We’ve been testing our new structure for about a month now, and it’s going well. I continue to weigh in about what should be included in projects or who various team members can go to if something is not being done efficiently, but having a couple of people taking charge of teams seems to be making my life a bit easier.

Still, the transition was a little tricky, and I’ve learned a few things from the shift that I think any leader can consider if you’re feeling like it’s time for a major tweak in company structure.


1. Be Transparent

From day one, I was transparent about the company’s flat-management structure. When I would interview new candidates, I would be sure to explain that no one had a “boss” and that I hired people who I felt could manage themselves. But when I started moving toward a more traditional structure, I wasn’t quite as forthcoming.

In hindsight, I realize I wasn’t entirely confident about the decision, so I sort of eased in, which turned out to just be confusing for everyone. For example, I spoke to individuals about taking on manager-style tasks versus announcing it to the whole team. I was worried that a large announcement would ruffle feathers if I told everyone that they had new bosses. However, since I didn’t tell everyone about the new structure, there was confusion about what the procedure was for getting things approved or determining priorities. I got the feeling that everyone could sense that a transition to a new management structure was happening, but they lacked concrete proof, so no one was totally sure what was going on.

But once I made finally made an official announcement about the change, everyone got on board, and any resistance or reluctance to work with a manager was alleviated.

I learned that when it’s time to adjust company structure, the more honest and upfront you can be with your employees, the smoother the transition will be. Hold meetings, answer questions, and listen for the positives and negatives so you can continue to restructure and test until you find a system that works for you and your employees.


2. Continue to Find Ways to Harbor the Best of the “Old Way”

When you shift your company’s structure, there will be a learning curve. And while there will be plenty of changes that make everyone’s lives easier, there will also be habits that are harder to break or perks that employees feel like they’re losing in the new order.

After four years, my employees were comfortable sharing all of their opinions and ideas for the business with me. While I value their input, now that I’m dealing with 18 employees and a much larger company, I just can’t prioritize every single idea, and I tended to hear the same thing over and over. I really needed this change in structure to streamline the process.

But my employees weren’t so keen on losing their ability to stream ideas directly to me during this management shift.

So, I decided to hold a monthly ideas meeting, where everyone can write down and then discuss them all with me. I also have an ideas “board” that is a shared list in Wunderlist where everyone can contribute to and then I arrange the ideas and make notes. Both of these allow me to continue to give people a venue to share their ideas with me—without disrupting my workflow.

Whatever it is, see if you can find ways to keep some of your employees’ favorite things about the way you used to run things, even as the company grows and changes.


3. Be Part of the Change You Want to See

We have reverted to our old ways a few times. Since I sit at the receptionist’s desk, everyone can hear my conversations, and sometimes people who have nothing to do with whatever is being discussed will feel free to chime in (as they did when we were flat). When that happens, what should be a three-minute conversation becomes an hour-long debate—which is what I’m trying to avoid.

If I want people to respect the new structure, I have to set the example and call my managers into not-so-public meetings where we can hammer out the details that they can then take back to their teams.

To be honest, I hate meetings (here’s why), but in order to make this change work, I have to shift the way I manage, too. And I’m confident we’ll find a natural balance to this new not-flat but not exactly hierarchical setup.



If you’ve started to notice that the structure you imagined or set out for your company is shifting, don’t panic. Take these three tips, and begin testing different structures. There’s no one size fits all, and there’s no need to get caught up in traditional or nontraditional structures—just find what works for you and your employees.


Photo of building structure courtesy of Shutterstock.