Empathy is the solution to management problems
There's nothing worse than a CEO who doesn't get it.
I want to start out by saying that I’m damn happy at my current place of work. It’s almost annoying how culturally alienating it is to work at a company where my boss isn’t powerless and the CEO isn’t actively harming the future and trajectory of the company. This isn’t about my current role at all, except to the extent that I’m able to see how valuable it is to have an excellent leader in power.
This is about what I’ve been seeing on Bluesky recently. I’ve mostly switched over to there for my microblogging fix. I scroll Twitter when I run out of things to see on Bluesky, but things are good over there. I’m happy with the crowd I’ve fallen in with and the content is beginning to flourish. But there’s quite a lot of content I’ve been seeing around this holiday season about how stupid and clueless some people feel that their CEOs are. I’ve been one of those people before. I’ve been in the side chats during all hands meetings where everyone is saying the things to their work friends that they wish they could say to the CEO who’s blustering on about how great a job sales is doing or how hard it was on them to raise that last round while no one’s had a raise in two years and promotions are always just a quarter away.
I thought it was inherent in the job of a CEO to catch flack for doing the right thing for long term growth even if it meant doing things that didn’t quite make sense in the short term. Perhaps it’s how we’re taught to think about CEOs—they’re in the role because they’re better able to strategize and do long-term planning than the rest of us. They’re wiser. They see a bigger picture than we do. The people who are complaining about these decisions just don’t understand the whole situation. But then I actually got out into the work world and realized that no, sometimes they’re just extremely charismatic people who can put together a good deck and had some success at a previous role. More often than not, they’re probably a little too confident in their own abilities, because if they weren’t, they wouldn’t be seeking out roles that involved being responsible for making sure the company continues to be a going concern and can pay its employees every two weeks. They don’t have to be subject matter experts, they don’t have to have any technical knowledge, and they don’t have to be geniuses. They need to have subject matter experts and technical experts and leaders from across the organization around them, and they need to listen to those people so that they can make informed decisions.
The problem is when CEOs don’t listen to the other leaders around them, and never take the time to check in with department leaders, or, in my dream, the plebs doing the work every day, to make sure that they’re not driving the train off the tracks. There are plenty of reasons why they think they don’t need to do this. They’re busy. It’s a big organization. They’ve created adequate feedback mechanisms to make sure that they know when things are going wrong. They’ve hired a “Chief of Staff” to talk to people for them and tell them what’s going on (yeah this one happened). Sometimes these things work out, sometimes they don’t, but they never will if the CEO doesn’t actually want to know what the people who make up the organization they lead think about what’s going on. It’s easy for all of these structures to become window dressing designed to placate people if the CEO and other leaders don’t actually take the words of their employees seriously. And when that happens, I think it comes down to a lack of empathy.
Now, I’ll say that most of my work experience has been at organizations at or under 50 employees. I’ve been in startups for eight years now, and that’s probably the space that I’m specifically writing about. I don’t think Jamie Dimon needs to be checking in with tellers at a branch in Frisco, Texas on a regular basis, but there is someone in that organization who functions as the CEO of that branch, or that region’s branches, and there’s someone who’s the CEO of the CEOs of the region’s branches and those intermediate leaders need to stay connected to what’s going on at that level and need to be empowered to affect change in some way.
I spent the final two years at my last company constantly trying to get feedback to the CEO there. I wasn’t the only one. It was really clear to everyone doing the daily work and interacting with clients that things weren’t going smoothly, and it didn’t seem like management was aware. We were dealing with a lot of turnover, and we weren’t getting those roles backfilled quickly enough, or at all. We were spending more time talking about make-goods than we were about product innovations. People felt (and were) under-compensated, and department leaders weren’t really empowered to do anything about that. The culture was completely bankrupt and no one that I talked to could do anything about it. And still, I was discouraged from talking to the CEO, because feedback was supposed to rise from employee to manager to lower level leaders to upper level leaders to the CEO. That’s the system and we have to use the system.
But the feedback usually didn’t make it up through the upper level leaders because they didn’t want to take it to the CEO. He didn’t want to hear it. He heard about people’s feelings through causal conversations and thought that people were just being dramatic. They didn’t want to put in the work to make things successful. Right before I left for my new role, we got an eleven page State of the Company document that was riddled with accusations that people weren’t pulling their weight and that’s why we were dealing with so many problems. I can still remember the rage I felt as I made my way through a document that was completely disconnected with the actual situation on the ground and entirely unaware of it. I felt helpless, I felt insulted, I felt angry, and I felt like this situation was hopeless. It made it easier to leave, I’ll tell you that.
When I was interviewing for my new role, a word came up unprompted by me from the CEO of the new company, as well as from others I spoke to at the organization. Empathy. This company was started by people who had worked in the roles that our product was designed to help. They knew what the pain points were because they had lived them. Our product exists to make those people’s lives better. The products that we build are all in support of that one goal and it guides what we do. The goal is born of empathy, and we have that guiding value because of our CEO.
When I talk to our clients and they ask for a feature in the product, I can tell them honestly that I’ll pass that request on and let them know what the product team says. I know the product team is oriented toward making our tools as useful as possible for our clients, not just because it’s good for renewals, but because it’s annoying to have to click 15 different checkboxes on a page when there isn’t a Select All box and they don’t want our clients to have to deal with that annoyance. When I tell clients in onboarding that it’s our job to take work off of their plates, I’m not just saying it to say it. It’s something we talk about internally. We want to make as much of our process feel like it’s automatic for them, even if it takes more work on our side, because our job is to take the load off of them. It’s not lip service, it’s a mandate from the top, and it’s a mandate we’re all bought into.
Recently, we had a situation pop up that I wanted to talk directly to the CEO about, because I didn’t want him to feel like he had to be in Leader Mode in front of a lot of people when I was telling him about it. I sent him a Slack message and we had a meeting scheduled for the end of the day. He listened to me, he thanked me for bringing it up, and we talked through potential solutions right then and there. It wasn’t something he was unaware of, but he still let me talk. He took me seriously. By the end of the conversation, we didn’t have anything fixed, but I felt like we could fix it, because we had someone at the helm who could see problems without feeling like the mere existence of those problems were an insult to his ability to lead. You can’t fix problems you don’t know about.
Bad CEOs are so ubiquitous that I didn’t even realize there was such a thing as a truly good CEO until I was hired by one. Not everyone can, should or wants to be a CEO, but anyone can be a leader. What I’ve learned in this past year is that the foundation of being a good leader is having empathy for the people you’re leading. Think of them as real people with real lives and valuable points of view. Listen to them when they voice concerns, and advocate on their behalf when it’s appropriate. Empathy won’t magically solve every problem and prevent new ones, but it’s hard to solve any problem without it.