“You need to understand yourself to be a good leader.”
I met Dan Pupius, Head of Engineering at Medium, through our participation in the same coaching program. Medium is a foundational piece of my business, so I’d investigated their culture and already appreciated that they “walked the talk,” especially on transparency. For this Leading By Example interview, Dan suggested we include his frequent collaborator Jennifer Dennard, who leads org design and culture initiatives at Medium. I enthusiastically agreed.
I’d love to start by talking about anything that resonated with you from previous Leading By Example stories.
Jen: I read your interview with Cecilia and what struck me was the power of asking for help. It made me reflect on something that a mentor once told me, that asking another human for help is an incredibly kind act. I now go out of my way to ask other people for help, regardless if they are my peers, my juniors, or my seniors. It lets other people know that they matter.
That’s great. What about you, Dan?
Dan: What resonated with me was why diversity in the workplace is important, especially in the context of feminine versus masculine behaviors. One of the things I saw elsewhere in the industry was that, even within a fairly homogenous industry dominated by white men, certain types of personalities still succeeded over others. You had to act a certain way in order to progress. I didn’t like that. When I came to Medium, I wanted to make sure people didn’t have to play those games in order to succeed.
Can you talk a little more about your experiences? What exactly did you come up against that you didn’t like?
Dan: I’ve been in environments that were very argumentative and aggressive. A lot of discussions came down to win-lose arguments and it felt like you had to argue your case to get anything done. There was a lot of, “I’ve been here longer than you and I am a higher rank than you, therefore you have to give me all this data in order for me to believe you.” The people who succeeded in meetings usually had the loudest voice. It would be hard to get a word in edgewise, especially if you were not comfortable competing to be heard.
“The people who succeeded in meetings usually had the loudest voice.”
Were there things that you’ve done consciously at Medium to try to avoid that?
Dan: At Medium, we are trying to cultivate an environment where everyone’s voice is heard, including those who may be more introverted. Because we are a writing platform, a lot of information is communicated in writing. We use an internal tool called “Hatch” that’s basically a private version of Medium. That helps democratize things because everyone — from Ev to a junior engineer — is writing there.
Jen: We want everyone to be on an equal playing field, so we’ve primed the culture in such a way that speaking up is easy for everyone. The way we structure meetings is a good example. One of our more common meetings is called a “tactical meeting” and we start those with a check-in round where everyone explains how they are feeling. This helps set the tone for sharing.
“We start those [meetings] with a check-in round where everyone explains how they are feeling.”
Then we move into agenda building. Basically we go around the room and give everyone a chance to share any tensions they think we need to discuss. A tension is anything where there is a discrepancy between where we want to be and where we are. A tension might be, “We are scrambling to find desks for new hires. We need to think about a system to streamline that process.” Or, “This spreadsheet hasn’t been updated in awhile. Whose responsibility is that?” We actually go around the room several times to be sure everyone has a chance to contribute. This is just a small way we make sure everyone is taking ownership over what is going on at Medium, but as it becomes embedded in our culture, it has effects across the organization. Now I see junior engineers who feel comfortable speaking up in high-stakes meetings. I haven’t observed that at other companies.
In March Medium’s Head of Operations announced you were moving away from Holocracy, in part because it assumes that employees are totally rational and divorced from emotions about, say, their job title or sense of advancement. How do you think about the place of emotions at work?
Jen: It’s inevitable that emotions show up at work. One way we’ve addressed this is by making it a priority to give feedback at a time when people are more likely to be relaxed and receptive. If people are in a heightened emotional state — say coming in from a high-stress meeting or in a large group setting — that is not the ideal time for personalized feedback. Getting outside the office to a quiet, neutral zone is usually a more effective way to give feedback so someone can really hear it.
That’s great to hear you are thinking on that level. Do you also assess potential hires for emotional intelligence or maturity?
Dan: Our interview process is set up to specifically screen for empathy and awareness. That’s critical to the human environment we want to create here.
That sounds great, but also difficult. What does it actually look like to “screen for empathy and awareness?”
Dan: We do a work history interview where we ask pretty awkward, uncomfortable questions. For example, we ask candidates about a challenging time they had at previous job. If a candidate responds by talking negatively about their former colleagues, we get a sense that this candidate may not be very good at seeing things from other people’s points of view.
“I spent ages early on thinking about what makes a good software engineer.”
Empathy wasn’t always a part of the interview criteria. I spent ages early on thinking about what makes a good software engineer. I came up with the acronym C.A.R.E., which stands for: Curiosity, Awareness, Resoluteness, Empathy. It really struck a chord with everyone here so we decided to put those qualities into the interview rubric.
Jen: One of our company values is around building trust. So we also screen for softer skills like mentorship experience or lateral leadership, meaning how someone can influence an organization without having overt power or being the loudest voice in the room.
Why is trust important to a business’ success?
Jen: Trust is the glue that holds a team or company together. If I don’t trust that others are doing their work, it drains my mental and emotional energy. I may be quietly anxious or I may waste my time micromanaging them. If you think in terms of productivity, an untrusting environment is a huge waste of time and energy, which will ultimately impact your business.
“You can never see the whole battlefield at once, so you can’t solve problems from a singular point of control.”
Dan: Trust has a very practical purpose within software development, particularly because we’ve moved beyond highly specced-out, waterfall-driven processes. We’re now dealing with complex systems where multiple marketplaces, user needs, and third-party black-box systems need to work together. Traditional management techniques aren’t effective in those systems. Without trust and a distributed sense of ownership, it’s almost an intractable problem. To put it in military terms, you can never see the whole battlefield at once, so you can’t solve problems from a singular point of control.
Have either of you worked on teams where you felt like trust was low in a way that hurt success or agility?
Dan: I have been on teams where senior, high-level people became incredibly overworked, controlling, and aggressive towards those below them. That ended up being disempowering for other employees because they couldn’t do their job without being shouted at by this senior colleague. Over time the employees become less and less proactive and the senior level people felt the need to work harder and grew even more aggressive. It was a vicious cycle that atrophied the company’s progress.
Jen: It’s easy to say, “This person’s work output wasn’t that great, so why should I trust them?” Versus looking at it from the opposite point of view: “If I had trusted that person to do their job, their performance would have been higher.” Trust can be this self-fulfilling prophecy. When people really trust each other, it elevates their functioning to a higher level, which then elevates the work they produce and helps build up the entire company.
Obviously I think a lot about the idea of “leading by example.” In this case, I imagine you can’t just tell your employees to trust one another. You have to live it, embody it, and trust other people yourself. How does leading by example relate to your efforts to build trust into the company?
Jen: I think the only way to drive change is to lead by example, to teach and empower others through the global impact of small actions. When you’re in a fast-moving workplace, it’s easy to dismiss the importance of taking a few extra moments to consider how you respond to an email, for instance. I actually put a lot of thought into my communications: when they happen, who I include in the conversation, my tone. I know that by setting that example, I ultimately can have a big impact on the org.
Dan: I think demonstrating trust is also a habituation thing. If people are conditioned to ask the boss for everything, then they are less likely to be proactive. As a leader, you have to reinforce independence and proactivity. For example, I don’t really want to pay any attention to budgets and I’m not very good at it, so I have given responsibility for that task to Madeline. If anyone asks me, “Can we sponsor this event?” I direct them to Madeline because I trust her to take care of it.
“First, I ask them to come up with five explanations for why the other person may have done what they did.”
Also, when people come to me during a one-on-one meeting with a complaint about someone, I will ask them to do an empathy building exercise, even if I think their point is completely valid. First, I ask them to come up with five explanations for why the other person may have done what they did. For example, if someone sends you a really sharp email, you might say, “Maybe he was emailing from the store while his baby was screaming, maybe he’s tired, maybe he’s having problems at home, etcetera.” Then you choose the most reasonable answer out of the five. It doesn’t mean you ignore what happened, but it gets people to understand things from the other person’s perspective. Instead of solving the problem for them, I coach them into solving problems for themselves.
That’s such a big thing. We all have off days, so you have to encourage people to give the benefit of the doubt.
Dan: Absolutely. If you foster an environment of trust, when one person has a bad day, it doesn’t derail things as much. For example, if you slept badly one night and then the next day you blew your gasket in a meeting, you don’t have to spend the next three weeks repairing the relationship.
So you’re leading by example. Are there other ways you help team members build empathy?
Jen: We offer coaching for people who are moving into a leadership position or dealing with other people as a primary part of their role. We have a couple different coaches, from more therapeutic to extremely tactical business-focused, depending on what a person needs help with. The goal is to give individuals support on issues they may not be comfortable bringing to their people manager.
“I feel like coaching calms our organization.”
I feel like coaching calms our organization. It gives us an outlet to talk about things with individuals who are not a part of the company and who have more distance and a different perspective than a co-worker or lead.
Do you mind if we talk a little bit about your personal experiences with coaching? I think coaching is really important, especially as people move into leadership roles. I think all founders should have coaches. I’m a big fan of it. In fact Dan and I met through Pathwise coaching.
Jen: I started working with a coach based on Dan’s encouragement. Before that, I was working alone on the people operations team and I didn’t have anyone I could bounce ideas off of. Coaching is like having an outsourced brain that I get to talk to for an hour. I get to air my thoughts in a way that enables me to take a step back from the situation. That’s very helpful, particularly in situations where I’m juggling a lot of different interests and have to maintain a high level of discretion.
“I get to air my thoughts in a way that enables me to take a step back from the situation.”
For example, I am currently leading feedback initiatives for different levels of our org, from the most junior folks to the most senior. Having someone to talk through this process with is particularly helpful to make sure my moral and ethical line is what I want, while also thinking strategically.
Totally. Dan, when you recommend that a colleague sees a coach, what’s going through your mind?
Dan: So much of management is about effectively dealing with other people. For the most part, managers aren’t trained in that. A lot of successful managers learned interpersonal skills on the job. Coaching just accelerates that process. Also, a lot of management training is outward facing — tools and techniques to motivate people — and what often goes missing is the inward-facing training. You need to understand yourself, your biases, and your own communication foibles to be a good leader. That’s where coaching can really help.
Do you have any examples of uncomfortable work situations you were better able to work through because of your own self-awareness?
Dan: When we did our annual engineering summit, we played this game which is basically a group Rochambeau tournament. If you lose, you have to be the other person’s biggest fan. By the end of it, you have two dozen people cheering each player on. It was super triggering for me and I wanted to run away. While it was happening, I was using what I learned in Pathwise to internally explore the emotions of what I was feeling. I realized it probably goes back to growing up in a town in the UK where there was a lot of football violence. Crowds could get incredibly rowdy and aggressive and I hated it.
“Standing up for others and making sure our company is inclusive is the least I can do.”
Jen: Recently I was in a meeting where it felt like the men in the room were speaking at me. It was a combination of the tone they used and the happenstance of the group dynamics. During the meeting, I sat there reasoning with myself: “This is making me uncomfortable. I know it’s not personal but I really don’t like how I’m being treated.” What was most interesting was that, because I was triggered, my functioning dropped. My ability to think and work in that context was lower than normal. It made me realize that, when other people get triggered, their functioning drops, too. So if our whole company’s functioning drops a little, that’s really problematic in the long run. The biggest takeaway I had from that experience is that it is critical to train people to be more aware of others.
The way I see my role is that I err on the side of being more PC at work than I would normally be in person. I do this to pull the whole org in the direction of being more inclusive. Sometimes it makes me uncomfortable to be that policing voice that says, “No, we shouldn’t use that phrase. It’s not sensitive towards others.” Sometimes I’ll have to say those things four or five times in a meeting. At that point it becomes a joke and I’m comfortable playing along with it. However, I have a hard time doing it and I don’t enjoy feeling like an outsider in a situation when I’m with peers or coworkers. It is difficult.
That probably helps you empathize with people who feel like outsiders.
Jen: Yeah. The way I see it, I’m incredibly privileged — I’m white; I grew up relatively well-off — so standing up for others and making sure our company is inclusive is the least I can do.
