Squarespace's Yaphi Berhanu: How leaders’ words shape the team

Squarespace senior engineer Yaphi Berhanu, illustrated by Matt Peet

Illustrated by Matt Peet

Out of touch. Disconnected. How many leadership difficulties are variations on these themes? It’s true that tech leaders have to have a different perspective than pure contributors—they’re managing individual health and team performance in conversation with organizational goals. 

But keeping in touch—that is, using the power of their words to build relationships—is an essential part of building a psychologically safe team. And Yaphi Berhanu, a Senior Software Engineer at Squarespace, understands the importance of communicating between tech leaders and ICs as well as anyone, because he stands with a foot in leadership and a foot in contributing at the same time.

“The leadership in my role is in terms of leading projects, mentoring other engineers, providing guidance,” Yaphi says. “At the same time, it is also on the individual contributor track. So it's leadership from the perspective of a senior engineer rather than specifically a manager.”

For Yaphi, psychological safety is a baseline. His teammates need to feel free to bring up ideas, ask questions and make mistakes. That’s how the team benefits from all the ideas and skills and enthusiasm within it. Psychological safety is not the goal; it’s the standard by which he measures the health of his team, and his own performance as its mentor.

In this interview, Yaphi discusses the power of a tech leader’s words to shape that safety. The higher leaders move in their careers, the more weight behind their words, so leaders must use language even more deliberately to ensure the right outcomes, to keep their teams motivated and to unify teams behind solving problems rather than inadvertently pitting teammates against each other (or themselves.)

Rising leadership status means being more deliberate with words

All of Yaphi’s insight into building motivation and safety into a team grows from one single seed: Leaders must be deliberate with their words. And the more they advance in their careers, the more impact their communication has.

“The littlest things you say sometimes have the biggest impact,” he says.

The potato chip parable

Yaphi recalls a story he read somewhere—let’s call it a parable—to illustrate this moral.

One day, a group of employees knocked on their CEO’s door to show him the packaging they had created for a new line of potato chip products. The chip bags were a bold red. The CEO liked the bags. But he said, in the most offhanded way, “I’m curious what that would look like in blue.” So the employees went back to work, and they returned a week later with a blue potato chip bag. The CEO was startled. He barely even remembered wondering what the bag looked like in blue. “You know,” he said, “I actually liked the red bag.” But when the CEO had mentioned blue, the team stopped production. The bag-making machines ground to a halt, designers redid the packaging and the week’s delay cost the organization thousands upon thousands of dollars. 

All because of one innocent comment that swung a bigger stick than the CEO realized.

Not all comments from leaders will steer teams so disastrously off track. But everything they say carries weight. “In creating a healthy team culture, it is important to be aware of what you’re asking your team to do,” Yaphi says. “I’ve been in these situations. You’re asked to do something that makes perfect sense. Write up a doc with that good idea, or make a couple tickets for that. They align with the team goals and all that. But they are treated as if they will take zero time.”

These sensible-seeming requests add up to entire days’ worth of work. They may make sense in isolation, but in the bigger picture, they chew into a team’s efforts. And they typically come from a constructive impulse—wanting to spread good ideas or make sure team members get recognition for their ideas.

Busting out of the potato-bag pitfall

Yaphi has plenty of times caught himself falling into that trap of creating more time-sucking work for his team—even though he dreaded that happening as a contributor. So he came up with a few strategies for avoiding inadvertently wielding the power of his requests as a leader.

  • Just share the ideas yourself. “Act as their amplifier,” he suggests. When a team member has a great idea, asking them to share with the team can feel like redesigning a potato chip bag—you’re unintentionally asking them to create a complex document or presentation. So just share the idea yourself, give credit to the originator and support them in that way.

  • Make clear that optional requests are actually optional. Direct language matters. “You can say, if you want to informally announce this in the next team standup, then feel free to. But it’s not an assignment,” Yaphi says. “Also, make it clear that it would be a short thing and not some big presentation.”

  • Weigh your words before you speak. “In the more general case of being careful about accidentally assigning things, I stop to think anytime I say something to someone that requires them to do an action that they were not going to do before I opened my mouth,” he says. Think through: what steps are actually involved in this request? What time commitment am I actually asking for here? Then articulate the real parameters to the person you’re speaking with.

Using language deliberately in these ways is about more than saying what you mean as a leader—it’s equally about making sure the team understands what their expectations really are.

Leading others as you would have them lead you

Using words deliberately as a leader, and listening carefully to the team’s needs feeds directly into Yaphi’s golden rule as a leader, which is… well, the Golden Rule: Do unto others as you would have them do unto you. While Yaphi stresses the importance of this rule, he notes that this is just a foundational principle, not the finish line. 

“One of the biggest things is setting the tone by example,” Yaphi says. Demonstrate that it’s safe to make mistakes by admitting your own. Ask the questions that sound obvious, so other people learn to feel comfortable asking. Get vocal when giving credit to people, especially if their work may be invisible to others.

“It’s really just about being the kind of person that you want to be on the receiving end of,” he says.

Yaphi offers some examples of the Golden Rule that embrace aspects of life-on-the-job that we all want, that help us all thrive, but that leaders can sometimes lose sight of when they are focused heavily on outcomes and projects—forgetting, to some extent, the human element. 

  • Keep work interesting and engaging. The situations where Yaphi has seen motivation lag usually boil down to a lack of fulfillment. “In any work,” he says, “fulfillment comes from this: Do I find this interesting or challenging enough to text my skills, while also not being so impossible that it becomes a wall?”

    So when allocating work to his team, he takes into account which pieces of the project his teammates will find interesting, and which will help them grow—all while avoiding too much monotony.
  • Oversimplifying matters can devalue a team’s work. Yaphi recognizes that we gain confidence in our knowledge when we’re comfortable with a piece of technology or a concept. Many leaders have gained such deep knowledge and interest in their careers. So when a team member voices their struggles, the answer may seem simple (or worse, trivial)—and a seemingly harmless, helpful, straightforward response can actually come across as dismissive.
  • “They’re going through some difficulty,” Yaphi says. “Maybe it’s a situation where they’ve seen something that you haven’t seen, and you’re kind of saying, ‘Oh, that’s simple,’ without realizing the full scope. Making an assessment about someone else’s work without the full context, yet with an expertise that makes you credible, can be more damaging.”

    In short: treat teammates’ problems as seriously as you’d like yours treated.

    “It's so interesting,” he notes, “in technology in general, how there are so many things that sound really simple that are very complicated. And sometimes the things that sound extremely complicated are extremely simple.”
  • The words not said are as powerful as the words said. Much of the talk about psychological safety circles around active problems. But sometimes, Yaphi recognizes, the problem is a simple error of omission.

    “Even if you’re not saying anything harmful or doing anything harmful, not doing things—like being publicly vulnerable—still sets the tone,” he says.

    This void allows more room for imagination, and not in the constructive way. Yaphi recalls earlier in his career when he carried a strong, self-imposed sense of needing to appear a certain way. That need for a perfectly polished exterior came without any specifically detrimental things being said or done by leadership.

Reframing disagreements as “us against the problem”

Perhaps we can all agree: Disagreements are a healthy part of the creative process for developers. We can test out different approaches and debate different strategies, all with the goal of reaching the best course forward. Many times, leaders discuss the importance of unifying after the debate has ended—some form of “disagree and commit,” where the team moves forward as one even if individual ideas are discarded along the way.  

For Yaphi, though, it’s not about coming together after a disagreement. It’s about coming together before.

The nature of development work means that product visions and user experiences lead to a lot of options. “That’s a good thing,” Yaphi says. “There are a lot of different trade-offs that need to be made. We need to see what the compromises are and how we can work together to come to a solution. But the biggest thing I do is to make sure that it’s us against the problem instead of us against each other.”

Imagine the team sitting at a table, disagreeing about how to address a problem. They can be sitting on opposite sides, banging heads. Or they can be sitting on the same side of the table, facing the puzzle together. That’s Yaphi’s goal.

“How do I make it us against the problem?” he says. “The first thing that I do is I make sure that the other side feels heard. What is their point of view? What are the goals, what are their concerns? I try to get a mental picture of that. And then I start bringing up questions that I have. Instead of just coming out and saying that I disagree, I'll say, ‘So I see that this is your goal. One thing I'm concerned about is how we should address that.’”

Everyone—including Yaphi himself—becomes more willing to listen because they’ve been listened to. “We’re a lot more willing to say, ‘Oh, I hadn’t thought about that, but maybe here's what we can do. Maybe we can compromise on this piece, or maybe we can pull back this or change this.’ And now it's a conversation where we're working together on the same side.”

The recap: Build communication, not weapons

Tech leaders can choose to take psychological safety as a baseline requirement for their teams, rather than an end goal in itself. After reading Yaphi’s advice, check out how other leaders are cultivating psych safety.

  • Be more deliberate with your words as your leadership status rises. Yaphi emphasizes that words coming from leaders carry inadvertent power. Leaders need to communicate their expectations ever more clearly, as well as finding ways to empower team members without requiring unnecessary work from them.

  • Do unto others. Most tech leaders have also been tech contributors, but their perspectives shift along with their responsibilities when they take on leadership roles. Yaphi encourages them to remember what being an IC was like, and to treat them the way they liked to be treated. His examples include keeping the work interesting and engaging as much as possible, acknowledging the struggles of teammates instead of inadvertently dismissing them and recognizing that words unsaid can be as powerful as words said.

  • Frame disagreements as us vs. the problem instead of us vs. each other. The ways that leaders handle healthy disagreements frame the debates. Are team members pitted against each other to champion their ideas? Or are they collaborators, testing out different approaches to the same problem? 

The words we use as tech leaders shape the teams we work with, and the realms they work in. Yaphi’s insights demonstrate that extra care from leaders in shaping those words—before opening their mouths or firing off emails—can help guide them away from unintentionally weaponizing their language and, instead, toward creating healthier, more motivated teams.