Leadership Is a Skill. Here’s How to Master It.

Management may be the logical next step in your career, but the skills to be a leader are anything but intuitive. These experts offer a few tips on how to get started.

Written by Sunny Betz
Published on Aug. 30, 2021
Leadership Is a Skill. Here’s How to Master It.

Years before entering the Silicon Valley startup world, Skye Thompson learned what strong business leadership looked like from his mother. The senior program manager of San Francisco-based fintech company Human Interest grew up in the woods of northwestern Washington State, where he watched his mom turn their ten-acre hobby farm into a wedding venue. Her ambition and commitment were massively inspiring and he carried those lessons with him once he became a tech industry leader. Above all else, she taught him the value of having a vision.

“When you’re running a small business, there’s an element of showtime that’s needed — the same goes for leading an engineering team,” he said. “You have to keep their eyes on the road and connect them with the bigger picture.”

Skills You Need to Be a Leader

  • Self-awareness: Recognize your strengths and how you need to improve
  • Storytelling: Build a common vision to inspire your team
  • Curiosity: Make it your mission to seek feedback and learn every day
  • Mentorship: Help your employees reach their full potential
  • Fearlessness: Make peace with the unknown

The responsibility of carrying out a company’s vision rests squarely on a leader’s shoulders. Not only do they have to create budget proposals, deliver market performance reports and delegate tasks, they also have to keep their teams cohesive and motivated. It’s a skillset that’s unique to leadership roles, where managers find themselves balancing their team’s immediate goals with the goals of their organization.

We spoke with several leaders within the tech industry about the skills they most frequently use on a day-to-day basis, and each agreed that the most important thing leaders can do is inspire their teams. The best way to do that is to lead by example.

“I think it is crucial for individuals entering a leadership role to not focus so much on being a boss and more so an inspiration and model to follow,” said Jared Shaner, chief revenue officer at Boston-based e-commerce company Trellis Commerce. “Nothing will inspire employees more than being the hardest worker and most humble person on the team.”

Whether you’re a CEO or an engineering project manager, here are a few underrated skills that you’ll need to master in order to be a strong leader.

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To a seasoned engineer or developer, moving into a leadership position may seem like a logical next step in their career. While that may be the case, management roles require an entirely different skill set than those expected in an early to mid-level role. Leaders have to not only succeed at their own immediate tasks, but are also responsible for helping their employees meet their goals as well — managing those expectations isn’t intuitive for someone new to leadership.

“It’s not a no-brainer,” said Thompson. “Just because you’re good at something technical, doesn’t mean that you’re going to be good at managing a technical team.”

Like with any new skill, you have to be real with yourself about what you’re good at and how you need to grow. Don’t act like you have all the answers, but also don’t be too hard on yourself when you struggle. The requirements of a management role can be frustrating and challenging to learn, but with time and self awareness, they can be mastered. To get a clear picture of your strengths and weaknesses, encourage honest feedback from your peers and carve out time for introspection.

“Just because you’re good at something technical, doesn’t mean that you’re going to be good at managing a technical team.”

“At our organization, every quarter, we meet as a leadership team and talk about our goals for ourselves,” said Annie Raygoza, director of client services at San Jose-based web design agency WebEnertia. “It forces us to look inward and to identify areas where we need to grow.”

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Leadership skills like time management, delegation and responsibility are common sense. But some traits and talents are more difficult to pin down. Thompson said that storytelling, while often overlooked, is one of the most valuable skills to master as a leader.

“It’s not even thought of as a skill. People think it’s just an innate talent,” he said. “But anybody can learn to be a storyteller.”

“One way to view brand management is that it’s external storytelling — it’s telling the world who you are and what you do.”

Telling the story of who your team is, where you want them to go and how they can get there is crucial — it’s how you keep everyone interested and focused. When you can build a narrative about your company and show your employees how they shape that narrative, you build trust and excitement not only within your team, but with your customers as well.

“One way to view brand management is that it’s external storytelling — it’s telling the world who you are and what you do,” Thompson said. “Workplace culture is a really important factor in management, and a good definition for culture is internal storytelling.”

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Some managers may feel they’re supposed to have all the answers, and that learning is reserved for teammates earlier in their careers. However, even CEOs of major tech companies have room to grow — it’s just a matter of discovering what those skills are.

“I feel that one of the best traits of a leader is their ability to be a sponge and to learn from everyone around them,” said Shaner.

Seeking out and responding to employee feedback is a central task for any successful leader because it helps you get a clearer idea of what your team wants and needs. It also provides insight into gaps in your leadership, as well as what you’re great at. Curiosity can be immensely rewarding, even if it reveals that you have a lot to improve on.

“I feel that one of the best traits of a leader is their ability to be a sponge and to learn from everyone around them.”

“My management style is definitely more hands-on, because I like to have full clarity on everything,” said Raygoza. “Being really curious and getting into the weeds a little bit helps me understand my employees better, and what makes them tick.”

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Mentor Mentality

Most of the job of being a leader, beyond writing monthly reports and organizing project schedules, is to help employees be the best they can be. Sometimes this means becoming a formal mentor — but oftentimes, you can simply ask your teammates what they want and do what you can to help them along their professional journey. It doesn’t matter whether an employee wants to climb the ranks at your company or move onto another role altogether — as their manager, you need to keep their best interests at heart and guide them toward their goals. 

“Sometimes employees really want to start doing something, but they just don’t understand how or where to begin,” said Raygoza. “We have to exude patience, and be supportive of those people, because nobody is just born knowing everything.”

“Give [your employees] opportunities to lead, fail and pick them up along the way.”

Let’s say an employee shares they want to take on more responsibility and move into a leadership position. To realize that dream, help them get firsthand experience. The idea of handing off more responsibility to someone less experienced is scary, but every manager was once a newbie. People only learn by trying things out — embracing a teacher mentality means letting your teammates build skill through trial and error.

“I think it’s important for people to have real experiences where they fail and learn,” said Jason Lapp, COO at San Francisco-based software company Beautiful.ai. “Give them opportunities to lead, fail and pick them up along the way.” 

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The stakes are higher for managers. Not only are they responsible for their own performance, but also for their whole teams. If things don’t go according to plan, leaders have to be prepared to take the heat for it. In the tech world, nothing is promised — big changes can happen overnight, and many startups roll out unprecedented products without knowing what the future holds. A truly effective leader has to make peace with the unknown.

Growing up in the woods with a Mount Rainier park ranger for a dad, Thompson learned to embrace uncertainty and self-sufficiency early on. He said dealing with the unpredictability of nature during his childhood helped him better handle the rapid changes of the Silicon Valley startup scene later in his life and fearlessness is a trait no leader can afford to overlook.

“Our brains convert uncertainty into risk, and the initial reaction might be fear,” he said. “It’s so important to go through that fear and to cope with uncertainty.”

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