It’s a good question: What is leadership, really? Is it the power to bully people into action, or the talent to coax the best out of employees? Does leadership inspire or intimidate? What are its limits? Built In talked to six tech leaders to discover how they define leadership and how their careers have helped them shape that definition.
10 Characteristics of Leadership
- Inspiring employees to be their best
- Seeking help when challenged
- Recognizing and dealing with setbacks
- Making and sticking to tough decisions
- Commitment to learning
- Solving problems
- Knowing that they don’t know everything
- Empowering employees
- Nurturing employees
- Finding balance between authority and consensus-building
“A good leader has the skills to share personal experiences, enabling and inspiring growth of others,” said Olga Kupchevskaya, vice president at Los Angeles-based MyEtherWallet, which helps users with blockchain management. Leaders, she continued, use clear vision, a strong sense of accountability and effective communication to encourage their team to succeed.
There’s more to her definition of leadership: Leaders are able to recognize setbacks, make necessary changes and even abandon old processes and goals if needed. Leaders are determined to produce the best work and won’t let challenges discourage them. And leaders are not afraid to ask for help, because they’re eager to learn and grow. “They aren’t afraid of people being better than them; rather, they take pride in discovering new ways to succeed,” she said.
Kupchevskaya has been a leader for several years. At first, she had imposter syndrome, feeling that she didn’t know enough and perhaps wasn’t doing enough. Over time, she came to realize that tech changes so quickly that there’s no one who understands everything fully all the time.
This knowledge freed her to be open to trying new technologies, get rid of old management methods, and completely change the production process without being afraid of making a mistake. “In the end, we’re all learning to be better at something,” she said.
Leaders Make Tough Decisions
“Leadership is about making bold decisions, sometimes tough and painful ones,” said Andres Garzon, CEO at New York City-based Jobsity, which helps companies scale software development operations.
“Leadership is about making bold decisions, sometimes tough and painful ones.”
He offered an example from his own career. He had sold a huge project to a VIP client and was chosen to be tech lead on the product. He gathered his team and asked for information in order to understand the problem. Some team members were hesitant to collaborate; a few even blocked Garzon. “I had to do a one-on-one with them and almost force them to help,” he said. Once he had the information he needed, he put deadlines on all deliverables.
In a meeting after the first deadline, he fired a programmer “because he didn’t take deadlines seriously,” Garzon said. The team was shocked at his hardball tactics, “but they also got the message that I wasn’t playing around,” he said.
When people complained to Garzon about the pressure and his style, he got them together in a room to explain his behavior. “I told them, ‘if we don’t make the deadline, all of us will be fired, not only him: what do you guys prefer?’” The talk helped the group feel aligned with the goal and got their attention, he said.
At the first demo, the client was impressed with the results and told the team she’d never seen so much progress on a project in such a short time. Garzon’s response: “It would have been impossible without the effort of the talented individuals next to me,” he said.
He at once got internal reassurance that his decision worked, and credited the team for the results. “At that exact moment, I became a leader,” he said.
Leaders Keep Learning
“Real leaders work for their teams. They are problem solvers,” said Amber Oler, vice president of customer success at back-office automation company eFileCabinet. Oler sees her job as supporting her team both in their roles and future career plans, while making sure her team’s goals and priorities align with the overall vision of the company.
“Real leaders work for their teams. They are problem solvers.”
Oler, who is starting her fifth year as a leader in the SaaS space, has learned from her mistakes. Once, she was called out for assuming that other people shared her knowledge of an issue, process, or even a desired outcome. “Don’t expect others to know; don’t assume you know everything,” a former manager told her. “Not only did I grow from this moment but it also made me appreciate and adopt radical candor,” Oler said.
Failure also taught her about leadership. Oler failed to take the right path with two employees because she felt intimidated and was answering to two leaders with conflicting needs. “That was a hard one to recover from,” she said. Oler stepped out of the leader role to improve communication, seek coaching skills and learn to manage conflict.
“The change taught me to stop trying to be right and start trying to learn,” she said. “A successful leader can’t know everything, especially when cross-departmental collaboration is needed in a holistic strategy, which in SaaS is always the case.”
Her ability to keep learning serves her well these days, as eFileCabinet teams work four-day weeks with the option of working remotely. Oler said she needs to be flexible and available for her teams, both existing ones and new ones. “We are collaborating internally on a level like never before,” she said. This requires me to constantly reprioritize the actions our teams take and when to be sure we never fall out of alignment with the company vision.
“Leadership is about creating vision, strategy, and processes that connect brilliant people to big problems,” said Andrew Cron, chief scientist and senior vice president, science at 84.51°, a retail data science and analytics company based in Cincinnati.
He notes a huge difference between leading a company and leading its workforce. Both are critical to a business’s success, and at 84.51°, the two are separate. Leading a company entails setting a vision and goals and developing the strategy to get there. “Leading a workforce is about people,” he said. “It’s ensuring we’re finding, developing, and placing the right talent.”
Cron, recently promoted into his role, is charged with spurring innovation at the company. One of his jobs as a leader is to continue to recruit and retain top talent to add to his established research team. Another is to create cross-functional teams where researchers, engineers and clients work together from the start on projects “instead of ‘throwing something new over the wall,’” Cron said.
Before he landed in a leadership position, Cron viewed the post as “more of a commander of a team, the person who always found a way to get things done in the right amount of time while maintaining high quality outcomes,” he said. That’s still part of leadership, but more important is empowering the right groups of people to work cross-functionally, as a single unit, toward a big goal,” he said.
He’s devised his current leadership philosophy from a history of being both poorly led — “zero context, connection or air cover” — and being well led by a person whose first priority was championing great data science product. “Our team had high visibility, morale, and impact due to our leadership connecting and empowering the talent,” he said.
The demands on leaders have changed as 84.51° has grown. During initial quick-growth phases, the company took on more and more work by hiring more and more people to do that work. “We can’t scale to the next level through people alone,” Cron said. Instead, leadership will need to invest in systems and processes that enable talent to work more quickly and minimize duplication.
It will also need to provide teams the strategy and support to stop work. “It’s incredibly easy to start new projects, but extremely hard to end them,” Cron said. “It is critical that we empower our people to make the calls to let go of some initiatives that don’t have the impact we need to scale.”
“Leadership in a corporate context is bringing together incredible talent and bringing the best out of that talent,” said Ronnie Kwesi Coleman, CEO and co-founder of Meaningful Gigs, a Washington, D.C.-based startup that matches Africa-based professionals with tech design jobs.
Meaningful Gigs was founded in 2019, and has grown to 13 employees. The initial team of three people did everything themselves. “Each of us was wearing 100 different hats,” Coleman said. As the company grew — it now has 13 employees — the three co-founders started focusing more on team building and less on doing everything themselves.
“When we found the right people and got the best out of them, they could do better than I could, and it would allow me to do what I’m best at and what’s important for the team and the company,” he said. As the company continues to grow, he’ll stay on that path, hiring more leaders and adding layers of management.
Coleman has been led well and poorly, once by a task master who got much accomplished but failed to build goodwill in his organization, and another by a leader who worked to build trust within his team. “I worked a lot harder for that leader because I felt that he had my best interests at heart,” Coleman said.
“The more I matured as a leader, the more I realized I needed to just find the right people for the job and help bring the best out of them.”
Coleman started leading his own teams 15 years ago. He first led by example, thinking that marked good leadership. “I’d try to do everything and just have people watch and follow,” he said. “The more I matured as a leader, the more I realized I needed to just find the right people for the job and help bring the best out of them.”
Leaders Find Balance
“Leadership occurs when individuals cede some control over their own destiny because they believe another person can better judge on the group’s behalf what needs to happen to produce the best outcomes for the collective,” said Adam Judelson, president and COO at Los Angeles-based startup mePrism, a data economy platform intended to empower consumers.
Judelson began his leadership career as a drum major for his high school marching band. His job was to lead and motivate about 130 peers in practice and in competitions. “I had to learn which tactics motivated or deflated people through mentors, experimentation and fast correction,” he said.
He calls leadership a precarious balance: If the leader is too authoritative, team members will take back individual control and abandon the leader. If the leader operates purely as a consensus builder, they’re effectively facilitators and the group might not achieve its highest potential.
Leadership also conveys the ability to focus. “Leaders must ensure that the group knows what it’s working toward; this scope frees the mind and our emotional selves to do our best problem solving,” he said. He offers construction as a metaphor: “You supply nails, wood and hammers, but you must also inspire the group to build a house,” he said.