Entrepreneurship for Engineers: How to Grow into Leadership

Building a company means becoming a leader. You’re committing to building a team, and you have a vision about a change you want to make in the world and a product or service you’re going to offer that will make that change — and hopefully make you rich in the process.

In talking with founders for this column, a couple of themes emerged. First, leadership is about rallying people around your shared vision. Most startup employees are taking a pay cut by joining the startup — your first experience of leadership is convincing those employees to make a bet on you and the vision you have.

Second, leadership is actually a lot more complicated than most non-leaders assume. There are hard choices to make, and sometimes being a good leader is going to mean being a villain in the eyes of your team. And while being a good leader does not require you to be an asshole, it is also possible to be a good leader, who motivates their team and builds successful companies, and be a jerk.

Let’s dive into some of the themes.

What Is Good Leadership?

“If the business is successful, if I can provide a productive work environment for people and bring the valuable product to market that customers use, I kind of feel like I’m a successful leader,” said Madhuri Yechuri, founder and CEO at Elotl, a multi-cluster nodeless Kubernetes platform. “The leadership comes as an after effect, rather than a well thought out, intentional process.”

Some founders approach leadership with more intentionality — but generally agree that the success of the business is one of the most important concerns for a good leader.

According to Charity Majors, co-founder and CTO of Honeycomb.io, good leadership means inspiring people to go where you’re going, to believe in your vision — and to do so by minimally coercive means. As Majors told The New Stack, “You actually lose leadership points every time you have to throw your weight around.”

Hard Calls and Dirty Work

A huge part of leadership, however, is having to make decisions that will not please everyone — or even decisions that will please no one.

“Ultimately, as a CEO, as a founder, it falls on you to make tough decisions,” said Wei Lien Dang, partner at Unusual Ventures and co-founder of StackRox, which was acquired by Red Hat. Founders have to make all kinds of tough calls, from product decisions to fundraising decisions to layoff decisions.

In the case of job cuts, one of the trickiest spots leaders have to navigate is letting go of someone who is well-loved but not effective. “You can’t tell the team, oh, this person is leaving because they failed in XYZ ways,” Majors said. “You owe that person their dignity and their privacy. You really just have to suck it up, expect it to be kind of painful, and hope you have earned enough credibility that your team won’t just quit and that they’ll take your word for it.”

(In addition to protecting a fired employee’s privacy, not talking to colleagues about the reasons why the person was dismissed also protects your and your company from legal jeopardy down the road.)

Founders — and leaders — have to think about themselves as being there to facilitate others, which can mean doing all the dirty tasks that no one wants to do, Yechuri told The New Stack.

“Pick up the dirty tasks that are not fun for others to do,” she said. “So they know that you’re not just talking the talk, you’re walking the walk as well.”

Balancing Responsibilities

It’s easy for individual contributors to say that good leaders care about their team members, but the reality is more complicated — leaders, good or bad, have a responsibility not just to individuals, but to the well-being of the entire team and the financial success of the company. And sometimes these interests are in conflict.

For example, a founder once told me they had a team member who wasn’t a good fit for the company anymore. Instead of terminating the employee quickly and cleanly, the founder told the employee to start interviewing for new jobs but to stay on the payroll in the meantime.

It ended up taking longer than expected for him to land elsewhere, and not only was it an expensive move for a small startup but also was terrible for the rest of the team’s morale.

The founder had wanted to do the right thing by that one employee, but in doing so ended up hurting both the overall business and the remaining team members.

Hierarchies Are Unavoidable

“I really think you can’t be an effective leader without a basic understanding about how power structures work and how they influence people psychologically,” Majors said.

Even if you, like Majors, try to make your organization as flat and non-hierarchical as possible, people will still see you as the boss and they will act accordingly. And so should you, to a certain extent: “You can be friends with your team, just like parents can be friends with their children. But ultimately, the formal relationship has to come first.”

And ultimately, a part of being a leader is taking responsibility. It’s up to you to put systems in place so that the information you need reaches you; it’s up to you to lead by example and actually live the values and principles that you espouse.

Transparency Equals Trust

“Transparent communication and honest communication is highly valued and important,” Dang said — and both Majors and Yechuri talked about the importance of transparency as well.

In fact, many of their most painful leadership dilemmas were situations where transparency was not possible. Deciding how transparent to be is one of the challenges of being a leader that never entirely goes away.

Yechuri expanded on the connection between transparency and trust: “I think transparency goes a long way because the more transparent you are with the team, the more the team trusts you, and they trust the decisions you make, and you have to make a lot of hard decisions along the journey.”