Great Leaders Step Back To See Patterns - An Interview with Melissa Leffler

Melissa Leffler is the VP Engineering at Drift, a chat software and conversational marketing platform based out of Boston. Melissa was at the helm of various technology companies before landing at Drift, which was/is undergoing rapid growth. In this interview, she talks about her experiences at each stage of her career, how working at Drift was different and what it takes to be an engineering leader.

Below transcript edited for clarity

Could you tell us about your role and what Drift does?

I am a Vice President of Engineering at Drift, the leader in conversational marketing. Drift has over 150,000+ customers across the globe.

I'm currently managing a team of 75 engineers, development organization - where engineers own quality and continuous deployment.

You have been an Engineering Leader at 5-6 technology companies, what have you picked up from these experiences?

There are always things to learn. A few aspects that hold across all company sizes and stages:

1. Development processes that dictate how you build software are critical. And as long as you have the right communication channels, follow the agile manifesto, have the right people, and give them context and autonomy, you should be successful.
2. It doesn't matter how experienced or how successful a company is. There is no standardized way of building stuff. You need to figure out what the company is looking to accomplish in the current context and find the best way via people, processes, tools, and discipline to support that goal.
3. Perhaps most important, Leadership Values, or Principles, are critical. You can have high growth, a high performing team, but if you are not in alignment with the values of the CEO and the company, you are going to have problems. It's easier to demonstrate these values when the team is small, but it's essential to document and consistently communicate as the company grows. At Drift, for example, we use leadership principles to influence our decision making, performance management, career growth, and how we interview. It also helps us stay excited about Drift and what we are accomplishing. We are looking to build an enduring company in Boston, that everyone wants to work for, and so we have our eyes on the long term.

Love to hear a story where you learned a lesson as an engineering manager?

I have picked up more learning at Drift in the last six months than in my previous six years of my career. At Drift, everyone strives to be a curious learning machine. We don't believe in pivots, we believe in constant learning by iteration.

I felt that my ability to involve people and collectively make decisions was my strength. But one thing I've learned at Drift is that it is not always right.

If you have the right people, right processes, and culture, you let individuals make the right choice for the company. One of our leadership principles is "Seek Feedback, Not Consensus." At previous companies, in striving to bring everyone along, I was too consensus-based.

Lots of Engineers aspire to be Engineering Leaders, but many struggles to scale themselves individually, what are your thoughts there?

My very first boss after college said: "I will be working for you one day. You were born to lead." He thought that I could look at a problem in a holistic way, not just my piece of the puzzle.

At Lotus years ago, I was first approached to be a manager. I declined because I wanted to become an architect. I wanted to build a strong technical foundation before I became a manager. However, after I turned down the role, they put me under someone who wasn't the right fit. So, two months later, I went back to the leadership team and agreed to take that role.

My advice to aspiring engineers and engineering managers would be this: Make sure you build a strong technical foundation early in your career. This foundation will help you go to a deeper depth on strategy and problems, ask the right questions, evaluate choices, and help guide the team in the right direction.

Women have less than 13% representation in Engineering Leadership roles. What can be done to improve this number?

I bought Lean In when it was first published. But I actually didn't read it for a couple of years, since I think of myself as a technical leader, not a female technical leader. But, I figured out that women who are in successful leadership roles should figure out how to give back and pay it forward.  

As Sheryl Sandberg said, women don't take their seats at the table. Leaders need to build the right kind of culture, and team dynamics where women can develop, and female voices are celebrated. I mentor several women who have tremendous potential. My advice would be:

1. Find the right opportunities where your voice can be heard more
2. Give your best in every situation, and
3. Find a good coach/mentor that can help provide the right mentorship.

Drift is undergoing rapid growth. As an Engineering Leader, when do you invest your time to make the most impact?

Scale (platform as well as organization) and team culture are my top two priorities.

Most of the folks at Drift are early in their careers, and many are first-time managers. That's why I'm so focused on career growth, employee experience, and management training.

We also continuously think about growing our platform, maintaining high reliability, analyzing customer usage metrics, and maintaining our bias for action in delivering value.

What approaches do you take to groom your reports to grow and evolve as leaders?

My most important job is to grow my next level of managers, who in turn will help managers and others who report to them. To make that happen, I like to have access to both quantitative data (eNPS of company and manager) and qualitative feedback (do double, triple skip-level meetings with people).

For example, we have a lot of smaller teams with individual tech leads, and many of them are first time managers. We started monthly training for managers where we cover topics on how to conduct productive 1-1s, performance management, how to focus on career growth, etc.

Could you tell me a specific aspect that's unique to Drift's Engineering culture?

Our product and engineering groups are organized into smaller teams of 3 engineers. Often two teams will roll up into a squad, which has a Product Manager, Designer, and Customer Advocate. These teams own specific quarterly goals they create themselves. We give the team a high-level vision, and the team determines tactics and executes.

The ability to look at customer usage by everyone on the team and see the impact of product changes gives everyone the ability to see the impact of their work. This feedback is incredibly powerful.

We let these small teams decide on what and when they release to customers, but our culture focuses on the ship quickly so you can get customer feedback. This way, all members of the team stay close to the customers and data to help accelerate outcomes.

As a closing note, what would be those 2 or 3 words of advice you give to aspiring Engineering Managers/Leaders?

Have an open mind to every situation. Listen and understand the whole thing before you respond.

Lean on others and think in terms of the team. Be a "multiplier" and not a "diminisher."

Have strong values. Surround yourself with people who respect them, and bake them into your culture

Melissa, thanks for your time and insights. Interacting with you was really enlightening for us and we, the BeautifulCode team really appreciate it.

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