Impactful People from 5+ Years at Lyft: What I Learned Watching the Company Grow from 300 to 5,000 Employees

First day at Lyft, March 2015

When I reflect back on five and a half years at one of the fastest growing, highest profile startups of the late 2010s, I think more about people than projects. In many westernized cultures like the US, we tend to value individualism — the notion that someone is a “self-made” person. But the reality is that everyone relies on support from other people. Every project I worked on at Lyft, even if it was “my project,” was a collaboration with those who supported me on my journey. Were I a car, these people were the infrastructure that enabled me to go places. This post is dedicated to these people.

“…people will forget what you did, but people will never forget how you made them feel.” — Maya Angelou

I want to tell you stories of person I enjoyed working with at Lyft. There are so many. Instead I’ll stick to a few that standout¹ while providing a summary of what I think makes someone generally successful in their role.

The 4.5 Styles of Individual Contributors (ICs)

Every IC is a bit different. But when I look back on those I really enjoyed working with, they fit into one of these four and a half categories.

  1. Someone who is supportive and collaborative. This person will stay late with you to finish a project. They stand by your side and help.
  2. Someone who can produce a high volume of output. This person will take on tasks no one else wants to do and get things done with perceived ease. They do a lot of work.
  3. Someone who will say what everyone is not saying. This person will sometimes be blunt but will always say some deeper truth the group was afraid to face. They say the hard things.
  4. Someone who can define a shared direction and plan. This person talks about vision with team members and stakeholders and they like to plan. “ is when vision and planning are two different people. They set the vision and help get everyone there.

True to what I learned from the categories above, every IC actively adds something valuable to the group. They do so in their own way, but no style is more important than the other. The group becomes dysfunctional if one style is missing or it is too mono-stylistic.

I have immense gratitude for those I’ve worked with who embody the styles I do not. They enabled me to perform better and made my job more fun. The following story is about someone in the supportive and collaborative style.

Standing By on Launch Day

This is a familiar story for most engineers. It’s time for launch. The code goes out. The code has an unexpected problem. If you’re lucky, you’re doing this early in the day so you have plenty of people around to help. But in reality that is not always true.

The large open office, with glass walls, and wooden top desks, sat mostly vacant. It was evening. I was typing away as fast as I could. A few of my teammates had to leave early but one stayed late. This person was preparing to pack up and go home to their family. I could hear the shuffling of a backpack and readjusting of items on the desk. But then the packing paused.

I had a problem. Thankfully it was a small bug. But I was stuck. My teammate leaned over, “I noticed as I was catching up on messages that we have an issue in the latest deploy, have you had any luck figuring it out? Want some help?” Those last three words were like a soothing bath for my ears. “Yes please,” I said.

They unpacked. We both jammed on our laptops. We got stuck. We tracked down someone else who was still online who was able to help us. Finally we figured out a workable solution, made the fix, and made the deploy.

During this time we hopped between each others’ computers, drew on whiteboards, walked around the office, and chatted about life while we waited for the automated deploy process to complete. I hesitate to call it fun, but it was fun. We made quick progress on fixing the bug, but we did it in a way that did not add more stress to the situation. Actually, the presence of this other person made the situation less stressful. They had made it clear they were going to stick with me until we figured out a solution, even calling home to let their family know it was going to be a later night.

Thankfully late nights were rare. But this teammate’s desire to simply be by someone’s side as they tackled huge projects and confusing bugs was not rare. This person did this for me countless times, ranging from “let’s figure this out” to “what if we tried it this way” to “need some help with that” and countless other catch phrases. They made me feel like I always had someone to call for backup. And honestly, I can’t imagine a better kind of teammate to have.

Engineering Managers (EMs)

It does not feel good to be a bullet point on someone’s to-do list. People know when the person interacting with them genuinely cares. You must find a way to believe in each person and truly see their unique value. By doing so you become interested in them. This interest allows you to support them by lining up projects that help them grow while standing behind them in case anything goes awry. This is a quest to better others. Yet in doing so, you better yourself — we are all connected. Further, the trust you build with those around you gives you access to crucial information from the frontlines that no one else in management can access. You will be able to see things before others and most importantly you will be able to support those around you before they admit they need help.

If I could distill the best engineering manager into one word it is: support. In the first story below you will meet my first manager. They believed I was more capable than I believed I was. In the second story below you will see how this quality of believing in me continued through my last manager at Lyft.

Seeing the Best Version of Me — My First Engineering Manager

I was a new member of the engineering team at Lyft. My manager had helped me transition from my technical role on the growth marketing team. I had completed several smaller projects. Now it was time for My First Big Project.

But I was still new. And I liked to hesitate. I liked to see the end before I took the first step. Because of this, I undersold what I was able to do.

My manager noticed this. They never questioned my ability. They surfaced people to help me when I got stuck. They always had the next project lined up for me, which was a tiny step more complicated than the one I had just finished.

My First Big Project was one my manager suggested I work on. We were rebuilding our internal system for managing the documents a driver needs to use Lyft. It was a three person team. I owned the internal interface our operations and support teams would use. Literally thousands of people, every day using the tool I made. No pressure.

Our first standup meeting. My teammate to my left starts talking. They list what they are working on, “Writing a spec for document data structure and api.” Next teammate over, “Writing a spec to do the migration of the old documents to the new documents.” Now our product manager, “Setting up user research interviews for you all to see how documents are used.” Next, our manager. They skip. All eyes on me. <insert Tina “uhhh” from Bob’s Burgers meme> then I say, “Writing a spec for the internal web interface.” Back to our manager. “Great! Nice work everyone. Let me know if any blockers come up.” I made it, alive. And I made it through every standup and subsequent set of tasks thereafter, also alive.

There is a concept in psychology called cognitive dissonance. It’s a comparison of reality against the perception of reality in your brain. A greater dissonance means the perception and reality have a greater difference. Everyone has some level of dissonance.

My manager perceived me as capable of handling any tasks. The reality is that I’ve been able to handle the tasks I’ve been given. I perceived myself as being unable to do most tasks. Thus, my manager counterbalanced my internal dissonance. They perceived me as more capable than I perceived myself.

This is what setting people up for success looks like. There are so many managers who fall short on it. You need to see a person as capable. You need to see the best version of them and line up opportunities to allow them to execute on this best version so they can believe it themselves. You need to be thoughtful about the next step you provide to make sure you’re not pushing them off the deep end. And you need to show up, every day, for that person, acting as a guardrail to catch them if something falls off course.

It’s simple: If you treat someone as the best version of themself and stand behind them, they usually act as the best version of themself. The opposite is true too.

My manager did this for me every time, for every project, for the multiple years I worked with them.

Seeing the Best Version of Me — My Last Engineering Manager

I started the day with a broken toe, the day I planned to tell my new manager I was leaving Lyft. I hadn’t slept well because of the pain in my toe and I jumped on a virtual doctor call at the earliest hour the service was available. Seven hours later, I had an x-ray and awaited a treatment plan. I had to reschedule my meeting with my new manager several times — I sent them a message letting them know what was going on.

I had met this manager only once so far, they were new. Because our relationship was so new, I had been anxious about breaking the news about my leaving because I was unsure how they’d react. Certainly, I reasoned, no one likes to hear about someone quitting.

I explained my reasoning to my manger — after taking some time to reflect on my last few years of health challenges, I feel a calling to use my skills to improve how people interact with their health and healthcare systems. Their reply was, “I’m so excited for you!”

I was not expecting that. We spent most of that meeting talking about how excited they were for me. They were interested in my plans and I was interested in learning from their experience listening to what calls to them. They understood me. But more than that, they supported me, in the best possible way a manager — or frankly, any person — could in that moment, by cheering me on and wishing me success in listening to my inner wisdom. Anyone can work a job, they explained, but I am choosing to take a risk and follow a calling. And that’s scary! Especially given the person I was in the story above, from five years ago — the one afraid to take a leap of faith.

Even during my last week, with a manager I barely knew, the manager showed up and saw the best version of me. I had grown. And while that meant leaving Lyft, I felt like I was leaving with the same sense of support that had helped me grow in the beginning.

Product Managers (PMs)

The best product managers understand how technical systems are built, have business experience, and value people. They can articulate a concise, well-defined vision rooted in patience, consistency, flexibility, and kindness. The kindness is most effective when it does not come from self interest, but instead through empathy and genuine interest in the success of others. We forget that, especially in the Silicon Valley bubble. The fast pace makes it easy to treat people like disposable objects or blockers along your path.

The teams that I have stayed with the longest were the ones where I felt like I mattered and where I felt like those I worked with were valued regardless of their role. I undoubtedly did my best work on these teams. Let’s meet a PM who did not rephrase what people said and involved them in decision making in the story below.

Support the Momentum Without Injecting Your Opinion

It was the end of a week-long offsite. Forty people were crammed in a room with mediocre airflow. We had spent the last four days in breakout sessions. The days were meaningful, with fun activities afterwards. But we were still a bit tired by the end of it all. We needed a volunteer to help us make sense of all the observations and feedback from the week.

This was not my first experience like this. What often happens is that a PM in the room gets up, gathers feedback from everyone while writing it on a whiteboard, and shapes actionable goals, to later prioritize or drop. To the close observer, the goals end up looking an awful lot like what the PM wants to do and the feedback is grouped in that way. This experience essentially renders the entire week useless — feedback becomes confirmation bias. So, I was expecting something similar.

A PM volunteered to write the ideas on the whiteboard. People in the room provided feedback. But then something interesting happened. The PM was simply writing down what they heard, instead of paraphrasing and not immediately grouping it. Everyone’s feedback went up as their feedback, not the PM’s words. Upon completion, the PM asked for volunteers in all roles in the room to come up and help categorize the items. This representative committee presented these to the room to gather additional feedback and ensure ideas were properly represented. Later actionable goals were made and prioritized. This was again shared with the group for feedback.

The PM wasn’t injecting their own ideas about what the team should be working on. They let the most important project emerge on their own. They wrote our exact words. They were a cheerleader for all the ideas in the group. This also made us all more open to hearing the PM’s ideas of how the feedback could be grouped together into goals. It was genuine interest in the success of the team and how each person could contribute to that.

Executives/VPs/Directors

A good organizational leader should care about the people in their organization more than their ego. Leaders who cultivate curiosity and ownership — essential ingredients for innovation — invest in feedback channels so people feel heard, are open about decisions with their team, relentlessly ask questions to understand, and realize that every person has something valuable to contribute.

A helpful way to think about feedback channels is to fill a matrix of public, private, verbal, and written.

Leaders should model open communication by acknowledging mistakes and asking questions to learn more — simply be an honest, genuine person. Leaders define communication norms through their actions. See the Lunch with the CEO story below.

When I’ve seen people in this role be successful, their role is about creating organizational structure that makes it easy for people to step forward. Think about how I am able to talk to my manager’s manager’s manager in the Seek to Understand story below.

Seek to Understand

You know that awkward furniture offices have to make the space look fun but isn’t really that practical? That was this room. Delicately perched at the edge of a strange chair, I had my first one-on-one meeting with my manager’s manager’s manager, sitting slightly diagonal across the room, over something that resembled a coffee table.

Despite the furniture, the conversation took off. I wanted to start a mentoring program for engineers. It was something a growing company needed to continue to grow. I had identified a group of engineers to start with and had developed an initial plan to test the program. “Tell me more about what you’re noticing,” they said. I reply. They ask, “Why do you think that is?” I reply. “Tell me more about how you’re thinking about working on it.” I reply. And the conversation proceeded something like that, with them occasionally suggesting a few ideas and options to consider.

We then went broad. “What else are you thinking about?” “How else do you think we can support engineers?” This launched a brainstorm of ideas, which they then helped categorize into memorable chunks that we decided the organization could work on, with my mentor project being a piece of it.

The meeting concluded. What the heck just happened? My brain scrambled to find the replay button.

The first time I met this manager was in a group setting. They were new. They set up meetings with every team. Those meetings were a chance for them to ask the team questions and the team to ask them questions.

The second time I met this manager was during an issue I had trying to change teams. They asked me questions about what I wanted to do and what happened.

This manager recognized there is something to learn in each interaction. They recognized that the learning is sometimes a few layers deep — the issue is not always the presenting symptom. They see solutions as collaborative. They chunk complexities in order to reduce the complexity. Conversations almost felt like a form of therapy or coaching instead of trying to convince the other person.

The result? I felt heard. They got valuable information about what it’s like to be on their team. I felt like a valuable member of the team whose voice matters. They got someone who is excited to work on their team and therefore does better work. It’s win-win. “Seek first to understand” in action.

Lunch with the CEO

I joined Lyft when it was just over three hundred people. At that time, Lyft was known as “those cars with the fuzzy mustaches on them.” Bright-eyed and bushy-tailed my first few weeks at a San Francisco startup, I was eager to uphold a Lyft tradition of setting up a “coffee chat” with many people. I asked for one with our CEO, Logan.

I sent what must have been a very shy but excited sounding email to Logan’s EA. A day later, I had an invite in my inbox. It was several weeks away but I didn’t care, I was levitating with excitement that I got a reply.

During quiet moments in the day, my mind would drift into what I should talk to him about. I came up with some questions. And I waited.

The day finally came for my meeting. The wait was over. Just kidding. We had to reschedule. Life is that way sometimes. He is the CEO after all. I got a new date and I was excited our meeting wasn’t removed from the calendar. This happened three more times.

Several days later, I got caught up in my work and worked through the beginning of the lunch hour. My team had already eaten. So I walked to the cafeteria and I got my food. The large room was full of large communal tables, all mostly empty.

I got about half way through my plate when someone walked over to ask if they could join me at my communal-sized table of one. It was Logan, the CEO. He apologized about having to reschedule our meeting so many times and he asked if we could eat lunch together now instead.

Stunned that he knew who I was and confused that he was apologizing, I stumbled through some form of a yes. We ate lunch together. I’m a slow eater, but I went especially slow, so as to not finish my plate before him. I wanted to talk to him and here I was. No empty plate was going to cut that short.

It was perhaps an unremarkable conversation. He did not reveal some secret revelation about the universe nor did I. But, it was a meaningful conversation. I’ve always valued people’s actions over their words. And here he was, showing me that he cared enough to know who I was and to be concerned about making sure we met. And mostly I remember how he made me feel: that I mattered and my curiosity mattered.

Three years later Logan tried out a Lunch With the CEO program for the company. Lyft was a few thousand people by this time. He met with various teams over lunch. My team was one of the first. We shared some details about our lives and drifted into talking about work. He asked a lot of questions, “Tell me more about this feature you just launched…What excites you about it?”

He seemed to know the details of what our team had been working on, and what we plan to work on better than most of us on the team. He did his research and he was speaking from a place that cared, both about us and about what we were making.

During that lunch, he saw my teammates and I as people he could learn from. That made us feel like we mattered and had ownership over what we did. I can’t imagine a better impact that a CEO could have on their employees.

It still happens. Just a few months ago a few members on my team stayed for dinner and ended up having a similar experience of Logan joining the table to eat with them.

Final Thoughts

People ask me about how my role has changed during my five and a half years. Mainly, it’s that I wear fewer hats but I’m able to go deeper. But the one constant has been the organizational values.

I joined Lyft for one reason: It was one of the few tech companies that talked about the human impact of the service it makes. This has not changed during my five and a half years. Was transportation and ride sharing interesting to me? Sure. But so were many other technologies.

Mission is a company exists in the world. Values are a company exists in the world.

Lyft’s mission: Improve people’s lives with the world’s best transportation.

Lyft’s values: Uplyft others. Be yourself. Make it happen.

Mission gets fuzzy in Silicon Valley. startup is out to “change the world.” While I applaud those efforts, the statement becomes noise. Every company has a world changing mission. Few companies talk about their values.

Values need to be consistent across every touchpoint a person has with a company, whether as a customer or employee. Each of the people in the stories I told embody at least one of the Lyft values.

Is Lyft perfect? No. Is it always true to its values and does everyone always have a perfect experience? No. But the one unifying factor across every person I enjoyed working with was that they were more interested in supporting others than boosting their own status. There are an overwhelming number of people like this at Lyft, from CEO to IC. It is why I think Lyft as an organization and service will continue to be successful for the long haul. And it’s a learning I will take with me throughout my life.

Thank you once again to my many teachers at Lyft and the many more teachers still yet to come throughout my life.

1 The stories are true. But like any story written after the fact, the exact details may have been modified by my memory. Please accept them as such. To preserve anonymity (except the CEO story), I remove identifying information including gender — this is also to support the idea that can be these people.

I’m a design and growth focused product maker on a mission to make the world feel more human. Learn more: http://seanbolton.me/