This story was recorded in April, 2020. Learn more about Rick on his Linkedin.

Tell us a little about your current role: your title, the company you work at, and generally what sort of work does your team do?

I’m the Strategic Advisor to Uber’s Vice President of Infrastructure, which means I’m part of the Infrastructure leadership team along with the engineering directors and org-wide Program Managers. Infrastructure Engineering at Uber is about 700 people across six sub-organizations like Metal which handles our data centers and servers, Storage, Developer Platform and so on. I work with the VP on things like technical strategy, cultural strategy and special projects.

Strategic Advisor is a wide ranging role, for example I might work on:

• assessing our technology needs over the next two years
• helping prioritize innovation in the roadmap for the next six months
• digging into important areas without a clear owner and helping streamline the ongoing related projects
• learning how the engineers are feeling before or after a big organizational change
• talking to two teams who need to agree on something but are very far apart and seem like they’re having communication issues, figuring out how to help them find an effective path forward

It’s just a really, really broad role that’s a mix of engineering, culture, psychology, organizational design and strategy. There are two ways that I describe it, both from pop culture. The first is like being the Hand of the King in Game of Thrones, and that’s the best analogue I have for it. The second is Leo McGarry from The West Wing, who always said, “I serve at the pleasure of the President.” In my role, I say that I serve at the pleasure of the Vice President of Infrastructure.

Although right now it’s just me, previously there were two of us in the Strategic Advisor to VP Infrastructure role, and we would split the work based on our natural affinity to the projects. She often focused more on projects related to managers and leadership while I focused more on IC’s and engineering projects - though we still managed to do things in both areas

The Strategic Advisor role is a bit unorthodox; it was created by Matthew Mengerink a little while after he started in the VP of Infrastructure role. To my knowledge, our org, and the office of our CTO, are the only orgs which have a role of this type. Matthew created the role because of the value of having full context from within the engineering teams themselves , and he wanted to create that feedback loop to inform his decision making.

It’s a particularly valuable role in Uber’s Infrastructure organization because it’s a really, really broad organization, and I help serve as a synthesized view across all of it.

How does this role compare to a TPM role?

This is an interesting question, because I was just thinking about the distinction between Chief of Staff and my own role the other day. Within the Infrastructure Leadership Team, we have the strategic advisor and program managers, and in the past, we’ve also had someone who filled a Chief of Staff role.

The way I see it, the program managers are an organization-scoped operational role. They're working at a high-level, ensuring that the major programs and areas within Infra are progressing along and evaluated at a regular cadence, operationalizing efforts + initiatives, etc. The Chief of Staff role was one which ensured that the entire leadership machine was working well together - that all the people, groups, messaging, etc, involved in running and leading Infra were operating effectively.

My strategic advisor role is more about taking broad domain knowledge, both technical and cultural, getting into the details of the problems on a personal and organizational level, and then mixing in engineering acumen. From that I’ll synthesize a set of recommendations or insight which I deliver to either the organizational leader or the entire leadership team. Day-to-day, the vast majority of my work is done directly with the org director and with the PM's - delivering recommendations to the director of the org, and then, with his input and approval, working with the PM's to turn them into a reality.

How do you think about the importance of remaining aligned with your sponsor?

It’s funny, because that alignment is key - almost a necessity - for the role. Matthew and I are very aligned on our principles, values, world views, emphasis on emotional intelligence, approach to execution, and philosophies. On so many things we’re lined up, such that it’s almost a symbiotic relationship.

Alignment with the sponsor is really critical to be effective, but it’s more than just the dispassionate connection between Strategic Advisor and Vice President. It’s also about the connection between Rick and Matthew as people, and making sure that’s a good fit.

In my role we’ll often go weeks without being in the same room together, but I still have to operate as if I’m his direct proxy. So I go into a room and think, “What would Matthew do here? What is the question he would want to ask? What guidance has he given on this problem?” Because I can’t always run back to him for clarification, it’s essential to develop and maintain a deep understanding of his world view. That’s essential for me to retain the very deep trust required to be his representative and effectively carry out his strategy and vision. People need to be confident that I’ll always give the same answer that Matthew would give if he were there.

It also means that I have to truly understand his goals, intent, values and principles, to make sure that I’m ready to stake my reputation and credibility on pushing them forward. Often, part of my role involves advocating for or translating his vision and/or implementation to engineers, sometimes when supplemental context isn’t always known. When I do this, I have to make sure that I not only understand the logic and value of what he’s doing, but that I also believe in it myself - otherwise, advocacy becomes hard, not to mention disingenuous.

This is something I really struggled with a lot when I started in the role. Matthew would constantly tell me, “You’re my representative; you should feel free to push on and perform things using my name and role.” That was difficult for me because I’ve never been in a role like that before. Previously I’ve always operated using my own name and reputation, and now I was operating under the aegis of the Vice President and everything which that carried . Over time I’ve learned how to be deliberate with using that hammer, since you don’t want to overuse it.

I’ve also learned that I have to let folks know which hat I’m wearing sometimes. I love to mentor people, but sometimes folks aren’t sure if they’re getting the strategic advisor working for the benefit of the organization and company or the mentor, working for the benefit of that person and their career; I try to let them know which role I’m currently in within a particular conversation. If I meet with someone I’m mentoring, they might want to get advice about changing teams, or even leaving the organization or the company, and they want to know which perspective I’m giving advice from.

What does a “normal” Staff-plus engineer do at your company? Does your role look that way or does it differ?

I think the biggest difference is that other senior-plus engineers work primarily on technical work. They are leaders, so they do get into the realm of emotional intelligence, communication, collaboration, conflict resolution, evangelism and so on, but still 80% of their daily efforts are driven by technical concerns.

Whereas with me, there might be weeks where I’m focused on a project around group psychology or organizational design. Technical concerns are not always the pure focus that drive my day to day - though they are always there, if even just in the background.

How do you stay aware of reality on the ground now that you’re developing less?

When I was an engineer I could do this passively, because you’re in the code, trying to push commits, dealing with the friction of provisioning and operating services, etc. That approach doesn’t work anymore, since I’m not touching code very much; so now, gaining that data and awareness requires an active process.

One thing I’ve done is continue to sit next to my old team so I can hear them work. Maybe they’ll complain about a service’s stability, or a gap in our tooling, and it’s helpful to keep hearing that.

I also constantly ask folks questions about their developer experience. I keep a list of people in my head of folks who are good at surfacing problems and giving feedback on approaches, and I reach out to them frequently. Sometimes these reach outs are more structured, literally a survey for input, and other times it’ll just be a quick message checking in.

I also tell folks to send me non-critical path work that doesn’t have a strict timeline, and I try to use that as an opportunity to stay fresh in writing actual code. I have to be careful not to get in the critical path of our actual product though, because I know I won’t have much bandwidth to maintain the code going forward.

How have you sponsored other engineers? Is sponsoring other engineers an important aspect of your role?

One of the things that’s special about this specific role is that it’s essentially a built-in mentorship with the Vice President. When I got started, he asked me, “What do you want to do in five years? What are you aiming for?” At the time, I really didn’t have clear answers to those questions. For a long time my perspective has been that being able to write code, in our current time, puts you in one of the best positions in the history of humanity, in terms of job security and trajectory, and that seemed like enough for me.

As I spent time thinking about my goals, what I really came away with was that I love being a visible reference for other engineers, especially other minority engineers, and helping people here at Uber or earlier in their career. I especially enjoy helping people who are just getting into the industry, and might still be a little intimidated by it. That’s a huge part of what drives me, and this role has helped me realize and admit that to myself. Before I didn’t accept that as a valid purpose, but I realized that if it’s what you love, if it’s what you’re passionate about, then you have to go for it.

Another reason mentorship is important to me because throughout my life and career, I’ve had six people that I consider key mentors. Each of them, at various times, have provided massive impact and influence upon my life - I would not be anything close to who I am without their past and continued guidance. And I’m both extremely grateful for them and also constantly aware of how much they’ve guided me. So, I always recognize the power of a mentor and want to make sure I can provide that for others. And sometimes, mentors don’t even know how their words or actions change you, the ripple effect they can have, even years later. So, I always try to make myself available for others as a mentor, because you never know when you can have that type of life-changing impact on someone, or how. It might just be the right word, the right perspective, the right push from you, at just the right time for them.

I’ll always tell people, “Seriously, if you need me, just come ask for help.” This is one of the most exciting parts of what I do, and there are a few different ways I try to make myself available.

One is that I give an Engucation (what happens when you blend engineering and education into a single word) class every month to most new hires in engineering. That class is called “Lessons + Questions” and it’s literally just a place where they can ask me anything they want about Uber - technical, cultural, whatever - and I’m as candid as possible. At the end of that, I let people know my email and that they’re welcome to reach out. A good number reach out to me after that and I give them advice on their careers, working at Uber, or whatever. Other times I’ll have people who just run into me while I’m around the office and ask for advice.

I want to be visible as a Black engineer, showing others that we are here and this is doable. Once I realized this was an important motivation for me, I knew that I had to get better at public speaking, because that’s such an important way to scale myself as a role model. Public speaking used to terrify me. I used to hate public speaking. But because it’s such a key way to reach large numbers of people, I told myself I had to learn to like it, and since then I’ve learned to be an effective public speaker and have actually fallen in love with it. It’s now one of the most exciting things I do - it’s like a roller coaster; everytime I do it, I get nervous, but it’s a thrilling, fun type of nervousness and I get a huge rush while I’m doing it.

Do you think about building your external brand?

I have a couple of friends that spend time building their external brand, one of whom is getting back into it right now. He realized that his work at Uber was so intensive that he’d pushed external work to the wayside.

I’m a bit more passive about it. When I’m involved with something that gets written up publicly or I give a public talk, then I’ll post a link on LinkedIn, but I don’t write my own content at all. I think about doing it, and I’m interested in doing it, but I don’t. I tend to think through speaking, so writing this way requires a lot of preparation to organize my thoughts, and I’ve not spent much time doing it externally so far.

You first got the title strategic advisor at your current company. Were you hired as a strategic advisor? If not, what was the process of getting promoted to that role?

My path was completely unorthodox. It wasn’t planned, and there really isn’t a reproducible pathway to it, more of a fortunate series of events. Previously Rob Punkunus was in the same role, and when he decided to leave he was asked by Matthew to suggest potential successors. He suggested me and Kate, and both of us ended up serving in the Strategic Advisor role.

Matthew and I had already had several positive interactions before that, where we’d started to identify that we had similar views and values. For example, at one point we had a rash of nasty comments submitted anonymously to our Questions & Answers meeting, and it really bothered me to see our culture heading that direction. I stood up and spoke at one of the Q&As asking folks to find a more constructive way to surface their concerns, and I think that resonated with Matthew.

When he first suggested that I take the role, I had a ton of imposter syndrome about it. I tried to get him to rescind the offer, thinking it wouldn’t be a good fit, but ultimately I did accept and have been in the role since.

What two or three factors were most important in you becoming a strategic advisor? How have the companies you joined, your location, or your education impacted your path?

In addition to Rob’s recommendation, the most important factor was doing visible work that aligned with Matthew’s values. One project I worked on was joining the working group to understand and improve SRE’s culture back in 2017. The working group was already planned before Susan Fowler’s blog post went out, and our first meeting was coincidentally three days after she posted it. I really think the culture working group did some great work, work which myself and the other group members are extremely proud of and over eighteen months we really moved the culture of a hundred person organization in a meaningful way.

Additionally, I’ve always just been personally fascinated with things in the realm of both culture and human psychology + behavior. In my career, at the companies I’ve worked at, culture + group psychology has often been the hidden x-factor that turns organizations from good to great. I’d already been satisfying my own personal curiosity in the area with books and papers on things like behavioral economics, behavioral science, etc, so that natural interest has helped nudge me towards where I’m at now.

Can you remember any piece of advice on reaching Staff that was particularly helpful for you?

Throughout my career people have always told me that I’m much more impactful and have more potential than I realized. I never listened to that, and for me, as well as many other engineers, especially engineers that are minorities, we spend a lot of time doubting ourselves. It’s so easy to only see the bad parts. We might not recognize when we’re in a meeting and speak passionately about something, and that people are really listening to us. It really helped to have people keep telling me that I didn’t realize the impact I was having, that my viewpoints were not only valid, but actually influential in the organization.

Another thing that’s helped is having mentors. Specifically I like mentors who are constructively antagonistic. What I mean by that is that they throw me into things that utterly terrify me but they’re certain I’m ready for. They’ve helped push me way beyond what I thought was possible for me. These have generally been managers who I’ve worked with, but where we’ve been able to mutually learn from each other.

What about a piece of advice for someone who has just started as a Staff engineer?

This goes back to how I got where I am based on having a broad set of interests in organizational psychology, culture, mentorship and so on, in addition to the technology. I’ve never been a pure engineer that’s just deep in the code 24/7. I’ve never been that person, and I had to make my peace with that.

For me it’s been important to follow my passions. Recently that’s been around mentorship, but it’s also been around other things like machine learning, which has always been a hobby of mine. I love how machines can generate insights that mimic how people think - it’s the perfect marriage of my interests in technology + psychology.

So I have these passions that I stoke, and then when opportunities to align those passions with something the company needs arise, I take them. For example, my previous team at Uber was generating insights into fleet utilization for capacity planning purposes, and that was a great chance to pull together my interest in machine learning and site reliability.

Small companies give you the chance to do many different things, but at a certain size companies also give you the unique opportunity to specialize in your passions, and that for me has allowed me to maintain both impact and passion despite never being the person to sit beyond the keyboard and knock out code all day.

Did you ever consider engineering management, and if so how did you decide to pursue the staff engineer path?

It’s something that I think about sometimes, even now it’s something I’m thinking about. It’s on my list of possibilities, and throughout my career folks have asked, “Have you considered moving into management?”

What I want to focus on right now is becoming effective as a high-level, big-picture leader. Eventually I’d like to develop the people management skill set too, maybe somewhere in the medium future. The thing that appeals to me is that human behavior excites me to no end, and people management is a great opportunity to spend time on that.

What are some resources (books, blogs, people, etc) you’ve learned from? Who are your role models in the field?

You know, for the first two-thirds of my career I used to love reading as much technical content as I could. I would be on YCombinator or my RSS feed all day reading about distributed systems, reliability, etc. These days I’m much more into reading about behavioral economics, behavioral science, human psychology, organizational strategy and so on. Some people I really enjoy in those realms are Daniel Kahneman, Tim Harford, Dan Ariely. There are also some amazing podcasts out there - Freakonomics, Choice-ology, Hidden Brain.

Also, last year I started compiling a reading list of books about the human brain and behavior which I share with anyone who’s also interested in the topic(s).

I do still keep up with r/linux and r/programming on Reddit, which have replaced RSS feeds for me in discovering new things to read.