As a part of our series about the five things you need to successfully manage a remote team, I had the pleasure of interviewing Siddharth Rao. He is a Staff Software Engineer and a Technical lead in the Revenue Product Organization at Twitter. He’s led several teams at Twitter that work across their ads stack. As a technical lead, Siddharth’s job is to define the technical strategy of the teams he’s leading, mentor and grow engineers, and design products used by advertisers across the globe.
Thank you so much for doing this with us! Before we dig in, our readers would love to get to know you a bit better. What is your “backstory”?
My journey into engineering started when I was in fifth grade with the BASIC language. The fact that I could build something that me and my friends could interact and play with was fascinating. It started with quite simple programs but soon enough, I started putting building blocks together and writing rudimentary video games like Snake and Pong. Writing software all throughout high school, I knew exactly what I wanted to do with my life and therefore, choosing an area of study was extremely simple during college. I graduated from University of Washington in Seattle in 2017 and joined Twitter as a Software Engineer right after.
At Twitter, I started in our Advertiser Experience team where we owned and built ad campaign creation, editing, and managing software for advertisers across the globe. Over the multiple years here, I’ve led front end, full stack and platform teams, all inside our Ads org. After our Advertiser Experience team, I worked in our Revenue Platform organization for some time, leading the Callback team. That team builds systems that allow us to store and retrieve ads data for analytics. Then, I moved back to Revenue product where I’ve recently led our Web Formats and Ad Targeting teams.
Can you share the most interesting story that happened to you since you started your career?
One of the most interesting things I’ve done at work was led the engineering team behind Twitter’s Ads Transparency Center — this was the product that provided transparency to users across the globe about ads being run on our platform, especially focusing on US Elections. The scope and impact of the project was mind blowing when we started building it out and it was one of the most impactful things I’ve done at Twitter. Being able to provide everyone across the globe with tools to increase transparency in ads — something that is generally a black box to everyone — was extremely rewarding and humbling!
Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?
One of the funniest things at the beginning of my career was that I was always afraid to ask any team member about any doubt I had with my work. I was always extremely worried about the optics of asking questions and was hesitant to be a burden for anyone. I would spend countless hours worrying if asking questions is the right thing to do or not. As I have progressed in my career, I have come to realize that it’s not only normal, but encouraged to be asking questions as a new hire!
What advice would you give to other business leaders to help their employees to thrive and avoid burnout?
One of the best realizations for leadership is to deeply understand that everyone has different needs and goals in life. If leaders start expecting all employees to work as much as they personally are or as little as they are, then they are asking to be lied to. It is very important for leaders to take a step back, and understand the different needs of their employees. I personally never ask anyone to work any certain number of hours. That’s the completely wrong metric to use, especially when conditions at home can be extremely varied, even within a single team, let alone a larger organization.
A better way to think about this problem is what really brings your employees happiness and create space for them to live their life that way. For some people, spending more time with family brings them joy. For some, spending an extra hour or two at work is what is fulfilling. Great managers and leaders should respect different ways of working and provide space for all employees to be able to find the right balance for themselves. One rule of thumb I personally use for myself is the amount of creative hours — I believe I have around 5 creative hours in a day and I try to dedicate at least 4 of them to work and use the remaining for personal time. Again, this might not be the right metric for everyone or even the right balance. Strong leaders understand this and create space for their direct reports accordingly.
Ok, let’s jump to the core of our interview. Some companies have many years of experience with managing a remote team. Others have just started this, due to the COVID-19 pandemic. Can you tell us how many years of experience you have managing remote teams?
This would be our first! While I do not have experience managing a fully remote team, I’ve led teams in the past that were spread across 4 time zones. So there are always periods where we had to do async work or rely on someone to fix the problem when they would wake up. COVID-19 has really accelerated us in a direction we were already moving!
Managing a team remotely can be very different than managing a team that is in front of you. Can you articulate for our readers what the five main challenges are regarding managing a remote team? Can you give a story or example for each?
Here are the five challenges that I believe any leader running a remote team should think about:
- Onboarding: How you bring on an employee to the company and the team will shape their. It is extremely important to do this right. Enabling them to ramp up to the codebase, team processes, and helping them learn different ways in which your company operates is of paramount importance. Onboarding has always been a hard problem, but with COVID, this has become excruciatingly difficult to solve.
- Decision Making: For the success of any company, it is important that decisions are made in a principled fashion and made quickly. There are certain classes of decisions which require you to take a much longer timeframe to get to resolution, but most decisions at most companies should be made fairly quickly. Being remote is a huge deterrent to this if companies do not have the right set of principles and methodologies laid out.
- Getting Connected: One of the most important aspects of joining the workforce before COVID was being able to be connected with a lot of smart individuals. In a company of larger size, this obviously becomes a problem — connecting with your co-workers as a new employee becomes quite hard.
- Chance meetings: A lot of growth in my career had been because of ‘chance’ meetings. These are meetings that happen unintentionally — think meeting someone in the cafeteria and discussing a business problem. That allows you to learn more and outside of the domain that you work on day to day. Remote makes this hard, if not impossible!
- Planning and Roadmapping: Planning for the next 6 months, 1 year, and beyond is extremely important for any company. With everyone being remote and in different time zones, it becomes really hard to align everyone on the same page and come up with a roadmap. Every company needs to be bullish on their vision and aligning on that vision generally requires hours and hours of communication between leadership.
Based on your experience, what can one do to address or redress each of those challenges?
There are multiple processes a company can adopt to help with each of these things. It’s also important to know that we are still learning and our teams still adapting to this new way of working. But here are some things we’ve found to be useful for each:
- Onboarding and getting connected: We have created an extensive document outlining each and every task one needs to do during onboarding. More importantly, our team sits in a virtual hangout room for the first few first days of a new employee. This enables us to create a space where the new employee can ask questions right away and not be blocked. This also has helped us a lot in getting better at collaboration as a team! We also encourage all managers to keep their calendars open for the first day of a new employee — this ensures that they are always available to answer any question right away
- Chance meetings: This is extremely hard to replicate, given that almost all meetings during COVID and being remote is intentional. There are no kitchen hours, watercooler meetings, etc. However, we do have scheduled social hours for teams where folks can either eat lunch together or get some drinks in their own homes. This has sparked some conversations about projects and problems at work that we could solve, but we haven’t been able to find the right answer here!
- Planning and Roadmapping: We recently finished a planning cycle and it went quite smoothly that what I had expected. I was organizing for 15 teams to submit their roadmaps and organize around 50 people in the company to work together on creating what we would do for the next 6 months. We used a simple excel sheet for checking in and keeping track of progress for all teams across different dimensions. We had a singular communication channel for announcements and for anyone to ask any questions! Then, we held office hours to respect multiple time zones and answer any questions anyone had about the process. In all, a progress tracker, singular communication channel, time zone agnostic meeting times did the trick for us!
In my experience, one of the trickiest parts of managing a remote team is giving honest feedback, in a way that doesn’t come across as too harsh. If someone is in front of you much of the nuance can be picked up in facial expressions and body language. But not when someone is remote. Can you give a few suggestions about how to best give constructive criticism to a remote employee?
Absolutely correct, different people have different preferred ways of receiving feedback. Some folks prefer to have feedback delivered on video calls while others might want it in written form. The first task of a strong manager is to understand and know these preferences and give feedback in the right channel. Being remote should not mean that there’s a homogeneous way everyone needs to operate. I think being remote has given the opportunity to everyone that there could be multiple ways of operation, even in feedback.
The precursor to feedback should be expectations. Early communication is key here. Being remote means that you might not be able to course correct on a random day when you see the employee and give them a quick feedback. Expectation setting needs to be well thought out and done at a very early stage. This sets the employees up for success for when feedback is due and they understand what is expected from them!
Can you specifically address how to give constructive feedback over email? How do you prevent the email from sounding too critical or harsh?
One way we solve this problem is provide the feedback in a virtual meeting with the employee — this means that we only send them the email when we are in a meeting with them directly. Then for the next 30 minutes, we sit in the meeting room, and the employee goes over their feedback. This creates an environment where they can simply ask questions and clarify any questions that they might have about the feedback. We call these ‘silent meetings’, where the goal is to do a read over of a certain document but providing an avenue to ask questions if needed.
The second most important thing we can do is learn to use the right vocabulary over email. As you mentioned, sometimes words can sound quite harsh if not accompanied by human emotions and physical presence. The most important fundamental to understand here is the goals of the feedback — to help someone grow. There are certain tips one can utilize to frame their sentences to sound less critical too — for example, simply replacing “Why” with “What” goes a long way: example: “Why did you decide to do that” with “What made you choose this direction” is a lot smoother and ends up giving you the same result!
Can you share any suggestions for teams who are used to working together on location but are forced to work remotely due to the pandemic. Are there potential obstacles one should avoid with a team that is just getting used to working remotely?
The most important obstacle is getting used to everyone’s working schedule and being understanding of that. Everyone has different working conditions at home — pets, kids, parents, etc. These different conditions mean that everyone’s throughput at work, work times might be very different. Office provides consistency while remote work provides the opposite. In these cases, it is extremely important that leadership understands this, provides time for everyone to get used to the different (or new) way or working, and normalizes these conditions of working across the whole company.
What do you suggest can be done to create a healthy and empowering work culture with a team that is remote and not physically together?
I would categorize this into 3 things leaders can do:
- Communicate excessively: When teams are physically together, communication naturally takes places and doesn’t require a catalyst. However, when individuals are within the walls of their homes, each and every conversation needs to be intentional. My advice is to increase the amount of these intentional conversations, or at least the chance of these conversations. To everyone I directly work with, we have recurring check-in calendar invites — whether or not we join this, this provides an opportunity to ask questions. This becomes especially important with new employees — creating a space for them to ask questions and not relying on them to initiate these conversations is a great way to unblock them and enable them to onboard them without hurdles.
- Ensure priorities are crystal clear: I recommend everyone in a leadership position to clearly lay out the priorities of the company or the organization and have them in a central place for everyone to be able to glance at it every now and then. This reinforces what is important and helps with focus. As individuals are remote, it becomes increasingly important to make sure that the entire company is using the same lens to look at ideas and prioritizing with the same principles in mind. Any conversation that is not relevant to the top N priorities should not take place, and this is a fantastic method to ensure that.
- Ensure you enable all employees to find their right work-life harmony: This is straightforward — respect different ways of how people like to work and live their lives outside of it. This is also the most misunderstood concept in our industry. People inherently like others around them to be similar to them. However, most organizations would be a lot more productive if they realized that creating space for diverse ways of life would benefit everyone. Understanding that different employees have different living conditions and creating space for them to be happy with the balance of work and life will enable them to excel at work and be happy!
You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. :-)
I’m a firm believer that education is the silver bullet. Unfortunately, a lot of traditional education systems like high schools, universities, colleges are built upon the wrong fundamentals and end up rewarding people for the wrong reasons. The problem then permeates into our society, where everyone places a large amount of value into something that isn’t quite that valuable. An analogy I use here is college degrees being similar to AAA securities that brought the housing market down in 08. The other major issue with these institutions is their lack of ability to create a strong working force — they are leaving millions of students in large amounts of financial debt without any prospects of job opportunities. Only a very few majors being offered by these universities generate the jobs that make the tuition costs somewhat reasonable.
To me, it seems like society values degrees. However, societies don’t quite care if you really went to a 4 year college to achieve that. If people were allowed to take standardized tests like the SATs and prove their proficiency in a certain field, which is what a degree fundamentally does, we don’t need individuals to spend a fortune actually going to colleges.
Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?
“A little bit of slope makes up for a lot of y-intercept” by John Ousterhout has always stayed with me. It fundamentally says if you were to plot your own knowledge over time on the graph, it becomes obvious that it doesn’t matter where you start. What matters is how much you learn — how much “slope” you have. As long as your slope is larger than someone else, you will always surpass them!