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Lena Reinhard of CircleCI: “Ask questions”

Ask questions. This is one of the most powerful tools of an effective manager. The basis for managing well is listening, observing, taking note of what motivates your teammates, and digging into the responses to your questions. I usually gather questions before I meet with my team members one-on-one so I am prepared and can […]

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Ask questions. This is one of the most powerful tools of an effective manager. The basis for managing well is listening, observing, taking note of what motivates your teammates, and digging into the responses to your questions.

I usually gather questions before I meet with my team members one-on-one so I am prepared and can guide the conversation toward understanding them better. Asking questions helps you adjust your leadership style to the individuals on your team. It also ensures that they feel understood and heard, which are important pillars of inclusion and belonging.


As a part of our series about the five things you need to successfully manage a remote team, I had the pleasure of interviewing Lena Reinhard, Vice President, Product Engineering, CircleCI.

In her 15+ year career, she has built and scaled high-performing engineering organizations and helped distributed teams succeed. Lena is passionate about helping teams increase their effectiveness and business impact, and scaling culture for organizational performance and health.


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”?

I have a background in finance, arts, and media, but have always gravitated towards leadership. My first tech job for a small SaaS startup was intended as a short-term copy writing gig and turned into a role as marketing and key account manager, running project management, account management, and marketing.

Around the same time, I started contributing to open source projects, and shortly after co-founded my first software company and became a CEO. I started managing distributed, fast-scaling engineering teams, quickly realizing that I really enjoyed this work, and that it was a good match with my prior experiences and background.

Can you share the most interesting story that happened to you since you started your career?

My first formal leadership role was as CEO of the company I co-founded. I’d been consulting for the founding team with research and assessments towards the founding process and business setup, and one day, on the way back from lunch, they asked me whether I wanted to become CEO. I thought about it and said yes.

The transition into leading an engineering team for the first time was a challenge in a multitude of ways. At the time, our team was building software to support Ebola outbreak response teams in West Africa. The work itself put a high level of stress and other psychological challenges on everyone on the team. It was also a distributed team across several countries in Europe and West Africa, operating in a critical space during a pandemic.

My work required bringing as much focus and order as possible to this, while building out this team a lot and as fast as possible, but also maturing our practices quickly on the fly. Due to the parameters we were working within, a lot of it was about staying flexible and adapting as we went.

The other crucial aspect was creating and holding space for the team to deliver high-quality software, learn quickly, focus, and build resilient systems of technology and humans.

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?

I learned a lot of hard lessons when first starting out. Due to the intense nature of the work and environment, I had to lead largely intuitively and in reactive ways. This meant that I didn’t have a good sense of what it would take for others to be effective in this role and work. It put a huge strain on myself, and also inhibited my ability to delegate effectively and build out better structures for the team. A colleague who I worked with at the time once told me after we’d both moved into different roles, “You don’t understand what makes you good at this, which means you’re not able to bring it out in others.” This hit me because it was true, even though I brushed off the first part as an odd compliment at first.

I had to learn how to delegate effectively and invest in developing leaders around me, to be able to run teams and organizations more effectively. I believe that it’s our biggest job as leaders to pull people up around us: remaining a critical part of a technical or human system can lead to feeling a sense of relevance, but actually is a terrible sign. The thing that tickles our ego the most is the sign that we’re not doing as well as we could; and to me, that’s the essence of what leadership means in a nutshell.

What advice would you give to other business leaders to help their employees to thrive and avoid burnout?

Focus on communication, expectations, and trust, to help teams avoid burnout during uncertain times. I think a lot has to do about being clear and transparent, while maintaining a bigger picture and a sense of purpose and impact, and continuously reminding employees of that. It’s on us as leaders to build organizational structures that provide the scalability and flexibility that organizations need especially in times of high uncertainty and change.

But leaders also need to take care of themselves, too.

A manager’s role typically requires a lot of critical and strategic thinking, problem solving and effective communication. I start every day with some strategic planning, while I have a freshly caffeinated brain, and before I dive into the more tactical aspects of the day-to-day work, this really helps me maintain sight of the big picture. In order to keep myself energized and sharp for my teams when they need me, I plan out my daily schedule based on my energy levels, and make sure to take breaks.

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?

I’ve been building, growing, and leading distributed engineering teams for the last 6+ years. Now, as VP of Product Engineering at CircleCI I have the pleasure leading a globally distributed team of 70+ engineers and developers spread across 3 continents and 9 time zones. All of whom are working to help our users solve the world’s most challenging software development problems through CI/CD.

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?

I often describe my work life every day as being made up of millions of pixels. My teams are distributed across the globe, and most times, my teammates are reduced to pixels in Zoom meetings, Slack chats, and emails. We bring different backgrounds, experiences, communication styles and collaboration preferences, and many more differences to the (virtual) table. Much less happens organically through osmosis, or at the literal water cooler, but at the same time many of the challenges all teams face, like communication and collaboration, are exacerbated when we’re distributed across locations and time zones.

Here are five ways I combat those challenges:

  1. Build trust. The first step in creating structure is building relationships. At CircleCI, for example, we’ve built structures such as regular pair programming rotations and engineering talks to help our distributed teams do that.
  2. Structure around how you collaborate. As our engineering department has expanded, we’ve moved to a more streamlined engineering delivery process. But each team decides how to implement day-to-day processes such as daily standup meetings, planning sessions, or collaboration. Every team has specific needs, and they know how to best address them.
  3. Remove blockers. We all know how frustrating it is to be stuck. Building pathways — for example, setting up regular pair programming rotations, investing in self-serve information access, supporting each other across teams, and establishing knowledge-sharing — can help keep things moving forward.
  4. Continuously improve. Use retrospectives to discuss and improve how your teams work together. Blameless postmortems are also a great tool to help understand problems and drive solutions. Code reviews, mentoring, and knowledge-sharing can help team members learn from each other. How you talk about learning — especially the way you discuss mistakes — matters. These decisions will fundamentally shape the culture of your teams and determine whether people feel safe or threatened in their core needs.
  5. Drive toward alignment. Communicate strategy, direction, and relevant tactical details to your teams — and remember that it’s almost impossible to over-communicate these details. Always repeat what’s important.

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?

The foundation of being a good leader relies on building trust-based relationships. Here are a few ways to start:

Ask questions. This is one of the most powerful tools of an effective manager. The basis for managing well is listening, observing, taking note of what motivates your teammates, and digging into the responses to your questions.

I usually gather questions before I meet with my team members one-on-one so I am prepared and can guide the conversation toward understanding them better. Asking questions helps you adjust your leadership style to the individuals on your team. It also ensures that they feel understood and heard, which are important pillars of inclusion and belonging.

Connect to the bigger picture. Creating an impact is an excellent motivator, so make sure the members on your team understand how their work helps users or supports other teams. While goal-setting frameworks like OKRs can help with this, it is also crucial to align initiatives with higher-level goals and connect them clearly with user value.

Give feedback. One of the best things you can do as a manager is to support your team members’ growth. Give feedback regularly to help them understand where they are and how they can grow — by course-correcting where needed and setting new goals in areas in which they excel.

Also, managers need feedback too: Don’t forget to ask your team for feedback so you can also adjust as needed.

Can you specifically address how to give constructive feedback over email? How do you prevent the email from sounding too critical or harsh?

I would generally advise to choose the feedback medium based on the employee’s preference — have a conversation about feedback preferences in your first 1:1, and stick to those: the more aligned feedback delivery is with what works for the employee, the better the odds that it will land. Here are three tips to help you get there:

  1. Use conclusive communication: When I send messages to my distributed team, I make an effort to set up the conversation so they can reply and then that interaction is over. I also always consider the time of the day when I approach people.
  2. Set expectations and over-communicate: Distributed organizations in a high growth stage have a lot of ambiguity, which is challenging. My job is to create clarity and provide the leaders and teams in my organization with context so they can make their own decisions.
  3. One way I do this is through recurring emails: a weekly overview sent to my team, highlighting what’s been top of mind for me, exciting news, as well as upcoming events or strategic topics I’m thinking about.
  4. I also utilize recurring meetings with my direct reports. Recurring meetings are often looked down upon. But, by making sure that these meetings are always useful for all parties involved, I find them helpful. Not only do they encourage relationship building, which is an important investment, they provide an outlet where people can expect information, which reduces uncertainty.
  5. Trust your team and resist the urge to micromanage: To do this I create a culture of visibility and accountability by using shared goals, as well as goal trackers and weekly one-on-ones. I focus on results over effort by setting clear goals on outcomes and making sure people achieve those, and have the support they need to do so. However, it is crucial to lead with trust, and go into relationships offering a portion of trust; more trust can be earned, but don’t start on a trust deficit.

I’ll throw in a bonus tip: build strong relationships. The better your relationship with your employee, the higher the trust, and the more frequent feedback delivery, the more natural feedback will feel: instead of being an uphill battle, it becomes part of your working relationship.

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?

Don’t try to replicate one-to-one what you used to do in person; instead, figure out what purpose your activities served, and build to achieve this purpose. One example to illustrate my point: if people miss the watercooler, it doesn’t necessarily mean you need a virtual one. What was the watercooler good for? — A space for spontaneous interactions with people beyond one’s own team, build connections, and maintain a sense of belonging to a larger team? — If that’s it, then how do we achieve that?

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?

In a world that is more remote-first than ever, I encourage everyone to think about how they are communicating with others on their teams. Here are a few tips to consider:

  • Stay humble, and make space for others. Just as we try to connect in many small ways, there are small ways we can become better collaborators throughout the work day. For example, we can avoid dominating conversations, even when they are written communications. Open up space for others and invite them into conversations by asking, “What’s your opinion on this? I’d like to hear your thoughts.”
  • Make a deliberate effort to get everyone in your team involved in the conversation, and listen well to what they have to say. When we build trust with our teammates through strong communication, it provides the basis for our collaboration as a team.
  • Build foundational relationships. Collaboration is not just about the output of work, but also one of the best vehicles that distributed teams have for relationship-building. My engineering teams often use the pair programming technique, which helps them strengthen relationships with their teammates and makes teams more resilient. Pair programming also helps us avoid knowledge silos and distribute information — and it’s a really great tool for onboarding new teammates.
  • Grow together: An even better way to connect and communicate as a team is by helping each other grow through constructive feedback. In distributed teams, this can be really difficult to do well. When we mostly see each other on screens, it becomes difficult to have harder conversations. I have a template I co-opted from the book Feedback and Other Dirty Words by M. Tamra Chandler that I often use as a starting point. I’ll ask my team to discuss our feedback preferences in this format, then discuss the responses as a group. We use what we learned to give each other much more meaningful and specific feedback.

Thank you for these great insights!

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