From Zero to CTO – Meet Lena Reinhard

Name: Lena Reinhard

Current position: VP of Engineering at CircleCI

Bio: I’m the VP Product Engineering at CircleCI, the leader in continuous integration and delivery for developer teams. Over my 15+ year career, I’ve been building and scaling high-performing engineering organisations and helping distributed teams succeed, starting with my own startup to corporates and NGOs.

I am an international keynote speaker on topics like leadership, DevOps transformation, and organisational scale, at conferences such as O’Reilly Velocity, The Lead Developer, CTO Summit, and QCon. I am passionate about helping teams increase their effectiveness and business impact, and scaling culture for organisational performance and health.

In other news, I enjoy spending time in books and in nature, and always strive to learn something new. I’m currently focused on how to play the piano and keep houseplants alive.

Hi Lena, thanks for chatting with CTO Craft today. Tell me about your life before leadership – what kind of roles and projects did you work on?

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 copywriting gig and turned into a role as marketing and key account manager. I ran project management, account management, marketing, and helped out with anything else that needed help. Around the same time, I got involved in a few open source communities, and shortly after, co-founded my first software company and became a CEO. Around the same time, I started managing distributed, fast-scaling engineering teams, quickly realising that I really enjoyed this work, and that it was a good match with my prior experiences and background. 

How did your first leadership position come about, and was it intentional on your part?

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 a CEO. I thought about it and said yes. 

My first formal engineering leadership role was more of a transition than a conscious decision. I’d been brought into the organisation as a consultant to get the team’s delivery into a better state and ended up taking on team leadership and scaling shortly after. Situations like that, where the scope of my role and responsibilities rapidly expand almost overnight have occurred many times in my career, and have always been exciting.  

How did you manage the transition? What came easily / what was difficult?

The transition into leading an engineering team for the first time was a challenge in a multitude of ways. Our team was building software to support the 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. 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. This taught me the value of a truly great team. 

What was your biggest failure in that first leadership role?

I learned a lot of hard lessons in that time. Due to the 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 me, and also inhibited my ability to delegate effectively and build out better structures for the team.

What made you keep doing it?

First of all, I always love a good challenge, and building technical and human systems has a lot of good ones. I also like a lot of variety in my work, and this space offered a lot. I’d received really helpful feedback from my teams that encouraged me to grow further, both in terms of building on my strengths and becoming a better leader. And lastly, I just really enjoyed it.

Tell us a fun fact that nobody knows about you

I love good notebooks and pencils. A few years ago, I bought a 20-pack of the Pilot G-1 0.5 and unfortunately, my plan to get through the next decade with those got spoiled because I’ve misplaced at least half of them in the meantime. My other favourite pencil is the Sakura Pigma Micron Fineliner 0.5.

What are the three key skills you think every lead needs?

I believe that leadership and management are two distinct traits, where management is about coping with complexity, and bringing order and predictability. By contrast, leadership is about handling ambiguity and change. I believe that organisations need leaders at all levels, so these are applicable no matter whether you’re in a formal leadership role or not: 

  • Self-management – Understanding and managing our own instincts, thought patterns, energy, time, and our operational horizon; 
  • Systems thinking – This is crucial, both at the technical and human level. It requires maintaining a strong context of the organisation around us and a solid connection with the bigger picture and long-term view, as well as staying connected with our teams and the people in them; and
  • Leading through context – One of our most crucial tasks as leaders is to bring up others around us, and the more they’re able to operate autonomously and deal with higher degrees of ambiguity, the stronger our team and organisation will become. 

What have you learned about acquiring and retaining talent?

Over the last year we have had over 5,000 candidates pass through our engineering hiring process. Our main goals for interviewing candidates are:

  1. Identify the best candidates and invite them to join our company; and
  2. Provide all candidates with a positive experience.

To achieve these goals, I rely on consistency and structure. I use a structured interview process with standardised questions; we design all our roles and job descriptions and evaluate candidates based on our Engineering Competency Matrix.  I try to get as many different perspectives on a candidate as possible, and make sure that everyone who’s involved in the process has a say in the hiring decisions we make. I find it important that interviewers are trained on topics like unconscious biases, how to run an interview, and how to utilise behavioural questions. 

When it comes to retaining talent, my team and I work hard to empower every individual on our team to be autonomous and take ownership of the projects they have hands in, and enable the people closest to the problem to have the right context to make decisions. We put a lot of emphasis on continuous learning and growth for everyone on our teams through structures around topics like career discussions, goal setting, internal transfers, and stretch opportunities. 

How do you motivate your team and manage their stress levels?

I think there are a few crucial aspects to motivation specifically: I think big picture connection is really important and helping people understand their impact on it, as well as how their work matters (to our customers, company goals, etc). I’ve also found just reiterating vision and direction frequently really helps. 

When it comes to managing stress levels, I’ve found these approaches really useful: 

  • 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. 
  • Set expectations and over-communicate – This is especially important for people struggling with anxiety or depression. Distributed organisations in a high growth stage have a lot of ambiguity, which is challenging. This can mean dealing with lots of information at all times and can increase the odds of anxiety. My job is to create clarity and provide the leaders and teams in my organisation with context so they can make their own decisions. 
  • 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-to-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. 

How do you manage your own stress levels and productivity?

I’ve found a few approaches crucial: 

  • Schedule your day around your energy – I always encourage leaders to be mindful about how they structure their day; instead of only focusing on time spent, look at what activities are energising or draining to us. Being fulfilled at work is not only about managing our time, but also about managing our energy.  There’s an exercise I do where I map out my schedule for the day with the intention to identify my energy levels and what increases or lowers my level of energy. As I go through the day, I’ll put a “+” next to the tasks that energised me and a “-” next to the tasks that drained me. That way, I’m able to recognise what emotions come up throughout my workday and plan around them.
  •  Practice boundary-setting – It can be very difficult to set boundaries, especially in high-pressure situations or when dealing with larger organisational challenges. As leaders, we have a responsibility to build sustainable work environments for our staff and ensure our teammates have the space they need to lead balanced lives.

How do you stay in sync with other parts of the business?

Context is one of my most crucial tools for being effective in my role. A few ways: 

  • Recurring meetings and discussions to shape out strategy, discuss, or collaborate in working sessions. These include other executives, my peers, staff, and different groups that get together regularly;
  • Provide regular reports and updates via email to the rest of the company;
  • Regular check-ins with my management team in particular, oftentimes also async; and
  • I read a lot of information across company departments, both Slack and email. For me, an important part of my work is to maintain a sense of what’s going on around me – often not even actual information I need at this moment, but processing events around me to maintain a strong pulse on the organisation. 

 Where do you see yourself in five years’ time?

I have many, many ideas, and leading distributed, fast-growing organisations and supporting leaders within them will be a big part of it.  

And finally, which product do you wish you’d invented?

The Karaoke machine: something that brings music and joy to people, and brings people together. I don’t necessarily wish I’d invented it, I’m just very glad it exists.

Thank you so much, Lena!


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