What led you to transition from a systems administrator to a leadership role?
‍What I realized is that I wanted to be where the conversations were happening. Early on, I was just taking tickets from the product team. I wanted to understand the business metrics behind why we were building certain things and what the customer experience was. I got a role as a lead engineer in health tech and worked directly with nurses in a hospital. Seeing their day-to-day experiences connected me to the impact of my work on customers, which was incredibly fulfilling.

‍What are the key skills needed for an engineer to secure a leadership role and influence decisions?
‍The core skill is being a translator and communicator. It's about helping engineers translate their work for the business and customers. Understanding business metrics, customer experiences, and go-to-market strategies, and translating these into engineering terms is critical. Being a great partner and maintaining a customer-oriented approach are also essential.

‍What challenges did you face when transitioning to leadership?
‍One of the hardest things was understanding what level of technical detail to provide to non-technical stakeholders. I focused on starting with a partnership mindset, trying to understand where stakeholders were and bridging the gap to where we needed to be.

‍How do you ensure engineers are spending their time effectively on the right projects?
‍It starts with aligning with core business metrics and understanding what needs to be moved to see external impact. This alignment often involves close collaboration with the executive team, the CEO, and go-to-market strategies to pinpoint critical tasks, then translating these into actionable engineering goals.

‍What strategies do you use to keep engineers motivated and invested in driving business forward?
‍Connecting engineers directly with the impact of their work is crucial. For instance, allowing them to see customers using the product or new features, or having stakeholders share how the product is used in the real world. Hiring people who care about the customers and facilitating regular interactions with them helps maintain this connection.

‍How do you handle technology decisions that don’t pan out as expected?
Regularly evaluating technology choices is essential. Understanding what scale we built for and whether our tools can handle increased scale is part of our ongoing assessment. Communicating the need for replatforming or making significant changes back to the organization is about framing it as a necessary step for growth, not just tech debt.

‍What measures do you take to manage your engineering teams effectively and watch for burnout?
‍We use quarterly surveys and one-on-one meetings to gauge how engineers are feeling and understand any underlying issues. It's important to create an environment where feedback is valued and acted upon, ensuring that the team sees their input leading to real changes.

‍How do you manage a remote or hybrid team effectively?
‍Regular touch bases, daily stand-ups, and sprint planning meetings are vital. I emphasize the importance of one-on-ones, where the agenda is driven by the team member, allowing them to express their needs and concerns. Treating hybrid settings like remote settings ensures inclusivity, using sync documents and virtual meetings to keep everyone aligned.

‍How do you balance driving company performance with maintaining a healthy team culture?
‍Team health comes first. A healthy team is more productive and motivated. Sacrificing team well-being for short-term gains leads to poor quality output and ultimately, the need to redo work. Setting realistic goals and ensuring the team voluntarily signs up for them helps maintain both productivity and morale.

‍What did you wish you knew when you transitioned from developer to manager?
‍Transitioning from a VP role to a CTO role was enlightening. I needed to focus not just on tech success but also on being a strategic partner for the broader business. Understanding the market and the economics more deeply was crucial, and it was a steep learning curve that required me to continually learn and adapt.

‍In the age of AI, how do you balance innovation with protecting intellectual property?
‍Data privacy and governance are paramount when integrating AI into business operations. It's crucial to start small with AI experiments, ensuring that customer data privacy is respected and secured. The focus should always be on improving the customer experience and supporting business goals, not just on the technology itself.

‍Looking forward, what's the key to building and managing a successful remote or hybrid team?
‍Regular communication, setting clear expectations, and using tools that enhance collaboration without requiring physical presence are essential. For hybrid environments, treating all participants as if they're remote ensures inclusivity and effective participation.

‍How do you handle decision making in technology choices?
‍Acknowledging that not all technology decisions will scale as expected is important. Regular reevaluation and willingness to pivot as needed are crucial. Framing these adjustments as essential for growth rather than setbacks helps in maintaining team morale and stakeholder support.

‍What's your approach to balancing high performance with a healthy team culture?
‍I prioritize team health above all because a motivated and healthy team naturally achieves high performance. If a team is overworked, the quality of work suffers, and it leads to burnout. Managing workload in a way that promotes well-being and sustainable productivity is key.

‍Can you share a memorable project that had a significant impact on you?
‍Working on ShaperTools, a vision-powered woodworking tool, was one of my favorite projects because it combined deep technical challenges with immediate, tangible results. It allowed me to engage directly with product development and see the real-world application of our work, which was incredibly rewarding.

‍What advice would you give to new leaders in tech?
‍Focus on continuous learning, be open to feedback, and understand the business impact of your technical decisions. Building strong relationships with your team and stakeholders is just as important as technical acumen.

- Brad Taylor