How I Manage My 1v1s

Introduction

Managing a team of talented individuals is both challenging and rewarding. As the leader of an organization comprising around 40 Data Platform Engineers, Data Engineers, and Data Scientists, I’ve developed a structured approach to conducting one-on-one meetings (1v1s) that (hopefully) fosters growth, collaboration, and satisfaction within my team. In this post, I’ll share my philosophy, strategies, and the challenges of effective 1v1s, ensuring that each team member feels supported and valued.

People Management

At the heart of my management style is a strong belief in people management. To me, it’s a multifaceted discipline that prioritizes the well-being and development of each team member. Here are the key components, listed roughly in order of importance:

• Maintaining good personal relationships: Building trust and rapport is foundational. I achieve this by scheduling regular informal check-ins, celebrating personal milestones, and being approachable. This time is dedicated to understanding my team members as individuals, not just professionals.

• Radical transparency: I maintain an unusually high level of transparency with my team. I believe in openly sharing information about organizational developments and decisions because I respect my team members as adults who deserve to understand the context. This approach empowers them to make informed decisions for themselves and their families.

• Discussing day-to-day issues: Addressing practical matters, such as office seating arrangements or rumors about organizational changes, helps maintain a transparent and comfortable work environment. These conversations keep the team grounded and informed.

• Performance management: Setting clear Objectives and Key Results (OKRs) at the beginning of the year and regularly reviewing progress ensures that everyone is aligned with our goals. This structured approach helps in tracking performance and achieving milestones.

• Career discussions: Regularly discussing career aspirations and development opportunities helps in nurturing long-term growth. I work with each team member to identify their career paths and provide the resources they need to advance. Having said that, I also make it clear that everybody's long-term growth and career trajectory is their own ownership — their manager is only a guide.

• Promotion discussions: Transparent conversations about promotion criteria and providing constructive feedback support career advancement. I believe in clear and honest dialogue to help team members understand their growth potential.

• Positive feedback: Recognizing and celebrating achievements, such as giving kudos for a job well done, boosts morale and motivation. Positive reinforcement encourages continued excellence.

• Negative feedback: Addressing areas of improvement promptly ensures that performance issues are managed effectively. Constructive criticism is essential for personal and professional development.

• Ask me anything: Encouraging team members to ask any questions fosters an open and communicative culture. This openness ensures that concerns are addressed promptly and transparently.

• Technical support: Whether it's assisting with a challenging bug or directing them to the right resources, I provide the necessary technical guidance to empower my team [if I can].

My philosophy is to have a 1v1 with everyone who directly reports to me or rolls up to me. While this approach might not be feasible for managers overseeing hundreds of people, it works well for my role. Additionally, being a "hub-like" manager within our company structure provides me with more context on ongoing projects, giving people value in these meetings.

Of the 40 people who report to me, about 30 are full-time employees (FTEs), and the remaining 10 are contractors. Approximately half of the organization operates fully remotely, while the other half follows a hybrid model, spending 2-3 days in the office each week. Personally, I’m in the office four days a week, balancing remote and in-person interactions.

I don’t hold 1v1s with contractors. Over time, I’ve learned that it doesn’t work effectively. Contractors are trained by their companies to treat me like a client, which prevents honest personal conversations. Similarly, I find that OKRs don’t resonate well with contractors, as their focus is often project-based rather than long-term growth.

Cadence and Optionality

Scheduling weekly meetings with 40 people is impractical and inefficient. Instead, I tailor the meeting frequency based on individual needs:

• Every 2 weeks: For junior team members who require more guidance and support.
• Every 2 weeks: For those in high-stakes or high-pressure projects, ensuring they receive the necessary attention.
• Every 4 weeks: For mid-level employees who are progressing well but still benefit from regular check-ins.
• Every 8 weeks: For senior team members who are on track and require less frequent interaction.

Additionally, I emphasize that 1v1s are optional by default. Team members can cancel meetings if they feel they don’t need to discuss anything specific. However, if there’s something important to address, I proactively reach out to ensure the conversation happens.

Related Meetings

To complement personal 1v1s, I schedule two types of additional meetings:

• People updates: Meetings with people managers who report to me to discuss how their team members are doing. This ensures that I stay informed about the well-being and performance of everyone in the organization.

• Team/project updates: Meetings with the entire team, or sometimes just senior members, to discuss the progress of deliverables and overall project health.

Note: I believe it’s crucial to separate personal 1v1s from team/project updates to maintain focus and clarity in each type of meeting.

Overall, I manage 41 meeting series encompassing 1v1s, people updates, and team updates. The distribution of cadence (every 2, 4, 6, or 8 weeks) allows for a balanced and manageable schedule.

With these cadences, the 41 meeting series translate to approximately 9.1 meetings per week, totaling about 4.5 hours weekly. While this may seem substantial, it’s manageable thanks to a simple yet effective system I use — a spreadsheet to track meeting series and their cadences. This tool helps me calculate and monitor my meeting load, preventing overwhelm. If cadences become too frequent, I adjust by identifying people or projects where I can afford to connect less often.

My Challenges

As a manager, I juggle around 25-30 meetings per week, with about 10 scheduled by myself (as shown above) and an additional 20 coming in externally. The primary challenges with this many meetings include:

• Interruptions leading to cancellations: The company’s culture emphasizes urgency for managers at my level, often requiring me to prepare documents on short notice. This results in the need to cancel downstream meetings unexpectedly.

• Tardiness: Similar urgency issues sometimes cause meetings to run over time, creating a domino effect that makes me late for subsequent meetings until I can regain some free time.

• Preparedness: With back-to-back meetings, there’s often no time to prepare adequately for 1v1s. Large Language Models (LLMs) could be a significant help here by tracking previous discussions and providing quick 3-bullet reminders at the start of each meeting.

• Listening skills: Some team members are incredibly patient and good listeners. However, I’m naturally a problem solver, and once I feel I’ve heard enough, I tend to start discussing solutions. This isn’t ideal, as it’s important to listen to the other person's full perspective before contributing my own thoughts. Continuously working on this aspect is essential for better communication.

The issues of missed or late meetings are particularly problematic for remote employees. While in-office team members can visibly manage interruptions, fully remote employees might not understand the reasons behind sudden changes, leading to confusion and frustration.

Conclusion

Managing a team of 40 individuals, both in-person and remote, comes with its unique set of challenges and rewards. My approach to 1v1s—prioritizing personal relationships, active listening, and tailored meeting cadences—has fostered a supportive and effective work environment. With a structured system to track meetings and a commitment to continuous improvement, I’ve been able to maintain low churn rates and high retention over the past 50 months.

While no system is perfect, the strategies I employ have proven effective in nurturing a cohesive and motivated team. By balancing structure with flexibility and addressing both professional and personal needs, I strive to create an environment where every team member can thrive. As I continue to refine my approach and leverage new tools, I remain dedicated to the ongoing growth and success of my organization.