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The Process of Scaling Small to Medium Sized Teams

Mission / Vision / Charter
Scaling Team
Different Skillsets
Company Culture
Internal Communication

11 January, 2022

Nikita Ostrovsky
Nikita Ostrovsky

Head of Infrastructure and Site Reliability at Patreon

Nikita Ostrovsky, Sr. Manager. Site Reliability Engineering at Peloton Interactive, shares how he has grown multiple small teams to medium-sized teams, hiring new candidates and creating a psychologically safe environment.

The Challenges of Growing Small Teams

A major part of my last four roles has been taking smaller teams of around 4-5 members and turning them into medium-sized teams of 10-15. In my opinion, scaling teams from small to medium sizes is the most challenging aspect of team building. Building teams from scratch typically involves technical problems, whereas growing much larger teams revolves around organizational and communication-focused struggles.

In both of these areas, I’ve found that I had more support when growing a team from small to medium sizes; not to mention it’s the most exciting. Medium-sized growth requires hands-on attention, direction for problem-solving, and hiring struggles.

Creating a Foundation and Scaling the Team

Hitting the Ground:

The first thing I do when entering a small team looking for growth is to understand what struggles exist within the team. I identify any existing problems and with strong consideration for ones that would be amplified when scaling the team. Some teams maintain their environment well but undergo a tremendous amount of toil work. Other challenges I’ve encountered were on the execution of new products, cultural issues, communication failings, planning issues.

Often these problems need to be addressed before the team can function or be scaled healthily in any scenario. Based on the team's situation, I work towards a solution, working with the individuals to find the best result for the entire team.

Understanding the Perception:

While working with teams, I begin by understanding their perception within the entire organization. I often learned if they were well respected or not, and based on that viewpoint, I tried to adjust that opinion. No matter the perception, I worked to build trust for the team as we would begin to do less support and more development during the growth period. Building a strong viewpoint of the team was essential to receive buy-in for the scale-up.

Growing the Team through Hiring:

The next step was to actually begin growing the team. After the foundation was set, I researched values that were successful for the team and optimized an interview pipeline that focused on these values. I chose to separate my team from the general interview pipeline and collaborated with my team to build and maintain our own. I’ve learned that this strategy only works under specific circumstances, depending on what values are necessary for the team.

Building a Healthy Culture:

As part of the hiring pipeline, I added organizational fixtures into the team. Specifically, these were mission and vision statements, north stars, and long-term roadmaps. Inter-team structures consisted of team policies, communication standards, leading patterns, and meeting rituals. It was essential to understand that when a team changes from 4 to 8 members, there is a 50% culture change. As it continued to grow, the culture was never the same, and I was thankful that I had pre-built these structures for a healthy environment for new hires.

Tips for a Healthy Team Culture

  • When growing a team from 4 to 15, the dynamic changes from each individual being in contact with everything to a few people being in contact with specific things. That structural change engages many challenges, and designating key team leads is vital in mitigating these potential pain points.
  • There is no time to take a risk on candidates during the initial hiring process. I’ve found it’s better to lose out on a rockstar than to take on an extra five interviews. Stay small, focused, and look for individuals who fit your organization. One bad hire can have catastrophic side effects on team culture

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