Leading Larger Teams

Jay Haque
6 min readSep 27, 2020

My team is growing for a handful of people to a few dozen seemingly overnight. It’s nothing I haven’t handled before but this particular time it is different. Having that prior experience, and comparing it managing a small team, allows for reflection and incremental improvements.

It’s important for all leaders to learn and to be open to the idea that the way it was once done, may not be the best way forward. So, what did I learn and what will I change?

Delegate Decisions, Including Big Ones

It’s hard to lead major transformation efforts without being involved in decisions; whether it’s a rip-and-replace enterprise computing project, consolidating large data centers, or adopting a cloud-first strategy, there are hundreds of decisions to be made along the way. The transformation nature of the projects lead to potential disconnects on the vision as work unfolds and leaders can ensure cohesion by “holding the line”- knowing the payoff will be worth it.

This latter point is an essential part of leadership, but the countless decisions can be a heavy burden and should be mitigated. In fact, as a leader, it’s vital that I increasingly encourage and support these decisions being made by team leads. Let’s explore why.

  1. Leaders can be myopic and absentminded of their own biases. Announcing view points and positions early can sway a teams discussion. It’s hard to ask teams to disagree with you or prove you wrong (even in a an environment where dissent is encouraged) then it is to reserve your opinions and let the conversation develop. Leaders will have a more holistic view when they empower their team leads to make big decisions.
  2. You can’t foster the next generation of leaders if you don’t let them lead. Team leads will operate respective to the bosses style and if that style robs them of big decision-making then their development is stunted. It’s not only the decision itself that adds value to their careers, it’s everything around it — negotiating with and convincing peers, rallying direct reports, managing up, addressing the details, weighing the value proposition, etc. Yes, some have a natural knack for these things but many benefit from developing the skills over time.
  3. A strong, resilient, high-performing team consists of people that trust each other. That trust is developed over time through trails and tribulations through which colleagues, at all levels, witness the journey and outcomes. When team leads are empowered to make decisions and carry them out they build a portfolio of successes that develops a strong reputation. This in turn, highlights the capabilities of the team and fosters great trust.

Let me say these points in no way absolve a leader of accountability. Even as I support and encourage big decision making by my teams leads, I am ultimately accountable for the outcomes. As such, it’s important as a leader to keep your ear close to the ground and be aware of decisions so that they can can fully supported or, if necessary, changed.

Accept How Others View You

I know members of my small team well; their likes and dislikes, about their families, their favorite foods, sports teams, movies, etc. This professional friendship enables a strong rapport that yields a level of candidness that is extremely valuable. Unfortunately, it has the opposite effect when leading a large team. I know this because I’ve tried to be as engaged in a larger setting before, here’s why it doesn’t work:

  1. There are just too many people. If I were to have 30 minute 1:1s with each person that would require 20 hours of my week. If I stopped and chatted with everyone for just a few minutes it would require a similar amount of time. Now, this doesn’t mean you should be cold — always be friendly, respectful, inquire about their well being, and have an open door.
  2. The same fluidity does not exist in larger teams. In a small, tight-knit, teams, communications are highly fluid thanks to the candidness and strong rapport between members. Pivots are easier as team members can quickly exchange information and make changes on the fly. I argue that this fluidity disappears for leaders of large teams as the number of participants is too large. Take for example, assigning a task a non-direct report; in a small setting any issues with this are brought up immediately whereas in a larger setting, they’re not. The team members accepts the task, changes priorities, and gets to work (it’s for the bosses’ boss after all). What task was pushed back? Can the team member deliver the task as requested? Who is going to pick up the slack if necessary? All of these things can be addressed but it will take much longer than it would have in a smaller team.
  3. You are viewed as the boss and that’s OK. Given the first two items it’s easy to see how a leader mare appear unapproachable. This has little do with the leader and a lot to do with the social dynamic — how do you combat it? By taking advantage of opportunities where the dynamic is advantageous to relationship building. Attend company events and actively seek dialogue, be genuine in conversations when/if they happen outside of these events, encourage team leads to provide team members an opportunity to communicate up.

I don’t think I’d be wrong to say that most of us, at some point of our careers, had meetings with leaders that made us unnecessarily anxious. For many of us, it takes time, exposure, and experience to change our perspective; ensure your team has these opportunities; create them if necessary.

Adopt an Input/Output Flow

In my past experience with a large team I led three business areas, all relatively well automated and all led by talented managers. The information flow was manageable — a quick scan of emails and alerts was sufficient to keep a pulse on things. This new endeavor is twice as large; 100’s of tickets, dozen’s of projects, 1000’s of systems and alerts, and many clients. How does a leader keep track of it all? For those that have led service organizations the answer is simple — KPIs! But what about everything that can’t easily be measured? Developing an input/outflow of information with team leads is essential to maintaining overarching awareness and sets bidirectional expectations so that everyone is in the know. I’ve not yet implemented this, but here are my thoughts:

  1. Identify the KPIs that matter and automate the collection and publication. This is low hanging fruit in mature organizations. Ticket data alone provides a good insight into the performance of the service organization. SLAs and proper categorization of tickets help highlight areas of concern and team members can live by the motto “if there isn’t a ticket, it didn’t happen.” This may not paint a complete picture for larger teams, in which case leaders need to identify new KPIs and must avoid those that can not be automated. I realize how that sounds, but I’ve been there — slaving over a spreadsheet for hours to produce metrics! Granted, sometimes it is unavoidable, but these should be rare occurrences.
  2. Establish a team communications strategy and support its adoption. Where does the team mainly communicate? When are business-as-usual conversation happening? When is an out-of-band heads-up a good idea? When is an after-hours call warranted? Your SLAs and system/process automation will help guide some of this—the outliers need attention. Pick a toolset (email, Slack, Teams, or a combination) and stick with it. Draw those team members that are lagging on the selected platform(s) into conversations. Be serious in respecting work/life balance and set expectations accordingly.

As some of this is new for us, or just not formalized, I’ll provide an update once our input/output flow has been operational for a couple of months.

In closing, there is a lot of ground to cover when your team grows and there are purposeful shifts that must take place to keep operations running smoothly and to aide the forming of the new team. I hope these points will be beneficial to others as they make the switch.

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Jay Haque

Director of Infrastructure & Operations @NYPL (views my own)