How to 4x your team size without it (& you) falling apart

“A rising tide lifts all boats”

In November 2020, I started at Wise as an Analytics Lead, responsible for a team of 7 Product Analysts.

By February 2021, my team had already doubled in size, leaving my calendar with a sea of blue slots with no time left outside of 1–1s either with my team or the product managers they were regularly working with. It’s magical how much of a wakeup call Time Insights on your gmail can be to start thinking about how to scale yourself and your team.

I remember blocking “thinking” time on my calendar at 4pm every day for at least an hour for a few weeks to draft out and visualize my own values and principles as a leader, what I wanted my organization to stand for, and what foundations I’d build it upon. That map is a post for another time!!

I had joined Wise to be able to do exactly this…Being able to play a critical role in scoping, building and growing an Analytics team was exactly what I wanted to do and this was where I exactly wanted to be. But… time wasn’t on my side and I wanted to make sure I got it right. Ideally the first time around…okay, maybe second!

Over the last two years, we ended up with 4.5x my original scope. Today, I am responsible for 6 managers and a team of 32 analysts, and we will only keep growing.

While there is still so much I am yet to learn, here I attempt to share back my wins and failures that led me to embrace some core principles of how I approach building teams.

So let’s dig in…

Building a healthy team requires intention at each step (…a lot of it!)

When a company is at its hyper growth stage, there is more to build than the people who can build them, more ideas to execute than the people that can turn them into actions, more to understand than the people who have the headspace and the time to meaningfully dig into the problems and the opportunities.

So we hire….to add more force to acceleration. However, as one of the leads on my team like to say adding more horses to the carriage doesn’t lead to innovation. You ask yourself when it’s time to build an engine.

I’ve come to learn that when it comes to building that engine around your team, the process is, in fact, no different than building a great product. Each team or collection of teams needs a why and a how, people who will build it properly and the right foundation for scale.

It needs a vision, a building framework, force (people) and a strong foundation(values).

You need to think carefully about how this living organism you’ve set in motion will continue to evolve. I’ve always felt the responsibility (and the pressure) of directly impacting many people’s professional lives on a daily basis, and I think that weight is a good, healthy thing. If you aren’t invested in what you are building, how can you be trusted as a leader?

So let’s break this apart…

I. Vision

Each team, no matter its size, needs a reason for existing. A vision or a goal, no matter how small the scope, that this collection of people are there to accomplish.

Common sense? You’d think so. This seemingly simple question is actually one of the hardest things to get right and I’ve seen many organizations not be able to effectively answer it, causing a trickling down effect on the rest of the pillars.

The test is actually quite simple. “What is the main problem you are solving?” → If a group of people can’t give you a single sentence answer to this question, you’ve got a problem.

Creating a strong vision is hard because it requires that we are very clear on the core problems we aim to tackle and solve. The single most important and broad problem becomes the company’s vision whereas the building blocks of that broader vision becomes the pillars we create underneath. Ideally we work backwards from there until we hit the smallest unit of problems we care to solve. The existence of a logical chain of problems going from large to small in your organization means people and teams who are tied to each tier of the collective problem-set are clear on what they are here to do.

One of the early mistakes I’ve made at Wise and very quickly learned from was thinking about people problems in isolation. When you work with an embedded model (meaning one analyst per each product team), you need to think about growth in line with the vision of that product area and let it guide the pods of problems you staff against.

Seeing the team vision as a collection of problem units also allows us to be agile, growing, shaping or reshaping teams as the sets of problems get more complex without straying from the overall vision.

My key learning here to any Lead looking to grow their teams is to get very, very clear on the day to day problems and priorities of the broader organization you belong to. When you get to a multi-layered understanding of the problem space you operate in, you can be very thoughtful about where you invest as a leader when growing your team.

Last but not least….a strong vision orients teams to the future while making it easier for them to track against it.

As an Analytics Leader, I am also biased towards the importance of this because a vision or a clearly laid out problem statement around a team makes it easier for us to identify the health metrics we’d set in place to ensure we are heading in the right direction.

II. Organisational Framework

A strong organizational framework, a.k.a, how you build out your teams, allows for flexibility and scale without threatening the integrity of the overall structure.

There are so many angles to this depending on your functional area/domain. So I’ll work through my own example to show what this could look like.

When I joined Wise, I had a team of 7 individual contributors (analysts) and now we have a team of 6 managers and 32 analysts. We did this with 3 organizational principles in mind.

Principle 1— Each pod/team we create should have a unifying theme(vision) in a domain that enables meaningful collaboration and shared learning.

• When your company is growing, you have to make an intentional decision on where to invest and where to grow your teams. At Wise, analysts are embedded into product teams. So if there is a clear product need that needs to be filled with an analyst and we currently don’t have the resources to support that product area, we look to bring in an analyst. As the number of analysts grow, we have to be careful and intentional about the support framework we are laying to ensure scale doesn’t jeopardize quality of work or the quality of the guidance and coaching we give to the people we’ve hired and should be investing in to do the hard work. The best way to do this is to think about the collection of problems that have the most synergy together to start breaking down the bigger team into pods. This means that a team that was initially one big team around solving all core consumer problems may now break into multiple pods around each of those consumer problems.
• People who work on very different problems can only provide so much guidance. Let synergy be your friend when building out your teams. There is more collective learning and growth that comes from bringing people together who are working through similar or related problems than any single Lead can provide.

Principle 2 — Each lead should not have more than X direct reports to be able to stay close to each of their directs in a productive way.

• Every organization will have a version of this magic number (3–5 usually) and I think the number only matters within the context of your organization but my principle here is this: It’s not your team’s fault that now you have more people to manage and less time to give back to each one. As you scale your team, the people in your team should not be negatively impacted by the growth and should, in fact, feel no change in the level of support they get from a lead. When this becomes hard to sustain, it means it’s time to bring in more leaders to share the work.
• I experienced this problem very quickly at Wise where I had become a blocker myself to many analysts I wanted to enable simply because I couldn’t get back to them fast enough.

Principle 3— Each analyst, senior analyst and a lead should have clear growth paths as much as possible within the organization.

• One of the biggest threads to a team’s sustainability and scalability is attrition, and one of the biggest attrition risks for an organization is the people’s ability to see themselves growing there. A big mistake many leaders will make is to only bring people externally to meet the steep headcount demands instead of taking the time to invest into the existing people in the team and growing them to take up the bigger, chunkier problems in the organization. Ideally, you should have a well balanced strategy of internal and external moves.
• Development plans exist for a reason! If you have someone on your team with aspirations to get to the next level, make sure you work through a clear plan for them to get there with a clear set of expectations. It’s okay if you end up hiring externally because they aren’t ready…BUT, you better have a detailed development plan with them on what you expect to see and how they are tracking against it. People will leave if they don’t feel invested in. You would too.

III. People

The number one thing to stress here is that if the people on your team or your future hires become an after-thought and are seen as a means to an end to close the gaps in your business or product, you are doomed to fail.

When it comes to your team growth strategy, you have to first and foremost take stock of who you already have. These are the people who are already invested in you as a lead and your organization. It’s your job to do right by them.

• What are their current skillsets?
• What are their strengths that you can harness and lean on?
• What are their weaknesses you need to help them with or complement?
• What are their development goals and aspirations?
• How far are they from the next milestone they’ve set for themselves?
• Do they have the tools and the opportunities they need to close those gaps?

The answers to these questions help you define your strategy for growth through external hires?

• What are the experiences and skills you need to hire for that your current team cannot meet at all or in the time required?
• How will these skills complement your existing team?
• What are the experiences and skills your team has but you need more of in your growing team?
• How does the seniority and aspirations of the people you bring in externally blend with the people you already have?

If you have a team with other managers who are closer to the ground, make sure you ask them to work through these with their teams as well.

While it’s impossible to plan for every permutation of outcome within your team and you can never predict when a team member might decide to leave, my approach has always been to plan for an outline that does not hinder the growth of the people I already have on my team while growing the team with people with a fresh perspective who will make everyone better and complement the sustainable development of the broader group.

IV. Values

When a team is small, they are more contained and much easier to manage and shape. As a lead, you can have a direct influence on the culture you instill within the team by being directly involved in the day to day of your team, staying close to everyone in your org with regular 1–1s, setting the ceremonies and processes with input from your team that better everyone.

As you start introducing skip-levels to a team, things change. The more pods exist, more layers become inevitable and layers mean distance from the original source of the values and principles…you.

There are two key things here to ensure that your team culture and experience remains intact and only continues to evolve and prosper.

Rule 1 — Focus on buy-in and ownership, and not rules and processes.

One of the most important responsibilities you have as a lead is to make sure that the people you have on your team are connected not only through a shared vision of what they are there to do but also, and even more importantly, a shared set of values that they want to uphold.

As a leader, my values are:

• Empathy and genuine care; Sense of security
• Honest and transparent communication; Shared ownership
• Investment and personal connection; Mutual respect
• Empowerment without being overbearing; Autonomy
• Reliability, dependability and trust when needed for support; Trust

As I build my team with more leaders with their own sets of values and principles, it is key that we discuss and create a shared sense of ownership around the values we want to collectively spread across all the pods and layers we’ve created. This cannot be achieved or will always be limited if done through forced structure and process.

One of the mechanism I’ve found to be really helpful to achieve this alignment is making sure that you have a close working group of your direct report managers who meet regularly to discuss issues that come up within our teams. We do this by meeting weekly as a Leads group with an open agenda that isn’t dictated by one person where everyone can bring in a topic that’s top of mind.

Rule 2— Continuously learn from those you’ve trusted to lead and feed those learnings back into the engine.

A team is a living and breathing thing that evolves with the people within in. Over the years, I’ve learned a tremendous amount from the individuals or managers within my teams. As they each bring their own views, approaches and practices to the table, feed it back into the broader engine you’ve created so that everyone benefits from it. The more you enable those around you to share, the more learning and growing you will see.

My goal has always been to build an evolving and sustainable engine that not only betters its members but sets an example to the rest of the teams and organizations, ultimately pushing everyone to be more intentional about why and how we invest into our biggest asset, our people. I hope these general rules come in handy to any Lead having to work through how to scale their teams and build a healthy, thriving team!

I’ve tried to touch on many important themes there that are worth exploring individually, and I intend to do so in a few follow-up articles. In the meantime, I’d love to hear your thoughts and feedback!