A CTO’s Toolkit: 3 Tactics to Scale Yourself & Your Team with One Medical

Kimber is the CTO of One Medical, a $5B+ company making high-quality healthcare more accessible. Kimber joined FirstMark’s CTO Guild to share her perspective on building a team through a public financing, leading through a pandemic, and much more.

Implement Scalable 1:1s to Stay in Tune with a Growing Org

A great leader makes sure they understand how their organization is doing at every level. Leaders gather candid feedback, identify issues with process, systems, or culture, and collaboratively develop and implement solutions to help their team scale. And the single most important tool for a leader to accomplish this goal is the 1:1 meeting.

Kimber has thought and written extensively about conducting great 1:1 meetings. You can read more in a series of blog posts here, here, and here. Two of the most important pieces of advice Kimber gives are to:

• Treat 1:1s as sacrosanct: as a leader, you have many competing demands for your time. But allocating time for 1:1s should be considered non-negotiable — and all of your front line managers should understand that, too. It’s essential for a healthy organization to create time for bidirectional feedback.
• 1:1 agendas should be driven by report: setting aside the time is not the only requirement in order to have a successful 1:1. An equally important piece is clearly aligning on responsibility and expectation for what happens. Kimber believes the best format for 1:1s is to have an agenda driven by direct or skip-level report. Obviously, a manager can and should bring items to discuss that are top of mind. But overall, it’s important to give your team control of the content so they feel empowered to bring up topics that may have otherwise been hidden.

As a company grows, the regular cadence of 1:1s will necessarily evolve. The first step in that evolution is a move to rotating skip-levels. This means continuing to host skip-levels on a 1:1 basis, but doing it at a less regular cadence — say, every 3–4 months.

Eventually, your team size will reach a point where even rotating skip-levels can no longer scale. When this happens, how can leaders still cultivate 1:1 connectivity with everyone in the org?

Enter “Coffee with Kimber” (or 1:8 meetings). Team members meet with Kimber in a group setting, with roughly eight team members at a time. The conversations have loose structure to them, creating a trusted space to talk about what’s going on in the organization, victories, losses, and open questions and concerns. These are similar in nature to an alternative structure many leaders embrace (“office hours”), but rather than being hosted on opt-in basis with no agenda, they retain the sacrosanct nature and loose structure of an effective 1:1 meeting.

Rotating skip-levels and “Coffee with” enable leaders to continue to get signal and create a holistic picture of what’s going on across the organization.

Scale Yourself through Creative Delegation… and with Vacation

Knowing how to allocate and maximize your time is an evergreen concern for every leader. For Kimber, finding mutually beneficial areas to delegate was a major turning point for scaling her time. Put differently, delegation is something every leader must do; but when you delegate in a way where everyone benefits (the leader, the new task owner, and the organization as a whole) you’ve found a major unlock for scalability. Two specific tactics to bring this to life:

Deliberate Delegation

As a leader, you will frequently identify work that needs to be delegated. Effective leaders are of course deliberate in selecting a new owner for that work. One under-utilized lens, however, is to think about who in the organization would view owning this work as a growth opportunity.

If someone views owning the work as a growth opportunity, you have found an opportunity for mutually beneficial delegation. And when a team member treats work as an opportunity rather than an obligation, you tend to see their best work, the application of enthusiasm and creativity, and contribute to their long-term growth.

One example: running the all-hands meetings became a time-consuming task for Kimber — time that she began to believe was much better spent on other priorities. Kimber delegated the work to team members who had personal goals of becoming better public speakers.

Initially, the transition came with some bumps, as both the new owners and the team at large experimented and iterated on a new formula for the meeting. But eventually, the all-hands meetings got materially better, because the new owners were enthusiastic and intentional about creating culture, cadence, and traditions that made the most of the time.

Going on Vacation

One other surprising way to scale yourself as a leader? Vacation.

When leaders take a longer vacation (perhaps two to four weeks), they are effectively forced to experiment with new management systems. These forced experiments will uncover opportunities for a more permanent handoff of responsibilities.

Most effective leaders do this naturally, but in preparation for several weeks away from the office, you will need to create a clear map of all your responsibilities, who should own it while you’re gone, and provide documentation on tasks and projects.

When you return, refreshed and ready to get back to building, you’ll learn something interesting from the experiment that was conducted while you were out. And you can ask yourself, “Should any of those changes become permanent? “

In summary, deliberate delegation and a well-timed vacation are two tools that leaders can use to scale themselves. This is critical in a fast-growing organization, and also critical to give you the space you need to grow as a leader. Mechanisms like these will ultimately help you create a high-functioning and high-performing organization.

Design for Rapid Adaptation via Multipurpose & Reaction Teams

In the earliest days of a company, a small handful of engineers will very naturally work together, with tight coupling, coordination, and focus. And at the opposite end of the spectrum, larger companies create structures where small, dedicated teams have clearly defined ownership of specific pieces of your product and infrastructure.

But how do you organize your team when you’re somewhere in between those two ends of the spectrum?

Kimber has developed two tools that growing teams can leverage, which can be applied in different contexts to achieve different goals.

Multipurpose teams

In our org, we created multipurpose teams that we named after colors to avoid siloing. A “color team” is the idea of creating a team with a fixed personnel makeup, but a variable mandate. Color teams are particularly useful when specific sub-projects (say, an infrastructure migration, or the development of a new feature) are big enough and important enough to be owned by a team, but where they’re not so big that they require the permanent assignment of a team. This gives organizations the best of both worlds: the productivity, collaborative, and culture that arises from a group of employees who work well with each other, coupled with the flexibility to rapidly change the specific mission and mandate of a team that’s essential in the fast-changing startup environment.

Reaction teams

Another framework Kimber’s team uses to address rapid change is the reaction team, which enables you to tackle short-term, urgent issues without chartering an entirely new long-term team.

When an urgent priority emerges, the reaction team will typically draw one or two team members from a variety of teams across the org. Those original teams will still be sufficiently staffed to continue to focus on their core priorities. And at the same time, you’ll be able to assemble a team that can wholly focus on executing against the critical short-term need.

Of course, this does create some stretching and friction across the organization, so reaction teams should be used sparingly and intentionally. But by having a well-understood process for reaction teams, you’ll have a tool that lets you continue to execute against both urgent short-term priorities and your long-term roadmap.

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