The great tightrope act

By thoughtfully balancing ideas and inputs during the planning process, engineering managers can enrich team impacts and business outcomes.
Part of
Issue 19 November 2021

Planning

As a software engineer at LinkedIn, I took product roadmaps for granted. Every two weeks, a carefully scoped task landed in my lap—a bite-sized morsel within the larger three-course meal of the team’s quarterly goals and the company’s business vision. All I had to do was turn a well-thought-out design spec into some code and tests. 

But as my responsibilities shifted from individual contributor to engineering manager (EM) at Strava and then at Calm, it was a shock to discover the complex, time-consuming role I would play in creating those nicely plated, beautifully broken-down Jira tickets—the result of meticulous product planning. 

In its simplest form, product planning entails artfully translating a few high-level business KPIs into a balanced suite of projects for the engineering team to execute. Typically, engineering managers take a back seat in these conversations, tasked primarily with portioning a project into engineer-comprehensible action items. But an EM who can communicate fluently across teams and drive engineering alignment in a way that prioritizes both business outcomes and developer happiness can help craft a far more effective roadmap—one that scales up non-technical teams’ impact while maximizing the engineering team’s efficacy and enthusiasm.

Where EMs fit into the planning process

Product planning tends to encompass two broad phases, which I like to think of as “entropy” and “order.” During each phase, the EM contributes to the roadmap by estimating technical feasibility and representing the engineering team in conversations about product direction. The goal is to gather information and inputs, align on priorities with sundry stakeholders, and craft an engineering roadmap that matches the needs of the company with the capabilities of the engineering team.

Phase one: Entropy

In this part of the planning process, a product engineering team’s product manager meets with non-product cross-functional teams to understand what they need from engineering. (The EM is sometimes part of these conversations too.) Meanwhile, leadership channels requests through their respective business verticals, while engineering teams brainstorm product ideas. 

This stage requires the EM to navigate the clamor of product requests and understand the nuances of other business functions—how an ad network works, for instance—in order to provide back-of-the-napkin estimates of engineering implementation. By keeping an open mind during this process and being generous with their time and energy, EMs can build solid relationships with other teams, contribute to an environment that promotes idea-sharing, and nurture stronger, more fluid partnerships down the road.

Phase two: Order

Once all product ideas are on the table, EMs are accountable for more accurately estimating how long each potential project will take. (They might facilitate this sizing exercise themselves or delegate it to a tech lead to guide individual contributor estimation exercises.) Meanwhile, the product manager, with a variable amount of input from the EM, determines each project’s priority level so the EM can create a timeline and assign tasks. 

Though engineering projects are notoriously hard to estimate, during this phase EMs make their best attempt to allocate the team’s engineering resources to priority projects. With the help of Google Sheets, Asana’s Timeline, or other Gantt-like visualization tools, EMs account for every engineer’s work in each sprint in a given time frame. Using visualization tools can also help illustrate to partner teams and other stakeholders what trade-offs the team is making.

Activating EMs in the planning process 

Engineering management is something of a tightrope act. It involves balancing requests and inputs from leadership, product stakeholders, other teams, and engineers to achieve an equilibrium that delivers on a business’s objectives while also taking into account individual engineers’ skill sets, career aspirations, and personal passions. By being conscientious and forward-thinking about how to leverage their team’s capabilities, EMs can level up their involvement in the planning process, contributing to a robust roadmap that enhances the product, reduces tech debt, and motivates engineers to do great work. 

Build buy-in around non-negotiables

At every company, leadership will have certain pet projects they’ll want EMs to allocate resources to, no matter what. The sooner an EM and their fellow team leads can identify these projects (flagging technical limitations or raising product considerations as needed), the sooner they can start generating buy-in from engineers by emphasizing the positive impacts of the project. 

During one of Strava’s planning periods, for example, product team leads and engineers were eager to build features such as training plans and race projections. However, leadership firmly believed that activity integrity—ensuring activity metrics like pace and location accurately represented real-world values—had to be the team’s top priority in order to build trust with athletes (what Strava calls its users). Focusing on activity integrity meant we’d have to deprioritize the training features we were more enthusiastic about.

Knowing our engineers were motivated by tackling technically challenging problems and creating rich user experiences, I worked with the team to build an engineering roadmap they’d find fulfilling. Through 1:1 conversations and team brainstorms, we decided to focus on flagging incorrectly labeled activity types, removing wonky GPS values from an athlete’s personal records and leaderboards, and giving athletes more control over what would display on their activities (pace, heart rate, etc.). These tasks supported leadership’s activity integrity goals—plus, engineers were excited to work on them.

Bridge the development chasm

A vital skill EMs can bring to the planning process is the ability to actively and empathetically collaborate with non-product partners to help amplify their business impact. Doing so can lead to novel product insights that product or engineering teams alone might not have considered. 

In a recent planning cycle, for example, my team at Calm met with the international team to discuss how to best serve their markets. During this conversation, we realized we could expand our English-only search functionality to help collect better data about what kinds of content international users were looking for. As part of this effort, I worked with other team leads to design and instrument search analytics to capture the most desired content by country. This work represented a valuable user-first approach to optimizing international markets, and prioritizing it allowed us to contribute both to the product as a whole and to the international team’s objectives. 

EMs often find themselves overwhelmed with meetings during “planning season,” but it’s important to create space to communicate with folks outside of product and engineering, hear their goals, and consider their priorities for the product roadmap. These conversations are an opportunity to build stronger, more collaborative relationships across teams while also enhancing business outcomes.

Advocate for your engineers

One of the most important things an EM can do during the planning process is empower engineers to work on the projects that matter most to them. Crafting a roadmap that pairs engineers’ personal objectives with product and company goals can yield measurable gains both for the business and its people.

Recently, one of the engineers on my team was interested in taking on a challenging refactor of a data modeling framework. However, it would require collaborating with an infrastructure engineer, and because the project would have no user-facing impact, it didn’t fit into our product roadmap. Still, knowing the engineer was passionate about the project and that it would improve velocity for backend product engineers, we were able to plan a six-week embed so the engineer could work on the refactor in the second half of 2021. 

These are the kinds of projects an EM should keep an eye out for. Even though this kind of work is rarely prioritized in a product roadmap, it’s an opportunity to make space for an engineer’s goals and aspirations while also producing business benefits—in this case, by reducing tech debt.

Another illustrative example: In 2019, Strava began planning to move its most popular free features behind a paywall. Before we made this transition, we wanted to build trust with athletes by shipping several sought-after features. During this period, leadership kept the roadmap fairly unconstrained so Strava engineers—many of them athletes themselves—could drive a product roadmap that encompassed our top user requests, including a training log and weather on activities. EMs then slotted these bottom-up ideas into an organized roadmap. 

When the time came to make the risky paywall move, this strategy paid off: The new features were responsible for a large portion of paid subscriptions. Trusting engineers’ product intuition not only resulted in a win for the business, but also a more energized engineering team.

Finding the balance

From entropy to order, intuition to fruition, EMs contribute invaluable perspectives and technical context at every stage of the planning process. They can harness the skills and inputs of their teams to deliver consequential projects, facilitate conversation and collaboration between engineering and non-engineering teams, and create strategic opportunities for developers to operate with more independence and creativity. The end result is a roadmap that balances product priorities with positive human impacts. 

When my team is seamlessly executing sprint after sprint, delivering business value while also advancing their careers and working on projects they care about, I can take a deep, calming breath, knowing I’ve done my job as an engineering manager—which is about so much more than portioning out project morsels on Jira tickets.

About the author

Melissa Huang is a senior engineering manager at Calm and a self-described physical and mental wellness nut. When she’s not running, she’s meditating or managing development teams.

@meowlissa10

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