Executing a plan perfectly is nearly impossible.
It's unfortunate, but true. Product managers know all too well that a completely immaculate product roadmap would take a miracle. Unforeseen circumstances will develop despite one’s best-laid plans. But the best remedy for tumult and keeping teams aligned is not strategic brilliance, but rather people skills.
“I’ve found it most important to set up all teams to transparently communicate their progress and obstacles. If this information is readily available and consumed, teams will naturally lean in to support each other and adapt to the latest information,” said Samar Shah, head of product for fintech firm Digit.
We touched base with Shah and another product manager to offer insight into team alignment and how to weather unpredictable changes to the product roadmap.
Skydio is a drone manufacturer and autonomous flight tech company.
When developing a product roadmap, what steps do you take to ensure there’s alignment across teams from the get-go?
I firmly believe in close collaboration between product, design, engineering and marketing. This is the core group that I work closely with when developing a roadmap. A question I try to answer early in the process is, “What should the balance be between building new features and reducing the technical and design debt that has inevitably accumulated?” Asking that question early and trying to strike a balance upfront helps alleviate contention down the road.
Once initial thoughts are assembled, it’s important to widen the aperture and solicit feedback from a broader set of teams. Customer success, sales engineering and sales leadership are typically the next set of folks I’ll turn to for input and feedback. These teams bring a diverse set of perspectives that help pressure-test initial assumptions.
Once that collection of teams is aligned, the final step I take is to ensure direct buy-in from the executive team. I share initial direction and high-level priorities with them early so that any course corrections can be accounted for before briefing on a more detailed course of action.
How do you maintain alignment throughout the development cycle?
Routine, detailed written communication is the key to maintaining alignment throughout the development cycle. If your team is small, you might get away with informal verbal communication and still keep everyone on the same page. But as soon as you start working on several threads simultaneously or have more folks involved then can fit into a single conference room, it’s time to start writing things down and keeping them current.
I routinely turn to two types of documents to help with this: weekly team meeting notes and launch plans. We routinely capture current priorities and the context for decisions that have been made so that we have a historical record of both, and everyone knows where to look for the current state of things. These documents also become incredibly helpful when conducting retrospectives. As for the launch plan document, it doesn't need to be massive. A basic, written, cross-team coordination of activities leading up to a product launch can help ensure that quality assurance, marketing, documentation and enablement activities are all coordinated. This process also helps to quickly identify any gaps between teams.
As project needs shift, how do you reprioritize the roadmap and keep teams aligned?
The only thing certain about priorities is that they will change. New opportunities will present themselves, new challenges will be encountered, and inevitability, roadmaps will need to be adapted.
One of the best ways I’ve found to address this is to be diligent about capacity planning when building a roadmap and to only commit 75-80 percent of available capacity to planned items. This ensures that there will be spare capacity available to handle escalations or entertain late-breaking, time-sensitive feature requests from important customers without having to sacrifice the priorities you’ve fought so hard to get in alignment. If, by some miracle, everything goes as planned, that spare capacity can easily be reallocated to bug-bashing and tech-debt burndown.
All of that said, there will be times where major course corrections will be needed due to unforeseen events. When this happens, it’s best to run an abbreviated process to reprioritize the roadmap: Start with a small team to devise a revised plan, circulate that plan for feedback from a wider audience and then brief the leadership team on the intended course.
Routine, detailed and written communication is the key to maintaining alignment throughout the development cycle. ”
Digit is a fintech platform for saving and investing.
When developing a product roadmap, what steps do you take to ensure there’s alignment across teams from the get-go?
The first step is making sure everyone understands how our mission to make financial health effortless for everyone translates to our product strategy. We opted for a business model that transparently maps to our mission: Members pay a monthly subscription for our automated financial health platform. This drives our product strategy to deeply understand the most important financial needs of our members, build a product roadmap that intelligently solves these needs and ultimately increase the impact our members receive from the subscription. We kick off each planning cycle by aligning on companywide product goals and creating a portfolio of metric-based milestones.
We share drafts of goals early to allow time for cross-functional feedback. Once everyone is aligned on our companywide strategy and goals, we rely on each product team’s expertise to chart the roadmap. Digit product teams are made up of dedicated product managers, engineers, designers, data scientists and business stakeholders. Each team owns a different mandate and domain within our product experience and they work together to ensure that our collective roadmap will ladder up to reach our company goals.
How do you maintain that alignment throughout the development cycle?
We use Coda to maintain a collaborative hub that houses our master product roadmap and the status of each initiative. We operate our roadmap as a living, breathing stack rank, so mid-cycle changes to priority are immediately reflected. Dynamically linked team-level views allow each of our product managers and team leads to drive their own team-level planning, while automatically keeping the master roadmap in sync on the latest status.
Even then, it can be overwhelming to stay up to speed with everything in flight. To help with this information overload, we run a weekly heartbeat meeting that is broadly attended and allows each team to share their most important priorities and how they are trending toward their goals.
Once everyone is aligned on our companywide strategy and goals, we rely on each product team’s expertise to chart the roadmap.”
As project needs change, how do you reprioritize the roadmap and keep teams aligned?
Roadmap reprioritization usually occurs through a series of decisions based on new information: “We just learned X, so we should take Y action.” Our favorite way of getting from X to Y is with a written memo. A well-written memo can lay out the new information, how it changes our prior strategic assumptions (e.g., “we underestimated the technical complexity of this project”) and how it impacts our ability to reach our goals.
In most cases, we can still reach our goal if we shuffle prioritization or adjust team resourcing. Less frequently, the latest information may require us to revise our goals. We ask our project leads to outline the different decision options and make a recommendation. This allows other stakeholders to read and deeply understand their thought processes. We believe that asynchronous processing leads to stronger thinking and levels the playing field for everyone to express their opinions, so we wait to gather written feedback before holding live discussions. Similarly, we don’t force decisions in meetings and let project leads break from a meeting when they have enough input to sleep on it and make a decision.
