AMA: HubSpot Former Senior Director of Product Management, Fintech, Zeeshan Qamruddin on Product Roadmap Planning

Ultimately, communicating about your product should tie to the outcome that you hope to drive. When pivoting a product, I've found it's most helpful to be honest about the process the team is going through. Sharing less information with higher quality is far more valuable than any other course of action in these scenarios. For example, when our team was stuck in a rut due to poor Org Design and a mountain of tech debt, we went to our executive team with a clear message. We needed time to unravel and unwind much of the legacy issues from the past. We believed that by taking this time, we would be able to position our teams in a way that would allow an exponential increase in our teams ability to solve their core issues (around interwoven code and tech debt). We did not have an explicit understanding of exactly how long this shift would take, or what the outcome would be, but we did commit to regular updates on our progress. Setting these very vulnerable expectations and committing to continuous communication brought our customer (the leadership team) along on our journey.

This is often the case for companies in a hyper-growth state, especially as they look to find a clear fit in the market. Where I've found success with leadership is by helping them understand the trade-offs in our teams focus. For example, when planning out our team's work, we lean heavily on research and a few key metrics to prioritize. When faced with requests from leadership that may not align, we try to create an apples to apples comparison (though not always perfect) to help bring clarity to the trade-off. Two things are critical here: * Being clear about the capacity of the team, and the realistic implications of having to trade-off (vs attempting to do both simultaneously) * Leaning on data wherever possible. Data is not biased, and likely will help leadership understand your perspectives if the segment that you're looking to focus on differs from the ask.

Roadmap communication is often just as critical as developing it in the first place. Our team has a number of internal stakeholders that are directly impacted by the decisions we make. When we consider the level of detail, we try to anchor Goals and Plays. Goals ensure that we are focused on the right thematic areas, and our goals are prioritized before the start of the year. We socialize our goals and their priority level to help teams understand where we will be focusing, and why. Plays are a level deeper, tying to actions that we will take, features that we will build, and tangible deliverables that will help move the needle on our goals. Plays offer us the ability to understand effort, timing, and dependencies, which can then be socialized for everyone else to see. This empowers our teams to understand who is doing what, and when, for a quarter or half-year at a time.

These are prime scenarios for a Product Leader, as they can use their own research and perspectives to help C-Suite understand the most beneficial bets to place. With a new leadership group, teams have the opportunity to reset on the legacy items that plagued them in the past. For example, upon taking over our Product Area in my current role, the first step that I took was to present a clear perspective on where our team could go. Because there was no leadership team from which I was taking the reigns, the company needed a point of view to be presented and owned. Painting the picture of what our team could be, the steps we would need to take to get there, and outlining how that would directly benefit each of them allowed C-Suite to provide support around an informed perspective.

Finding the right balance of leadership input to infuse in roadmap planning is always a challenging endeavor. What has been most effective in my career is coming to the table with a clear perspective and reasoning for prioritization. As a leader, staying in tune with the business should allow you to preempt those initiatives that are top of mind for your executive team. It is absolutely not an exact science, but building a bridge between 1. The company/executive priorities and 2. The areas that you would like your team to invest will create an organic overlap for the top items on the roadmap.