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Interview: Lenny Rachitsky

Lenny is a former product lead of consumer supply growth at Airbnb. He writes a popular weekly e-mail newsletter that has a ton of useful information for product managers and founders.

How did you transition to product management?

I started my career in engineering before co-founding my start-up in Montreal, Canada. When Airbnb acquired it in 2012, I joined as an engineer. Over time, I found myself gravitating more and more to a product manager’s responsibilities: running meetings, building roadmaps, and driving metrics.

Product management is often thankless, nerve-racking, and all-consuming but I can’t imagine having another job. PMs are always closest to the center of the action and have a disproportionate amount of influence over key decisions.

Can you describe how roadmap planning at a company should work at a high level?

I like to use what I call the “W framework” to think about planning .

First, it’s important to realize that there are two basic groups involved in building roadmaps:

• Leadership : Generally the executive staff of a company.
• Teams : The people executing the actual work.

Figure 9 . The W framework for roadmap planning.

What role does each group play in the planning process?

The framework is shaped as a “W” because leadership and teams take turns in the planning process:

1. Leadership provides context to the teams. Leadership produces a high-level plan that includes the mission, vision, goals, and strategy of the company. The strategy should be a short narrative that explains how the company will win in the market by investing in key product areas.
2. Teams respond with a proposed plan. Teams need to read through leadership’s plan and fill in the details for each product area. A team’s plan includes the vision and strategy, a list of OKRs and key projects, resources required, and risks and dependencies.
3. Leadership shares an integrated plan. Leadership uses each team’s plan to flesh out the overall company plan. This plan includes information on which product areas are being funded, goals and timelines for each area, and which investments were cut and why.
4. Teams confirm their buy-in. Leadership shares a draft of the overall plan with the teams and ensure that team leads are bought in and ready to execute. This involves getting more feedback from the teams and iterating before sharing the plan broadly with the entire company.

Can you describe an individual PM’s role in this planning process?

As an individual PM, you are responsible for driving the roadmap for your team (step 2) based on leadership’s guidance. To do that, you need to have a well-defined vision and strategy that clearly outlines how your team will contribute to the company’s priorities. Ideally, your strategy will have three pillars that you want your team to invest in.

Once you have these pillars, coming up with individual features to build is a matter of ideation, prioritization, and communication.

• Ideation: Start by gathering ideas from everyone on the team. Run a brainstorm meeting and meet with team members to give everyone a chance to share their ideas. Collect these ideas into a single document and organize it based on your team’s strategic pillars.
• Prioritization: Prioritize ideas using three criteria: 1) Expected impact; 2) Cost; and 3) Risk. I suggest following the 70/20/10 rule: Roughly 70% of resources should go to low-risk, immediate impact work. Roughly 20% should go to risky, long-term bets. And roughly 10% should go to delightful features that the team is excited about building.
• Communication: Communication is really important throughout the planning process. When drafting your roadmap, get feedback from your team and bring them along on the journey. Once your team and stakeholders are bought-in, share your roadmap and strategy widely. Make sure it's easy to find and the single source of truth. Always keep your roadmap updated when things change (e.g. dates, priorities, blockers).

Any other advice on roadmap planning for product managers?

Here are a few more tips for planning:

1. Begin with the problem. Crafting and aligning on a problem statement with your team is the single most important step for planning. A great problem statement starts with the user need.
2. Focus. To design a plan that has a real chance of success, you need to put your resources behind a small number of bets (ideally no more than 3). If you spread your priorities like peanut butter, your most impactful ideas won’t receive the funding they need to thrive.
3. Start early. Think about what your team should build in the next quarter long before the planning process begins. Most successful teams get way ahead of planning and accurately anticipate leadership asks.
4. Listen. Listen to your teammates and talk with customers to gather the best ideas for your roadmap. Review past data-dives and research findings to understand the most impactful areas that you should invest in.
5. Get buy-in from teams you will depend on. Make sure teams you depend on see and buy into your plan early.