The importance of thinking like a disciplined investor when managing multiple products.

Ever felt like your roadmap was a bit all over the place? 

Found yourself in endless discussions with stakeholders debating your roadmap?

Creating a strategically sound roadmap isn’t easy, but if you want to lean into a product leadership role, you’ll need to play a significant role in shaping your roadmap.

PMs and Product Roadmaps

Driving the roadmap process is a high-exposure responsibility and that’s always a double-edged sword. Owning the roadmap is a great chance to be seen, have an impact, and demonstrate your strategic capabilities. On the flip side though, you’re staking your reputation and political capital on something that’s very difficult to “get right” and extremely subjective. Plus it’s a tough process.

Many product managers are tasked with “owning their own roadmap,” oftentimes that doesn’t play out and even if it does, someone needs to coordinate those team-level roadmaps across the full product suite.

Most product roadmaps end up being crafted from a long list of potential projects. Those projects are then ranked by a process that spits out a prioritized set of projects that are then roughly estimated and a “cut line” is drawn for how far you think you’ll get down the list. (A cut line is basically how far we think we’ll get down the list)

In a small organization, that’s not a terrible process. Of course, it depends on what your prioritization method looks like but there’s plenty of ways to do that rigorously.

The Challenges of Product Roadmaps

As your organization grows and you have more than one product team or more than one product, the process starts to break down and expose some blind spots. 

Firstly, it becomes exceedingly difficult to reason about the absolute priority of a given project against every other possible thing that could be done. It’s never easy, but as your organization grows, that issue compounds.

Secondly, you’re likely to over-invest in particular areas. The biggest downside of over-investing in certain project types is that it compounds over time to create a strategic weakness or blind spot. The kind of projects you over-index for end up crowding out other projects and drive your product in a direction you may not be actively aiming for.

How do you avoid this pitfall without manually adjusting your prioritization approach all the time?

Enter the Product Portfolio

You might be familiar with the investment principle of diversification? Essentially, that says that by spreading your investment across multiple things you’re less exposed to the risk of one going bad. There’s more to it than that, but basically it’s that investing in different but related things will get you a better result.

As a product leader, I recommend thinking of your roadmap like an investment portfolio. Not every project is going to be a winner. Many will have a small impact, a few will have a big impact, and some won’t have any impact. That’s okay, though. (If all your projects succeed, you’re playing it too safe and leaving value on the table… but that’s another story).

How to Create Your Product Portfolio

How do you apply portfolio thinking to your roadmap? The best place to start is to think about how you want to split your investment between different projects. If nothing immediately comes to mind, I’d suggest thinking about short-term projects, long-term strategic projects, and foundational/platform projects. Then decide how you want to balance your investment across those categories (e.g. 30% short-term, 20% foundational, and 50% long-term).

Short-term and long-term projects are pretty self-explanatory. Keep in mind, your long-term projects should expect an outsized payoff compared to the short-term ones.

Foundational or platform projects are the ones that make all your other projects or products better. Often these are internal tools, product processes, or engineering experience projects. Engineering experience projects are ones that help make your engineering team more productive. Usually, your engineers will have a pretty long wishlist of things that can be prioritized here (better CI/CD is a common candidate).

Once you’ve chosen your categories and established your investment balance, you can plan for the team you’ll have own those projects. Then you can work to prioritize a sub-roadmap for each category. If you use the example categories from above, you’ll have 3 roadmaps and 3 cut lines. 

Taking this project sets you up to have a strategically driven roadmap and at the same time makes it much easier to prioritize since you’re comparing apples-to-apples and working with a much smaller list for each prioritization set.

There are many ways to leverage portfolio thinking in your product strategy and roadmaps, but this is an important starting point. Try it out and let me know how it goes!

About the Speaker
Tatari Product Leader

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