What are some of the lenses your look through or principles you apply when prioritizing a roadmap? How are they weighted relative to each other?

When I prioritize or stack rank a list of items, I typically find it helpful to understand how each item can (a) deliver customer impact and (b) increase engineering happiness. Additionally, I also find it helpful to understand each item's level of (c) feasibility, (d) urgency and (e) effort. 

I weigh customer impact and engineering happiness at 50:50 -- after all, you need to make your customers happy while also keeping your team excited. Things that are less feasible are often pulled down the list. Whereas things that are higher urgency or less effort might be pulled up the list. At the end of the day, prioritization is an art. 

There are countless product management prioritization frameworks available, such as RICE (Reach, Impact, Confidence, Effort) and MoSCoW (Must have, Should have, Could have, Won't have). That being said, my favorite is a simple, four-lens model that my very first HubSpot manager taught me.

• The Market lens - How differentiated will our offering be compared to other solutions in the market that are solving a similar problem?

• The Business lens - Will prioritizing this initiative allow us to make progress against our higher-level business objectives?

• The Custom lens - How big of a need is there for this feature? Are 80% of our customers asking for it, or is it solving a more niche problem?

• The Technical lens - What's the overall level of effort? To what extent will this create or reduce tech debt?

While it won't always work out this way, in general, you should prioritize features that strongly align with several (or, ideally, all) of these lenses.

This is a great question. I've been using some variant of cost-adjusted impact scoring to prioritize roadmaps for over 20 years now. Every market, buyer, product and strategic context is different, so there's no one size fits all methodology. RICE is an example of one popular approach, but I prefer something more tailored for the specific situation.

Essentially, as an organization we will pick 3-5 outcome measures according to the needs of the business. Examples might be new business growth, churn mitigation, internal efficiency, COGS reduction, etc. The key is to focus on business outcomes here - the what, not the how. So while "system usability" is a great how metric, I'd pick something like churn mitigation or new business impact instead, since system usability would impact either.

Next pick your cost measure. It could be FTE weeks. story points, R&D spend, whatever. Put all of your scores into a matrix and trade off the benefits and the cost. You can weight your impacts differently if some are more important than others. That will net out a cost adjusted impact score, and give you an apples to apples view of priorities.

A few caveats. This approach is a tool, not a panacea. A good product manager is already doing this work in their head whether they realize it or not, so this is as much an opportunity to "show your work" as anything else. You should go blindly picking up whichever has scored the highest. But it will give you a starting point and help you build transparency and trust with stakeholders.

There are lots of frameworks available for prioritization. The key is to find the one that works the best for your product function and the needs of your stakeholders. Most frameworks are directional and product folks should use product sense and intuition to build a roadmap that makes the most sense for their customers and stakeholders.

Some things that I consider

• Business impact

• Customer painpoint solved, not all customer pain points are equal

• Investment to build

• Cost savings for the business

• Defensive feature a.k.a absolutely need this to be at par with competition

• Offensive feature a.k.a sets us ahead of the competition

• Company strategy

A number of these are interconnected eg: if a feature solves a big customer pain point it most likely will return in a big business impact. How you weigh them against each other will depend on your product function, company strategy and your organization's role in it.

I think there are a lot of frameworks when it comes to prioritization. At the end of the day, what is important for me is a combination of

1. prioritization

2. sequencing

to arrive at a confident and well executed roadmap.

Whatever be the framework, there are several signals to utilize

1. Feedback criticality from customers

2. Important of the product/ feature in the product maturity cycle

3. Competitive pressure or innovation

4. Upwards input/ company alignment

5. ROI (Cost benefit analysis)

1. I like to start with the product stage, context, and strategy. From these, and your customer data you should be able to determine your priorities

   • With an early stage, pre-PMF product, you may be prioritizing learning about your customer needs and how well your product is meeting those needs above all else.

   • When you know your product is meeting some people’s needs or providing some valued entertainment, you can focus primarily on increasing engagement and retention. How can you make your product better in ways that result in longer user sessions, more repeated user sessions?

   • When your retention curves look good for 30+ days (and ideally 90+ days), it may be time to focus more on growth.

2. You may have a more complex product though. E.g. one with a creator or developer or seller ecosystem and a 2-sided marketplace dynamic. 

   • In these cases, you should be aligned on a strategy that includes sequencing (e.g. how are you getting high quality content to begin with in order to engage consumers? Or, how can you increase awareness and users enough to become an attractive marketplace for producers?)

3. Funnels also make great lenses. 

   • New user acquisition (by channel and campaign, and the UX flow for each)

   • Retention over time

   • Conversion or upsell funnels

   • Social growth (if any)

4. Things like speed of learning, speed of improvement, and iteration velocity also matter to winning in the long run. So you may need to think this through as well. 

   • Example: Is your tech debt getting so high that you’re wasting a ton of time dealing with regressions? Is this driving customers away or leading to low review scores?

Roadmap items are execution against product strategy. Therefore, considerations for prioritizing roadmap items should include (1) support of the overall strategy, (2) innovation, and (3) delivering against customers' needs. One is not more important than the other; rather it's an aggregate of the these considerations.