Roadmap Prioritization for Overworked Product Teams

A treatise on how to maintain team morale and motivation in the face of overwhelming odds.

In my 20+ years as a product leader, I have worked with many different compositions of product teams across just as many types of scenarios. Though the faces and the projects may change, prioritization, morale, and motivation are always a concern even when not actively a problem to solve. Whether at a five-person startup or a team within an international conglomerate, the universal truth is that people are governed by incentives and have incredible adaptability & resolve… until they don’t.

Why Doesn’t “Ruthless Prioritization” Work?

The phrase “ruthless prioritization” has been bandied about extensively in PM circles, especially when facing a shortage of resources (whether people, time, or capital). Conceptually it makes a ton of sense to advocate for the killing of sacred cows and to give teams the freedom to do “what is right”, but often this doesn’t change the shape of prioritization. If you think back honestly, how often have you killed a core roadmap item when push came to shove? In two decades of experience, I can count my example instances on one hand (not counting wholesale pivots). That’s because, without a significant change in macro-context, your roadmap probably looks the way it does for a reason.

Must Do, Should Do, Want to Do

What then, are the reasons projects end up on our roadmaps? I posit that three key drivers are behind any effort we consider undertaking:

1. Things we MUST do — This is top-down strategic work and the reason your team exists in the eye of leadership. In the integrity space, it’s the identification and mitigation of harms to users. In privacy, it’s protecting data and meeting legal requirements. For growth teams, it’s about moving metrics up and to the right. These projects usually have large external incentives behind them and have significant ramifications for the company and the team if not executed on.
2. Things we think we SHOULD do — As leaders, we have a more granular and informed perspective on what needs to happen than those driving top-down strategy. There is work that we can see “should” happen that no one else really understands the context of. We feel an obligation to fulfill these unplanned for needs and a responsibility to ensure their execution. We also make commitments to others to support dependencies — making us feel a duty to execute on them.
3. Things we WANT to do — This is work that we are personally motivated to prioritize. Whether it will potentially have a positive financial / career impact or is work that we just enjoy doing, we have reason to desire these projects to be prioritized. We’re also used to letting these items fall by the wayside to make sure the items above get done.

Balancing the Humours

Loosely translated as “a reason for being”, Ikigai [which I will not do justice in explaining herein] is a concept that explores the multiple reasons humans do what they do. Any purpose (or even potentially objects) can be classified as something that you love, something that the world needs, something that you can be paid for, or something that you are good at. A purpose could sit within a single classification, several, or (if you’re so lucky) all of the classifications — representing a rare and wondrous situation where all of the incentives align and you find your “reason for being”.

People that are able to find that ideal purpose can dedicate their lives to it, achieving personal fulfillment while making an impact on the world around them (and somehow also paying their bills in the meantime).

While maybe not as philosophically deep, the work that software product teams engage with also requires balance. Projects that exist too far from the overlapping portion of the Venn diagram can tip the scales in aggregate, pushing the equilibrium necessary for teams to function into a downward cycle of work-life balance discussions and protestations about the need for headcount.

A team that spends all of its time focused on MUSTS will invariably feel unfulfilled and unhappy. One that focuses only on SHOULDs will spend all their time explaining why their work is needed. One that only works on WANTS will quickly lose support from leadership. There is a natural balance point for every team and finding it takes time and persistent transparent communication.

Doing More to Find Fulfillment

Prioritization typically takes input from the incentives in top-down order — with externalities making MUSTS the highest priority, then SHOULDs that we feel responsible for doing, and finally WANTS that will give us fulfillment.

This default prioritization, paired with universal resource constraints makes it common for teams to see their entire bandwidth saturated with MUSTs long before SHOULDs or WANTs are considered. This leaves teams with a choice: 1) Choose to execute on only the MUSTs and have an unhappy team that feels unfulfilled and unable to do things that they see as important, or 2) Choose to do more to make room for SHOULDs and WANTs. I have seen teams choose to burn out time and time again — they volunteer to be overworked in order to do things they feel responsible for or are personally motivated to see happen.

Above, we see several potential roadmap compositions. The Balanced model is what many of us think of as ideal. It strives to reduce commitments to MUSTs and make space for SHOULDs and WANTs to allow the team to have an impact while also feeling fulfilled. Your team will feel that they have agency and the ability to control their destiny! But let’s be real, how often does it work out that way? It’s almost a guarantee that the MUSTs will end up as high priority and the WANTs will sit in the backlog until they get officially depri’d.

Then, your team will be Unfulfilled. The MUSTs have pushed out anything that isn’t coming down from the top and you will end up dealing with staff retention issues as people who have been down this road before start to peel off.

That’s when you’ll decide that “stretch goals” comprised of SHOULDs and WANTs can be taken to help balance the bullshit that has eaten your roadmap. You’ll make a decision to Burn Out your team in the hopes that the opportunity to work on things they WANT to will outweigh the constant crunch mode that you end up in. Spoiler — it won’t.

Instead of “ruthless prioritization” we should flip that thinking on its head and strive for “ruthless alignment”. Working to identify the WANTs of the team, agree on SHOULDs, and match them with MUSTs to achieve an Aligned roadmap. What if you actually hired people based on their alignment with the SHOULDs and MUSTs in the queue? What if you proactively dropped MUSTs that don’t fit the profile of your team’s incentives and fulfillment? Teams that ruthlessly curate their priorities based on the alignment of what they feel a responsibility to do and what fulfills them can move mountains.

Get In the Zone

Have you ever wondered why small startup teams seem to move like lightning? Or, how people like Zuck or Bill Gates did so much so quickly in the early days of their companies? The reason is because the best startups achieve a deeply aligned set of priorities and reach a flow state that makes it nearly impossible for them to STOP working.

The cliche of the startup founder writing code for 20 hours straight to prep for a demo with a VC and loving every minute of it is a reality for a lucky few. An engineer that can build a better mousetrap and has the opportunity to change the world while maybe getting rich along the way will happily work until they drop. They have found the overlap between doing the thing they love, impacting the world, and making money. Their WANTs, SHOULDs, and MUSTs are all in alignment.

This is also why you start to see a degradation in efficiency as startups move from founders to initial hires and then expansion of the team at scale.

That alignment of incentives becomes smaller and smaller as the company grows, with the economic opportunity and sense of impact on the world receding from the center of the Venn diagram. That magic Elon feels that lets him sleep under his desk and think of it as a privilege is not felt by the Tesla line workers. It’s a job to them — it’s a purpose to him.

If you want to ship faster and have a team that can’t wait to log in every morning, then creating alignment between prioritization incentives is your next step.

Manufacturing Alignment

How can a software product team create alignment on their roadmap?

Have a Principled and Defensible Charter

One of the beautiful things about product teams at modern tech companies is that charters and responsibilities are as fluid as water. This reactive planning model is thought of by some as optimal, allowing rapid response to emerging context shifts and the picking up of dropped balls. Unfortunately, this “loose approximation of a charter” approach not only creates an opportunity for extensive and continual thrash but also makes your team a dumping ground for externalities.

It is imperative that your team charter have an opinion, be rigorous in creation, and garner strong leadership support. Only when you have a distinct and stable true north can you navigate successfully over a long period of time. This is your chance to make sure that the work contemplated is both impactful and fulfilling to your team- if your charter doesn’t line up with their needs, then what’s the point?

Just Say No to Misalignment

As with most things, the top of the funnel is the biggest lever for making an impact. Assuming that you’ve gotten your charter in order, you should have a set of principles that guide your prioritization process from brainstorming to level of effort estimation to mashups with dependency teams to leadership reviews. Throughout this process, you should be able to clearly define items that don’t align with what is impactful and fulfilling for your team, and reject them.

There are a bunch of ways to do this: You can refer to your charter and explain why the project doesn’t fit your principles. You can offer to consider this for the next half. You can point the ask at another team that has more overlap of charter. Whatever you do — don’t just accept it. Even if it comes with headcount — do you want to sacrifice the long term morale and productivity of your team just to get a couple of engineers that are going to be unhappy as soon as their boots hit the ground?

Build an Aligned Team

Team composition is everything. Your charter and principles need to match your team’s incentives to achieve real alignment. If you’ve got a great team, then changing your charter is the way to go. If you’re building (or rebuilding) a team — then you’ve got a few paths to success:

• Hire the right people — Too often have I seen people pull the trigger on anyone that shows remote interest in their work. Even when surrounded by top talent, incentives should be overriding criteria in hiring. It’s better to have one engineer that will love their work than two that are going to be looking at other roles as soon as they’re able.
• Be open about your work — Tricking someone into joining your team because you need to fill seats never ends well. If they love working with users, but your charter is all backend platform stuff — you need to tell them that. If they join on false pretenses or uncorrected assumptions, they’re going to nope out asap.
• Help people find work they love — Help others find work that will fulfill them, even if it’s on another team. Low morale is contagious and it’s better to spend a little more time recruiting than dealing with productivity problems.
• Ask your team what they love It’s amazing what happens when you ask an engineer what they would like to work on. They’ll be dismissive at first, but with persistence, you can start to understand where opportunities for priority alignment exist. Harness individuality and varied personal incentives to create a resilient team.

Communicate

Communication cures most ills, and ensuring that you have both vertical and horizontal transparency will go a long way to defending your roadmap and building your team. Be deliberate in your communication upward and outwards and make it clear to your partners that building an aligned roadmap that will facilitate team fulfillment is your goal, and you need their help to achieve it.

MSW Framework

The best way to make sure that you’re building an incentive aligned roadmap is to apply a rigorous process to prioritization. Impact and level of effort estimation can help identify what the lowest hanging and shiniest fruit are, but doesn’t take your team’s preferences into account. Explicitly defining these inputs is necessary to generate a clear agreement.

Start with three columns of indexes with scores from 1–5:

1. MUST — External, strategic, or leadership prioritization goes here. I suggest a scale ranging from 1 = “There is little obligation to do this” to 5 = “Negative consequences are imminent if this is not done”. Bring leadership into the discussion on items to get macro-context and help them understand your process.
2. SHOULD — Call out things that there is good reason to do, even if not aligned with larger strategy or incoming demands. Consider a scale from 1 = “We don’t think this is important to do” to 5 = “It’s imperative that someone do something about this”. Even if it’s work that you wouldn’t want to do, this is what you see as important.
3. WANT — This is the place to make your personal preferences clear. Ask your team to bid on what they would like to work on or find fulfilling. Try a scale from 1 = “I hope I don’t have to work on this” to 5 = “I’ll be sad if I don’t get to work on this”. Feel free to ask team members to force rank projects individually from most exciting to least and aggregate that in this index

All three indexes being equal, there is limited benefit to the framework as things that are a MUST have the same footing as WANTs. This however still tells you what projects have aligned incentives.

Weighting these indexes can be done however you like, but should consider the level of stress on the team currently as well as the strategic urgency of the problem space. Integrity and privacy work is inherently higher risk, so MUSTs might be weighted higher — but a team that has been stretched for months working on things that everyone hates probably ought to over-optimize on WANTs for a half.

Over time, you can learn and iterate on the weighting model or adjust the indexes to fit the stage and composition of your team and optimize for long term impact and resilience.

Elasticity & Resilience

Even with your best efforts, you’ll probably have a half that gets inundated with top-down demands that upset the apple cart. What can you do to help your team survive and bounce back?

Spread that shit around

FDA guidelines allow some disturbing amounts of disgusting things in the food we eat. In their wisdom, they choose to allow up to 5 mg of mammalian excreta to be present per pound of sesame seeds! Yum! No one likes the idea of eating mouse poop, but in aggregate these small amounts are indistinguishable to the consumer and have no ill effects. So too are shitty projects on our roadmaps. If one engineer gets a full spoonful of excrement, they have reason to complain — if everyone splits up that 5 mg, no one will bat an eye.

Bounce back before you break

As a geriatric millennial, I had a metal slinky as a kid. Being hyperactive and destructive — I decided to stretch it as far as I could and utterly ruined it for its intended purpose. This is how our teams react to being stretched for too long as well. If you find yourself in an overbooked half, you better make sure the next one is relaxed or your team’s default state will become stretched and useless.

Recognize sacrifice

Resilience comes from convincing yourself that your compromise will result in a larger positive outcome. At the team level, that requires making it clear to those who sacrificed that their contribution was impactful and appreciated. Even in situations where financial rewards aren’t possible, calling out those that went above and beyond is the bare minimum. The worst thing you could do is punish someone for deviating from their typical role to meet a challenge that was thrust upon them.

Putting It All Together

The key to building a resilient team that has high morale and even higher productivity lies in creating alignment between the various incentives that drive your work. Be like a startup and focus on priorities that create clear overlaps between what your team WANTs to do, what they believe they SHOULD do, and what MUST be done.

1. Create a principle-driven charter informed by what your team thinks is impactful and finds fulfilling.
2. Be deliberate in prioritizing alignment, no one else is going to do it for you. Use a framework and get your team involved.
3. Recognize misalignment and fix it by changing team members or dropping priorities.
4. Build resilience by distributing the misaligned work, giving your team a break, and recognizing those that went above and beyond.
5. Learn from your team by communicating clearly and often. Share your intent to build an incentive-aligned roadmap with leads.
6. Iterate on your approach over time to refine your method for driving the alignment of incentives.