I watched a product team present their quarterly roadmap last year. Twelve initiatives, each one carefully justified with user research, stakeholder alignment, and estimated impact. Everyone in the room nodded. The CPO signed off. No questions.

That’s when I knew the roadmap was wrong.

Not factually wrong — the initiatives were reasonable. But a roadmap where nobody pushes back is a wishlist wearing a strategy costume. If nothing on the roadmap makes someone uncomfortable, nobody is making hard choices.

Strategy is a sacrifice

The word “strategy” comes from the Greek strategia — the art of the general. Generals don’t get to fight on every front simultaneously. They choose where to concentrate force, which means choosing where to be deliberately weak.

Product strategy works the same way. Every initiative on a roadmap consumes the same finite resources: engineering time, design attention, management bandwidth, organisational energy. Saying yes to one thing means saying no — or at least “not yet” — to something else.

The hard part isn’t building the roadmap. It’s defending the blank spaces.

The portfolio lens

I treat every roadmap as a portfolio — allocating effort like capital, with expected returns and hard trade-offs.

When I evaluate an initiative, I’m asking four questions:

  1. What commercial lever does this move? If the answer is vague (“improve user experience”), the initiative isn’t ready.
  2. What’s the expected return and time horizon? Some bets pay off in weeks. Some take quarters. Both are valid, but you need to know which you’re making.
  3. What are we choosing not to do? Every initiative has an opportunity cost. Name it.
  4. How does this compound? The best initiatives create leverage — they make the next initiative cheaper, faster, or more impactful.

If a PM can’t answer these four questions for their top initiative, the thinking isn’t done yet.

The discomfort test

Here’s a diagnostic I use: after finalising a quarterly plan, I look at the room and ask — who’s uncomfortable?

If Marketing isn’t slightly uncomfortable because a campaign-supporting feature got deprioritised, the plan is too safe. If Engineering isn’t pushing back on a technical bet that feels risky, the ambition is too low. If Sales is perfectly happy, nobody cut a customer request that wasn’t strategic.

Discomfort doesn’t mean conflict. It means someone’s priorities didn’t make the cut — and that’s exactly how a strategy should feel. The alternative is a plan that tries to please everyone and delivers for no one.

The kill decision

The most undervalued skill in product leadership is the willingness to stop something that’s already in progress.

Sunk cost bias is real and powerful. A team has spent six weeks building a feature. There’s momentum, pride, invested energy. Killing it feels like waste.

But the question isn’t “what have we spent?” It’s “knowing what we know now, would we start this today?” If the answer is no, the only waste is continuing.

I’ve made a few kill calls that I’m proud of — not because they were easy, but because the team saw that we were serious about investing resources in things that matter, not just things that were started.

What this means in practice

If you’re a product leader looking at your current plan, try this:

  • Name the sacrifices. For every top-3 initiative, write down one specific thing that didn’t make the cut because of it.
  • Find the discomfort. If every stakeholder is happy, you’re not making hard enough choices.
  • Apply the kill test. Look at your in-progress work. Is there something you wouldn’t start today?

Strategy isn’t about having the best ideas. It’s about having the discipline to choose — and the conviction to defend those choices when the room gets quiet.

The roadmap-as-portfolio framework is part of how I think about product decisions.