Strategy Is Never a Priority
Every year we know exactly when next year begins, and every year the plan for it is late. We blame the day-to-day, and it does take its share. But the real reason sits deeper, in how our brain reacts to work this uncomfortable, and once you see it, you can work around it.
In one of my workshops, I opened with a product version of two truths and a lie (that game where people say two sentences and the other participants have to guess which is true and which isn’t). At that workshop, last December, one of the participants said, “Our roadmap for next year is ready.” The whole room laughed, because it was obvious that this was the lie.
Nobody is ever ready on time. But why?
I mean, we all know exactly when next year is coming. It isn’t a surprise, and yet every year most of us reach the last few weeks without a plan for it.
The common explanation is that it’s a matter of priorities. The day-to-day takes up all the time there is, and next year can always wait another week. That is true, but I don’t think it’s the whole story.
Strategy is harder than most of us are willing to admit. It gets us way out of our comfort zone, and so, when the time comes to prioritize, our brain quietly pushes it aside, because it would rather avoid it altogether. We think we prioritized, but we were played by our brains and strategy never actually made it onto the list. If you’ve ever found yourself thinking about next year’s plan, sighing, and moving on to something else, that’s exactly what I’m talking about.
The root of the problem is discomfort, not priority. Here is why it feels so itchy, and what we can do about it.
Strategy always comes with uncertainty
When I was Head of Product at eBay, I was walking out of a management meeting with the VP R&D, my work husband at the time, and he told me, “You’re not good with uncertainty.” I laughed, and he said he meant it.
It stung, but he was right. I thought I handled uncertainty well, while deep down it made me very uncomfortable. That mattered, because I wanted my next role to be VP Product at a startup, where uncertainty is most of the job. I knew that if I didn’t work on it, it would become my glass ceiling.
I don’t know anyone who likes uncertainty. It’s scary.
But uncertainty is at the essence of strategy. In fact, the definition of strategy is a high-level plan for reaching your goals under uncertainty. So if there is no uncertainty, you don’t need a strategy. You need a very good plan, however complex the work is. A heart surgeon doesn’t do strategy for an operation (or at least so I think. My knowledge in this area is based on Grey’s Anatomy. 22 seasons, and counting! Don’t judge).
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In product, the uncertainty is built in. When you are asked for next year’s plan, you are already navigating the unknown. And whether they told you or not, you are being asked for a strategy, and a large part of the work is understanding that uncertainty and finding a way through it.
A different level of thinking
Even when there is little uncertainty, strategic work is hard. It requires a different type of in-depth thinking. You need to make connections that don’t exist yet, and to take a goal everyone thinks is already clear and make it sharp enough to act on. It is abstract thinking about areas you can’t see well yet, pieces that don’t seem to connect, and contradictions that won’t resolve on their own.
Add to that the fact that there are hardly any good examples of roadmaps and product strategy. They aren’t among the Harvard business cases you would study during your MBA, and companies don’t share their internal plans that easily.
So for most of us it is not only hard but also unfamiliar.
As I wrote above, the fact that it’s hard is a feature, not a bug. It requires us to think it through, and that’s the core of the work.
The first step is always the hardest
Since the discomfort won’t go away, we want to trick our brain into making progress. I found that what helps most is breaking the work into smaller questions and taking them one at a time.
To get there, I usually like to start by creating a long list of the open questions I have in my head. There is something about writing the questions down that makes them feel more manageable. Maybe articulating them is already actual progress, and maybe just seeing them, instead of carrying them in our heads, relieves the load. The list can be messy, with overlapping questions in various areas. It’s fine, the point here is completeness, not accuracy.
Then you can choose the questions you feel more comfortable dealing with, because the other ones aren’t lost.
Our brains have an amazing trait: once the work has started, it’s much easier to keep going. It’s the starting that is so hard (I have three kids with ADHD, trust me, I know).
If taking the easy questions isn’t doing the trick either, you can start with even simpler tasks, like opening the strategy document and naming it, or tidying up your research library. The brain still sees it as work that has started, and that immediately reduces the fear level.
No matter what you choose, you should start.
Next year will arrive in less than eight weeks, whether you are ready or not. The next time your brain says there are other, more important things to do, tell it that you know better.
Our free e-book “ Speed-Up the Journey to Product-Market Fit” — an executive’s guide to strategic product management is waiting for you at www.infinify.com/ebook
Originally published at https://infinify.com on November 5, 2026.
