Why PMs Aren't Driving Strategy (And Why Workshops Won't Fix It)

A couple of years ago I sat in a strategy workshop where a facilitator spent about an hour walking product managers through where they sat in the market, opportunities, threats, etc.

It was good content, solid delivery and nicely polished slides.
They also ran an activity with post-it notes where the team voted on the most promising opportunities and got a basic heatmap but the energy was quite low. That kind of energy you get when people can't wait to go back to their desks.

I checked in with the CPO 6 months later but the problem was still the same - PMs still weren't driving strategy or even motivated to explore this. They were great at shipping but kept waiting to be told what to build, not on details feature level, but more holistically.

"They just need to think more strategically" is a sentence that I and I'm sure you have heard a lot.

It always pops up in performance reviews, in leadership offsites, in 1:1 where the manager is trying to be helpful and the PM leaves with a vague sense that something important was said but no actual idea what to do with it.

The diagnosis is usually right, more or less. The fix almost never is and I've been trying to work out why for a while now.

BJ Fogg spent years testing a theory about why behaviour does or doesn't change. He was mostly looking at personal habits, exercise and flossing and things like that, but the pattern holds further than that.

The short version is that a behaviour only happens when 3 things are present at the same time.
The person has to want to do it. They have to be able to. And something has to trigger it right now, not in theory.

If you pull any one of those out and the behaviour doesn't happen.

Let's start with motivation. Most PMs who aren't thinking strategically don't think it's their job. Not because they're incapable but because the incentive system points entirely somewhere else: delivery, velocity, features shipped, etc. Keeping the roadmap from turning into a backlog swamp and making sure stakeholders are happy. And sometimes PMs feel more safe in the delivery space as it's more predictable and less vague.

I've watched smart PMs get narrower and narrower over 12 months because the gravitational pull of the delivery machine just dragged them in, not because anyone pushed them down but

You won't have a deep conversation about where the market is going during a sprint review, most of the time you spend talking about what shipped and what didn't.

Ability is real too and I want to be clear about that. Strategy is a craft, actually, not just a mindset you switch into. Most PMs were never shown how to find a genuine insight versus a restatement of a brief. Nobody explained what it means for a strategy to have a diagnosis and guiding policy.

So. The prompt.
A prompt is the thing that should make something happen today rather than eventually. And what I keep noticing is that PM rituals are wired entirely for execution like your typical sprint reviews, stand-ups, Weekly check-ins , etc.

None of those meetings have a moment where someone turns to the PM and says "so what's your actual read on where this market is heading?". Big question, I know but The strategy question does not exist in the schedule. It's not in the agenda. It's not in the template. The prompt is just absent.

I've watched PMs do the strategic thinking privately on their own time and write it up then send it into a Notion doc with a catchy title. 3 people give it a thumbs-up and it's never opened again.

I said earlier that ability is real and needed, and I still think that is true, but the more I ponder this, the less certain I am that it is the main issue.

I believe motivated people with regular prompts tend to find their way to the skill. When the skill sitting there unused is basically the same as not having it at all.

Anyway. I've seen this work exactly once at a company that sort of stumbled into it rather than designed it.

The CPO started asking one question in every quarterly review: "where do you think this market is going in 12 months?" And then waited. Didn't accept "we're focused on retention" as an answer. The first couple of times the PMs scrambled and gave non-answers and left looking flustered. Third quarter, the answers got interesting. By the end of the year two of those PMs were doing the thinking that used to stop at the CPO's desk.

That's motivation plus prompt, in one recurring moment. And yes, you still need the capability side too but it's the one that already gets all the workshops.

I don't have a clean resolution here, honestly. Most organisations aren't set up for this and changing the setup is genuinely hard and the people who have the power to change it don't always understand what exactly they'd be changing.

But I'd start with the prompt. It's the one nobody's looking at.