jade rubick

Some shoulds for strategy

2025-09-12goal-settingprioritizationproduct-management

I’ve been having some conversations recently on strategy, and have been reading some strategies (product, corporate, and departmental). I’d like to share a few observations of what is essential for great strategy.

Strategy should feel uncomfortable

Strategy needs to make explicit choices. Unless those choices are uncomfortable, it’s probably not sharp enough. And thus it’s not a fully articulated strategy.

A personal example of this was when I was leading up an innovative new analytics product. We had poured a ton of work into making a completely new type of analytics product possible. We were excited about what it would do for customers, and the business.

And then, a new product strategy came out. It made it clear that the focus was on the core product, and explained why that was important.

We had to ask ourselves: do we cancel this work? Do we delay this other product line too, which was about to be released? We chose to do so, and it sucked, but was the right decision. That product never saw the light of day, but we chose an approach that was better for the company. This was good strategy work!

There are some rare exceptions to this, when you’re the first to exploit a new opportunity. But usually strategies should hurt. Or at least be uncomfortable.

Strategy should outline “the diff” against now

A strategy document should outline where you are at today, and where you need to be. It should articulate what the gap looks like.

It’s common for early versions of a strategy document to describe a set of goals. You benefit by going further: where are we at today? Where do we need to be, and why? And importantly, what does that gap look like? This paints a stark picture that then is filled in with your prescription for addressing the path to success. And that path to success is the heart of your strategy.

If you don’t outline “the diff”, you won’t create an argument for your path forward.

Strategy should tell a story

Great strategy is storytelling. It should explain and make sense of the situation.

For example, I imagine most product strategies this year are about AI. But these strategies need story-telling. “Times like these are times of disruption. If you look at previous disruptions of the past, that has been when great companies have emerged. For us to take advantage of the moment, we need to respond to this disruption better than our competitors. We have to make sure we’re best positioned in our response. Here’s what that means…”

Don’t just say what you’re doing, but paint a picture of a narrative. And the narrative ideally should be exciting or scary, like a real story.

More on strategy

I have a longer piece on product strategy that is a good companion piece to this.

Let me know

If you find this useful, or you have feedback, I love to hear it. And I’m happy to help with strategy work!

Thank you

Strategy should be uncomfortable was a distillation of something I had been thinking about, but was driven home by Molly Graham in a LinkedIn post. She in turn was quoting Claire Hughes Johnson, of Stripe, who said “Strategy should hurt”.

Image by chiến nguyễn bá from Pixabay

Jade Rubick

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