TBM 221: Strategy = Insights^Conviction

And why generic strategies are rarely what they seem on the surface.

I had a fun debate with a friend recently about product strategy. The question was whether a strategy needed to be unexpected and novel to be effective. "Sometimes the simple and obvious strategies are the best," they argued. "You don't need to reinvent the wheel; it is mostly execution anyway. We just need to [some generic strategy]. That's what [popular VC] tells all of its portfolio companies!"

There was something about that perspective that bothered me. Getting shit done is an exercise in deciding what NOT to do, and the policies that nudge those decisions in the right direction are what I would expect from a well-tuned strategy. 

It's easy to look at a company and say, "Oh, they're running the X playbook, totally expected." It is much harder to figure out—from the outside—where and how (and why) they said the uncomfortable NOs. For example, to "go up into the enterprise" (a common play), did they prioritize certain hires over others, pause efforts, or commit to re-tooling? Is the effort getting 70% of new funding or 10-20%? Has it been elevated to a board-level metric? Will someone lose their job if it doesn't proceed as planned?

And what's the twist?

Do they have some unique insight or capability that will help them "go up market", Triple-Triple-Double-Double, "become a system of record", "start a PLG motion", go Bluesky, go niche, land-and-expand, create a flywheel, or create network effects? How will they succeed while so many others—an uncomfortably high %, even among skilled teams—have failed?

Consider a prompt and example:

Prompt:

You are likely expecting us to ______________ . And you're right. What may not be as _____________ is __________________.  

Example:

"You are likely expecting us to develop advanced features and integrations to cater to enterprise clients. And you are right. What may not be as immediately perceivable is that instead of simply scaling our existing product for the enterprise market, we're also creating a suite of flexible, modular components that can be mixed and matched. This 'Lego-like' approach allows enterprises to tailor our solution to their specific needs, thereby reducing unnecessary complexity and costs and making our solution appealing even to smaller departments within larger organizations.

However, we have had to refuse the traditional approach of offering one-size-fits-all enterprise software solutions loaded with extraneous features. We believe in allowing our clients to choose what works best for them rather than imposing a prepackaged product.

This also calls for a deep commitment from us. We are not simply developing a product; we are revolutionizing how software is designed for enterprise. Every feature, every module, and every piece of our solution is being crafted with coherence and adaptability in mind. We understand this path won't be easy, but we firmly believe it is the most valuable way forward for us and our clients."

Even this is pretty "ho-hum"—who doesn't want modular components? I've certainly heard my fair share of this preemptive rationalization (literally "Lego blocks') for closing some big enterprise deals over the years—but it does show some bite and conviction. The proof would be in the pudding.

Sometimes everyone expects you to do something, but they underestimate:

• Your unique insights

• Your conviction for committing to the new course

• The challenge of doing the seemingly obvious thing

• A unique twist for getting it done (tooling, capabilities, partnerships, etc.)

• Timing and sequencing (you'll do it earlier or later than expected)

• How different elements of your strategy interact and support each other

• The existing strengths that make the seemingly obvious thing possible

• An emerging trend that makes the expected much more impactful/relevant

• What you said NO to make it all possible

So, in a sense, my friend is right and wrong. 

Yes, "Sometimes the simple and obvious strategies are the best."

But no, that's not the whole story, and that is what makes strategy fun. In a sense, strategy is stubbornness and conviction, and it is both the details and the broad strokes—the diagnosis, guiding policies, and "coherent actions" (Rumelt).

Underpinning how we “execute” is likely a strategy as well…