https://www.octopusintelligence.com/the-move-makes-no-sense-until-you-ask-this-one-question/
The Move Makes No Sense: Until You Ask This One Question: Weekly Winning Strategies
You’re knee-deep in competitor analysis. You’ve got tabs open like a conspiracy theorist. SEC filings. Product changelogs. Archived pricing pages. CEO Twitter rants. You’re not here for inspiration—you’re hunting for asymmetry. And then it hits you:
You find something that doesn’t add up.
A pricing change that seems irrational.
A product launch that no one asked for.
An executive hire that contradicts their stated strategy.
Silence from a company that just raised a round.
This is where most analysts freeze. They stare at the move, confused. They try to explain it away. Or worse, they label it “a mistake.”
You ask the only question that actually opens doors:
“In what context would this situation look right?”
Because that’s how you reverse-engineer the real strategy—the one they don’t talk about. The one the press won’t cover. The one that shapes what happens next.
Confusing moves aren’t mistakes. They’re signals with missing context.
Most companies don’t operate from strategy decks.
They operate from pressure.
Internal burn rate
Sales targets missed for three quarters
Technical debt choking their product velocity
Investor demands post-funding
Quiet customer churn they won’t acknowledge publicly
So when a competitor makes a move that looks wrong, your job isn’t to scoff.
Your job is to ask:
What set of conditions would make this move logical—even smart?
Examples: Same move, different context, different meaning
Move: Competitor kills their freemium tier.
On the surface, that’s suicide in SaaS. Why cut the top of your funnel?
But ask yourself:
“In what context would killing freemium make sense?”
They’re shifting to B2B, and free users only burn support hours.
Their activation rates are abysmal, and freemium pollutes the pipeline.
They’re trying to clean up gross margins ahead of acquisition talks.
Their product is finally strong enough to justify a paid-only model.
Each of these is a plausible scenario. And if you dig, you’ll probably see which one it is. But you won’t see it unless you ask the question.
Move: A young startup launches a half-baked AI feature.
Everyone’s doing it, so you roll your eyes. But then you ask:
“What context would justify shipping something that unfinished?”
They’re collecting prompt data to train a proprietary model.
They’re planting an SEO flag for early discovery on AI-powered [category].
Investors are squeezing them to show “AI progress” on the next deck.
They’re trying to preempt a competitor’s upcoming release.
The feature isn’t the point. The timing is.
This isn’t just guessing. This is strategic modelling.
Ben Gilad talks about competitive intelligence not as “finding secrets,” but as understanding why a company moves the way it does.
That means context is everything.
It means knowing what’s press release theatre and what’s internal reality.
You don’t assume the move is stupid. You assume you don’t yet understand their constraints.
And once you do, their roadmap becomes more predictable than they’d ever want to admit.
Real example: Superhuman AI
On the surface, it is another AI writing assistant. It looked like a crowded play. It looked late to the party.
But ask: In what context would launching Superhuman AI in 2023 make sense?
Major email platforms (Gmail, Outlook) were too slow to integrate AI workflows.
Knowledge workers were copy-pasting into ChatGPT and wasting time.
No one had built an in-context co-pilot for high-frequency communication.
Suddenly, the move isn’t “crowded.” It’s surgical.
They weren’t playing the GenAI feature game.
They were targeting a narrow, high-friction workflow, shipping faster than incumbents.
Context reframes everything.
Another one: Beehiiv’s expansion into monetisation (2023)
Everyone thought they were “just another Substack clone.” However, they started building native monetisation tools for newsletter creators.
People asked, “Why? The audience is too small.”
But again, I ask: What context makes this move make sense?
Substack was leaning into culture wars and identity politics, not business tools.
Creators didn’t want to stack Gumroad, Stripe, ConvertKit (now called Kit), and Patreon.
Newsletter writers were turning into solo businesses—and needed stack simplification.
The move looked small from the outside.
From the inside, it was a direct shot at creator tool fragmentation.
That’s not a feature. That’s a wedge.
How to use this question in practice
The next time you see a competitor move that breaks your model, run it through this 5-step process.
- Document the move.
Don’t overthink it. Just write it out in plain English.
“They just launched an enterprise plan, even though their ICP is startups.”
- Ask: What context would make this logical?
Brainstorm 3–5 possible answers. They don’t have to be pretty. Just real.
Their CAC is rising, and they need bigger ACVs.
Investors are pushing them to expand into B2B.
They’re copying a peer that just raised on an enterprise narrative.
Their churn is brutal, and they think larger firms will stick.
- Look for support signals.
Scan hiring, pricing, site copy, and partnerships. Anything to validate your theory.
New hires from Salesforce? Yup.
Is blog content shifting toward procurement and security? Yep.
Case studies with enterprise clients? There it is.
Ask: What happens if this works? What happens if it flops?
Game it out. Think like a founder. What’s the risk/reward curve?Reposition your narrative.
Now that you see their move clearly, you can react surgically.
Either:
Block it with feature parity
Flank with a more differentiated offer
Or ignore it entirely and press where they’re still weak
Final thought
Most competitor analysis is pattern matching.
What did they ship? Who did they hire? What’s their pricing?
That’s fine—but shallow.
Real leverage comes from interpreting moves that don’t make sense… yet.
Every time you find yourself staring at a decision going,
“What the hell are they thinking?”
That’s your edge.
That’s where the alpha lives.
Not in consensus but in confusion.
So, train yourself to pause.
And ask the one question that unlocks everything:
“In what context would this situation look right?”
The faster you get at answering that, the further ahead you’ll be—before anyone else even knows the game has changed.