The Right Competitive Intelligence Questions: Weekly Winning Strategies
The Right Competitive Intelligence Questions: Weekly Winning Strategies
The right competitive intelligence questions and the good questions aren’t just intellectual exercises or quick lists with little thought.
“Erm, what’s their turnover? What’s their pricing? And erm what is their strategy?”
Especially if you’re a founder, chief revenue officer, strategist, or solopreneur trying to grasp your competitors and their actual and perceived growth. These questions are the tools for cutting through the surface-level noise and revealing the machinery underneath. Ask the right question, and you get access. An edge. A lever.
Most teams are still doing reconnaissance from a hilltop, squinting through binoculars. But that’s not your job. You’re not just trying to see further — you’re trying to break in. Crack the fourth wall of your competitor’s strategy. To do that, you don’t need better data. You need better questions.
Not Smart. Sharp.
Too many teams waste cycles asking “smart-sounding” questions that make you look good in a meeting but don’t shift your perspective. “What’s their TAM?” “What’s their UVP?” These aren’t real questions. They’re parroting. Theatre.
What you need are questions that create strategic tension:
They force clarity.
They challenge lazy assumptions.
And they drive action.
Let’s take five investigative, speculative, productive, interpretive, and subjective questions and rebuild them with a real edge. The kind of edge I’ve used working with early-stage startups and later-stage scale-ups where strategic misreads cost millions.
- Investigative Questions: What’s Actually Going On?
This is where you start. But not with their homepage or positioning. You look at movements, not messages. Interrogate behaviour.
Don’t just ask, “What’s happening over there?” That’s too soft. Refine the signal. Ask:
What changed in their product roadmap in the last 6 months, and what does that imply?
Where are they hiring? Where are they not? What bets does that suggest?
What topics have they gone quiet on — and why?
Take Cortex, an AI brand compliance tool that launched in late 2023. Earlier, they hyped up multi-language support. Lately? Silence. And their job boards show zero localisation hires. That’s a shift. Likely a pause on international expansion. Maybe LATAM’s on ice. That’s not trivia — that’s a hypothesis you can act on. If you’re building in adjacent markets, knowing they’re pulling back gives you room to move.
- Speculative Questions: What If They Moved First?
This is where things get interesting. Where most competitive analyses stay observational, you shift into simulation. Game theory. Imagination with teeth.
Ask:
What if they changed pricing — who would they squeeze?
What if they partnered with [X]? What would that change in the ecosystem?
What if they’re deliberately tanking metrics to win a land grab?
These aren’t fantasies. They’re controlled stress tests. I use this framework constantly when modelling what aggressive founders might do — not what they say they’re doing.
A stealth competitor to Canva called PixelTag quietly added enterprise integrations in late 2024 — without a single public announcement. Could be feature creep. But what if it’s a strategic pivot toward enterprise design automation? If your positioning assumes they’ll stay in the SMB lane, you’ll be caught flat-footed.
- Productive Questions: What Should We Do About It?
Competitive intelligence is useless unless it drives action. And most teams stop before it does.
You’ve spotted signals. You’ve speculated. Now, it’s time to use what you’ve learned to pressure-test your own strategy.
Ask:
How can we counter-position in a way they can’t follow?
What move would force them to react to us, not the other way around?
Where can we build so that they won’t chase — by design?
Unifydb, a zero-setup data warehouse launched in early 2023, saw Snowflake dominating with tech, but also burdened by confusing pricing. So UnifyDB built its entire onboarding experience around one promise: predictable cost. They didn’t try to out-tech Snowflake. They flipped its strength — flexibility — into a weakness: unpredictability. That’s how you turn product insight into strategic leverage.
- Interpretive Questions: What Does It All Add Up To?
Now, you zoom out. Synthesis. The strategic read.
You’ve got tactical data. But you need to figure out what it means in the broader context. This is where you stop thinking like an analyst and start thinking like a CEO.
Ask:
What are they really optimising for — growth, retention, or optics?
What tradeoffs are they making — and are they even aware?
What assumptions about the market are they betting on — and what happens if those assumptions shift?
In 2024, GrowthLoop, a data-focused martech startup, built buzz around “composable CDPs.” It hit the hype cycle hard. But look deeper, and you’ll see it was all tied to centralised cloud infrastructure. What happens if the trend swings to edge computing or decentralised data models? Suddenly, their go-to-market looks brittle. Not because of a product flaw, but a strategic blind spot.
- Subjective Questions: What’s the Emotional Weather?
Markets aren’t just rational. They’re emotional ecosystems. And smart operators know how to read the mood, not just the map.
Ask:
Are customers anxious, bored, or overwhelmed — and how’s that affecting adoption?
Are early adopters bragging about using the product, or staying quiet?
Is the market chasing novelty, or craving safety?
This is subtle but powerful. Shifts in sentiment often signal strategic openings before behaviour changes.
Juniper, an AI meeting notes tool, stalled after its launch in 2023. Too much competition. Until they changed their positioning to “no hallucinations, no fluff.” Why did it work? Because the market wasn’t asking for smarter AI. It was scared of unreliable AI. Juniper didn’t win by shouting louder. They won by tuning in.
The Meta-Question That Cuts Through Everything
There’s one question I’ve used in every competitor war game I’ve run — from fintech to SaaS to consumer health.
“What would we do if we were them — and we wanted to destroy us?”
It’s uncomfortable. But it strips away ego, wishful thinking, and internal dogma. It forces radical clarity. When you answer this honestly, you reveal the pressure points of your own strategy — the places you’re exposed to and pretending you’re not.
Final Thought on the Right Competitive Questions
Strategy isn’t analysis. And competitive insight isn’t about being clever — it’s about being clear. Sharp questions do more than reveal information. They force decisions.
Most companies do competitive research like it’s a school project. They collect links. Build slide decks. Show their work. But real insight? That’s earned. Through repeated, focused, sometimes brutal inquiry.
So stop asking what your competitors do. Start asking what their moves mean.
Most importantly, ask what you’re going to do about it.
Let’s talk…