Challenge · Positioning
Why a broad question rarely names a challenger
A challenger runs its first AI visibility check, types the broadest question in its category, and finds the market leader named and itself missing. That result is real. It is also the least useful question a challenger can start with.
By Prasad Hassan, Founder & CEO · 12 October 2026 · 6 minute read
A broad question such as "What is the best CRM?" asks an assistant for the safest answer for everyone, and the safest answer is usually the brand that the most pages already write about. In most categories that is the market leader. A challenger rarely wins that question early, and many do not try to. They compete on narrower ground, where their positioning makes them the better answer: a segment, a type of buyer, a use case, an integration or a price point. "What is the best CRM for a ten-person recruiting agency?" is a different question, and the assistant now needs a product built for that buyer. Choosing that ground is a positioning decision, and it should be made on purpose. Measure the narrow questions you chose, keep a few broad ones alongside, and expect the broad ones to move later.
Why does a broad question favor the market leader?
An assistant answering a broad question is trying to give an answer that suits almost anyone who could have asked it. It builds that answer from what the web says about the category: comparison lists, review sites, forum threads and the vendors' own pages. The market leader appears in most of them, because it has been around longest and the most people have written about it. A newer product appears in fewer, so it is easier to leave out.
That says nothing about which product is better. It means the broad question is weighted toward whoever is already best known, and a challenger checking only that question will look invisible even while it wins the buyers it was built for.
What makes a question narrow enough to win?
A question gets narrower each time the buyer adds something about themselves. Each addition is a place where a challenger can be the better answer, provided it really is. The usual ones:
- Segment. Company size, industry or stage: "for a ten-person recruiting agency".
- Buyer. The role asking, and what they answer for: "for a head of sales with no admin support".
- Use case. The job the product is hired to do: "for tracking candidates across several open roles".
- Integration. The tools it has to work with: "that works inside Google Workspace".
- Price point or market position. "Affordable", "for a first CRM", "for teams moving off spreadsheets".
- Market. The country or region, written into the question, because chat assistants have no country setting.
Is being this specific a choice or a compromise?
For many challengers it is a choice, and often the right one. Positioning means deciding who you are for. A company that has chosen to serve one segment better than anyone should be measured on the questions that segment asks. Being named first for "the best CRM for a ten-person recruiting agency" can be worth more to that company than appearing fifth on a list for "the best CRM".
The narrow questions are also where buyers with a real need tend to be. Someone who names their team size, their tools and their problem has usually done some of the thinking already, and is closer to choosing.
The test for each question
Would a buyer in the segment you chose actually ask this, in these words? And when they do, is your product genuinely the better answer? If the first is no, the question measures nothing useful. If the second is no, the work is in the product or the positioning before it is in content.
How do you turn your positioning into questions?
- Write down the choice you have made: the segment, the buyer, the use case and the position you take against the leader. One line each. If the team cannot agree on these lines, settle that first, because every question depends on it.
- For each line, take two or three broad category questions and add the detail that makes them yours. Use the words buyers use, taken from sales calls, support tickets and review sites.
- Keep a few broad questions, unchanged, as a control. They show you when the narrow wins start to carry into the wider category.
- Check where the leader is named in the narrow answers too. A narrow question where the leader still comes first is a contested question, and it is worth knowing which ones those are.
- Freeze the set and measure it over time, so that a change in the score comes from a change in visibility and from nothing else.
Does winning narrow questions help with the broad ones?
It can, though nobody can promise when. The pages that win a narrow question, such as a comparison written for one segment, a customer story from that segment, or a review on a site that segment reads, also become part of what the web says about the wider category. Over time, a challenger that owns several narrow questions gives an assistant more to draw on when the question gets broader. Treat that as a likely side effect, and keep measuring the broad questions so you can see whether it happens.
Pick the questions your positioning says you should win, and measure those first.
What to do this week
- Write your positioning as four lines: segment, buyer, use case, and your position against the leader.
- Turn each line into three questions a buyer in that segment would ask, in their words.
- Ask each question in two or three assistants, several times, and note who is named.
- Add three broad category questions as a control, then leave the whole set alone for a month.
If you are an agency
Challenger clients often arrive upset about one broad question where the market leader is named and they are not. Showing them the narrow questions their own positioning should win, and where they already appear, turns a bad score into a plan. It also brings the positioning conversation forward, which is useful work in its own right and hard for a client to do alone.
How we do this ourselves
Brand DNA holds your positioning, your category and your competitor set, and the questions Signal AI Visibility Optimization (AIVO) tracks start from it, so the set reflects the segment and buyer you chose. Competitor Signals shows which positions nobody in your competitor set is occupying. AI Search Visibility runs the whole set on a schedule across the assistants your buyers use, and shows which sources each answer was built from.