The questions worth asking about a competitor (and the ones that waste your time)
Start with the one that hurts: why would a reasonable person choose them over us? If you cannot answer that without insulting the customer, you do not understand your competitor.
Most competitor questions are bad. They are either unanswerable, like what is their burn rate, or useless, like how many employees do they have, or self-serving, like why are we better.
Here are five that are actually worth the hour.
Why would a reasonable person choose them?
Start here, because it is the one that hurts.
Not why do people choose them, which invites you to say things about marketing budgets and buyers being fooled. Why would a smart, well-informed person, who understood both options properly, still pick them?
If your answer involves the customer being confused, misled, or stupid, you have not answered the question. You have defended yourself, which is a different activity that feels similar.
There is a real answer. There always is. Find it, and then decide whether you can live with it.
What do their unhappy customers say, repeatedly?
One complaint is noise. The same complaint nine times is a structural weakness, written down by their own users, in public, for free.
That repeated complaint is the most actionable thing in competitive intelligence, because it is specific, verifiable, and did not come from your own marketing imagination.
What are they hiring for?
Because that is what they will do next, months before they do it. A job post is the earliest honest document a company produces, and it is public.
What did they stop doing?
Nobody asks this. It is the best one after the first.
They used to blog weekly and now they do not. The integrations page has not changed in a year. The ads stopped. There was a whole product area they used to talk about constantly and now they never mention it.
Every one of those is an abandoned bet. Somebody killed it. That tells you either that the thing does not work, in which case do not try it, or that they gave up and left an opening, in which case take it.
Absence is data and it is nearly free to collect.
What would have to be true for them to beat us badly?
This is the pre-mortem, and it is uncomfortable in a productive way.
Imagine it is two years from now and they have destroyed you. What happened? Not vaguely. Specifically. They went downmarket and undercut you. They shipped the one thing you kept deferring. They hired the person who was your only real advantage.
Write down the three most plausible versions. Then go look at whether any of them are currently in progress, because sometimes they are, and you have been carefully not noticing.
The test for any other question
What would I do differently depending on the answer?
If both possible answers lead to the same Monday morning, drop the question. It is not intelligence, it is curiosity with a business justification, and you have client work to do.