Dear SaaStr: Should Your Ask a Prospect What Competitors They Are Looking At?
Yes. And in 2026, more than ever.
You’ll find 90% of the time you’ll want to not just tell a prospect who you are competing with, but do so aggressively. And box the competition out at the start.
- “Great to learn about your business! Is there anyone else you are looking at to _______?”
- Then, the sales rep looks up the latest tear sheet or FUD (Fear, Uncertainty & Doubt) on that competitor.
- “Ah. [Competitor 1] doesn’t really have a functional mobile app today, so that can be a challenge.”
- “Ah. [Competitor 2] is about 1/10th the size of us. Good for very small businesses, but not someone you can trust for bigger deals.”
- “Ah. [Competitor 3] doesn’t remotely have the level of security that we do. We’re fully _____ compliant.”
- “Ah. [AI-native Competitor 4] launched 14 months ago. Cool product, but they don’t have integrations into your billing system yet, and they’re still on a single-tenant architecture.”
Etc. Etc.
If you don’t do it, your competitor will.
FUD can be annoying. But it works. And you know what works even better? Truly, really knowing the competition.
And then being a true ally of the prospect. Showing where you’re stronger, and where they are. Few things build up trust faster than that.
In 2026, this matters more than ever for three reasons:
- The competitive set has exploded. Vibe coding and AI-native tooling means there are now 5-10x as many competitors in most categories as there were in 2022. Your rep may not have heard of half of them. The competitor your prospect is evaluating may have launched 8 months ago. If you don’t ask the question, your rep is flying blind. Even if they know the legacy competitors cold.
- Buyers fact-check FUD in real time. LLMs make this so, so easy now. The new B2B buyer has a ChatGPT tab open during the demo. They’re testing your competitive claims live. They’re asking the AI to explain technical concepts while you’re presenting. They’ve already researched your top three competitors before the call. If your FUD is wrong, even a little, the buyer catches it instantly and your credibility collapses for the rest of the meeting. The bar for accuracy on competitive claims is much higher than it used to be. Train your reps accordingly.
- “Do nothing” and “just use Claude” are real competitors now. In a lot of categories, the alternative isn’t just another vendor. It’s the prospect deciding to build something themselves with AI, or just route the workflow through Claude or ChatGPT directly. That’s a real, growing category of competition. Ask about it. “Have you considered just building this internally with AI?” is a fair question to surface and address head-on. If you don’t, the prospect will quietly evaluate it on their own and you’ll lose deals you didn’t even know you were in.
Whatever you do, address competition up front. Usually, in the first few discovery questions.
If you don’t ask, you won’t know which tools in your sales toolkit to use to compete, win, sell, and close. Don’t be shy. They may say they aren’t looking at anyone else or any other way to solve the problem. Then OK, no need to address the competition much more. But ask. Ask somewhere early in the conversation.
And one more thing for 2026: ask again at the second meeting. Buyer journeys are shorter and more dynamic. The competitive set in week 1 is often different from the competitive set in week 4. An AI-native upstart shows up in their LinkedIn feed, a peer recommends a new tool, ChatGPT suggests three options they hadn’t considered. Re-checking the competitive set isn’t paranoid. It’s just current.
And a really, really great conversation about competing with the ex-CROs of both Brex and Divvy here:
Don’t Trash The Competition
Once upon a time, a couple of cars were wrapped in Divvy branding and parked outside the Brex office in San Francisco. This was how deep the rivalry ran.
While a little good-natured harassment between competitors is always a good time, should competitors stick to their strengths and not mention each other to customers or play on the negatives about another company to gain an advantage?
“The right move is never to trash your competition. Humans pick up on that fast,” says Snow.
(Us vs Them image from here)
