The skill: Know when a competitor is in the deal, position on your strengths instead of their weaknesses, and control the evaluation criteria so the comparison favors you.
Most deals have a competitor. Sometimes it's another product. Sometimes it's a spreadsheet. Sometimes it's "do nothing." The mistake founders make is either ignoring the competition entirely (leaving the prospect to compare on their own) or trash-talking the competitor (which makes you look insecure and gives the competitor free airtime in your conversation).
Know Who You're Up Against
Ask early: "What else are you evaluating?" or "Have you looked at other solutions?" This isn't fishing for gossip. It's essential context. If they're comparing you to a specific competitor, you need to know so you can position accordingly. If they won't tell you, that's a signal too — either they don't trust you yet, or there's no real competitor and the real competition is inertia.
Do your homework. Know your top 3 competitors cold: what they do well, where they're weak, how they price, and what their customers complain about. You should be able to articulate your competitor's pitch better than their own reps can. This isn't so you can attack them. It's so you can redirect the conversation to where you win.
Group Competitors by Approach, Not by Name
Don't position against specific competitors by name unless the prospect has already brought them up. Instead, group the competitive landscape by approach type. "There are three ways companies solve this problem: the manual way, the all-in-one platform way, and the purpose-built tool way." Then walk through the trade-offs of each approach objectively, like a consultant helping them think through their options. This does two things: it makes you look like a trusted advisor instead of a biased seller, and it lets you define the criteria without ever naming a competitor. By the time you've described the strengths and weaknesses of each approach, the prospect has already concluded which category fits their situation best — ideally, the one where you win.
Control the Decision Criteria
The single most important thing you can do in a competitive deal is define how the prospect evaluates. If the prospect sets their own criteria (usually "lowest price" or "most features"), you're in a commodity comparison. If you help them define criteria that map to your strengths, you've tilted the field.
Do this during discovery. "Companies in your situation usually evaluate on three things: time to value, depth of integration with your existing stack, and ongoing support quality. Does that match what matters to you?" Now you've set the frame. If those happen to be your strong points and the competitor's weaknesses, that's not an accident.
Positioning, Not Attacking
Never speak negatively about a competitor. It backfires every time. Instead, use the "we're different, not better" frame:
- Acknowledge: "They're a solid company. A lot of people use them."
- Differentiate: "Where we differ is [your unique strength]. For companies in your situation, that tends to matter because [specific reason]."
- Let them conclude: "I'd suggest evaluating both options against what actually matters for your team and seeing which one fits."
This works because it's confident without being aggressive. You're showing you know the landscape and trust your product enough to let the prospect decide.
When the prospect says "Competitor X does Y and you don't," don't get defensive. Ask: "How important is Y to what you're trying to accomplish?" Half the time, Y is a nice-to-have they'll never use. The other half, it's genuinely important and you need to address it honestly — either with a workaround, a roadmap commitment, or an honest "that's not our focus, and here's why."
Competitive Traps to Avoid
Don't get into a feature war. Competitors can always add features. You can't win a checklist comparison with a larger company. Win on the dimension they can't copy: speed of implementation, quality of support, founder-level attention, or a fundamentally different approach to the problem.
Don't match their pricing out of panic. If the prospect says "Competitor X is 40% cheaper," your response isn't to drop your price. It's to ask "What's included at that price?" and "What's the total cost of switching if it doesn't work out?" Cheap solutions often have hidden costs: setup fees, limited support, contract lock-in, migration pain.
Don't ignore the "do nothing" competitor. The status quo wins more deals than any named competitor. If the prospect is comparing you to their current process (however painful), you need to make the cost of inaction tangible. "You told me this problem costs you 20 hours a week. Over the next year, that's 1,000 hours. What's that worth?"
Do's and Don'ts
Quick Reference
- Ask "What else are you evaluating?" on the first call. You need to know.
- Know your top 3 competitors cold: their pitch, their pricing, their weak spots.
- Control the evaluation criteria. Set the frame during discovery, not during negotiation.
- Never attack competitors. Acknowledge, differentiate, let them conclude.
- Feature wars are unwinnable. Win on speed, support, attention, or approach.
- "Do nothing" kills more deals than any named competitor. Make inaction expensive.
- When they say "X does Y," ask "How important is Y to what you're solving?"
Written with ❤️ by a human (still)