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Want to steal a customer from your competitor? 99% of sales reps, 95% of CROs, and 99% of CEOs never ask the one question that would get it done. And it’s so, so simple: “What would it take for you to move over to us? What problem could we completely, 100% solve for you, so you’d switch?” That’s the question. Ask it. What Everyone Does Instead What we get instead is some version of “they’re better.” A competitive battlecard. A G2 grid with green checkmarks in your column. A LinkedIn comment that says “DM me and we’ll talk.” A cold email that opens with “I noticed you’re using [Competitor] and thought you’d want to see how we compare.” All of that is about you. It says nothing about the one reason this particular customer would go through the pain of ripping out a system their team already knows how to use. Switching is expensive in ways that never show up in the pricing conversation. Migration. Retraining. Re-integrating. Buying out the remaining term. And the political risk to whoever championed the incumbent two years ago and now has to explain the change. So being 20% better doesn’t clear the bar. Nobody moves vendors because your NPS is higher. They move when something is actively broken and their current vendor won’t fix it. Why the Direct Question Works Ask a specific question with no pitch attached and you usually get a specific answer, often by email, often within a day. People like talking about their problems. They especially like talking about the ones their current vendor is ignoring. And an email that doesn’t ask for a meeting, a demo, or 15 minutes on the calendar is the easiest email they’ll get that week to reply to. You’ll get one of four answers: - Something you already do well today. The gap is now one demo and a migration plan. Most reps never find out they were already the answer. - Something on your roadmap. Now you have a design partner with a logo and a ship date attached. That’s the most valuable roadmap input you’ll get all quarter, because there’s revenue riding on it. - Something you’ll never build. Walk away and count it as a win. You just saved two quarters of pipeline theater on an account that was never going to close. - Nothing, or “a lower price.” There’s no real pain here. Deprioritize. A cheaper quote is a renewal negotiation tactic, and they’re going to use yours to get 15% off from the incumbent. Three of those make you money. The fourth saves you a ton of chasing. Then Decide if You Actually Want Them Sometimes the honest answer tells you that you don’t want this customer. Maybe it’s a laundry list of one-off custom work. Maybe it’s “match their price at half.” Maybe it’s a problem that only exists because of how they’ve organized their own team. Maybe it’s five integrations you’d have to build and maintain forever for one logo. That’s a customer who churns in 14 months while consuming 4x the support load of everyone else. Finding that out in an email beats finding it out in month nine of an implementation. The Email Don’t overthink the copy: Subject: One question Hi [Name], You’re on [Competitor] and if it’s all running perfectly just ignore this. But if not, what are the top issues we could solve for you? We gotten 100s of customers to move over by solving problems like [X, Y and Z]. What’s the one problem we’d have to solve 100% to make it worth switching? If we can, we will do it for you. [Your name] No calendar link. No deck. No “quick 15 minutes.” You’re asking for a reply, and a reply is a much smaller thing to give you than a meeting. Founders Should Do This Themselves A founder-to-VP email gets read at a rate no SDR sequence will ever hit, and it gets a more honest answer, because the person reading it knows you can actually do something about what they say. A rep asking “what would it take?” sounds like a discovery question. A founder asking it sounds like an offer. Pick 20 accounts sitting on a competitor. Send 20 versions of that email. Do it once a quarter. That’s an afternoon of work and it will teach you more about your competitive position than any analyst report you’ll ever pay for. Getting the Answer Is Only Half of It You still have to do the work. Five things separate the teams that close switchers from the teams that just collect intel: #1. Go hyper-tailored. ABM it. Come back with 3-4 specific ways you solve the problem they described, for their business, in their workflow. If the prospect has to figure out what’s better about you, you’ve already lost. That’s your job. #2. Offer to do all the work of switching. The migration. The implementation. The integrations. The data mapping. The onboarding. Every one of those is a reason to say “not this quarter.” Take them off the table explicitly and in writing. There are products people would buy today if the vendor just said “I’ll handle all of it.” Almost nobody says it. #3. Build collateral for the switch, not for the category. A tear sheet on why you’re a good vendor is table stakes. What you need is a page that makes it obvious why changing is worth it. The bar for a switch is far higher than the bar for a first purchase, because you’re up against inertia, sunk cost, and somebody’s reputation. #4. Do buy-out deals. If they’re nine months into a two-year contract, give them 15 months free and sign them for a year after that. Zoom did this constantly against WebEx and GoToMeeting. Sales teams rarely love buy-outs. But nobody switches if switching means paying two vendors at once, and no ROI math makes a CFO comfortable with a double-billed line item. #5. Pay up on commission for steal deals. Competitive takeaways take longer and require more work than a greenfield deal. If comp treats them the same, reps will rationally spend their time elsewhere. Pay a premium for switchers and watch how fast the team finds them. Solve A Real, Top 5 Problem, For Real. And They’ll Take The Call. That’s the job when you reach out to steal a customer from the competition. Not better features. To solve a big problem that isn’t getting solved for me today. And do it for me, specifically. The only way to know what that problem is: ask. Almost no one does. They just … pitch features.
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