Your first call with a seller is part interview, part chemistry test. Don't waste it negotiating price, you don't have enough information yet, and price talk before trust kills more deals than it saves.
Open with context, not price. "Tell me about the route, how'd you build it, and what's a typical week look like for you?" Sellers who built something they're proud of will talk for 20 minutes. Listen.
Then work the diagnostic list:
- Why are you selling, and why now? (Listen for coherence, burnout, retirement, relocation, new venture. "I just want out" is a yellow flag.)
- Walk me through a typical week on the route, days, hours, hardest stop, easiest stop.
- What's your churn looked like over the past 3 years? Any month or quarter that was abnormal?
- How do you bill, auto-pay, invoice, cash? What's the mix, and what's your collections rate?
- What's your chemical and fuel cost per month? (You're testing whether they actually know.)
- What software do you use, and will the subscription transfer?
- Who's your backup if you're sick or on vacation?
- What would you do differently if you were keeping it for 5 more years?
- Will you stay on for a 30/60/90-day transition? Paid or unpaid?
- Are there any HOA, commercial, or vacation-rental contracts I should know about?
- Have you had any complaints, lawsuits, or insurance claims in the last 3 years?
- Is there anyone, a family member, employee, or competitor, who you've discussed selling to first?
You're listening for coherence. A seller who knows their numbers, owns their mistakes, and has a clean reason for selling is worth a premium. A seller who can't quote churn, dodges questions about billing, or pitches "growth potential" instead of facts is telling you what the diligence is about to find.
Ending the call. Don't make an offer. Set the next step: "If you're open to it, I'd like to see your account list with rates and start dates, plus the last 24 months of bank deposits. If those check out, I'll make a written offer within a week."
That sentence does two things, it filters out unserious sellers (they won't share the data) and it positions you as a buyer who underwrites instead of guesses.