Ask any salesperson in Chicago to name their least favorite selling activity, and “prospecting” will almost always come up first. Drill down further, and the most dreaded prospecting method of all is cold calling.
Why Salespeople Hate Cold Calling
Prospecting by phone is tough for three key reasons:
Prospects dismiss salespeople immediately. Many have a rehearsed list of excuses to get off the phone before the conversation even starts.
“Not interested” is the default response. Even if the prospect listens, they usually say no — regardless of how many features, benefits, or advantages the salesperson offers.
Salespeople sound like… salespeople. Too many treat prospecting like a compressed sales pitch, starting to “sell” within seconds of saying hello. Everyone ends up sounding the same: “We’ve got the latest…” or “We’re a leader in the field of…”
Your product or service may truly be the latest, greatest, and most cost-effective. But that won’t capture attention in today’s Chicago market.
The Real Problem: Treating Prospecting as Selling
Prospecting — especially cold calling — isn’t selling. It’s marketing. More specifically, it’s proactive, interactive marketing designed to start a conversation, not close a deal.
That means your approach should follow the same rules as an effective marketing message.
Four Elements of an Effective Prospecting Message
Identify your target market. Lead with “Our clients are typically…” or “We work with…” instead of talking about yourself or your company. Make it about them.
Address the problems they face. Highlight specific challenges your ideal prospects in Chicago deal with — things that will strike a nerve. Example: “We work with manufacturing managers who are finding it increasingly difficult to hit both production targets and profit goals.”
Describe outcomes you deliver. Keep it simple and focused on results. Instead of jargon-heavy explanations, use plain language: “We analyze your production process to identify bottlenecks and eliminate them.”
End with a call to action. Ask a clear, direct question. Example: “Would it make sense to invest five minutes on the phone to see if what we’ve done for other Chicago-based companies could help you too?”
Less “Pitch,” More Relevance
When you shift the focus from your company to your prospect — their problems, challenges, and desired outcomes — you stand out from every other salesperson making calls in Chicago.
Prospecting stops feeling like a dreaded chore and becomes an effective way to start meaningful conversations that lead to qualified opportunities.
Bonus Sandler Resource: Download this guide to learn about modern prospecting mistakes and how to avoid making them.
**Blog updated 9/15/2025**
