For years, salespeople have heard, “All you have to do is get to yes.” In today’s article, I’m going to tell you exactly why yes might be what you don’t want to hear. Think I’m nuts? Keep reading!
As salespeople, we have been trained to get to the yes. That’s all we want to hear! But I have to tell you something: sometimes yes is the last thing you want to hear come from a prospect’s mouth. Let me explain. In his remarkable book, Never Split The Difference, my man, Chris Voss, ex-hostage negotiator for the FBI, outlines three different kinds of yeses, and essentially confirmed something I have suspected for years. If you haven’t read the book, I recommend you get it. I’m not going to recreate it here, but what I am going to do is talk about the yes you never want to hear. And that’s the early yes.
Here’s why: people want to get rid of salespeople. A lot of them don’t have the backbone when you’re sitting across from them to tell you no. Think about it, what’s easier to do? We’ll tell them yes, right? We’re going to tell them yes to get rid of them. We’re going to tell them yes to make them go away. We’re going to do it early and often because we want to get this meeting over with as quickly as we possibly can. And the most comfortable, most non-confrontational way for us to do that is to tell them yes. Then when you leave, and you go away, guess what happens? They change their mind. Something happened in their business operations, “Oh, my incumbent agent came over and broke out a bottle of scotch and talked about his son that’s going to college.” And all of the things that we’ve read about in The Wedge, and it never ends. There are all kinds of excuses. The second reason we don’t want an early yes is because they’re milking’ us, man.
If you go in and you offer a ton of value at the beginning of an appointment, and you’re getting the reassuring yeses, guess what we’re doing? Boom, boom, boom. We’re beating our chest; we’re doing everything we can to make ourselves feel good because that’s what we do, right? These people are buying me. I’m the man. I’m the woman. I’m going to do everything I can to let them know just how awesome I am. And they’re going to continue to nod yes, because why? The ‘I don’t want to get rid of you,’ but more importantly, what if they just want you to keep giving them more and more information, showing how awesome you are so they can take it and later use it against you. The only yes you ever want in a sales call is the yes that ends up with a signed agent of record letter or applications at the end of the meeting.
That’s it, that’s the yes of commitment. Listen, if you’re getting early yeses and those yeses are turning into ruined opportunities, I think I just told you why. Practice listening more than you speak and don’t give up so much value in a sales call that they don’t need you. Show them enough to where they think you know just enough more than they do, that they need you going forward. Now isn’t a time to prove you’re an insurance expert, they’ve already assumed that that’s why they’re meeting with you. Take your time, slow play it, listen, repeat what they ask you so that they understand that you understand, and you’re going to get to the right yes. But if you get a quick one, you better course correct in that meeting as quickly as possible, but you’re never going to kill it in commercial insurance.
Until next time: kill or get killed!
Workers’ compensation is one of the most misunderstood and underestimated lines of coverage in the middle market. Too many producers view it as a commodity, something to quote, bind, and move on from. But as the market heads toward 2026, that mindset is becoming a liability.
For years, commercial insurance producers could survive by being good enough across a wide range of industries. They could write a little construction, a little manufacturing, a little hospitality, and a little habitational business and still build a respectable book.
The commercial insurance industry is in the middle of a quiet evolution.
While most conversations still revolve around premiums, deductibles, limits, and carrier appetite, a different category of risk transfer has been gaining traction beneath the surface—parametric insurance. It is not new, but it is finally becoming accessible, relevant, and actionable for middle market producers who are willing to think differently about risk.
In a recent episode of the Power Producers Podcast, I sat down with Brian Thompson from Descartes Underwriting to unpack what parametric insurance actually is, what it is not, and why producers who ignore it may be leaving their clients—and themselves—exposed.
This article breaks that conversation down into practical, producer-friendly language and shows how parametric insurance fits into modern middle market risk management.
The last several years have reshaped the landscape of property insurance across the country. While most national carriers have retreated from coastal states, wildfire zones, and other catastrophe-exposed regions, a handful of disciplined players have taken the opposite path—leaning into difficult markets with a strategic, data-driven approach.
For most entrepreneurs, the decision to start a business is rooted in the promise of freedom. Freedom from a boss, freedom to control income, and freedom to build something meaningful. Yet for many business owners, particularly in service-based industries and middle-market companies, that freedom slowly erodes. What begins as ownership eventually turns into obligation, where the business demands constant attention and the owner becomes the single point of failure.
The insurance industry is full of shortcuts. Some producers look for ways to streamline the quoting process, others avoid hard conversations with clients, and many rely on endorsements or extensions because they are “easier” than diving into the details. Nowhere is this more dangerous than in the world of cyber insurance.
Too many agents assume that a cyber endorsement on a BOP or commercial package policy is “good enough.” It isn’t. In fact, treating a BOP cyber extension as a replacement for a standalone cyber policy leaves clients dangerously exposed, puts producers at risk of losing accounts, and opens the door to costly errors and omissions (E&O) claims.
Cyber threats evolve faster than any other area of risk, and endorsements simply can’t keep up. If producers want to protect their clients and themselves, it’s time to understand why standalone cyber insurance is non-negotiable.
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