“What’s keeping you up at night?” And why do risk professionals – especially brokers – keep asking this question?

Are you still asking customers and prospects this age-old question to uncover current needs? Questions like, “What keeps you up at night?” are outdated. It’s time to offer a smarter exchange. 

In today’s world, you should come to the meeting with ideas to address the nightmare scenarios already traipsing through your client’s head, and you should propose solutions. Help them to know what’s lurking around the corner. 

Most of the savvy insurance brokers whom I talk to say CEOs and CFOs care about two things: what are the problems and opportunities which they can’t see themselves, and what are their competitors doing regarding risk mitigation which they are not. 

Do your homework 

Clients of all sizes keep saying they want you to understand their business and their industry. What can you do to stand out? Do away with the open-water fishing questions, or at least do your homework first. That means mine your client portfolio for insights. For example, if your client has 1,000 trucks in their commercial fleet, what is the benchmark experience, and how does your client become a positive outlier? Gather external data and research peers to see trends and spikes. I am no expert when it comes to specific industries, though Zywave has an arsenal of 1m loss data records mapped to companies and hierarchies. So, I can quickly tell what types of million-dollar loss events have hobbled your company and/or your peers. Why does your company keep having shareholder risk events like D&O claims at such a higher frequency than peers? Why is the severity of your company’s services and operations known losses aka GL and Auto so much greater? What can be learned from the giant breach of contract loss incurred by one of your competitors? I am all in favor of these types of broker-led discovery questions. Ask the questions your customer can’t answer from their limited internal vantage point. 

Go even further 

There’s clearly also a role here for AI to find correlations and connections among claims, loss events, and almost any large dataset which are not readily apparent. 

Sure, cyber risk and climate change exposures are on everyone’s mind – and they should be – but you’ll need to customize your one-size-fits all offering if you’re aiming to establish a long-term relationship rather than a transactional approach. 

It’s not always about selling insurance. At a higher level, you are protecting the balance sheet and you are protecting the brand. I recently listened to a top 10 brokerage CEO speak about the positive attributes of a career in insurance; I agree that there are many. For large- and middle-market companies especially, a proper insurance strategy is an essential element of a successful trajectory. The approach you take to put a strategy in place is crucial. So, bring that proactive line of thinking, strategizing, and solutioning to the table and dispense with the tired “What’s keeping you up at night?” approach to uncovering issues. 


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