Without doubt, asking smart questions is one of the keys to successful selling.

And for those selling complex products or services which require positioning or tailoring in line with the client’s business issues, it’s critical to use your questions to understand those business issues.

When I first started selling large consulting projects over a decade ago it was still common practice to ask very generic questions: “What keeps you awake at night?”, “What are your ‘red’ issues?”. Nowadays that just won’t wash.

Clients expect you to understand their business already, and to know the potential issues they and businesses like them may have (in your field). But it’s a fine line – they also don’t want you presuming you know more about their business than they do. They certainly don’t want to be told after 2 minutes that you can save them 20% of their manufacturing costs or that you can see that their biggest problem is staff retention. To do that is to simultaneously insult them (after 2 minutes I can see how fix problems you couldn’t Mr Client) and demonstrate your ignorance (they may already have tried what you’re suggesting, or their situation is different in some way).

What you need to do is phrase your questions so that they demonstrate your knowledge and prior research – but that don’t presume too much.

“A number of the clients we work with in your field are finding it critical to reduce their manufacturing costs to remain competitive. Is that an issue for you?”

“I noticed you have quite a high employee turnover rate compared to your competitors – what are the implications of that?”

Each of these questions can lead to more detailed follow-up probing to get to the bottom of the issue, its impact, and some of the potential root causes.

Help your clients understand their issues through smart questions and their perception of you as an expert will accelerate. Not because you’ve shown how much you know – but because you’ve shown how you can help them through that knowledge.

And please, don’t ask what keeps them up at night.

My answer to that question: “Nightmares about salespeople asking stupid questions they should know the answers to”.