How to Effectively Challenge Your Buyers in Sales: 3 Tips to Follow

In November of 2011, one of the most influential sales books ever came out – The Challenger Sale: Taking Control of the Customer. In it, as the title suggests, the authors cited studies showing that top-performing salespeople often challenge their buyers.

That’s bold advice. After all, one of the oldest adages in sales is that the customer is always right. Does it really make sense to challenge the person you are trying to sell to?

Well, sometimes, yes. But you need to do it the right way – because, if you do it the wrong way, you won’t just lose the sale, you’ll damage you and your company’s reputation in the process.

“As a seller, you don't want to be a ‘yes man’ or a ‘yes woman’, because that's not really valuable to your customers,” Sales Expert Lisa McLeod said in her LinkedIn Learning course, Sales Fundamentals. “By the same token, you also don't want to be a jerk and come across as really rude.”

The reason why you want to challenge your buyers is you want to be seen as a strategic partner to them. It’s impossible to be that strategic partner if you rubber stamp everything they say and never challenge their assumptions – because, then, you really aren’t helping your buyer grow.

But, you need to do it the right way.

Three keys to effectively challenging your buyers when selling.

In their course, McLeod and her co-Instructor, Elizabeth Lotardo, listed three keys to effectively challenging your buyers. They are:

1. You need to have a deep understanding of the industry you are selling into.

Here’s where it starts. Just like you shouldn’t trust medical advice from someone who knows nothing about medicine, to challenge your buyers, you need to really know the industry you are selling into.

What does this mean, in a practical sense? It means reading as much as you can about your industry. Staying on top of trends. It means learning from your other buyers, particularly the ones seeing success.

It’s unlikely you are going to be an expert on your first day selling into an industry – meaning, it’s difficult to challenge your buyers on your first day. It takes time. The more you learn about the industry you’re selling into, the more able you are to effectively challenge your buyers.

2. You need to really understand your buyer’s situation.

Building off of that, no matter how well you know the industry, you need to know your buyer’s business equally well. That requires strong discovery, where you get a clear understanding of your buyer’s current state, what matters to them, and what they are trying to achieve. 

Buyers won’t respond well if you challenge them before understanding them – even if your point is valid. Instead, first fully grasp their own unique situation, before jumping in with suggestions.

3. Your challenge needs to come from a place of kindness, with the intention of getting to a better outcome.

Even if you know the industry and your buyer, the intention behind why you challenge really matters. If you are being critical of your buyer to improve your own standing or for your own ego, it won't go well.

Instead, your challenge needs to come from a place of kindness, McLeod said. And, it needs to come with the goal of getting to a better outcome (and, no, a better outcome doesn’t just mean them buying your product).

The takeaway: Yes, challenge your buyers, when applicable. But earn your right to do so. 

Some people really want to be a boss. But, they don't put in the effort of learning how to be a great boss, so even if they get promoted to that role, they won’t be ready for it.

In the same way, you need to earn the right to challenge your buyers. That starts with doing your homework about the industry you are selling into. Equally important, you must understand your buyer and their goals. 

And, even then, if they are doing something worth challenging, you need to go about it in a respectful and constructive way. This leads to you serving your buyer, instead of your ego. 

“Challenges can be really beneficial to everyone, but only when these challenges or conversations are based on knowledge, a trusting relationship, and two kind and respectful people,” Lotardo said. “So don't be afraid to ask those questions that push boundaries to respectfully challenge an assumption that your prospect has made or to offer a new insight that might conflict with their existing point of view.”

Bottom line – challenging effectively can make you a better salesperson, as it'll help you build trust with your buyer. The key is challenging with credibility, and for it to come from a good place.

Looking to challenge your own thinking and improve as a salesperson? Subscribe to LinkedIn’s weekly sales newsletter to get the latest insights sent straight to your inbox.